I typically write 2 blogs a week. Those of you who are good at math may have noticed I’ve only been pumping out one per week these last few.
Here’s a timeline of my life starting from 24 days ago:
24, Took a weekend trip with a good friend to Iguazú Falls, Brazil.
21, Started working with a developer to revamp my website. (Here’s a sneak peek.)
19, Had my final Spanish lesson in Argentina. Said goodbye to my tutor and asked if we could continue working together online.
17, Took a couple’s retreat to Patagonia for the weekend with my lady, an Argentine, and a Brit.
13, Threw a going away party with all my Buenos Aires friends. Said my final goodbye to most of them.
12, Last day in Argentina. Said goodbye to the woman I was dating. Heartbreaking cab ride to the airport. Almost canceled my flight twice.
11, 16-hour return to the United States starting at 1am. Got a phone call that night telling me one of my best friends had killed himself.
8, Lunch with my mom, sister, and aunt for Mother’s Day. Tried to be present and loving while battling the emotional waves from leaving my favorite city and losing my friend.
7, Had several connect calls with friends from all over the globe who reached out in support. Refreshed and revitalized me.
5, Finished the first draft of my free YouTuber’s Guidebook.
4, Flew to Tampa, Florida for my community’s annual coaching retreat. Hung out with my mentor, met other coaches in person for the first time, and competed in various coaching challenges for four days.
2, Made $3300 in an hour and a half. Won the “Out and About” challenge.
1, Flew back to DC. Eighth airport in three weeks.
0, Sat down to type this blog.
After I email this to all of you, I will pack up my car, shower, and drive down to Virginia. There I’ll move into my aunt’s extra bedroom and live with her for the rest of the summer.
I’m doing this for three reasons:
to live frugally
to live close to family I don’t see as often
to focus entirely on work, fitness, and family time
I’ve been bopping around without a technical home ever since I moved out of my apartment in February. It’s felt like a year’s-worth of experiences has been condensed into a single month.
I feel ambitious, sad, and sharp.
Underneath all the hardships and challenges, I can’t help but feel immense gratitude. For the people in my life, for the projects I get to work on, for the body and mind I’ve been gifted and choose to maintain.
In the last week, I’ve sat down at this laptop three times to start writing a new blog. Each attempt lasted 5-10 minutes before I closed my computer and walked away.
I was planning on writing about leaving Buenos Aires and moving back to the United States. I would mention the biggest lessons I learned from my two months in South America. I would’ve told the emotional story of saying goodbye to my friends and girlfriend down there.
But on Thursday night, the day I flew back to my home country, prepping for bed after a long day of travel…I saw a missed call with a few Facebook messages.
“Hey man call me when you can. It’s about Tobias.”
I tried to come up with 20 different things it could be. But I knew. I hadn’t heard from this mutual friend in years.
I called back. He picked up immediately.
“Hey man,” he answered.
“Hey,” I replied. “What’s going on?”
He asked if I was sitting down. I closed my eyes and started crying.
The history of “salt and pepper.”
Tobias referred to our friendship as salt and pepper. You can imagine why. He used the 🤍&🖤 emojis when commenting on photos of us.
I met Tobias McCargo in the summer of 2014. It was customary for young folks in Maryland to spend the summer working and partying in Ocean City, the closest thing that state had to Las Vegas.
He trained me on my first day ever working in a restaurant.
At least…he was supposed to. He called in sick that day so I was bussing tables on my own. I had lied about having restaurant experience because I thought I wouldn’t get the job otherwise.
It was a busy day. I got ripped apart, like jumping into a pool of sharks.
So right out the gate, I was like, Who the hell is this Tobias guy? I’m pretty sure we’re going to be enemies.
Then I met him.
I liked him immediately.
He was funny. He was cool. Every single person at the restaurant knew and loved him. He knew everyone’s name and stopped to talk to each person as we walked around setting up the dining room.
But above all, he showed a level of kindness and givingness I had never seen in a human being.
If you needed help, he wouldn’t just tell you the information you wanted. He would stop what he was doing to personally show you step-by-step how to do something.
I needed guidance in setting up a room service delivery. So he organized the tray for me and joined me in handing it to the hotel guests.
Aside from a small group of high school friends, I didn’t know anyone in Ocean City. So he invited me to his house and introduced me to his buddies and a bunch of coworkers at our restaurant I was too nervous to meet myself.
As fate would have it, we lived on the same street that summer: Gull Way.
We spent that summer partying, skydiving, and making cash at the hotel during the day only to spend it all that night. Ever since then, he’s been one of my closest friends.
As the years continued, we went our separate ways. Many months would fly by without us seeing each other. The occasional text or social media comment.
But whenever we’d reunite, it was always like we’d just hung out the day before.
I was scared that maturity and age would dissolve our friendship. It was built on the foundation of drinking Yuenglings, experimenting with drugs, and staying up until 5am.
But as we got older, we got closer.
Tobias could party, yes. But he could also just talk to you completely sober for hours about anything.
He loved to read. We discussed our favorite Stephen King novels, our favorite anime shows, and polarizing topics like race, religion, and politics.
He was patient. He told you what he thought but always wanted to hear what you had to say. He gave everyone the benefit of the doubt. This man was friends with the world.
And above all, he loved to mess with people.
God forbid you fell asleep with your shoes on. He’d take a photo of you and post it to Facebook. He’d find a nickname you hated and call you it every time he saw you. But he had this magical ability to do it in a way where you had to laugh too.
One time we were setting up the restaurant for a banquet. I asked him where I could find linens for the big tables. He told me to follow him and we started walking down a series of halls.
After about four minutes, I realized he was just taking me in circles.
“Dude where the hell are we going,” I shouted. We burst into laughter. Two dudes hunched over in an empty hotel hallway unable to breathe because they were having such a fun time.
It was impossible to be mad at the guy. And if you ever were, he would apologize profusely because he never wanted to actually hurt anyone or make anyone feel like less.
So, what now?
There are a number of cliches you hear about when a close friend or relative commits suicide.
“I had no idea.”
“I feel like I could’ve done something to prevent this.”
“I’m sad and angry at them for doing this.”
They all hold up.
I feel guilty for not being more assertive these past two years when Tobias fell off the face of the earth. We went for a long time without talking on the phone. He had a history of disappearing from time to time.
But no matter how annoyed I got at his lack of presence, I knew in the back of my mind that we’d reunite and do what we always do. We’d sit at a bar somewhere, he’d buy the first round of beers, and we’d laugh and tell stories. I knew he’d be one of my groomsmen whenever I got married. I knew we’d go to a UFC fight together.
I’ll never get to see those scenes play out though.
I think about his girlfriend who was expecting a life with him. I think about his family being told this news over the phone. I think about all the thousands of friends and acquaintances he stacked up over the years…each of whom will feel a sharp pain learning that one of the greatest people they’ve ever met is no longer living on this planet.
I also think about when I tried to kill myself in 2017. It never hit me until now how utterly devastating that would’ve been for the people around me if it had actually worked.
I’m so sorry.
There’s still a shocking level of denial in me. I keep thinking, Well let me just call him. If I just call him we can sort this whole thing out. If I could just talk to him…
He reached out to me last month for the first time in over a year. I was in Argentina at the time and felt it would be easier to just set up a call when I got back to the States.
I’ve reread these texts a hundred times. I can hear his voice. It makes me cry every time.
We never set up that call. The logical part of me knows there’s no way I could’ve known what would’ve happened. But the emotional part feels like not calling him back will be one of my deepest life regrets.
Just one more conversation. What I would give for that.
Looking back, one thing I’m wildly grateful for is the number of times I said “I love you” to my friend. Every hang. Every conversation.
We were extremely vocal about how much we appreciated each other and the friendship we created. As two masculine men, it never felt weird.
Tell your friends you love them. Tell them why. When one of you leaves, you’ll only wish you said it more.
And please. If you are battling with anything that makes you want to do something drastic, call someone. A friend, a relative, a hotline…
My biggest hurdle growing up was my obsession with what others thought about me. I had to be funny, entertaining, and seen as a cool dude.
It didn’t matter if I actually was these things. So long as the character I was playing was performing well.
I tried to mask my insecurities in middle school and high school by being a class clown and by making fun of others for laughs. Come senior year, I started taking ADHD medication (which I didn’t need) and became twice as self-conscious. Only now, I was too timid to even talk to my friends.
Thank God TikTok wasn’t around back then.
I know none of this is all that unique. Who isn’t an uncertain and anxious mental mess as a teenager? But it seemed like everyone around me had everything figured out at the time. People knew how to be smooth. Guys knew how to get girls. My friends seemed to know things about business and politics I couldn’t comprehend.
But as we’ve all gotten older, I’ve been able to connect and reflect with the men and women I grew up with. Each and every one of them has said the same thing:
“I was super insecure in high school.”
Act 1: Learning something simple
Things got better when I went off to college. I stopped taking Adderall, stopped smoking weed, and started partying and making new friends.
I was becoming more confident. I was beginning to grow into myself. But not for the sustainable reasons I hoped for.
It was mostly the booze.
I still had no idea who I was, what I valued, and what skills I brought to the table. Maybe I could carry on a conversation, but I was still a wildly insecure person.
And once everything came crashing down in 2017, I failed out of college and moved back home. That was the darkest time of my life. But it’s also when I started becoming the man you all read from today.
My self-improvement journey began. I listened to Jordan Peterson’s lectures, started going to the gym, and built a meditation practice. Personal Development 101.
As I became more mindful and more healthy, I quickly embodied one of the age-old pieces of advice:
Stop caring about what people think about you.
It was freeing. I stopped looking at myself through the eyes of other people. I just worked on myself, did my job, and corrected myself when I made mistakes.
There’s a quote I love: “I am not what I think I am. I am not what you think I am. I am what I think you think I am.”
In other words, we have no idea how others actually view us. We just create stories in our heads that are our best guesses. So there’s no point in working tirelessly to figure it out. Should I try to put the puzzle together of what my coworker thinks of me or should I just show up, get my work done, and be as respectful as I can?
I started saying no to things. Derek Sivers calls it “Hell Yes or No.” When faced with a decision, if it’s not a “hell yes,” it’s a “no.”
It felt like I solved life.
Act 2: Discovering nuance
I quit my full-time job in 2020 to start my own freelancing business. I would eventually find life coaching and pursue that as my career.
In the coaching space, we often talk about the concept of people-pleasing: sacrificing your own wants or values for those of other people. It’s often a pernicious habit that drains us and keeps us from doing the things we actually care about.
But then I heard a coach say something that has stuck with me ever since. It was in the middle of a workshop I was running on people pleasing.
“I think people-pleasing gets a bad rep,” she said. “Obviously we shouldn’t be killing ourselves for other people all the time. But I think being a good friend or partner means doing things you don’t want to do from time to time. If you tell your friends you don’t want to go to dinner with them four weeks in a row…don’t be upset when they stop inviting you to dinner.”
This was the first challenge to my “only do what I want” principle.
I love my friends. I cherish my family. Am I jumping with joy at the prospect of every hang, every phone call, every event?
Of course not.
But I’d rather be a person who shows up for the people he loves than put every single decision through a matrix. I want to be able to say I’m sorry. I can set boundaries and make sacrifices.
So this concept of not caring about what others think about me…it was incomplete.
We have to care about what others think about us. It keeps us from acting like assholes, smelling like garbage, and letting our lives rot away. It’s what allows us to make friends and keep them. It’s what gets us hired. Life is significantly better when other people like being around us.
So I went from, “I don’t care about what other people think about me,” to, “I care about what the right people think about me.”
My friends and family. You guys, my audience. My podcast listeners. The folks who care about me and want me to continue to grow. I listen to these people. I use their feedback.
Act 3: Relearning
I’ve been in Buenos Aires for a month now. In one month, I fly back to the United States.
I’m dreading it.
The amount of growth and fun I’ve had here, the people I’ve met, the work I’ve gotten done…It’s been a pivotal moment in my life.
Among the many insights I’ve gathered in my short time here, one sticks out. I think about it when I’m in a taxi flying through the city streets, drinking coffee at an outdoor cafe, and sitting here in this coworking space.
Right now, I’m seated next to around 20 other digital nomads. They come from Europe, North America, and countries that neighbor Argentina. I know many of their names. I’ve partied with a few of them.
Most of them know I have a blog, a podcast, and a coaching business. They know about my travel plans, the wedding I’m in this summer, and my current career goals.
And none of them are thinking about any of that right now.
Not a single person in this room is wondering how I can get more YouTube subscribers, how I can charge more for my coaching, or where I’ll choose to live when the summer is over.
I’m the only person thinking about any of that. They’re all on their laptops reading Slack messages, coding features, or yawning through Zoom calls.
No one cares about how good my Spanish is. No one cares about how jacked I look. No one cares about how big my podcast is growing.
And if they ever do, it’s for a fleeting couple of seconds.
“Oh wow, you have a podcast? That’s awesome!”…Then they go right back to their own desires and insecurities.
Alex Hormozi has a quote I come back to once or twice a week:
We will always be the main character in our movies. So we sometimes make the mistake of thinking other people view us as lead or even supporting actors. But outside significant others and very close relatives, we’re usually just side characters at most and background extras at the least.
Does it make sense to obsess over the opinion of someone who views you as an extra in their movie?
It’s almost arrogant to believe we hold so much power. We act as though the comfort and emotions of others are in our hands. If I go into a cafe and speak horrible Spanish and it’s awkward for the barista…so what?
Did I ruin her day? Will she need therapy because of my horrendous vocabulary?
If so, she has much bigger problems to sort out.
Stop caring what people think about you.
But make sure you still act in a way that the people you love and respect enjoy being around you.
So long as you are a kind and respectful person, keep putting yourself out there and doing what you want. No one is thinking about you nearly as much as your anxiety is telling you they are.
I ask questions for a living. Coaching, podcasts, writing…
What makes a low-quality question?
