Last winter, I experienced my first serious bout of burnout. For a week and a half, I felt zero positive emotion and ran away to a cabin in the woods.
Luckily, I haven’t felt anything like that since. But I’m hyper-aware of the warning signs of overwhelm. Certain questions pop up:
am I avoiding things?
is there a ton of resistance?
am I excited by my projects or dreading them?
Since launching my new podcast back in August, I’ve been dancing with burnout once again. The show is called The YouTuber’s Guide to the Galaxy. I interview YouTubers with over 10k subscribers to dive into their creativity, share their strategies, and inspire new creators.
I was oozing motivation right out the gate. My expectations for output were high: one episode every other week, three clips per week, and three to five TikToks per week.
I kept that up…for two weeks.
It turns out, treating something like a full-time job is difficult when you already have a full-time job (my coaching business) and two side hustles (writing my book and leading my coaching community). There’s also this blog which is a fun lil proj.
But as I’ve been interviewing successful creators and entrepreneurs, I must admit I’ve been taken in by the glamor of sacrifice and hard work. James and Anthony Deveney sacrificed all their free time for a year to build their show, Raiders of the Lost Podcast. CupppaJoe5 has been working 100-hour weeks in his pursuit of becoming a full-time content creator. Ryan Twomey has uploaded a TikTok every day for almost two years.
Here’s what I learned while grinding away these last two months: I don’t want to do any of that.
It comes down to the essentialist question: What are the most important things in your life right now?
For me, my entire being is dedicated to building the life I want most. I have my dream job and work with incredible people. My physical health and relationships will always be my top priorities. I want quality time with my friends and family. I also need to work out at the gym and go to jiujitsu class. I’ve gone on a few dates with a woman I like and am curious to see where that goes. I play and study chess practically every day.
No matter how awesome it sounds to have a full-time podcast that makes me money and has a ton of listeners, I’ll never sacrifice these things mentioned above. I’m not willing to put in the level of work that my guests have put into their channels. And that’s okay.
So what will I do?
Well, the goal is still the same: 100 episodes. I have three episodes on deck and two interviews scheduled. The show goes on.
But I’m deleting the high-friction activities and doubling down on the low-friction ones. I hate video editing. So I’m changing the YouTube channel so that it’s only short clips of episodes and not full conversations. Then, I’ll be trimming down the podcast audios so they tell a much higher-quality story. Finally, I’ll upload one TikTok per week.
The goal here is to make things much easier for myself and to make it harder to quit. I’ll stop doing what I hate and do more of what I love.
I’ll leave you with these questions:
What are the three most important things that demand your focus right now?
What are you doing too much of that’s getting in the way of these things?
What aren’t you doing enough of?
This show has been my favorite creative project I’ve ever worked on. And it’s not even good yet. Just wait.
Awesome guests to come. If you want to check it out, all the links are here.
One Big Mac. One Spicy McChicken. One Large Fry. Delicious.
For the whole month of September, I consumed zero:
alcohol
sugar
pasta
bread
processed food
Doing 30-day challenges like this always enlightens me about portion control and cravings. I ate McDonald’s and didn’t feel ashamed because 80 to 90 percent of my diet is nutritious.
I eat primarily home-cooked meals, farm-raised meats, and organic produce. Fancy boy, right?
But the truth is I’m not well-versed at all when it comes to nutrition. The same goes for fitness.
I go to the gym three times per week, do jiujitsu two or three nights a week, and see a personal trainer twice a month. To someone who doesn’t exercise, that may seem like a lot. But I’m not doing intricate or complicated workouts. It’s all simple yet consistent.
And that’s the key word here: consistency. You are what you do consistently.
One fast food meal won’t make you overweight or out of shape. Consistently eating junk and never exercising will.
Just like one great workout won’t make you an athlete. Consistently making yourself sweat and eating mostly well will.
So, what are you doing (or not doing) consistently? What results are you getting?
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!
This week, I hit my 1000th coaching hour. That means I’m a certified Master Insight Coach. It took me one year, six months, and four days.
I’ve coached nearly 100 different people these last few years. This has given me a pretty good look at how we make decisions, what we’re afraid of, and our capacity for growth.
I’m lucky to have been able to coach some amazing people. Some of them I see myself working with for years and years to come.
Humans are infinitely complex and quite simple at the same time. We all have different personalities, strengths, and limiting beliefs. But we all want stuff, feel there’s stuff in the way of that stuff, and then either do something or nothing about it.
There are five major traits I’ve seen in the people who crush life. I see these folks as genuinely successful.
By “successful,” I’m not factoring in their income. I measure success by how fulfilled a person is by the life they’re creating.
Here we go.
1) Ownership
The top characteristic I’ve seen in people who move in the direction they want.
They don’t blame things outside of their control for their situation. They might mention them, but they quickly dive into what’s in their control to do something about it.
“Not everything is my fault, but it is my responsibility.”
The people who actually get what they want in life understand that if they want to experience change, they have to change.
2) Doubt, fear, and anxiety
“You’ve got to be fearless” is bullshit advice.
Humans are wired to stress about things. Only now, we don’t worry about getting attacked by animals; we ponder our purpose in life.
No matter how well a client is doing, they tend to still be afraid and doubtful as they level up.
“I don’t know what I’m doing.”
“Maybe I’m not cut out for this.”
“What if I screw up now that the stakes are higher?”
I’ve heard this all a thousand times. But they always get through it.
Which brings me to #3…
3) Doing the scary thing anyway
Successful people realize that they’re allowed to feel how they feel. Emotions come and go naturally.
But they don’t let these feelings stop them from doing what they want. They experience the growing pains of improvement.
It goes like this:
Step 1: I want this new thing Step 2: I’m going to take action to get it Step 3: This isn’t as easy as I was hoping Step 4: I don’t know if I can do it Step 5: I’m kind of doing it and it’s actually not that hard Step 6: I can do anything I set my mind to Step 7: Repeat
4) Committed and focused
The people who are most serious about improving their lives play full out.
They show up on time, are ready to take notes, and are eager to take action.
They are also prepared to invest in themselves. Not just with money, but time and effort as well. They make their well-being a priority.
5) Growth mindset
Those who climb the mountain know the only thing between where they are and where they want to go is time and effort.
They stay away from fixed phrases like “I can’t” or “I’m not the kind of person who…”
Deep and meaningful change is possible for every single one of us. The only way it wouldn’t happen is if we choose for it not to happen.
Take a person who is convinced they couldn’t run a marathon. They’re unlikely to start training for one. They won’t register for one to give them the incentive. They won’t find a training partner to hold them accountable. Six months will go by and they’ll be in the exact same place…thus proving themselves right.
Successful people realize the journey will be more difficult, uncomfortable, and complex than they originally thought. But they keep practicing and doing.
The hard becomes easy. Then they look to new challenges.
Which of these traits do you feel you have? Which do you think you need to work on? Reply to this email and let me know.
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.
Yesterday was the quarterly Baltimore Charm City Chess Tournament. I played in the U1400 section.
Typically, I compete with my buddy. But he was on a work trip so I was left to my own devices.
I got to the hotel early, as I always do. After signing in and dropping off my bags (my chess set and food), I took my usual stroll around the Johns Hopkins campus.
It always gives me anxiety walking on a college campus. It brings me back to my days of skipping class and feeling low status. Sometimes I feel insecure pacing by students as a 28-year-old man with a mustache.
But it was a lovely day. The air was crisper as fall approaches.
When it got closer to 10:30 I headed back to the hotel to see the first pairings. My first of five opponents was a teenager with a lisp.
Shit.
In the first game in my last tournament, I played against a four-year-old and nearly lost. I’m not proud of it, but losing to a kid has a particular sting to it.
But this teen was good. He slowly squeezed me until I blundered a piece and resigned. After losing, my mind flooded with excuses.
I’m tired. It’s not as fun without my friend here. I might leave early and enjoy my Sunday.
Fear of failure leads our minds to hilarious places. I texted my buddy, “Never again will I do a tournament by myself.” I was so salty!
If you’ve ever climbed a mountain or worked on a difficult project, you know this feeling.
Starting or launching a pursuit is exciting and novel. We have these shiny images of what it’s going to be like. Then we get going.
Nine times out of ten, it gets hard or boring or both. We have to push through resistance. We need to improvise and solve problems we didn’t account for.
At some point, we even question why we wanted to do this thing in the first place. That’s where I was at. All I could think about was losing my remaining four games.
But I stayed.
In game two, I demolished the poor guy and he resigned after 13 moves. Chess was fun again.
I texted that same friend, “Nvm just beat a guy in 13 moves my spirits have lifted.”
It’s wild how easily our states can change. It makes me question reality. How much of our perceptions of what is going on are painted or tainted by how we feel at that moment? I went from genuinely hating chess to being eternally grateful for spending a day playing my favorite game.