In my mind, it’s one that can be answered with a single word or sentence.
Do you like your job?
What kind of food do you enjoy?
What do you do for a living?
These run the risk of being answered immediately and mundanely. Not everyone is good at expounding or really running with a prompt. So I like to ask questions that force people to think and open up a bit.
What’s your favorite and least favorite thing about your job?
If you could hand-pick every meal you ate for a week, what would that week look like?
How would you explain what you do for a living without using the name of the occupation itself?
Not only do questions like these tend to get more juice out of the person I’m talking to. But they also bring a sense of fun. There’s nothing quite like being asked a question we’ve never been asked before.
So for me, a high-quality question is one that:
they don’t hear often
makes them think before answering
cannot be answered with a single word
My favorite question to ask people?
What have you been learning about yourself?
Not only does this meet all three criteria mentioned above. But you can ask this question to someone multiple times in a month and get totally different answers. It implies growth and awareness. It allows people to reflect on the direction they’re heading.
I ask this question to my clients, my friends, and myself. The results are reliably rewarding.
Here are some things I’ve learned in these 29 years. Hope you find one of them valuable.
1) Learn the names of employees at restaurants you frequent.
Find great servers, build relationships with them, and ask for them every time. It makes them feel validated to have a regular who prefers them, you can tip them well, and you know you’ll always be taken care of.
Ask them about their life. No one does that. 99% of customers don’t even know their name or they forget it after a night.
I went to the Chipotle near my apartment one to three times per week for two years. There was this quiet dude who was always working. His name is Mike and he was taking on extra shifts to take care of his mother who was sick.
Every time I went in there, I said, “What’s up Mike! How are you man? How’s your mom doing?” He’d give me updates and then pile two enormous piles of steak onto my burrito bowl, free of charge.
All it takes is spending five seconds to treat someone like a human being for them to want to go out of their way for you.
2) Ask 3 questions before stating your opinion.
When someone says something you disagree with, hold off on your counterarguments and rebuttals. It’s more important to ensure you know exactly where they’re coming from and why they believe what they believe.
Steelman their argument. Articulate their opinion so that they’re pleased with your summary.
This has three useful effects:
It makes them less combative and defensive.
You avoid arguing with things they don’t believe.
It slows things down and gives you time to decide whether or not you even want to pursue a disagreement.
A simple rule to build this habit is to force yourself to ask three clarifying questions before giving your thoughts. So you believe x because y?
3) In a group of friends, ask: “What impresses you most about every other person?”
When you’re hanging out with two to five people, this is a fun and wholesome game to play. Everyone takes a turn going from person to person and saying what they most admire about them.
No matter how close you are to these people, you’re bound to hear and say things you’ve never heard or said before.
Everyone feels more connected and heartwarming conversation ensues.
4) When you feel the urge to send an emotional text, wait 24 hours.
No one’s ever been told to “stay awake on it.” Get a night’s sleep and see if you want to send that same text tomorrow. You probably won’t.
I’ve saved myself from sending countless passive-aggressive or annoyed one-liners and paragraphs. These kinds of messages never lead to fruitful solutions. They never make the recipient go, “Oh you’re frustrated? I’m so sorry. Here’s why I was wrong and I’ll never do it again.”
All context is lost over text. If it’s that important and the feelings are still there the next day, call the person.
Don’t hit “send” when you’re in a state. That state will pass, but the message can’t be unsent.
5) Have your phone out of sight when watching movies or TV.
Two screens are too many. Just sit and enjoy the story.
Especially if you’re watching with someone else. It’s meant to be a shared experience.
Too much dopamine-searching weakens attention span and makes us less present. Do what you’re doing. If you’re watching a film, watch the damn film.
6) Know what success actually is.
What we think it is: Someone who is really good at something, doing things we could never figure out.
What it actually is: Someone who worked on something for years and years until we all see their polished results.
Just keep at your thing and eventually you’ll be amazing at it.
7) Buy expensive noise-canceling headphones.
Use them for work, to listen to music or podcasts while you cook, or just to quiet the world around you.
It’s one of the best purchases you can make. I suggest Bose.
8) If a book is bringing you zero value or entertainment, just put it down.
I used to have this rule that I had to finish every book I started. Slogging through boring pages was torture. All that rule did was take weeks (sometimes months) away from me reading something I might’ve actually enjoyed.
If it felt like a chore or a battle to get through the last three chapters, stop reading it. There are too many phenomenal books out there for you to be wasting your time on one that sucks to you.
You might hate a book but love it five years from now. But do your present self a favor and spend time diving into writing that fills you up.
9) Status is fun, but it’s a mirage.
Money. Clout. Reputation.
These things aren’t meaningless. I love making great money. I love building relationships with people who have wealth and power.
But these things will never complete us.
How many times do we have to hear rich and famous celebrities tell us being rich and famous does nothing for our happiness and fulfillment? Status can be fun but it will never be the final piece of the puzzle.
If your basic needs are met, if you’re healthy, and if you have loving relationships…and you’re still waiting on more status or success to be fulfilled, you will remain empty.
There’s nothing wrong with wanting to make more money or wanting a more interesting life. But real fulfillment comes from spending quality time with great friends and family, learning hard and rewarding skills, and being a grateful and healthy human being.
10) If you hate cooking, pick an easy and healthy meal to make every day.
It doesn’t have to be every day. Most days will do.
I love cooking…for other people. But when I’m home alone, I feel zero motivation to experiment or spend more than 20 minutes preparing a meal for myself. I just don’t care.
So, rather than wishing for more invisible willpower, I just choose a simple and nutritious meal I could make basically every day.
For a while, it was scrambled eggs with black beans and salsa. Protein. Carbs. Tasty.
Sometimes I’d use peri sauce instead of salsa. Sometimes I’d cook sausage instead of beans. Make it flexible and repeatable. This removes the headache of figuring out what to eat for at least one meal per day.
11) Frequently ask, “If I knew I’d die 10 years from now, how would I be living my life differently?”
Then do those things.
12) Set up regular hangouts centered around activities.
An easy way to consistently spend quality time with people and get out of the house.
Love knitting, board games, or walking? Find a friend or a group of people who enjoy it too. Then pick a day to regularly meet with them and do that thing.
Some examples from my life:
Thursday morning swims with a bestie. Tuesday night chess club. Sunday rock climbing with the bros. Biweekly phone calls with my friend living in Rwanda.
We expect our relationships to take care of themselves. Proactively scheduling things is a lovely and efficient way to ensure we actually tend to them.
13) Run errands without your phone.
When was the last time you left the house without your phone?
Next time you have stuff to do out and about, leave the black rectangle at home. You won’t be on-call. You’ll have no choice but to be present and engaged with your surroundings. You’re more likely to spark conversation with strangers.
Feel the peace that comes from spending an hour or two completely unreachable and offline. Nothing to compulsively check. Nothing to experience other than the world around you.
14) Write letters, not cards, as gifts.
Giving a $5 card with a sentence on it is such a common tradition and it has always seemed odd to me.
People do it for “the thought.” But there are so many other, more personal and meaningful ways, to express that sentiment. Namely, taking 5-10 minutes to write a letter.
Outline plainly what this person means to you, what you love and appreciate about them, and how they’ve helped you and made your life better. Then read it to them.
It doesn’t matter if this is on printer paper or on a notecard. It’ll mean so much more to them than a funny card with your signature on it. They’ll remember how it made them feel for years.
15) No one is thinking about you as much as you are.
From your perspective, you’re the main character in the movie. But for everyone else, you’re a supporting character at best and a background extra to most.
Stop obsessing over everything you do and say. Not a single person is thinking about you even 1/10th as much as you are. They’re just worried about being the main characters in their movies.
Go to the gym. Share your opinions. Apologize and improve when you make mistakes and get feedback.
Because no one cares as much as you do.
16) Take month-long breaks from booze and sugar.
Pick a month. I typically do January and October.
You’ll get excellent sleep, eat better, and have more energy and willpower.
Can’t do this? You might have a problem.
It’s crucial to prove to yourself you don’t need something like alcohol to have fun, be fun, or live an interesting life.
17) Keep a list of your friends’ goals.
What they’re working on. What they want most. Their latest wins.
Check in on them and see how these things are going. It takes minimal time on your end and they’ll feel seen and supported.
18) When you’re feeling stuck, answer these 3 questions:
What do you want most right now?
What’s in the way of that?
What’s step 1?
19) No one has ever been rejected into a coma or black hole.
The fear of being rejected is 100x worse than actually being rejected.
Ask that person out. Give that sales pitch. Ask for help.
The absolute worst thing that can happen is they say no. Now you’ve gone from not having that thing to not having that thing. You’ve lost nothing.
20) They’re not texting you back because…
They don’t want to.
People who are excited to converse and engage with us will prove it by continuing to converse and engage with us.
Short texts. No response. Never calling back.
These don’t necessarily mean this person hates you. You’re just not a priority to them right now. That’s okay. It doesn’t make them bad people. It just means you shouldn’t keep exhausting yourself to keep the conversation alive.
The number of times in high school and college I kept texting a girl who clearly wasn’t interested in me…I thought, Maybe if I just send the right text, if I just send the perfect joke…she’ll want to get with me.
Never happened. People who want to talk to you will talk to you. If they put in zero effort, stop being needy and move on.
21) The 10/80/10 rule.
10% of people will dislike you no matter what.
10% of people will love you no matter what.
The other 80% will decide based on how skilled you are, how fun you are, and how delightful you are to talk to.
22) Be an ESPN sportscaster.
Bring up the accomplishments and highlights of your friends and partners. Hype them up. Show them off. Congratulate them in front of other people and on your own.
“Look at this! Let’s see that again! Isn’t that incredible?”
They may seem embarrassed but underneath that, they’ll feel super supported and respected.
23) Never set a secret expectation for someone.
If you want something from someone, tell them. No matter how overt or passive-aggressive you are, they can’t read your mind.
Quiet expectations are a one-way road to resentment, disappointment, and unspoken tension.
Be clear and direct about what you want.
24) Be on time.
It’s the easiest way to show respect for others and yourself. It also relieves the constant burden of feeling rushed and frantic.
Being the person who’s always late to things is a childish reputation to have.
25) Download ‘News Feed Eradicator.’
Hate scrolling on Facebook but don’t want to delete it?
Download this browser extension. It hides your Facebook news feed. No more being hypnotized by the algorithm.
26) Keep a list of your biggest insights.
Realizations, discoveries, mindset shifts. What have you changed your mind about lately?
It’s like finding old photos of who you were and what you were working on in the past.
27) Tell your friends “I love you.”
Especially guys. You’ll wish you said it more when you die.
28) Under 50 and don’t like what you look like shirtless? Prioritize exercise and diet.
It’ll only get harder. Now’s the time.
Hire a trainer. Get someone to help you figure out what to eat.
Give yourself more energy, confidence, and brain power by taking care of your body. If you were responsible for taking care of someone else’s body, would you fill it with sugar, simple carbs, and processed foods? Would you make sure that that body was never active?
Be kind to your future self and take care of your present self.
29) The quickest way to earn someone’s respect is to be able to take a joke.
There’s a difference between bullying and poking fun.
If someone is messing around with you, laugh. Join in on the joke.
This shows people you don’t take yourself so seriously and that you’re secure with yourself. I struggled to take jokes when I was younger because I was wildly insecure. Every jab felt like a missile.
Now, I make fun of myself more than anyone else. Life’s short. Be less serious and more silly. You’re no God.
Hope you enjoyed some of these. Hope you disagreed with some of them. Email me and let me know what you think.
Earlier this week I shared the biggest criticisms I took away from my annual feedback review with my buddy. I’ve already been utilizing the changes I wanted to make and it’s been cathartic.
I didn’t want to do this but I feel it’s only natural I share the more tender and positive stuff. One of my biggest insecurities is coming off as arrogant or self-important…but here goes.
1) I practice a growth mindset.
Growth mindset: understanding that skill and talent come from consistent time, effort, and repetition.
Fixed mindset: the false belief that skill and talent are innate and unmovable—you either have it, or you don’t.
It’s the difference between, “I’m just not a musical person,” and “If I sit down and practice piano for 10 minutes a day, I could get pretty good.”
Connor, the guy I do this feedback exercise with, has commented on my lack of perfectionism before. I love to just dive into new projects or crafts, know I’ll be garbage at them, then break through that initial brick wall until I’m actually kind of good.
Theatre, chess, jiujitsu, rock climbing, coaching, content creation…
All these things were pretty painful at the start. I was either cringing at my lack of ability or getting humiliated in one way or another.
In those moments, our 100,000-year-old survival systems kick in. We feel anxious and want to give up. But that’s just a wall to get over.
And once we crawl up and over to the other side (after a few weeks or a few months), that awkwardness and clunkiness turns to fluidity. The problem is that a lot of people simply give up before getting over the wall.
2) I’ve built a life around only doing the things I want to do.
This one really hit when he said it. It’s my central operating system: creating the life I want by helping others do the same.
Joe Rogan is undoubtedly my biggest inspiration in how to live. Let me explain.
Love him or hate him, he lives an incredible life. He was pivotal in me taking control of my life back in 2017. For two reasons…
He was the first real masculine male figure who made being disciplined look really cool to me. Listening to his podcasts and YouTube clips gave an energy of, “Hey man. I love you, but you have got to get your shit together! You could be so much better than you are, and you owe it to yourself to start moving in that direction.”
His career was the first crystal clear example I’d seen of only doing the things you love and making great money from that. He’s a podcaster, comedian, and UFC commentator…and he has worked at these for decades and figured out a way to become rich from each passion.
In short, Joe’s work ethic and results made me think I could get good enough at the stuff I enjoy to make a decent living. I particularly loved his career trio: three different pursuits which offer tons of overlap and variety at the same time.
I’m actively trying to model that myself. My trio is:
If I just do these things for the next 30+ years, that would be my dream career.