With my newly-found momentum, I won the rest of my games—tying for second place and winning $100.
The winner and I played in my first-ever tournament last winter. We drew. I saw him and congratulated his performance.
These events always pump me up to improve my game and play more. If you’d like to see my actual games, here’s a link to a study I made. I even annotated some of them so you can see my thought process.
Having hobbies and activities that have nothing to do with work or money is rewarding and therapeutic.
What are your favorite things to do outside of work? Let me know.
(PS—Here’s my favorite final position from round 5. It’s rare to have the enemy king so deep in your own territory.)
It’s been a while since I emailed you guys a blog. 11 days to be exact.
While I’m sure some of you are delighted by this, it’s left me feeling guilty. When you subscribe to something, you do so because you expect value from it.
Some of you support the blog financially. Some of you neglect your children and careers just to read what I write. I’m so grateful.
The truth is, I put too much creative work on my plate at once. Here’s my to-do list from the last 30 days:
But now that I’ve crossed off a few of these items, I’m ready to clean up, reflect, and make sure this doesn’t happen again. I thought today’s post would be a good time to do an exercise I found on Instagram.
It’s called the AAR Method (after-action review) and it’s used by the Navy Seals. It’s a four-question framework. In sharing the model with you all, I’ll give my answers for each step.
1. What did I intend to accomplish?
I tried to move in the direction of what I want my work life to look like.
It’s threefold:
writing blogs and books
running a podcast/YouTube channel
having my one-on-one coaching business
To me, it’s a fulfilling cocktail of conversations and deep work.
2. What happened?
I started sprinting in this direction with no real plan and with little help. My schedule and timelines were up in the air. I got to things when I could get to them.
Problem was, I often felt creatively empty after spending hours of bandwidth on one or two things. I also felt the effects of task-switching. After hours of writing in the morning, coaching in the afternoon, and editing in the early evening, I’d be absolutely drained by 5pm.
3. Why did it happen that way?
I didn’t create any organized systems for keeping everything on track. With everything left to chance, my days were cluttered and sporadic.
I also just expected myself to be able to handle all this. There are these sexy Instagram-worthy archetypes of entrepreneurs doing a thousand things and working 12-hour days.
In reality, most of us have about four to five hours of deep, undistracted work in us each day. So putting eight hours of writing and editing on the calendar was destined to fail.
In summary: unrealistic expectations and a lack of organization.
4. What will I do next time for a better outcome?
Give each day of the week a theme. On these days, I write. On those days, I edit.
Some sort of digital system would also be useful for deadlines. I’m working on that with services like Evernote and Trello.
Finally, next time new projects present themselves, I’ll ask myself: “How much harder will this make things for me?”
I usually go to great lengths to keep from being busy or overloaded. I’d like to never get there again.
My favorite thing about interviewing creators is hearing the same philosophies or mindsets for different crafts.
I’ve sat down with YouTubers, founders, comedians, doctors, athletes, musicians, authors, and more. Here’s something they’ve all said.
“You have to enjoy what you’re doing. It’s okay to set goals and to want to make money. But if status, wealth, and success are your only driving factors, you won’t make it.”
Benjy Himmelfarb, a DC standup, said a comic’s first two years are just about getting comfortable on stage. As I’ve been interviewing YouTubers for my podcast, they’ve said the exact same thing.
When we start a new venture—a business, a new job, creating content—the beginning is mostly about figuring out how to get good and how to find our voice and styles. Nine times out of ten, the people who are doing the best are just the ones who’ve been doing the thing consistently and committedly.
Occasionally we see young phenoms who start crushing it immediately. But those are rare. We just think they’re everywhere because they get a ton of exposure.
Eric Rosen is one of the biggest names in the chess world and has 575k subscribers on YouTube. It took him a year of consistently streaming and posting to start to experience success.
Courtland Allen sold Indie Hackers—a community for online business owners—to Stripe for millions of dollars. But this was after 10 years of him starting companies that failed, coding every day, and being uncomfortable in Silicon Valley.
Courtney Maginnis has spent over a decade doing comedy in New York City. She’s worked with College Humor and Comedy Central and still works a nine to five to support herself.
Point is, building true skill and leverage takes time.
If the result is the goal, we’re just suffering while looking at the clock. As cliche as it sounds, we have to enjoy the process.
Right now, my YouTube channel isn’t that great. The first few interviews I used were for my book so they’re just grainy Zoom calls. I don’t know how to make good thumbnails. I have to refine my interviewing and editing skills.
But I’m loving the conversations I’m having and working on the show is the most fun I’ve had of any of my creations. So if I stick with it, I have no doubt it’ll be great. But what metrics are keeping me going?
The idea of 100k subscribers sounds amazing. But that will probably take years. That can’t be my compass.
So my one and only goal right now is to make it to 100 episodes. Once I get there, we’ll see how I’m feeling.
To end, I’m not suggesting we don’t set financial goals or look at metrics. I just don’t think doing something unfulfilling in the hopes for success is sustainable.
We don’t necessarily have to do what we love. But we should at least like what we do.
The second episode of my podcast is out now. It was the most nervous I’ve ever been for a conversation.
Eric Rosen is one of the biggest names in the chess space. He has…
575k subscribers on YouTube
225k followers on Twitch
an International Master title in competitive chess (there are only 4000 of these in the world)
This conversation was recorded for my book back in May. It took me about 30 minutes of talking to understand that it was real.
That may sound silly to most, but I’ve been enjoying this guy’s content ever since I got into chess back in 2020. I’ve seen well over 500 of his videos and I’ve taken all his online chess courses. Meeting him was wild.
He was so kind and so generous with the details of his journey and business. He took me through all his revenue streams, his processes, and his goals for the future.
I loved the conversation and I think you will too if you enjoy creating.
Send me any feedback you have! If you like the show, please rate and review it on your podcasting platform. That’s super helpful for bringing it to more people.
1) “What’re your thoughts on Roe v. Wade being overturned?”
If you’ve been reading this blog for more than a few months, you probably noticed I don’t touch on anything sociopolitical.
That has less to do with fear and more to do with the fact that it just doesn’t interest me. I’ll talk about anything in person. But when it comes to what I write and publish, this is a space for me to type about what I love.
Major insights. Business. Mistakes I’ve made. Doubts and anxieties I’m having. The things I’m creating. Building better relationships. How to live a fuller life.
These are the things that keep bringing me back to the keyboard. I’m sure this list will change but for now, the system is: sit down and write about what you know.
I don’t know much about politics or anything in that realm.
For me, that means I wouldn’t enjoy writing about it. And for you, that would be a disservice because you’d be hearing my half-baked thoughts on meaningful and often radioactive topics.
Lastly, I get a lot of emails and messages now. People send me their thoughts and criticisms after certain blogs.
I love every single one of them. I even save my favorites.
Last week, I got an email with feedback on my last piece on dying. In the article, I said that since we all kick it one day, we have no choice but to be present and appreciative in the here and now.
But in this guy’s feedback, he asked why that was the only choice. He correctly posed that someone could also choose the path of nihilism and hopelessness, which I didn’t consider. How cool!
Someone read something I wrote, gave mental energy to think about it, and then articulated thoughts to send me to challenge me and improve my delivery. It’s quite rewarding.
But I don’t have the interest or bandwidth to do this several times a week with people who disagree with me politically. I love responding to reader emails. But I don’t want to start Facebook comment wars with people. I simply don’t have the space for it.
So for now, I’m happy to keep that stuff closer to my chest.
2) “Have you ever felt addicted to anything?”
Oh yes.
Some roll their eyes when they hear this. But for about a decade, I was severely addicted to video games.
I don’t mean I played them a lot. I mean, when I was into a game, it would consume my entire life.
In high school, I’d hide under my bed so my mom would think I left for school only to stay home and play Skyrim or Call of Duty. I skipped and failed college classes to stay in and play Xbox. I’ve racked up thousands of hours of Runescape.
I haven’t played any video games since 2018.
Here was my vicious cycle:
Discover a game I loved
Take Adderall so I could play that game better and longer
Come down from that Adderall around 4 or 5pm
Drink alcohol—the only way to combat the crash
Be wasted by 8pm
Wake up hungover
Repeat
I’ve gone through a few periods in my life where I’d live this cycle for months on end. It was terrible.
I would feel my physical and mental health slip. Daily drinking. Poor sleep. Avoiding friends. Barely eating.
And it would all start with a stupid video game. Once I threw away my Xbox and deleted my Runescape account, the cycle stopped. There hasn’t been a day where I’ve been interested in going back.
Last year, I was teaching my buddy from high school how to play chess. Seeing how into it I was, he said, “You know what chess is for you, right? You replaced your video game addiction with chess.”