Anyway, it sounds almost childish. I just want to do the things I want to do, get better at those things, and repeat that process until I die.
I don’t really set goals. I don’t care about getting a certain amount of money or subscribers or clients. I just want to keep podcasting, writing, and coaching.
If something changes, I’ll pivot. But until then, the train keeps moving.
3) I’m an active listener.
Connor said, “When you listen to people, you make them feel seen and understood, never judged…which is sadly super rare in people today.”
I make a lot of eye contact and often reflect people’s words back to them. What’s funny is I don’t really notice any of that in myself. It must be programmed into me from 1300+ coaching sessions and hundreds of hours of interviewing people.
The biggest gift we can give people is curiosity. Asking people questions and follow-up questions is one of the best ways to make them feel good when they speak with you. It’s a heart-warming way to connect with other human beings.
Connor had a lot of other insanely kind things to say. But these were the three that meant the most to me.
We do this kind of feedback review each year. I’d highly recommend you do something similar with your friends. It can be as simple as two questions:
What’s something I can improve?
What impresses you about me?
What do you want feedback on? What answers are you scared to hear?
This is Connor. He hated me in middle school, is the reason I run my own business, and has been one of my best friends for 15 years. He and his wife run a kick-ass climate tech studio and startup.
Each year, we do a feedback review where we answer deep and critical questions about one another. (Here were my biggest takeaways from last year’s review.)
What’s something you haven’t told me for fear it might hurt my feelings?
How do you wish I was more like you?
How do you wish you were more like me?
What impresses you most about me?
What would you say at my funeral/eulogy?
No feedback is complete without an action item. So for each critique, I came up with ways to change. Here’s how it went…
1) I’m ugly.
*1) I send people sociopolitical links they’re not interested in.
I don’t feel identified with the conservative label. But most of my close friends are more liberal or left-leaning than I am, so it makes me feel like I stick out a bit.
And since I rarely seek confrontation and am rather agreeable, I tend to avoid potentially tense or divisive discussions.
But sometimes I let my opinions peep through. And when Connor brought up the fact that I have sent some podcasts and clips or made some brief comments, I realized something about myself.
I have a habit of sending people links. I tell myself and the person I’m sending them to, “Hey, I think you’d find this fascinating.”
But I discovered what I really meant was, “Hey, here’s something I wish you understood and internalized. Hope ya like it!”
It’s been my cowardly way of indirectly debating and making arguments. As though watching a 40-second YouTube short and avoiding any sort of long-form conversation would bring insight to my friends.
Worse yet, I’ve been coming to conclusions about what I think my friends’ opinions are. I thought, I have liberal friends. They must be blue-haired, mega-woke granola people.
But I have zero evidence to even begin to back that claim.
I called a few friends to apologize for hiding behind links, promising that if I had anything to say I’d just say it myself. I don’t have to have someone else make an argument for me in a podcast or YouTube video. I can construct my own opinions.
Furthermore, I realized I crave two contradictory things at the same time:
I want to have open and honest discussions and debates with my close friends about divisive topics.
I absolutely don’t want to have those conversations. I just want to chill with my friends.
One friend made a great suggestion while I was on my apology phone tour. I can pursue conversations like those by simply stating, “Here’s something I’ve been thinking about lately. Can I get your thoughts on it? I’d love to workshop it because it’s something I feel super passionate about.”
Respectful. Light. Welcoming…Instead of, Hey watch this clip, it’ll expose how stupid you are!Lmk what ya think. 😉
2) I hold people to the high standards I hold myself to.
In terms of honesty, communication, and discourse. And well, they don’t feel like high standards to me. They just feel normal and reasonable.
Firstly, I refuse to lie in any way.
I was basically a compulsive liar when I was younger—lying even about small and insignificant things—and it created a world of chaos for me. I had to remember what I said to each person in my life. And worse yet, when you lie all the time, you slowly begin to believe the lies you tell others, building a false world for yourself.
On top of that, one of my most significant life principles is open and candid truth-telling.
I will always tell my friends, family, and colleagues what is on my mind—so long as I can do so in a respectful and valuable way. I don’t just blurt out every thought that pops into my head.
I tell my close friends what they’ve done to make me feel hurt. I tell my family what they mean to me. I give brutally honest feedback to my fellow coaches (with their permission).
And I want others to do the same for me. Hence this entire feedback review.
Lastly, I try to remain kind and compassionate toward people even when they’re not in the room.
One thing I pick up on quickly is how often someone talks about others who aren’t currently present. Gossip is an enormous turnoff for me. It drains me and it makes me question how often the gossiper talks about me when I’m not around.
My goal is to praise others when they aren’t in the room. I’m not naive, but I try to remain positive and grateful basically 100% of the time.
All this is to say…I often expect these same values and practices from other people.
When one of my friends suggests I lie, I’m shocked. When I learn someone feels a certain way about me, I get frustrated that they haven’t brought it up to me yet. When I hear someone gossip, I think less about them.
I’m proud of these values but I don’t want them to make me feel disgusted toward the people in my life.
First, be mindful. Remind myself that my principles are mine and I’m not in charge of other people.
Second, continue being the change I want to see in the world. When someone lies, ghosts, or gossips…don’t judge or shame them in any way. But instead advertise what you would prefer: uncomfortable honesty, candid conversation, and praise. Lead by example.
In other words: make these boring and wholesome alternatives sexy again. It won’t guarantee people will become more like you, but it will continue to create a more positive atmosphere.
3) I don’t collaborate enough in disagreements.
This last one combines #1 and #2.
Not completely understanding the other person’s beliefs + feeling my way of thinking is supreme = subpar debates and discussions.
I love diving into potentially divisive and radioactive topics: race, gender ideology, sexism, etc.
But I have only been able to do so consistently with friends I already agree with. That makes me sad because I want to be able to talk about anything with anyone. It also means I stay in my bubble: not having my ideas challenged enough and not considering opposing opinions.
Part of this is due to the naturally uncomfortable nature of having these conversations…especially with friends. If you’re at a dinner party with four buddies, would you rather play CatchPhrase or debate police brutality in America?
But a huge component is my own lack of collaboration and questioning. I want to dive headfirst into my thoughts and point out other people’s errors. Folks love that.
When someone says something I disagree with, my internal emotional reaction is, That’s ridiculous, let me set this person straight. Turns out no one is interested in being “set straight” or educated.
People just want to be heard and understood. So…
First and foremost, I need to make it clear to people that they are completely free to share their thoughts and opinions without my judgment or condescension.
I can ask way more questions before I share any of my own ideas or counterarguments. Above all, I can find common ground.
Where do we completely agree? Where do our perspectives divert? What values and desires do we share?
I need to address these things before turning into a professor. No one wants to be lectured at. No one wants to attend a TED Talk against their will.
Finally, I have to get better at steelmanning.
Strawman fallacy: attacking a weak or incorrect version of someone’s argument, often straying from the actual points the person is making.
“You care about climate change? So you just want us to stop driving cars and having babies?”
“You’re pro-law enforcement? So you think cops should just be able to do and say what they want to innocent civilians?”
“You think pornography is bad for society? So you think we should shame women in the industry?”
Steelman argument: debating with the best possible interpretation of someone’s argument.
When you steelman someone, you articulate their opinions to the point that they agree with you. “Yes, that’s exactly what I’m saying.”
It’s hard to do this, especially when we vehemently disagree with someone. But it’s the best way to have a fruitful conversation.
I’m going to practice doing this. I can’t unload my thoughts before steelmanning the person I’m speaking with.
It took a few days for these criticisms to really sink in and for my defensive nature to fade. But I’m excited to put these changes into practice.
Later this week, I’ll share the positive feedback I received in part 2.
One of my besties and I do an annual feedback review. The goal is to be as honest and exposing as possible. Crying is encouraged.
I try to use different questions each year. Here’s 2023’s:
1. What’re you hesitant to tell me for fear it might hurt my feelings? 2. How do you wish I was more like you? 3. How do you wish you were more like me? 4. What impresses you most about me? 5. What would you say at my funeral/eulogy?
These reviews always teach me something I didn’t know about myself. They also prove that openness and being candid don’t kill us but in fact, make us stronger.
For all of my 20s, I would list family as one of my top priorities. But there was a problem.
From 18-23, I was a lost soul trying to find his way at college. My priorities were getting drunk, acting in plays, and scrounging endlessly to find ways to eat and pay my late bills. Then I failed school and didn’t know who I was, what I wanted, or what skills I could offer the world.
And from 23-26, I was reborn and dove headfirst into self-improvement. I started making money, working out, and building the habits for a strong and capable life. I did all the things I wanted to do and weeded out the things I didn’t. I pushed myself to new and scary heights. I crawled out of the hole of a life I dug for myself in my early 20s. I learned sales, started podcasting and making videos, and became mindful and stoic.
But something was missing.
In all those formative adult years, I never once felt like a good son, brother, or nephew. I would say I valued family, but my actions told a different story.
I called and visited when it was convenient or fun for me. I avoided helping my mom out with simple things around the house. I would say I was going to do things and not do them.
The strange part was that I knew this wasn’t the way. I felt slimy every time I told my mom I’d help clean out the attic, and then would stay at a friend’s house and show up hungover in the middle of the afternoon. It was draining and deeply disappointing to everyone involved. And she would say so.
This all tugged on one of my deepest-held fears: Am I going to be a neglectful dad? Will I be incapable of sacrificing my own desires for the sake of my family?
Then three huge things happened that changed everything:
I moved out of my mom’s house.
I started a life coaching business.
My grandpa started to decline.
In the summer of 2020, my friend from middle school reached out and asked if I wanted to get an apartment with her. She was also living with her mom at the time.
We moved into the apartment where I’m currently typing this blog in October of that year. I felt closer to my mom and sister almost immediately.
The place is only 16 minutes away from their house. But the space between us created room for us to miss each other.
But I still didn’t genuinely feel like I wanted to make quality time with family a priority. And that scared me. What was wrong with me?
My mom has done more for me than any other human being. Why didn’t I jump at every opportunity to help her with whatever she needed? Why didn’t I actually care?
Cut to April 2021. As part of my life coaching certification, we each got paired with a coaching partner. My partner, who is one of my closest friends today, was coaching me.
I came prepared with a question: How do I change how I feel about my family?
I was sick of my actions not matching up with my words. If I didn’t change my habits, I knew I’d regret it forever.
I wanted my mom to tell people that I made her life easier, more fun, and less heavy. I wanted my sister to see me as someone she could come to for anything. I wanted my dad’s side of the family to view me as an active and present member of the family.
So I asked my coaching buddy, “How do I change my mindset? Is it possible to alter how I feel emotionally? Can you force yourself to be motivated to do something you don’t feel compelled to do?”
He held space for me. He asked me incredibly powerful and thought-provoking questions. He helped me find the answers I already knew that were hidden beneath the surface.
By the end, everything was clear.
“I’ve been going at this all wrong,” I said. “You can’t just force your mindset to change. I have to change my behaviors first and let the beliefs come afterward.”
My emotions and motivations were out of my control. What I did, how engaging I was, how often I showed up…These were completely within my control.
So I added family time to my weekly system. When planning my week on Mondays, I couldn’t finish without having some form of quality time or conversation. Phone calls. Lunches or dinners. Visits at my mom’s.
What felt like a chore at first quickly became activities I thoroughly enjoyed. I wanted to do things with my mom. Our conversations were more fun. We laughed more. I was curious about how I could help her.
That’s been my journey these past two years. I’m about to turn 29, the age my parents were when I was born.
All those years I blew my mother off. I can’t get those back. While I’ve forgiven myself, it’s still my deepest regret. But I can do everything within my power to be a great family member now and from here on out.
When my grandpa started to noticeably decline in 2021, I changed my habits around driving down and visiting my grandparents. Once every two or three months. Because of that, I got way more hours in with them before my grandpa passed away last month.
If I didn’t do that, I’m positive I’d be thinking, I should’ve spent more time with him. I should’ve shown more appreciation while I had access to him.
But I didn’t. While I was down there with my dad, grandma, and aunts, all I felt was, I’m so glad I’m here. I’m so grateful I prioritized seeing him more this past year.
And I feel the same about my mom and sister.
Something heavy just happened with that side of my family—a story I’ll share in the coming weeks. But I was thrilled to see that my immediate responses have been: How can I be there for my mom? How can I make things easier for her? How can I show up for my sister?
These aren’t things I felt in my early 20s.
I got coached last week. She asked me, “Do you think your mom would say all the things you want her to say about you…today?”
With watery eyes, I replied, “Yes. I think she would.”
I hope that’s true.
Words are lovely, but you are what you do consistently.
You can change your values and motivations by changing your behaviors first.
Live in a way that would make the people you love say great things about you when you’re not around.
When I failed college in 2017, I got a job at the Cheesecake Factory. There I started making money, building strong habits, and getting my life together.
The first change to make? I wanted to be a kinder person.
That’s great. But how does one begin practicing that? Well, it wasn’t something I started doing more of; it was something I put an end to…
In other words, saying something about someone who isn’t in the room—something that would make me uncomfortable if he/she heard it come out of my mouth. In other words: shit-talking.
It’s one of the easiest ways to bond with people: over mutual hatred or frustration of other people like bosses or fellow coworkers. It’s fun. When we know they’ll never hear what we have to say, we feel brave enough to say whatever we want. This person is an idiot. That person is an asshole.
I bring up the Cheesecake Factory because that’s where I started my experiment. I swore to never say anything about anyone I wouldn’t say to their face. And, when I felt the urge to talk shit, I had to instead share something I respected about that person.
This was hard. At times, it felt impossible. Why would I force myself to say something wholesome about someone who brought me nothing but headache or anguish?
Well, it only took a few weeks for me to notice a shift in my thinking. In fact, I was beginning to see the world differently.
I know that sounds a bit fantastical, but it genuinely felt as though I was reprogramming my brain. I was in a better mood at work. Annoying things didn’t make me as mad for as long as they used to. I liked people more.