He was right.
I don’t think we ever delete our addictions. We simply shift the ways in which we exert that energy. Now, I’m addicted to creating a great life, spending time with the people I love, and helping others do the same.
3) “What’s your biggest fear?”
It’s always been some version of: I’m a fraud.
All the success I’ve had and am having is just a fluke and people will eventually catch on that I have no idea what I’m doing. That’s the fear.
I’m afraid I’ll be 37 years old and on the verge of eviction. I have no evidence that that would ever happen, but that’s the root of my underlying anxiety. Anything to do with money. When I see my friends getting married and having kids.
While I know it’s not true, deep down I think: You’ll never have the skills to do that. You’re a manchild.
It’s strange how we can have worries that we know logically don’t make any sense. But emotionally, it’s a completely different story.
I’m doing great and I’ve never been more fulfilled by my life—my friends, family, health, and work. But buried deep in the vault, that fear still lingers.
Thanks for all your questions! Please keep sending me stuff you’d like me to dive into next month.
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…”
I spent this weekend at the lake house. My grandparents were supposed to be there, but my grandpa was in the hospital.
He had a mini-stroke two weekends ago, got let out the next afternoon, then had to go back the following day because something was wrong with his liver.
Him being 81, none of this was shocking. But it was deeply troubling.
Since they couldn’t come to the lake, I left early Sunday morning to stop by Norfolk and see them on my way home. I’m so glad I did.
How many visits left?
Lake Gaston, 2020.
Almost exactly a year ago, I wrote a blog about the finite amount of time we have with people. The example I used was my grandfather.
Assuming someone lives to be 90, and assuming we maintain a relationship with them, how much time left do we have left with that person?
Well, we simply subtract their age from 90. Then, we multiply that by the average number of times we see them a year.
I see my mom once or twice each week. She’s 58. So that’s about 2496 more dinners and walks with her.
My family in Wisconsin and I see each other once a year or so. They’re in their late forties. So that’s roughly 42 more weekends at the lake with them.
I see my gramps about three times a year. He’s 81. So I have about 26 visits left.
Grapes and tuna fish sandwiches
When I got to my grandparents’ place yesterday, my grandpa was in the shower after just getting home from the hospital. Grandma made me lunch and we sat chatting at their dining table.
When my grandpa came out, he sat down next to me and held out his left hand. The stroke made him unable to use his right. I focused intently on him. He was visibly frustrated. Who wouldn’t be after losing their functionality?
“Dotty,” he signaled to my grandma. “Help me put in my hearing aids, just in case Dillan says anything worth listening to.”
We all burst into laughter.
It was a gorgeous day outside, so we set up the balcony chairs and sat overlooking the bay next to their apartment. Grandma made tuna fish sandwiches and got us a big bowl of grapes.
For 30 minutes, it was just me and grandpa out there talking about business, travel, and science. I always try to ask him questions about his past, his experiences around the world, and his fondest memories. It’s always a hoot to hear him tell stories about my dad and aunts when they were growing up.
Grandma eventually joined us and we just sat out there talking. I don’t even remember what we were discussing. It didn’t matter.
The only thing that mattered was I was there and we were happy.
Memento mori
That’s Latin for “remember that you’ll die one day.” It’s a reminder we could all use on a daily basis.
Many people shy away from any conversation about death and dying. Depending on peoples’ experiences, this can be a rigorous topic. It can come off as morbid and depressing.
But I think burying our heads in the sand when it comes to death is one of the most damaging and unhealthy things we could do. Meanwhile, shedding light on it and speaking about it openly brings with it so much opportunity.
Here are two reasons why.
1) It softens the blow.
My grandpa will pass one day. It’s possible that that happens before I get all 26 of my remaining visits with him. When that happens, I’ll be devastated.
But I won’t be crippled by it. I won’t collapse. I’ll look back with gratitude that I got to have conversations with him about Brooklyn on his balcony while eating grapes.
2) It makes it easier to be present and grateful.
When someone truly understands the simple fact that none of this will last forever…the only option is to be mindful and appreciative of all that they have.
How can I get into a comment war with someone…How can I get pissed at a server…How can I ghost a friend who’s texting me…when I know that I and everyone I’ve ever known will be dead one day?
It’s things like my grandpa being in the hospital that really wake me up. They remind me. Hey, don’t forget.
I’ve returned from this trip with renewed energy. I feel so lucky that I’m young and that all my friends and family members are alive and healthy. I get to do work that fulfills me. I get to meet beautiful women. I get to travel. I get to.
Every phone call. Every bit of quality time with people I love. They feel ten times as impactful.
I’m paying attention. I’ve been reminded. Thanks, gramps.
What is a strength of yours that is also a weakness?
My buddy asked me that last year and it led to a wild conversation. My answer?
“I obsess over the things I’m interested in.”
I’ve never dabbled. If I’m going to learn a new skill or embark on a new project, I commit to it 100%. Whether it’s a career path like building a coaching business or a personal hobby like chess or jiujitsu. If it stops being interesting to me, I quit and move on to something else.
How is this a strength?
Well, since I’m able to put my head down and stick with something consistently for months, I can learn things pretty quickly. I created a full-time coaching practice in nine months. I got cast as the protagonist in a play after my second audition ever. I became an advanced chess player in less than a year.
None of this is to brag. It’s just to emphasize the impact of commitment and consistency.
But how is this a weakness?
My hyper-obsession can get in the way simply because I get interested in too many things. This leads to suboptimal performance and occasional burnout.
We can do ten things to the first degree or one thing to the tenth degree. I also love this quote from Chris Williamson:
“You can have anything you want, but you can’t have everything you want.”
That’s a harsh truth for someone who wants a lot of things. But it’s true.
We can’t be an incredible parent and be in perfect shape and start a business from scratch and coach baseball and read tons of books and have a thriving social life and travel all the time and be a great musician and…you get the point.
Everything’s an opportunity cost. Time spent with our children is time not spent working on our side hustle. Time spent on our side hustle is time not spent with our children.
The question is: What are you willing to sacrifice?
Here’s an image to help illustrate this phenomenon—the Four Burners theory.
Since I was a kid, I had always wanted to be an actor.
I remember watching my favorites. Folks like Daniel Day-Lewis, Natalie Portman, and Christian Bale. I’d memorize scenes and perform them when I was alone. It was mesmerizing to me to be taken to a completely different world. What floored me most was knowing it was a set with actors, directors, and producers…yet finding it 100% authentic in the moment.
I wanted to do that for other people.
But when it came to taking opportunities, I wouldn’t. I avoided being a “theatre kid” in high school. I was too busy smoking weed and making fun of the theatre kids. I didn’t audition for anything during my first three years of college. I had a good reason not to.
I was terrified.
The semesters would pass by and I’d see flyers for the new shows being put on. Next semester, I’d tell myself.
Then, at the beginning of my senior year, I was walking through the liberal arts school. I happened to see a girl I knew who was in the theatre program. We chatted for a minute or two.
“What’s the play this semester,” I asked.
“To Kill a Mockingbird,” she replied. “The last day to audition is tonight at 6!”
Shit. I had nothing going on that night. Which meant I had no excuse to bail.
The day went on and I found myself back home watching the first season of True Detective. I wanted Matthew McConaughey’s swagger to inspire me. I sipped some whiskey to calm my nerves.
An hour or two before auditions, I convinced myself not to go. I wouldn’t know anybody. They’ve all been acting for years and I had no experience. The community and culture were probably already set in stone and I wouldn’t belong. I’d make a fool of myself.
Then I had an insight.
I wanted to be an actor. That was true. But how did I want to secure that for myself? I imagined the director knocking on my door.
“Hello,” he’d say. “I know you didn’t audition. But you strike me as someone who’d be really good at acting. Would you like to be in my play?”
I laughed because there was a 0% chance of that ever happening. No one was coming to hand me anything. I had to put myself out there and go for it.
I sighed and started walking to the campus. I tried to step fast enough to get there with plenty of time to settle in, but slow enough to not be covered in sweat.
As I panted through the building’s doors, I could already hear the cacophony of conversation coming from the theater. I followed the noise and to my horror, everyone was talking to everyone. I grabbed a script from the pile by the door and meekly took a seat toward the back of the stands.
I felt like the new kid in school who didn’t belong. I wanted to flee. Ten minutes passed and I thought, it actually makes sense for you to leave.
Then the director walked in. I expected the place to become silent.
It got twice as loud.
Students left their seats and walked up to start talking to him. I was screwed. But it was too late to weasel my way out. He took center stage and everyone sat down with their scripts.
At random, the director would pick scenes from the play and we would go up and cold read as any character. It didn’t matter who it was, guy or gal. The goal was to give him a sense of what we looked and sounded like.