The biggest thing? I saw just how frequently everyone around me gossiped about others. It’s like trying to stop using the word “like” as a filler word, then recognizing how often other people say it.
So that’s where it all started.
Cut to: today. I have absolutely zero interest in engaging in gossip or any conversation where we’re just badmouthing someone who’s not in the room.
I was at a party a few months ago and a raging shit-talk fest erupted. I left the room.
When my friends start criticizing somebody, I’ll go as far as to say something like: “Hey, thank you so much for trusting me and being open and vulnerable. But if we’re going to talk about someone else in this way, let’s set an intention. Let’s make sure we leave this conversation with a change or an action to take so we’re not just gossiping.”
You might be reading all this and thinking, Dillan…isn’t this all a bit overdramatic?
Well, I did theatre in college. So drama is in my blood.
Jokes aside, here’s why I think this is important.
I think gossiping is a slippery and cowardly slope to other deeper and darker habits. Comparison. Resentment. Insecurity.
That last one is massive. I’ve never known someone who is hugely secure, confident, and fulfilled by their life…who talks shit about other people. Gossip almost always comes from a place of insecurity.
Alex Hormozi said something in a 12-second video a few months ago that really stuck with me:
“People who are ahead of you in life are not talking shit about you. They’re not even thinking about you.”
The healthiest, most successful people I hang out with spend zero time gossiping. Instead, they congratulate people behind their backs. They highlight areas of admiration and respect, and any judgment spoken comes from them pointing out their own flaws.
No one who’s crushing it in life is leaving a mean comment online.
So I’ll leave you with two questions to ponder:
How much time do you spend talking about people who aren’t in the room?
How much of what you say about those people would you be comfortable with if they heard you say it?
Praise people behind their backs. Criticize people to their faces.
I’ve been connecting with strangers, coaching people, and staying in touch with friends for years. Here’s what I’ve learned about great conversations.
First and foremost, people love to feel important or interesting. It’s a basic human need—to feel like we matter and that people care about us.
That’s why we’d much rather talk to someone who asks us questions than someone who just talks about themselves. We all know people who only share their stories, their opinions, or their knowledge. Being asked zero questions can feel like we’re just being talked at. No matter how captivating or funny they are, eventually we want them to show some curiosity.
In coaching there are three types of listening: level 1, level 2, and level 3.
Level 1: listening through your lens
ex: “That reminds me of the time I did that. It was crazy!”
Level 2: listening through the other person’s lens
ex: “That’s crazy because you typically love doing stuff like that!”
Level 3: recognizing another person’s energy
ex: “You feel more excited than normal. What’s going on?”
When we converse with someone who only uses level 1 listening, we want to shoot ourselves. There’s no back and forth, no collaboration.
Want good conversations? Ask questions. Want great conversations? Ask follow-up questions.
Asking someone what they do for a living is common. Asking them why they chose that line of work, what they love and hate about it, and if they’d still be doing it if they had $1,000,000…most people don’t get asked those questions.
Follow-up questions make people explore and tell us more about their values, personalities, and decisions.
But all this doesn’t mean level 1 listening is bad. In fact, it’s necessary. Which brings me to the second principle of great conversations.
People want to feel a connection.
So while they’re powerful, don’t only ask questions. That turns a conversation into an interview. Some amount of self-sharing and inserting is needed.
What then, is the balance? Try this simple trick.
The 2-for-1 rule.
Ask two questions. Share one thing. Repeat.
If the conversation doesn’t seem to be flowing and they’re not asking any questions in return, take the lead. Ask a question. Then ask a follow-up question. Then share something about yourself.
This ensures that the other person knows we’re interested in them but also connects the dots between them and us.
“How was your New Years?”
“Sweet! How do you typically like to party or celebrate?”
“Yeah, I feel the same. My ideal weekend is a cabin in the woods with a dog and a book.”
Obviously, this doesn’t have to be followed like a script. But the idea is to ask more questions and to connect with the person we’re talking to.
Ask more follow-up questions.
Still share your own experiences, ideas, and knowledge.
Use the 2-for-1 rule: ask two questions, share one thing, repeat.
We give ourselves disempowering labels and attributes all the time. Here are a few I heard from some of my coaching clients this year:
“I’m a chaotic person.”
“If I’m not certain I can do something, I can’t do it.
“All I need is more confidence…I’m just unconfident.”
None of these are true.
They’re just excuses meant to justify why we haven’t been living the life we truly want. If we’re chaotic, it makes sense that our physical and digital lives aren’t organized. If we’re uncertain, it makes sense that we haven’t put ourselves out there to try something new and scary. If we’re unconfident, it makes sense that we’re waiting and putting things off.
In my coaching experience, I’ve seen people of all ages and careers drastically change their personalities, habits, and values.
Nothing is fixed. Nothing is set in stone. The only thing keeping us from doing what we want is whatever fear, story, or label we tell ourselves to keep us from taking scary action.
2) Men and women are different.
And that’s okay. Actually, it’s necessary.
There are noticeable, meaningful, and beautiful differences between males and females. That is true of all animals. And what blows my mind most is that that is considered a controversial statement in 2022.
We can start with physicality and work our way down. Height. Weight. Muscle mass. Bone density. Fist size. Hip width. Fat distribution.
These are all averages, of course. I know women taller than most guys I know. And I know men who are more feminine than some women I know.
Which is a great segue from hardware to software.
Anyone who thinks gender is entirely a social construct has never taken testosterone or estrogen.
In Carole Hooven’s book T, she points to research done on men and women transitioning. Without fail, the women who began taking testosterone reported heightened levels of sex drive and decreased levels of empathy and emotionality. And men who started estrogen therapy reported increased compassion and emotional connection to others. I doubt society was telling these people to change in this way.
And no, that’s not to say women are too emotional or that it’s okay for men to be sexual deviants. It’s just useful to look at what makes us different from one another.
We can also observe the spectrum of masculinity and femininity:
This can explain why men and women choose different professions, are often confused by the other sex, and are attracted to different characteristics. We’ll end #2 with that last point.
I’ve been single most of my life. So this year I became fascinated by what men and women are looking for on the dating market.
On dating apps, for example, men swipe right on (say yes to) 65% of women. Women swipe right on 3% of men.
That actually makes sense when we realize that women have way more to lose when pursuing a sexual relationship. They could get assaulted. They might get pregnant. They should be pickier than men.
Most women: “I want a guy who I connect with emotionally, who makes me feel safe, and who I can envision having a child and a ton of fun with.”
Most men: “See hot girl. Want hot girl.”
Moving on before I get canceled.
3) Porn is sexual junk food for the brain.
For the vast majority of heterosexual men, porn is not a good thing.
It weakens sex drive, makes men ashamed of themselves, increases the risk of erectile dysfunction and premature ejaculation, raises our tolerance so we crave more intense porn, makes talking to women even more terrifying, devastates men’s body standards and sexual expectations for women, and decreases motivation and willpower in other areas of our lives.
Quitting porn has been one of the best things I’ve ever done for my sex life and health. But it’s hard. Reading Brett McKay’s How to Quit Porn was super helpful.
A 10-year-old boy with an iPhone will see more gorgeous naked women in five minutes than a man 100 years ago would see in his lifetime. Our brains are not evolved to handle that kind of stimulus.
On the flip side, I don’t think porn is empowering to women.
People say, “sex work is work.” Sure, I think if you’re a consenting adult, you should be able to choose whatever life path you want. But if the goal is to get men to stop objectifying women, making more porn seems like an odd approach.
Banning porn would be wildly impractical and downright impossible. But I don’t think it should be free. I dread the day my son gets internet access and can find whatever he wants at any time.
For anyone who wants to learn more, but doesn’t want to read a whole book, I’d suggest one of these resources explaining your brain on porn:
Can anyone get in great shape? Can anyone pack up and move to Australia? Could anyone really go downtown and ask out 20 people?
But most people won’t. Most people (including myself) have a plethora of fears and stories stopping them from doing the things they’d actually love to do.
Different people have different starting lines, of course. It’s a lot easier for me to be moving to Argentina in a few months than it would be for my friend who has a one-year-old, two dogs, and a home to look after.
But if you live in the western world and are above the poverty line, you can really do anything you want.
One of my clients recently shared her fear of staying productive and healthy over the holidays. “I want to,” she said. “I really want to work out, eat well, and read over these next two weeks. But it’s impossible when you’re traveling and spending time with family.”
Then I asked, “If I said I’d give you a million dollars to have a super healthy and productive couple of weeks, what would you do?”
She smiled and told me working out, eating clean, and finding time to open a book would be effortless.
So again, we can do anything we want. The question is not: Are you able to do this thing? The question is really: How incentivized are you to make this thing happen?
One helpful model I like is asking myself, “If I knew I was going to die five years from today, what would I do?”
My answers to that question always lead me to do scary and fulfilling things. Flying to Vancouver to pursue a woman. Starting a coaching business from scratch with no experience. Moving to Buenos Aires. Spending quality time with the people I love.
In my experience, the people who do cool shit aren’t fearless; they’re courageous. Courage is being afraid but doing the thing anyway. Unfortunately, so many people wait until the fear goes away to live the lives they want. Then they wake up at 50 and wonder what they’ve been doing all this time.
5) Getting in great physical shape is the best thing you can do for yourself and your future family.
I got pretty cut this year. (Bragging? Maybe.)
And I’ve gotten to experience many short-term, superficial benefits.
First, I feel super confident with my shirt off. At the beach, on a summer run, changing in the locker room.
It’s not like women come sprinting out of the woodwork once I peel my v-neck off. But the internal peace I feel knowing that I’m good under the hood is hard to put into words. (The funny thing no one tells you is that when you start to get jacked, 95% of the compliments you get come from other guys.)
Second, I’m mentally sharper.
Many of us have experienced feeling like crap, then forcing ourselves to work out, and all of a sudden we feel awake and ready to go. Aside from the endorphins putting us in a better mood, we also know we just did something difficult and worthwhile. This makes us proud of ourselves and puts us in a more grateful headspace.
The actions needed to get in shape are actually pretty easy. It’s the patience and consistency that’s hard.
Here’s all I’ve done this past year to get a body I’m immensely proud of:
go to the gym 1 to 3 times per week
use the Fitbod app as a personal trainer to tell me what exercises to do when I’m there
eat well more often than not (avoiding sugar, refined carbs, and processed foods)
work out with my PT buddy twice a month
drink supplements like Creatine and Aminos (These are both legal, over-the-counter substances lol.)
That’s it. I just did these things almost every week.
None of them are difficult. It’s the “almost every week” part that’s difficult.
I hated going to the gym for an entire year. I needed my friend to go with me otherwise I’d leave after one set of one exercise. But once I started feeling and seeing real changes in my muscles and body fat…and once I got more familiar with all the machines and equipment and knew what I was doing, I was hooked.
The last superficial plus I’ll share is an example.
I had a lovely evening with a lady friend earlier this year. The morning after, she told me she really enjoyed grabbing my arms and feeling a good bit of muscle on them.
Is getting jacked necessary for being attractive? Absolutely not.
But in general, people are more sexually attracted to folks who are fit. We’re wired to think they’d make healthier offspring and it signals to us that they are disciplined enough to take care of themselves.
I’ll end this point with something more long-term. Here’s a quote from Dr. Peter Attia:
“If you’re over 40 and don’t smoke, there’s about a 70 to 80% chance you’ll die from one of four diseases: heart disease, cerebrovascular disease [stroke], cancer, or neurodegenerative disease [Alzheimer’s, dementia].”
As more of my friends have children, as I just spent two weeks in Virginia watching my grandpa die, and as another year comes to a close…I’m seeing more and more that my health isn’t just for me.
It’s for my future wife, my future kids, and everyone else. If working out and eating well today means I get one more year with the people I love most, it’ll be worth it. I want to be a 60-year-old man who can pick up his grandkids and play with them.
Freak things happen, but an unfortunate number of early deaths are simply because someone didn’t take good care of themselves.
That wasn’t my grandpa, and it won’t be me.
6) When you start something, it never ends up being what you think it’s gonna be.
I started this blog in 2019. It was meant to teach people about habits and self-improvement.
I avoided talking about myself because I was certain nothing about me was interesting. There was also a fear that people would think, who the hell cares about you and your experiences?
The opposite turned out to be true. The most successful pieces I’ve written have reliably been about my own travels, anxieties, and insights. I go back and read my early stuff and it’s like reading a crappy A.I. who copied other personal development creators.
I’ve also tried my hand at several YouTube channels. Vlogging. Sketch comedy. Mindset tips.
None of them stuck.
I even had two podcasts. One with just my friends and me BSing and one where I’d interview guests on their specific passions.
They both faded out because I didn’t really know what my message was or who the shows were for. All these things combined made me feel like I was a guy who could never finish anything. I couldn’t see things through. I feared I lacked enough grit and resilience to create something worthwhile.
Then this year, as I was interviewing creators for my book, I got an idea.
Now, I get to learn from some of my favorite creators in the space—how they started, what their systems are, and everything in between.
Little did I know, I’ve been building all the skills needed to do this all along. Interviewing, editing, uploading, recording myself, listening to my own voice, working with designers and engineers, sharing my opinions…
The next job you take, the next business you start, the next door you open…It probably won’t be the thing you take to your grave. But it will get you closer to whatever the next door is.
You just have to choose.
When you do, one of two things happens.
You love it, and now you know what you want to lean into.
You hate it, and now you know what you want to avoid.
Sitting around and strategizing over the perfect podcast idea is the best way to never start a podcast. But sitting down, hitting the record button, and uploading shitty conversations is the first step to having the podcast of your dreams five years from now.
Don’t worry about what it could be. Just choose something that sounds fun and start. You’ll learn what it’s meant to be along the way.
7) We can double our quality of life by prioritizing our sleep.
Another health one.