I sat in my seat pretending to look at my script because I was too horrified to go up. Then I noticed too shiny brown dress shoes next to my feet. They were attached to the director. I looked up.
“We haven’t seen you yet,” he smiled. “Why don’t you read for Scout?”
My plan to remain invisible had failed. I crawled up there and did my best Matthew McConaughey I could muster. I was sweating profusely.
But I did it.
After the first round, I stayed up and read for another character. It got easier and easier. No one was laughing at how stupid I was. No one whipped their phone out to start filming me. As it would turn out, everyone else was just as nervous as I was.
I went home and despite doubting I’d get a part, I was proud of myself. After years of thinking about going for it, at least now I could say I actually tried.
My actor friend messaged me a few days later while I was at work. I got a role. My first role in a play.
It was a small part. A side character with ten lines. I was elated. Ten lines? It’ll be impossible to forget them!!
That semester was my first experience being in a theatre company. I became familiar with the rehearsal process, learned my way around the back of house, and made new theatre friends. I also started taking acting classes.
It was a perfect timeline:
Got that first role in the fall of 2015.
Got cast as a protagonist in the following spring production.
Became convinced that I wanted a career in theatre after college.
Got cast in the more intimate play that following fall with a different director. He taught me how to tell a story and helped me drastically sharpen my skills.
But there was a problem.
Here’s the thing…
Clybourne Park, 2016.
As my years at university drudged on, I was doing worse and worse in school. I was skipping classes, not handing in essays, and using that time to sit in on acting classes. I was too deep into my major to switch to a theatre degree, so I had to improvise.
Obviously, this was unsustainable.
My girlfriend at the time was an actor too. That winter, we took a bus up to NYC and auditioned for grad schools. We had spent months preparing our monologues and resumes.
It was a thrilling and anxiety-inducing experience.
Hundreds of actors from around the country would wait to be called into a room. It was a small banquet hall where 50 people with clipboards were facing a small stage with a chair on it. We’d walk in, head to that stage, arrange it how we wanted, then introduce ourselves and perform two monologues.
We had two minutes starting when we spoke our first word. At the two-minute mark, the time-keeper in the back would raise his/her hand and say, “thank you!” Then the gods would decide our fate.
She and I both got several callbacks. It was an exhilarating way to spend a day: running around a giant Broadway hotel to different masters program scouts from around the globe.
Here’s the punchline to this drawn-out story: I got accepted into three different schools. One in Long Island, one in San Francisco, and one in Birmingham, England.
I couldn’t go to any of them because I flunked out of college that spring.
Emailing each of them back was one of the most depressing things I’ve ever had to do. But things got worse.
After an unsuccessful “college try,” I moved back in with my mom with my tail between my legs. I’m all for people living with their parents to save money and figure something out, but this wasn’t my choice. I was back to square one. No job. No real skills besides acting. A ton of debt.
A few weeks into that summer, that same girlfriend broke up with me. She had graduated and wanted to explore the world and herself. I was in a hole with no idea how to start digging myself out. It made total sense. But it crushed me.
Unfortunately, none of those events motivated me to begin climbing that mountain. In fact, in June of 2017, after stealing a bunch of prescription pain pills and anti-depressants from various people, I tried to kill myself.
That sounds awful. And it was. But it wasn’t out of intense depression. It was almost out of laziness.
I had so many things to figure out and repair. The second I thought about the first few steps, I’d get overwhelmed and would avoid anything and everything. It seemed truly insurmountable. So I tried to bypass it.
I’ve shared that story before and can go into more detail in a future blog. But all you need to know for this one is that it was my breaking point. My rock bottom.
My decision
To Kill a Mockingbird dressing room, 2015.
Waking up from that, everything clicked.
Whatever I had been doing up until that point clearly wasn’t working. Something had to change. Many things had to change. So I started at the beginning.
I began applying for jobs—bigger restaurants in my area. I opened a new checking account since my old one was closed due to prolonged overdrafting. I got a gym membership and started working out 2-3 times per week.
But the question remained: When would I have time to audition and perform in plays? There were numerous theatre companies in my area. How could I make it work?
I wouldn’t.
It was both one of the easiest and most difficult decisions I had ever made. I wasn’t ready.
I wasn’t prepared to pursue arguably the most grinding, unforgiving, and least lucrative careers in the world. I could barely take care of myself. I needed to grow up.