I’ve doubled down on my sleep this year and I feel like a God. Late nights and partying are still fun from time to time. But the benefits I get from consistent 8 hours blows everything else out of the water.
Being well-rested makes us more creative, motivated, and happy. Being stricter about bedtime, getting right out of bed in the morning, drinking way less alcohol…These simple acts have a compounding effect.
Here are easy ways to get much better sleep:
go to bed and wake up at the same times as much as you can (including weekends)
give yourself an extra hour in bed (if you want 8 hours of sleep, go to bed 9 hours before you wake up)
keep it dark before bed, and make it bright when you wake up
wear a sleep mask or use blackout curtains
avoid drinking anything before bed so as not to wake up to pee
keep your phone away during the first and last hours of the day
dial down caffeine and alcohol use
8) Dating apps suck.
I have several friends who have met awesome people on dating apps like Bumble and Hinge. I’m even going to be the best man at a bestie’s wedding this spring and they met on Tinder.
Whenever and however two people meet each other and fall in love, that makes me happy. But these are the exceptions, not the rule. And there’s a darker side to dating apps I wish more people would talk about.
Firstly, the experience is quite different for men and women.
Women get way more matches. This means they get more oddball dudes in their inboxes that they have to sift through. It also means they’re able to ghost several guys with ease.
I spent two months on the apps and it was terrible for my mental health.
I’m a fairly confident young lad. I like who I am. But after just a few days on one of these services, I felt as though I was an ugly and useless trash monster not fit for this world.
Above all, I’m afraid of what it’s doing for future generations. Dating apps, along with all other social media, are slowly destroying the need for a very important skill…
The ability to go out into the world and talk to people.
I mean really talk. Sit down face to face and have a conversation. Be able to debate, ask curious questions, look people in the eye, and share personalities and stories.
Teenagers today have higher levels of anxiety, depression, and anti-social behavior than we’ve ever seen. And I don’t think the remedy to that is to disincentivize them from going out and meeting people. Staying inside and staring at our phones just doesn’t seem to be the way.
Since the popularization of dating apps, fewer and fewer men are meeting women and having sex. That’s because we’ve created a “Facebook Marketplace” for dating. People scroll through, see if someone is hot or not, maybe get some idea of their hobbies or interests, and swipe yes or no.
Whereas meeting someone in person makes us much more likely to find them attractive. A picture tells us nothing about what it’s like to be in a room with them. I bet countless people have said no to a guy or gal on an app that they’d absolutely love if they met at a party.
I met some cool women on these apps. While it never blossomed into anything, I don’t regret my time with them. But the mental strain of the dating app rat race wasn’t worth it to me.
That’s why in 2023, I’ve set a goal to ask out 100 women. Face to face. Out and about.
The idea is to eliminate my fear of rejection through pure exposure. And obviously, it’d be great if I met someone awesome before getting to 100 invites.
9) Who’s in your hospital room?
My grandpa died last week. Prior to, I spent a week down in Virginia with my family to be with them and be by his bedside during his final days.
I’ll write more about him and that time in another blog. But this part is actually about something I learned from Kevin Hart.
My company got to see him speak in Philadelphia right before COVID hit. It was more of a self-improvement talk than comedy.
“Man,” he said. “They told me I might be paralyzed for the rest of my life. When I couldn’t eat or go to the bathroom on my own…you know what I had in that room with me? It wasn’t my fame, my house, or my Instagram following. The only thing in that hospital room with me were all the relationships I built over the years. My team, my friends, my family…”
Since then, I’ve used this as a model for living my life.
If I got in a horrible car accident today who would be there in my hospital room when I woke up? Those people have to be prioritized now.
While it was quite an emotional time, I could smile looking around grandpa’s hospital room. Seeing my dad, my aunts, my grandma, my stepmom, my half-brother…This group of people was just a representation of the life this man created and the lives he touched. He made every single one of us feel special.
That’s what I want to do: make the people in my life feel special.
10) I have no choice but to live a fantastic life.
Before my grandpa went, he told us all, one by one, what we meant to him and how much he loved us. He said he lived a great life and had no regrets.
And as I spent those days there, I would look at my grandpa while he was sleeping in that bed. My old man’s old man.
It didn’t take long for it to really sink in. That will be me one day.
A long long time from now, after Elon has taken us all to Mars…I’ll be an old man dying in a hospital bed. That inevitable fate is coming for me and every other person I’ve ever known, loved, and laughed with. I’ve known that and I write about it often. But seeing a physical manifestation of it was 10 times more powerful.
By truly understanding that certainty—that I will die one day, I felt only one thing.
I have no excuse.
Between now and whenever that day is, I have absolutely no excuse but to live a phenomenal life. How can I be rude to a friend, get pissed if a waiter gets my order wrong, or sit around wasting a day…knowing that it’s all going to end someday?
I feel so empowered to sit at this desk and work on projects I love, to charge more money in my business, to travel to other countries, to call my friends and family more, to stay in great shape, to learn more about the world and the people in it. There’s a fire under my ass.
This year, I’ve learned the importance of spending more time around birth and death. Playing with my friends’ kids brings an energy to the room that’s not possible otherwise. It makes me feel lighter and more joyful. It makes me imagine the kind of father I’m going to be.
Thinking and talking about death and dying makes me feel so present and appreciative of the people and opportunities I have at my disposal.
Some might think us all dying one day means none of this matters. I like to use that to my advantage.
Since none of this will really matter 500 years from now, why wouldn’t I go after what I want? Why shouldn’t I ask out a beautiful woman at a coffee shop? What’s stopping me from charging the kind of money I want to charge? Who cares?
Most of us go around waiting for permission to live the lives we truly want. But sometimes certain events can wake us up.
Thanks for waking me up, gramps.
Hope you got something out of that!
Please, dear reader, do me a favor. I’d love to know the biggest lesson you learned this year. Please email it to me.
Thanks for your support. Here’s to another year. 🥳
This photo is of me, my dad, and my grandpa. We’ve been told that each generation is brighter and more handsome than the last. (Not by many, though.)
I spent this weekend in Manhattan with a friend and his girlfriend. On Saturday, I got the call I’d been anticipating for the past year.
Grandpa was admitted to the hospital on Thursday (his fifth time since the summer). On Saturday morning, he decided he wanted to be taken off life support. He wanted to go.
I packed my stuff, canceled my Saturday plans in the city, and drove straight to Virginia. My aunt flew in from Wisconsin and my dad drove down from Pittsburg.
Since taking him off his heart medication Saturday night, we’ve all been taking shifts at the hospital as we wait for it to happen.
It’s all quite fresh, so I’ll save the whole story for another time. I feel guilty even writing about it now. It feels as though I’m using a dramatic moment for content. But this blog is about my experiences and what I learn from those experiences.
And that’s what I’d like to share today.
I’ve gotten thoughtful calls and texts from several friends and family members. One thing I’ve heard a handful of times is, “I know this is a really hard time for you.”
And I can’t help but think, well, it is and it isn’t.
I’ve spent a good amount of time crying this past week. In the car, with my family, on the phone…Realizing I’ll never have another conversation with him or hear another one of his jokes breaks me every single time. This is a wildly emotional time and when it finally happens I’ll feel a level of devastation no amount of stoicism can prepare me for.
But I won’t remember this as a depressing or hopeless time. Not even close.
I’ll remember being with my family. I don’t often get to be in a room with my dad and both aunts. But whenever I am, we’re all laughing and telling stories. It’s been a treat to smile with them, to hug them, and to cry with them.
I’ll remember the blog I wrote when I realized every visit counted with my gramps. That was the starting point for me to prioritize seeing him. Since then, I’ve tried to go down once every two months. I’m so so glad I did.
I’ll remember the last joke he told me. Sunday morning, my aunt put his glasses on him. I was at the foot of his bed. Once he focused his eyes, he said, “You’re telling me I gotta look at Dillan? Take these off.”
I’ll remember how awesome my dad and aunts are. Being there for him at his bedside, taking care of the logistics, and working as an effective and loving team.
I’ll remember the last real conversation I had with him. I stopped by right after he had his mini-stroke. We sat on his balcony, ate grapes, and talked about geography and travel. He asked me about my business and the book I’m writing.
I’ll remember getting pho with my aunt and talking about her dreams for the future.
I’ll remember laughing in the hospital room as my dad cracked jokes and my grandma and aunts told stories about gramps. We all went through our favorite photos, videos, and voicemails of the old man.
I’ll remember feeding him Dots like he was an insatiable kid in a candy store.
I’ll remember my revitalized appreciation for family. And how easy it is to forget what really matters until something like this happens.
And among many other things, I’ll remember the last thing he ever said to me as he lay in his hospital bed:
“Dillan, how you doin’ buddy? You’ve been an excellent grandson. I’m proud of the man you’ve become and of the success you’ve built for yourself. Your mom did an amazing job raising you. Give my best to her and your sister.”
These are the things that will stay with me forever. I’m grateful.
At some point, I’ll return home and continue writing these posts and making YouTube videos. That’ll be a strange time. It feels like everything should stop for a while. But I know that’s not how it works.
For those who’ve made it this far, thank you. If there’s anyone you’ve been meaning to call or spend time with, do it now.
You’ll never remember that weekend you stayed home because it was more convenient. But you’ll always remember sitting down and laughing with the people you love.
My roommate just announced she’ll be moving out in March. This sparked three emotions.
I’m super excited and proud of her for leveling up her life—starting a bigger and better job and moving in with her boyfriend.
I’m sad to end the best living situation I’ve ever experienced.
I can’t ignore the anxiety that comes from figuring out where to pack up and go next.
As you might’ve guessed from the title, I’ll address #3 in this post.
My immediate thoughts were on staying in this apartment, finding a replacement roommate, or getting a one-bedroom nearby. But hidden underneath was the reminder that I was supposed to move to New York City this fall.
Not only do I feel like I’ve given all my readers blue balls by not actually going. I also just have an itch for adventure that hasn’t been scratched. The last time I went somewhere totally new and had to rebuild myself, my community, and my skills, was when I studied in Germany at 20 years old.
That was eight years ago. Now, I’m (hopefully) much wiser, more competent, and more secure. If the immature boy that was Dill can live in another country, make life-long friends, and learn a foreign language…what’s stopping me now?
The obvious answer is nothing. Well, nothing but fear and excuses.
Cut to the chase
After the teaser email a few days ago, I got bombarded with texts asking where the hell I was off to. I must say making people wait for it brought me sadistic pleasure.
I’m moving to Buenos Aires, Argentina. 🇦🇷
Just for a few months. One of my besties has really helped me along with all of this.
“Do I go here for a year,” I asked. “Or do I stay put for another 12 months until I figure something else out?”
“Dill,” she replied. “You’re thinking in terms of one-year leases. Why don’t you lower the bar and just go somewhere for one to three months?”
She lived in Rwanda for years and met her husband there. Needless to say, this is someone I’m glad to have in my corner when it comes to living in another country.
When I confirmed my interest she started blasting me with articles and how-tos. I read every single one. Best South American cities for foreigners. Cheap Spanish classes online. How to secure health insurance and visas abroad.
What seemed like a nice little fantasy quickly became a set of clear-cut action steps. I renewed my passport and bought my plane ticket.
Why Buenos Aires?
I’ve been wanting to travel to Argentina’s capital city for years. It’s gorgeous, clean, and safe (especially relative to other South American cities).
But on top of that, it’s reliably rated as the #1 spot in the continent for digital nomads: people who can work anywhere in the world so long as they have a laptop and internet connection. As an online coach, a podcaster, and a writer…this is perfect for me.
For anyone interested, here’s a breakdown of the city from NomadList.
As with any place, there are tradeoffs. Let’s go through the cons first.
1) It’s a 10-12-hour travel day away from my friends and family.
You might be asking, “But Dillan, didn’t you say a few months ago your #1 value was close proximity to the people you love?”
Nothing gets by you, dear reader.
Yes, quality time with my peoples is something I cherish. That’s what the two-month excursion is for. 60 days will fly by I’m guessing.
Two friends have already shared ideas of coming down to visit. My birthday is right before my departure and my community’s annual coaching retreat is just after my return. There will be no shortage of friend time in these coming months.
Plus, Buenos Aires has a thriving and organized entrepreneurial community. Meetups, events, coworking spaces…It will be hard for me not to befriend like-minded individuals who also speak English.
I plan on taking a weekly Spanish conversation course. But with only two months, I’ll be leaning into my English-speaking compadres.
2) Uh, I think that’s it.
Some sites claim the internet is slow in South America. But others have said it’s no problem. So we’ll see.
Okay, the fun part.
1) As stated above, BA is a clean, safe, and beautiful city. It has beaches, high-quality nightlife and restaurants, and quaint and quiet suburbs.
Aside from the dirt-cheap public transportation, the city is incredibly walkable. I plan on living in the neighborhood of Palermo Soho, which at most would be a 10-minute walk to my gym and coworking space.
BA is said to feel more European than South American. It’s super organized and stylish. I’m certainly one of those things.
2) Same timezone.
Simple as that. I wouldn’t need to change anything about my schedule. Sessions, calls, sleep cycle…None of it shall be touched.
3) It’s ridiculously cheap.
The average cost of living (including rent, utilities, food, and fun)…is around $1000/month.
I pay more than that in rent alone.
A nice bottle of wine in BA is $3. A nice dinner? $9. The luxury one-bedroom apartment I’m looking at booking is $700 per month. It’s nicer than my current two-bedroom and costs $400 less.
The big reason I didn’t move to NYC was the disgusting cost of living. But now I feel like I’m being financially irresponsible for not moving to Argentina.
There are hundreds of reasons I could rattle off as to why I’m excited to sell all my belongings and fly to South America. The feelings of accomplishment, the new relationships, the skills I’ll develop.
But underneath it all, I’m just pumped to inject some novelty into my life.
I’ve grown into an entirely different human being these past five years. From attempting suicide, to starting to build my life, to working at a restaurant, to starting a blog, podcasts, and YouTube channels, to working in sales, to quitting that sales job to start my own business, to playing chess and doing jiujitsu, to making my business profitable and sustainable, to writing a book.
It’s been a wild ride. I’ve tried a plethora of new things and have been lucky that much of it has stuck.
But I’m still craving something to drastically take me out of my comfort zone. I thought it was New York. It wasn’t (not yet, at least).
So for now, I’ll be enjoying these holidays and the last few months with the best roommate I’ll ever have. I’ll sell or donate all my furniture, books, and clothes. I’ll continue to live frugally to save and invest my money.
A good friend sent me a podcast yesterday. It was a panel of academics sharing research on the relationships of friends.
I thought I’d go for a short walk and listen to 10-15 minutes of it. But it was so insightful and entertaining, I spent an entire hour just walking laps around my apartment complex in the cold and rain.
It’s called, “Time for a Friendship Reset?” by Aspen Ideas to Go. For anyone who wants to listen to it, it’s available on Apple Podcasts and Spotify.
They discuss how limited the research on friendships is. In doing so, they share relatable and digestible experiences we’ve all gone through in our friendships.
Here are a few of my biggest takeaways:
Men tend to bond with each other through activities and often avoid maintaining friendships with openness, vulnerability, and communication.
There’s a powerful script when trying to save an eroding friendship: Here’s why I loved our friendship in the past—you made me feel this way. Then it seemed like this happened and now I feel this way. I’m sorry I didn’t have to courage to say anything until now. How have things happened from your perspective? What can we both change moving forward?
It’s totally natural to feel jealous of our friends. The same is true of those who take up time with our closest friends.
Friendships are often more powerful than family relationships. While you can’t choose your family, friends are close bonds that are entirely based on two people choosing to spend their time, love, and attention with one another. There’s no contract like there is with a spouse or a blood relative. That’s also why it hurts so bad when someone chooses to let the friendship die.
If you check it out, reply to this email and let me know what you got out of it!
Since attempting suicide in 2017, I’ve been obsessed with living a better life. I’ve even made a career out of helping people improve theirs.
But for those of you who have it too good, are too fulfilled, and are looking to downgrade…here are 10 easy tricks to help you start living a shittier life today.
1. Talk shit about people when they’re not around.
By saying things about others you would never say to their face, it makes you more resentful and cowardly. Also, when you gossip and badmouth around friends, they’ll subconsciously wonder if you do the same to them when they’re not around.
People get drained by toxicity. This is a great way to decrease people’s energy when they’re with you.
2. Laugh at exercise.
67% of Americans are overweight. That’s totally fine. The number should be higher.
Exercise has a plethora of benefits: increased confidence and energy levels, mental clarity, heightened motivation and willpower, increased general attractiveness, lower risk of disease later in life, and more strength overall.
So it should be avoided at all costs. Try viewing it as this uncomfortable, sweaty activity only meant for athletes. Be confused as to why anyone would put themselves through physical strain. Making fun of it will make you feel better for not doing it. Tell people you love your body by doing nothing to protect or improve it.
This is a great way to feel worse physically and mentally throughout your day.
3. When in conversation, focus on being right.
99% of people know something you don’t. But they must never know that.
Act as though you are enlightened and have all the answers. This will make conversations with you boring and non-collaborative. Be the teacher, never the student. Don’t ask questions. Constantly preach your knowledge to others, especially when they don’t ask for it.
When someone disagrees with you, the goal should not be to understand where they’re coming from and find common ground. The goal is to explain why they’re wrong and you’re right. Shame them into believing this if you have to. That will guarantee they never will and it will disconnect you both entirely.
This is a great way to keep people from feeling safe to explore their thoughts around you.
4. Drink more coffee, soda, and booze than you do water.
75% of Americans are chronically dehydrated. Again, those are rookie numbers.
Consuming a lot of caffeine and sugar can increase anxiety and stress levels. Downing alcohol frequently weakens the immune system and lowers sleep quality. This is all a perfect cocktail (pun intended) for a shittier life.
Drinking water protects organs and tissues, carries nutrients to cells, and flushes bacteria from your bladder. Sounds awful.
Skip a cold glass of water and reach for coffee first thing in the morning. This is a great way to start the day in a manic state.
5. Avoid doing the things you think would be cool to do.
We all have things we’ve been talking or thinking about but have taken zero action on. Learning Spanish. Dance classes. Starting a business, blog, or podcast. Painting. Piano. Pickleball.
The more we avoid actually doing any of these things, the more regret we’ll feel when we’re older. The pain of longing is guaranteed to feel shitty.
There will always be 1001 reasons why it’s inconvenient to start something. Let those excuses keep you from having more fun, improving your skills, and being more fulfilled.
This is a great way to wake up at 60 and question why you didn’t actually pursue your dreams.
6. Start and end your day by looking at your phone.
If you’re looking to add compulsion and anxiety to your life, this is one of the simplest ways.
Rather than giving your mind space to wake up or wind down, feed it with notifications, news, and chaos. Reading, stretching, or meditating would make the rest of your day more peaceful and present.
Fuck that. Keep your brain spinning every waking hour.
This is a great way to never feel done and to be addicted to a screen.
7. Give in to most of your cravings.
We all indulge. But try to avoid moderation. Make indulgence a lifestyle. Give in to temptations several times a week.
Junk food. Porn. Entertainment. Booze.
Doing this over and over again will supplant this story that you’re addicted to your cravings. When really it’s just a habit you currently have that can be broken or replaced. But don’t let your mind know that.
Treat yourself to whatever meal you want. Skip exercises or difficult things. You’ve earned it. Your body doesn’t care that you’ve earned it but hey…you’ve earned it.
This is a great way to be less fit and powerless against your compulsions.
8. When talking to others, talk more about yourself than about them.
Being interested in others is the best way to make them interested in you. They’ll feel seen and heard. People will enjoy your company more. They’ll feel connected to you.
Steer clear of that. Avoid asking curious questions. Definitely don’t ask follow-up questions to prove you’ve been listening. Try to stick to your stories and your opinions. Keep it one-sided.
This is a great way to weaken rapport and have worse conversations.
9. Take responsibility for the emotions of other people.
There are 7.98 billion people on the planet. If you do or say anything that could offend, frighten, or rub someone the wrong way…you should be arrested.
You’ll never agree with anyone 100% of the time. So it’s best to walk on eggshells and muzzle yourself to avoid any confrontation or misalignment. Don’t be yourself. Definitely don’t ask for what you want. If there’s even a slight chance of someone else being uncomfortable, stay silent.
It’d be easy enough to apologize or have a conversation if you ever do hurt anyone. But it’s best to avoid it entirely.
This is a great way to remain a shell of yourself.
10. Stay soft.
View discomfort as the worst-case scenario. Challenging moments will strengthen you. They’ll sharpen your communication and problem-solving skills. Avoid that.
You should be triggered easily. We all care about things. But you should get unhinged whenever you see or hear something you don’t like or agree with.
Shun people who have differing opinions from you. Judge them. Question their morality and humanity. Try to shame others into believing what you believe. It’ll never work. But you’ll feel superior and enlightened.
This is a great way to stay mentally weak and to keep your head in the sand.
Hope that helps! Let me know if these 10 tips help you decrease your quality of life.
Receiving feedback from our friends, family, and colleagues is one of the quickest ways we can improve ourselves.
It can also be extremely painful.
Our egos can get hurt. Not everyone’s opinions are valid. We see what people really think about us.
But building thicker skin and understanding we’re far from perfect are some of the most valuable things we can do. I ask for suggestions for this blog. I do regular improvement sessions with my closest friends. It can be uncomfortable but it always leads to something better.
If none of that interests you but you want to make improvements in your relationships, health, or work…ask this question to the people closest to you.
What’s something you’re afraid to tell me because you think it would hurt my feelings?
The answers you hear may sting in the short term. But you’ll start being more mindful, improving skills, and seeing reality for what it is.
For the first time since starting my business in 2020, I’m busy.
It’s something I never want to be. Many Americans use the word “busy” as a fake complaint. They’ll groan about it while flaunting it like a badge of honor. How am I? Good! Busy. Super busy.
But to me, busy just means a person isn’t in control of their time. The number of tasks outweighs the available hours for those tasks. It implies a feeling of rushing from one thing to another.
So when people tell me something like, “You must be so busy,” I correct them.
“No,” I reply. “Just productive.”
This lands well with some people. With others, I sound like a douche.
Anyway, this month has been different. I have genuinely been busy and it’s been a shock to my nervous system. It’s the fullest my plate has been all year.
Coaching. Restructuring my community’s website. Chess tutoring. Jiujitsu class. My new podcast. Writing my book and these blogs.
You can have anything you want, but you can’t have everything you want. And this month, I’ve felt the quality of my attention and production slip. My bandwidth is being allocated to too many different things.
To add fire to flame, this is the most vacation I’ve taken in a single month.
I know that’s a terrible thing to complain about. But deadlines can make it difficult to be 100% present when you’re trying to get away. There’s guilt involved. The story that replays says, “I could and should be getting work done right now.”
Two weeks ago, I spent the weekend at my family’s lake house. Yesterday, I got back from a four-day stay in West Virginia with my mom and sister. This weekend is a trip to Deep Creek Lake with close friends.
It was the last night in West Virginia. Flooded with anxiety about getting everything done, I texted the group and pulled out of Deep Creek.
I woke up to a few responses saying they totally understood and they hoped to see me soon. That felt nice.
Then my buddy called me.
“What’s up man,” I asked.
“Yo dude,” he started. “Saw you weren’t coming to the lake this weekend. What’s going on?”
I shared about my workload and my fear of not being fun. He listened respectfully, told me he understood, then challenged me.
“I totally know how stressful deadlines can be, man,” he offered. “But I think now’s a great time to lean on your people. We got your back. And I think there are steps we can take to make this happen.”
He came up with a few ideas. They involved carving out specific times for me to tinker on my laptop while they took care of other things. He told me I could work in their van while they got the boat ready and could come pick me up.
“Fine dude,” I chuckled. “You win.”
I decided to go. But it had way less to do with his proposed solutions and more to do with the fact that he called me in the first place to get me to come. It felt like a slap in the face.
It said, Hey dummy, don’t skip out on memories with your friends. The workload will eventually end, but you won’t be able to get those memories back if you miss out on them.
His language was much lighter and kinder than that, but it had the same effect.
I’m lucky to have friends who push me to live a better life. It’s not something everyone has access to.
20 years from now, we’ll tell stories about drinking beer on a boat. Because no one ever tells a story that starts, “Dude! This one weekend, I stayed home and got a bunch of work done…”
A few years ago, one of my best friends—the guy I thought would be my best man—cut me out of his life entirely.
He stopped returning my texts and calls and never responded when I told him I wasn’t upset and only wanted to talk. To this day, I don’t know the reasoning behind it. I can only imagine there was something about me he felt would be better if removed from his life.
But I’m still in the dark.
It took me about a year of coaching, reflecting, and overthinking before I found closure. But I’d be lying if I said there wasn’t some sort of trauma as a result.
Despite that, it’s taught me a ton about friendships and all that goes into them. Here are two things I’ve learned.
1) A friendship is just another relationship.
A friendship takes a consistent effort to remain strong and healthy—just like a romantic partner.
In fact, friends are much stranger than significant others when you think about it. With a partner, sex is involved (hopefully), families are shared, and you may even reproduce together.
With friends, you’re basically saying, “Hey. I enjoy talking and doing activities with you. Let’s keep meeting up to do those things. We’ll never do anything romantic together, but we’ll still support one another as we live our lives.”
When we’re younger, it can be easy to take having friends for granted. In school, we’re physically forced to be surrounded by people our age with similar goals—be they playing the same sport, having similar hobbies, or smoking the same weed.
But as we get older, we go off to college. We move to different parts of the country or planet. Some people leave their previous lives behind. Others start families.
My 10-year high school reunion was this weekend. I absolutely love reconnecting with people from my past. It fires me up to see people grow and better themselves as the years go by.
One guy who was a bit overweight in high school lost all of it, is totally jacked now, and looks like a Calvin Klein model. I found myself teary-eyed as he took me through his journey. I told him I was proud of him.
Anyway, as we inch through our 20s our values and priorities evolve. When we add another human to that mix, a plethora of things can happen.
We’re almost guaranteed to change. Our friends are almost guaranteed to change. How do we know that these changes will align and harmonize with one another?
It’s out of our control. But whatwe can control is how present we are with the people we care about and how well we communicate what we want.
I have a number of friends I used to party with. But now that I don’t care for getting wasted and doing drugs, a huge chunk of my shared values with those people is gone. So naturally, we don’t spend time together.
The friends I used to go out with aren’t the same ones I talk to about my business ideas. Likewise, the folks I bond with over goals and growth aren’t the same ones I party with now.
Each relationship has its own role. And those roles change as we change. Keeping a friendship thriving takes effort, luck, and communication.
Speaking of communication…
2) It’s important to regularly check in with your friends.
By “check in,” I don’t simply mean reaching out. I mean reflecting on how the relationship is doing.
This can seem a bit dramatic to people who aren’t as willing to be open and vulnerable. But it’s one of the healthiest and most productive things my friends and I do.
It can be done in many ways.
On a small scale, simply telling our friends how much we appreciate them can make an enormous impact. Praising them behind their back. Letting them change our minds and inspire us, and telling them when that happens.
I tell my guy friends I love them. At first, they don’t know what to say but it quickly becomes a natural part of the conversation.
At the mid-level, it’s important to vocalize what’s working and not working with our buddies. This is where setting clear boundaries comes into play.
I talked with one of my close friends last year about how she made me feel belittled and patronized in conversation. We talked compassionately and respectfully about it for four hours. Last summer, I asked a best friend I’ve had since 7th grade to put in more effort. He went from doing practically nothing to calling me much more frequently.
It’s not about demanding our friends meet our expectations. It’s about creating agreements with them that allow the friendship to flourish.
My friends and readers of this blog know that I’ve been preparing to move to Brooklyn later this year. Mostly because I won’t shut up about it.
I did a two-week trial run in the city to see if I would actually enjoy the hustle and bustle of New York. Turns out, I love it.
Coming home from that, I felt elated, motivated, and driven to get myself ready for the transition. I was dead set.
Last week, I decided not to move. Let me explain.
Wait, but why?
For people who’ve been following this saga, I’m sure this seems anticlimactic. I mean, I’ve been writing about this since November of last year. The first blog I wrote about wanting to make the trek is still my most viewed piece, with 1000+ unique readers.
So what happened? Did I chicken out? Was I using people’s love for adventure as click bate? Am I a sleazy fraud?
Well, yes and no.
I can break it down into two main reasons for not packing up and moving my life to New York this October. There’s a logical reason and a more emotional one. Let’s hit them in order.
As soon as I got back from my NYC beta test, I felt it was finally time to stop procrastinating and crunch the numbers.
I put everything I could think of into a Google Sheet. All the purchases and fees. All the housing payments. Loads of furniture I’d have to buy. The U-Haul. I did my best to estimate what the first three months would look like for my bank account.
It’s been so easy to joke about the cost of living in New York, but seeing it all laid out in front of you is a completely different beast.
For what I want, rent would be $2.5k-$4k per month (not including utilities). Moving in would require the first and last month’s payment. Depending on the quality of furniture I got—couch, desk, chairs—it would all cost somewhere between $2k-$5k.
Sitting in this seat and looking at all the numbers quickly adding up, I got anxious. I know enough about myself and my business to know that I could continue to create income that would allow me to do this. I could figure it out.
But not comfortably.
When I told one of my buddies, he put it well.
“It sounds like you’d be in survival mode the first few months.”
He was exactly right. I doubt I’d become homeless. But during the first three to six months in Brooklyn, my main goal would be to figure out how to pay my bills.
For obvious reasons, I don’t want to do that. I want to go somewhere new and live my life. I want to go out and have fun. I’m looking to adventure. Counting every dollar doesn’t appeal to me.
After filling out the sheet, the thought occurred to me: What if I didn’t move this year? With that came a rush of relief.
Then I thought, Damn…my readers are going to roll their eyes.
I went to a best friend’s wedding a few weekends ago. The week prior, another best friend moved back to the area after living in Rwanda for years.
She brought back her husband, who she met there, and will be going to grad school in the fall. That week preceding the wedding, they came over and I met her husband for the first time.
I liked him immediately.
What I expected to be a quick hello turned into hours of sitting at my dining table and talking. My friend even used my office to take a call with her soon-to-be fellow students. Meanwhile, I sat and chatted with her husband and picked his brain on what he thought about the states. It was his first time leaving the continent of Africa.
Hugging them goodbye brought joy to my heart. There’s a huge difference between, “When will you be in town next,” and, “See you next weekend?” And that difference means the world to me.
My deepest-held value is spending quality time with those I care about.
I often think of the ‘hospital room’ scenario. If I got into a horrible car accident today, who would be in that hospital room with me when I woke up? It sounds dark but it’s a useful mental model for measuring how strong our relationships are at any given time.
Anyway, not only did this friend just move back here after years of adventure across the ocean. But another one of my best friends will be returning to the area at the end of the summer.
That means that in a one hour radius, I’ll have 14 close friends, my mom and sister, aunts and uncles, and my jiujitsu team.
I told my buddy all this on the phone the other day. What he said reassured me.
“You know, man,” he said. “There’s that statistic. 80% of people die within 100 miles from where they were born. I used to think that was depressing. But now as I get older, I realize…it’s really fucking hard to leave your friends and family.”
Ain’t that the truth.
Call me a chicken, but I’m finding it hard to justify leaving all of my favorite people on the planet. I’m under no illusion that we’ll spend the rest of our lives living 10 minutes away from one another. But at the very least, I feel the need to take advantage of this opportunity while I have it.
NYC is expensive and I love my friends and family. Maybe next year.
Around 30% of those I reached out to, all of whom I genuinely adore, responded to my message. Then, shockingly, they agreed to share their time and energy with me. But why?
Well, there are a few basic principles every cold email should have. There’s also a simple formula to make structuring this outreach fun and easy. I’ll share both in this post. Then, I’ll share the exact email I sent to Steph Smith, a badass content writer.
Caveat: There is no way to guarantee that someone will respond. Most people simply won’t and that’s okay! You’ve gone from not talking to them at all…to not talking to them at all.
Let’s start with the step-by-step formula.
Cold Email Must-Haves
1) A personal and human intro.
Anyone can tell when they’ve been spammed a copy and pasted message. It’s impersonal and robotic. It invokes zero motivation in the recipient because they know the sender doesn’t actually care—they’re clearly just sending that same message to the masses.
So right out the gate, it’s vital to convey that you genuinely know who this person is, that you’re familiar with their work, and that you respect them for it.
That way, they know they’ve just been emailed by a human being who is actually interested in their time or resources.
2) Why you’re writing to them.
Cut to the chase.
Who are you and why are you sending them this email?
3) A clear and simple call to action.
What specifically are you asking for?
Would you like their time? Their feedback? A reference?
Make the ask so understandable that they’ll have to say either yes or no. A great finisher question is: Is that something you’d like to do?
Highlight the value they’d be getting out of it. They need to know what’s in it or them.
Also, paint the full picture of exactly what it is they’d be saying yes to. How long would it take? How much effort would be required on their end?
Answer any possible questions or objections before they think of them themselves. Not only does this put them at ease and make it more likely that they’ll agree to the thing, but it also shows them they’re dealing with a professional who is prepared and organized.
4) Give them an out.
Most people, especially those of higher status or prestige, will have no problem saying no to a stranger. Again, they’ll likely just not respond. Which makes sense; they’re busy!
But, a subtle yet impactful thing to end on is something that gives them permission to say no. It can be as simple as: It’s totally okay if you don’t have the time or interest for this right now. Just thought I’d shoot my shot!
Never, ever say something assumptive like: Looking forward to speaking with you soon.
That comes off as passive-aggressive. The person will think, “Huh? I haven’t agreed to speak with you soon.”
Keep it light. It takes the pressure off them and shows them you’re not some needy person begging for their time.
Now that we have the structure, let’s move on to the most important concepts to keep in mind.
Key Principles of a Cold Email
1) Keep it short.
Less is more. No one wants to read a bunch of long paragraphs with no spaces in between. Would you be pumped to read a poorly-typed novel from a stranger when you have a million other things to do?
If a word, sentence, or paragraph can be deleted and have the email still make sense, scrap it.
If reading your message feels like a chore, they’ll likely just chuck it in the Trash bin.
While there’s a ton of psychology involved here, I’m not advocating for manipulating people.
Everything in your email should come from the heart. Remember, these are for people we genuinely respect and value. That also makes it easier when they don’t reply. It’s probably because they’re doing the work that we cherish. And if they do reply, it’s just an unexpected bonus.
3) Be persistent but not annoying.
Most of the time (but not always), I’ll send a follow-up.
I call it being “lovingly persistent.” Not pushy. Not needy. But staying true to asking for what I want.
At some point last year, Lynne Tye—founder of Key Values, stopped responding to my emails. I sent her a follow-up because I really wanted to talk with her. Not only did she respond and set up an interview, but she told me she massively respected my “persistence and hustle.”
To drive this home, here’s a real-life example.
Steph Smith wrote the book Doing Content Right. It’s helped me tremendously with the structuring and planning of my blog and book.
Here’s the word-for-word message I sent Steph:
Got introduced to your book/Gumroad course and I’ve been tearing through it. I’m stunned by the level of detail you put into everything you do. Thanks for helping me grow my blog! 😎
What’s the solution to overwhelm, poor health, and money problems?
I have no clue.
There are thousands of possible steps one could take to become more productive, more fit, and more financially stable. But these actions would depend on the person and their unique situation. What’s more, that person’s answers would change over time.
That’s because these challenges are infinite. They’re not problems to solve but instead areas to manage. They’re not games to win but instead fields to play on.
No workout would make us fit for the rest of our lives. No incredible conversation keeps a relationship strong forever. These things take upkeep.
I used to think if my business made over $10,000 in a month that I’d be set. I’ve had several $10k+ months over the past year and I’m still constantly money anxious. The stress hasn’t dissipated, it’s only leveled up as my bank account has. The fear used to be: Will I be able to afford rent next month? Now it’s: How long will I be able to keep this going before it all comes crashing down?
Making $10k was a problem to solve. It was finite. I either did it or I didn’t. The solution was to create enough value in my business that enough people paid me money in 30 days or less.
But the ambiguous feeling of “financial stability” is a battle that goes on forever. If I have a great month, I still have to show up to my sessions and I still have to type words on my keyboard. Then I do it all over again the next month.
We never arrive. But we often feel like we only need to check off a few more boxes in order to do so.
Even if we clean our room, we’ll either need to clean it again in the future or manage it in a way that it stays tidy.
In my coaching practice, I see a ton of people trying to find solutions to problems that actually need to be managed. Things like: finding a balance between work and personal life, practicing healthy habits, and making more money.
These things evolve as we evolve. What solves the problem now could get in our way in the future.
So when struggling with something, it can be helpful to ask: Is this a solving problem or a managing problem?
Two friends texted me today saying they missed the blog. One included a crying emoji.
Sometimes I go weeks posting every day. Sometimes I go a while without, especially if I’m away from home.
I just got back from living in Brooklyn for two weeks. The goal was to get an idea of what it’s like to live in the city before potentially moving there in October.
It was a lot.
I learned about the city and how to navigate it—both physically and emotionally. But I also learned a ton about myself—what I’m afraid of and what my values actually are.
And I’d like to reflect on both.
What I learned about New York City
Every day in Brooklyn felt like I was scribbling things down on an imaginary pros/cons list. I felt one of two emotions at any given time:
“I can’t wait to get back home to Maryland.”
“I never want to leave this place.”
There was no in-between. Let’s start with the negatives.
1) No established community
I had no clue how comfortable I was here in Annapolis until I went to a space where I didn’t know anybody. My mom and sister live 15 minutes away. Several best friends are within a 10-minute drive. I have an incredible roommate.
Throw this same man into a neighborhood of 150,000 people where he doesn’t know a soul…It’s daunting.
It took me three uncomfortable days to admit that I was lonely. My ego repressed the thought because I pride myself on being a social butterfly, someone who makes friends easily, and a guy who can strike up a conversation with just about anyone.
But I couldn’t hide from it. After a few phone calls with friends, I could physically feel how safe I felt talking with familiar voices. I tried to remind myself that any city that wasn’t Annapolis would make me feel that way.
I went out on my own a bunch. I got solo dinners a few times. I worked out and went rock climbing almost every day. I went to meetups.
But I didn’t feel at home. So I made it a mission to ask everyone I met in New York the same question: “How did you build community here?”
More on that later.
2) The cost
My buddy spent $450 in four days in Brooklyn. And he doesn’t even drink alcohol.
What the fuck.
I can’t speak for his spending habits, but I can confirm that if I went out all the time in New York, it’d only be a matter of time until I needed my mom to pick me up and drag me back to Maryland.
A beer that costs $3 elsewhere is $7 in New York. To guess the monthly rent of an apartment, simply take what you think it is and multiply it by two or three. I started laughing when a bartender told me my cocktail would be $21. She was not laughing.
3) The trash
It didn’t just stink. It also totally desensitized me to the sight of litter.
I was walking behind a kid and his mom. He opened his Dr. Pepper bottle and let the cap fall on the sidewalk. They both saw it and just kept walking.
Enraged, I extended my arm and prepared to bend down and pick it up. But then I looked to my right and saw ten times as much garbage scattered on the concrete. Regretfully, I just went about my day.
There was a sense of hopelessness. What would’ve picking up that bottle cap done to help?
(Sorry to my climate tech friends who read this blog.)
4) The homeless
It’s hard not to sound elitist here but this was quite the culture shock.
Someone asked for money on about half of my walks and subway rides. It wasn’t super bothersome. But what stung was having to deny empathy to so many people in such a short amount of time.
It hurt each time I declined a homeless man. But I looked around and everyone else seemed totally used to it.
“You have to deny your emotions in New York City,” my Brooklyn friend told me. “If you don’t, you’ll be drained every single day here.”
He was half kidding. But I thought about what it would be like if I gave change to every single person who asked for it. It’s a challenge that I have no answers for.
(I know, I know. How dare these homeless people make my life more difficult?)
1) The adventure
Every walk out of my apartment. Every subway ride. Every event. Every bar or restaurant. Every new connection.
My favorite thing about the city is the collective experience of living there. That may sound grandiose but let me explain.
Whenever I met someone new, I always had a conversation piece in my back pocket. All I had to do was ask three questions:
“How long have you lived in New York?”
“Why’d you move here?”
“How’d you build community?”
And voilà. Those three simple prompts would show me a person’s story, values, and personality. Once I told them I was planning on moving there, they couldn’t add me on Facebook fast enough.
Casey Neistat said, “People don’t live in New York City. They survive.”
If I were to ask those same three questions in any other American city, it would just sound like boring small talk.
2) The food
Some of the best meals I’ve ever had were in these 14 days. Israeli. Greek. Indian. Jamaican. Cantonese. All within a few blocks of one another.
And the fucking pizza. The hype is real.
3) No car
Not having to drive or park anywhere was the bliss I didn’t know I needed.
Sometimes you don’t know what’s nice to let go of until it’s gone. That’s why I deleted my Instagram a few years ago.
4) The discomfort
I’m sure that sounds weird. I was just complaining about that in the cons section above. Let me explain.
I put off using the subway in Brooklyn for days until I had no choice but to jump on it. It was nerve-wracking. Between my travel anxiety and fear of getting stabbed, I was quite shaken up.
But then I just got to my destination and everything was fine. After doing that a few times, not only did I become comfortable on the train but I really began to know my way around. The synapses were connecting. I was, as they say, learning.
It felt like I had conquered something. As though I had a duel with fear and I came out on top.
That’s exactly how I felt when I climbed my first rock wall last month. And when I built my coaching business last year. And when I placed in chess tournaments.
We’re scared of something. Then we do it. We don’t die. Then we decide if we want to continue doing it. If we do, we get better and eventually comfortable with it. If we don’t, we stay scared of whatever it is.
I choose the former. If I spent a year in New York and had a community and a plethora of new skills by the end of it, I’d feel like I conquered something vast.
What I learned about myself
I really thought I wanted to move to New York City. And this trip only confirmed that.
I have friendships I can strengthen in Brooklyn. My friend in Philadelphia is an hour and a half train ride away. Maryland is not far. I have so much growing and stretching to do.
On that note, it would actually be pretty hypocritical of me to not move there. I help people do things they’re scared of for a living. If I didn’t practice the same, I’d be like a doctor who refuses to see a doctor.
The first week was lonely, yes. But then I got to spend time with my peoples. A best friend came to visit. I chilled with my Brooklyn buddies. I got invited to a rooftop party. I met people. I went on a date and had a lovely time.
Packing up to leave on Saturday was a sad couple of hours. That’s how I knew. I didn’t want to leave. But I had my time there and it served its purpose perfectly.
I’m energized to set myself up for a colorful life there. I want to put myself out there. I have four months.
Coming back to my suburban apartment…it felt like I was coming home to a little country town. It was so quiet. I had to go somewhere and was pissed to realize I had to get in my car and drive there.
The next steps are:
find a place in Brooklyn
sell all my stuff besides the bed, clothes, and tech
make as much money as possible
spend as much time with friends and family as I can
enjoy the end of this chapter
And of course, I’ll keep you updated along the way.
I’m in an entirely new space so my survival instincts are keeping me on guard and it feels like I should be on vacation. But I’m working full days of sessions and writing.
One of my best buds lives in Brooklyn. But last week, he was quite busy until Thursday, so I had to entertain myself each night prior. I’m quite good at that, but it’s scary.
It feels like I’m the new kid at a school where everyone already knows each other.
I’m staying in Williamsburg. It has a stereotype of being the yuppy, stuck-up part of Brooklyn.
While I can’t speak for the 150,000 people who live here, I can say that folks don’t seem too thrilled to start conversations with a stranger. There’s no silliness. People seem calculated and reserved. Everyone’s hot and everyone knows it.
I’ve sparked conversations with people at the climbing gym and with a few at coffee shops. The vibe is very much not, let’s be friends.
And that makes sense.
There are 8.2 million citizens in this city. If everyone stopped and opened up to every person who started talking to them, it would be unsustainable. People are doing their own thing.
But after a few nights in a row of this, I was beginning to doubt my social abilities. Maybe I’m not as extroverted and conversational as I thought. Maybe I’m not a master at making new friends in new environments.
Then I went to a chess meetup.
Meetup.com is great. You give it your location and the kinds of activities or groups you’re looking to take part in. Then you just RSVP and show up.
I just typed “chess” and 100+ meetups popped up. The closest one was Tuesday night at a brewery in Gowanus, an industrial neighborhood of Brooklyn.
After putting off getting on the subway (for fear of getting lost or stabbed), I geared up my Google Maps and headed south. Navigating through the different stops and line transfers made me feel like an adult who had a mortgage and could start a fire on his own.
I made it there with no stab marks and only mild disorientation. I walked into the brewery and was greeted by a jolly bartender with tattoo sleeves.
“Hey! Are you here for the chess? Can I get you a beer?” I wanted to hug her.
She pointed me to the back table. It consisted of six people who waved at me and called me over. It was the first time anyone had been excited to see me since coming to NYC.
I had met my people. They were chess nerds like me and we discussed our journeys in the game. I spoke about my tournaments, which made me sound way better than I actually am. After about five minutes of conversation, I realized I wasn’t this unlikable country boy.
What I have been understanding more and more, is that New Yorkers are quite willing to open up. They just need a context in which it makes sense to do so. Meetups, shared interests, groups.
We started playing.
I won a few games, then lost a few. But what I loved was that people just kept piling in. There were close to 30 who dropped in with their chess sets or their dogs. Everyone was friendly.
My feeling was that if I lived here, I’d love to organize the event. Try different areas, hold tournaments, etc.
By the end of the night, I had added people on Facebook and even invited someone to a gifted coaching session with me. It was all I could’ve asked for.
Over the weekend, I spent each day with some of my best friends.
People say: “When you’re 10 years old, a year is 10% of your life. But when you’re 50 years old, a year is only 2%. That’s why time speeds up when we get older.”
I think that’s bullshit.
When we’re young, everything is a novelty. We’re learning about the world, about our environments, and about ourselves. We try new things: activities, styles, hobbies. We know very little.
Then as we get older, for better or worse, most of what we do becomes routine. We pick the things we like and we do them over and over again. Or, unfortunately, some of us become akin to factory workers; we wake up, go to work, come home, watch TV, wait until the weekend to have fun, and repeat. Our lives become familiar.
I do the same thing. Although I have the freedom of running my own business and creating my own schedule, I still have my own version of clocking in during the week.
So what’s wrong with this?
Well, nothing’s wrong with it per se. But it does allow our minds to shut off. Let me explain.
Habits are great because they let us go on autopilot for things we want to do (or don’t want to do). I’ve gone to the gym so consistently that sometimes it feels like I just wake up there.
And that’s my point.
You ever drive to work (or somewhere you go often), and when you get there you realize you don’t remember the journey? It’s because you’ve done it so many times your brain doesn’t have to be on guard. Meanwhile, if you took a different route to that same place, you’d be much more alert and mindful because you’d have to make new decisions.
That’s what happens to us in our week-to-week lives. When there’s no newness, when we’re doing the same things over and over again, we wake up one morning and realize it’s already May.
“Where the hell did four months go?”
Nowhere. Time moves at the same rate for each of us. Some just pay attention better than others.
So how can we be more mindful? How can we slow down time? Two ways.
We’ve covered newness a bit. In this lies adventure, spontaneity, and curiosity.
This is something I could use way more of. I’m a super scheduled person. So I’ve been trying to leave more unstructured time in my calendar.
Trips also help—especially last-minute trips. Surprise your partner. Surprise yourself. Take a weekend off, go to the airport, and take the cheapest flight to somewhere random.
Constantly change things. Keep doing the things you love but find different ways to do them. Do them with different people. Try activities that scare you.
I have a phobia of heights. Right now, I’m slowly using rock climbing to squash that fear through exposure.
As for gratitude, this is a habit that can be built quickly.
Not only can we begin our day by writing or saying three things we’re grateful for. But we can also just start telling the people in our lives why we love them and what they mean to us.
It only takes a sentence.
I try to do this frequently. They don’t always respond with the same sentiment. But that’s not because they don’t feel the same way. It’s because they haven’t built that habit yet.
Want to make a good friend uncomfortable? Tell them how they’ve positively impacted your life. Watch them scramble for words. It’s lovely.
Anyway, my two questions for you are:
How can you add more newness to your weekly life?
Where can you express more appreciation?
Answering these questions will help you create your own time machine.
When we look at famous actors, we don’t see all their failed auditions.
When we look at pro athletes, we don’t see the other 99% who didn’t make it to the big leagues.
When we look at a successful person, we see their highlight reel; we don’t see their embarrassing moments, their doubts, or their anxieties.
We often compare our insides to other people’s outsides. But we’re all terrified one way or another.
We want to live fulfilling lives and feel we’re spending our time well. We want to feel loved, feel important, and feel supported. This is true regardless of our occupation, geographical location, or income.
For years, I thought everyone around me had their shit figured out and I was the only person on the planet who was clueless. Then I got curious about people.
All it takes is asking someone a few questions to realize: None of us have figured out life. We’re all just winging it and are doing our best.
Don’t look to a person’s social media page to see how they’re doing. Look at their current fears and stresses. That will paint the real picture.
The goal is not to go out of my way to piss people off. I don’t want to do or say anything controversial just for the sake of being controversial.
But I noticed recently that most (if not all) of my writing has been curated for anyone and everyone. I’ve been painting with a broad brush in the hopes that any kind of person could sit down and enjoy my stories and lessons.
The consequence of that has been me avoiding certain topics I thought would be lost on most of my readers: the ins and outs of my business, hot takes, possibly-arrogant stories…
Then everything changed when the fire nation attacked.
Whoops. I mean, everything changed when I grew a mustache. Here’s what I mean.
I shaved my beard and left my mustache about a month ago. Since then, I’ve gone to a wedding, a bachelor party, and have gone out drinking.
The thing I noticed immediately? Mustaches are polarizing.
Some people (women) wanted nothing to do with it. Others went out of their way to say how attractive they thought it was.
Prior to that, no woman had ever mentioned to me in casual conversation how sexy she thought my face was. I realized that was because I was trying to have a face anyone could get down with.
I went from attempting to reach everyone to only spending time and energy with mustachers. They were bought in. They were my people.
Then I thought about other areas I could apply this.
When we polarize people, some folks naturally get alienated. Some hate mustaches. Some don’t care about business tactics.
But for the ones who stick around…the connection with them is 10 times stronger. It’s not about trying to get people to buy in; it’s about investing in the ones who are already bought in.
Lower quantity. Higher quality.
So what does this mean for us?
I’m guessing half of my readership cannot actually grow a mustache (ladies…and some dudes [sorry, gents]). But we can think about this as we create things and as we connect with others.
Do you hold any opinions you’d be uncomfortable sharing with the people around you? If not, that’s a problem. It could be a sign that you just go along with what everyone else thinks and that you have few values of your own.
When creating something, are you trying to make it so everyone can enjoy it (like I did)? When we build something for everyone, we build something for no one. Find your people.
In my coaching business, I have high standards for the people I work with. I want committed action-takers who show up on time and do what they say they want to do. That’s not most people.
And that’s the point. Most people shouldn’t work with me.
It’s not about the ones left behind. It’s about finding our people and giving them the world.
Naturally, people enjoy talking to someone who asks questions and expresses curiosity. We all want to feel heard and feel important.
Whether it’s conscious or unconscious, people notice pretty quickly when a person only talks about themselves. The first thing I detect in someone is how often they ask (genuinely curious) questions. If they never do, I almost always find them less interesting.
But there’s a limit.
If we only ask questions in a conversation, it can feel like an interrogation real fast. That tends to make people uncomfortable or feel guilty that they talked about themselves the whole time.
So what if the person we’re talking to isn’t a skilled conversationalist? If they’re not giving us much to work with…
We can use the “2 for 1” rule.
Two questions. One personal story or idea. Repeat.
This ensures a back and forth. It lets the other person know, Hey, I’m a human being too. I’ve been through stuff. I can relate.
Try it out with your coworkers or with strangers. Let me know how it goes.
This sounded a bit harsh and over-dramatic when I first heard it. It took me a while to actually get it.
We often play “stupid” games:
trying to be the smartest person in the room
looking really cool on social media
making as much money as humanly possible
being on our phone for hours each day
I have coaching clients who have played tons of these games. I’ve played tons of these games.
The question is: What does it look like to win the game you’re playing?
If you climb your way to being the absolute coolest person on Instagram (whatever that means), what would you be able to do with that? What would that mean for your life? What would that fulfill?
If you feed your phone addiction and make sure you never miss a notification, or respond to every email as quickly as possible, what would winning that game look like?
In my experience, the prizes of these games often include being kind of happy for a short time…then going right back to whatever our normal state is. After that, it’s feeling disappointed that this thing didn’t bring us enlightenment.
An even darker example is texting and driving, one of the stupidest games out there. 400 fatal crashes happen each year from driving while using our phones.
But what is ‘winning’ texting and driving? Not having to wait 10 minutes to see what our friend texted us?
In 2020, my mom was completely stopped at a red light waiting for it to change. A young man hit and totaled her car at 50 mph. He was texting.
I always think, I wonder what he was doing on his phone and I wonder if it was worth it? He played a stupid game and won a stupid prize.
So which games bring us awesome prizes?
For me—and I would argue for most of us—it’s all the cliche stuff:
being a great friend/son/daughter/etc
getting physically/mentally fit
being kind and curious
So, what games are you playing?
If you were to win that game, what would that look like? Would it be worth it?
One of my besties came over yesterday and we discussed building new friendships.
As we get older and as our relationships evolve or fade, we learn a ton about the kind of people we want in our lives. The people we surround ourselves with are a reflection of our own values and desires.
She’ll be moving to DC this fall. So I asked her what her red flags would be while building a community there.
When she asked me what I wouldn’t accept in a friendship, a few things came to mind:
We’re all human. We’re all allowed to feel unpleasant emotions. But it’s hard for me to tolerate someone consistently complaining about things out of their control—especially if they’re taking zero action to make it better.
Any sort of victim mentality is a no for me dog. I like surrounding myself with people who take ownership of the life they’re creating.
Similar to #1, I guess.
I can’t stand passive aggression or bullying. Not so much when it’s directed at me, but when someone is mean to other people.
It sounds almost childish, but it makes my blood boil. When someone’s condescending, belittling, or downright nasty…
3) Dry conversations.
This is now starting to sound like I’m building a job application for the role of “Dillan’s friend.” I’m just trying to point out the traits that would make it difficult for me to build a deep connection with someone.
Whether it’s a friend, colleague, or romantic partner…if we can’t sit sober for three hours and have fruitful conversation, it just won’t work for me.
Sharing experiences, insights, and ideas. Telling stories. Asking curious questions. If this stuff isn’t present, what the hell are we talking about?
Anyway, I’ll be accepting applications online.
What are your red flags when it comes to making new friends?