Many of the successful paid actors I know today have one or two (sometimes three) side jobs. They’re scraping by.
I didn’t want that. I don’t ever want to live anything close to paycheck to paycheck ever again. I didn’t know what I would pursue instead, but I knew it would be something much more likely to make a great living. I had an inkling it would be in the world of business.
So I haven’t done any sort of acting since failing school in the spring of 2017.
Will I ever be on stage again? Maybe.
Theatre will always be a love of mine. Going to shows is one of my favorite ways to spend a night out. I’ll always have a deep respect for the craft of acting and storytelling. I still act out my favorite movie/television scenes when no one is around.
But if I never act in another play again, I wouldn’t regret it.
I have so many other things I’m passionate about. My business. Creating content. Writing. Chess. Jiujitsu. Connecting with others.
I’m not the lost 23-year-old I was when I was…23 (that’s math). For now, I’m content with going to see as many performances as I can. I also have a bunch of old theatre friends creating their own shows and doing incredible work. Seeing them do their thing makes me smile every time.
For me, acting was like the perfect guy or gal you meet at the worst possible time in your life. It brought me tremendous joy, fulfillment, and friendships. But wasn’t the right time. I had to learn how to live first.
It wasn’t you; it was me. We had our time. Maybe I’ll see you again. 🎭
1) “What’s a question you wish someone would ask you?”
With all the time I spend being curious about other people, it’s so refreshing to have anyone ask me questions about myself and what I’m working on.
I run a life coaching business where I spend hours going deep into the minds and lives of others. I’m writing a book where I pry at people’s habits and insights. And I love it. I find people—specifically people who are doing things—fascinating.
But it can burn me out if I go a long time without anyone returning the favor. It’s a basic human need to feel important and seen.
So did I start this Q&A to fill a void? You be the judge.
My favorite question to ask and be asked is: What’s on your heart and mind right now?
It’s so broad and yet pointed and specific at the same time. It’s practical, emotional, and allows the answerer to be vulnerable immediately if they so choose.
So what’s on my heart and mind right now?
launching my new YouTube channel/podcast next week
the fact that I interviewed Courtland Allen, one of my favorite creators, yesterday
being pissed that I ordered a new car for delivery and it’s been delayed twice
getting in excellent shape and burning away my love handles
2) “How did you get into rock climbing and what level climbs do you do? #v1gang”
This made me lol.
Two of my besties took me climbing earlier this year and I didn’t love it immediately. I found it quite challenging, which pissed me off because they made it look so easy. So I kept coming back out of competition and ego.
As I improved and could enjoy it more, I thought it would actually be a great way to irradicate my phobia of heights. So I tried rope climbing.
This was a huge milestone for me. Climbing up that wall and being attached to a rope connected to my friend at the bottom was one of the most terrifying experiences of my life. My head was flooded with images of me falling and breaking my limbs.
But I made it to the top.
Coming back down, out of breath and coated in sweat…I felt triumphant.
When I lived in NYC for two weeks, I was an eight-minute walk from a gorgeous climbing gym. I went nearly every day, which would prove to be awful for my muscles and ligaments.
Although I got injured after those 14 days, I got way better at bouldering (shorter climbs without a rope). It was there that I did my first and only V4. So I would say V3s are my sweet spot between challenging and doable.
3) “What are some non-technical/intangible areas you’re thinking about and/or working on these days (e.g. attitudes or skills such as patience, listening, being more present)?”
The biggest thing I’ve tried to actively practice and improve this year has been empowering and praising people.
When someone impresses me. When they are clearly working hard at something. If they’re putting effort into things that matter to them.
I tell them.
It can be as simple as saying, “Hey, I want to acknowledge you for x, y, or z.”
Sometimes they just say thank you. Other times it makes their entire week. And on rare occasions, they tell me it’s exactly what they needed to hear. We never know where a person is at mentally.
A few months ago, at the end of a session, one of my clients took two minutes to do that to me.
“I just wanted to say,” she started. “That I know we’re here to focus on me and my dreams. But I’m so proud of you for pursuing yours. Building a business where you can help people and make money doing it. Creating stuff and only doing what you want to do without working for anyone else. It’s inspiring.”
My eyes teared up. No one had said anything like that to me before. And the last person I would expect that from was one of my coaching clients. I’ll never forget it.
We have the power to do that at scale for those around us. It could change their world.
4) “What are some of your favorite books and why?”
Here are five I love in no particular order. Follow me on GoodReads!
Essentialism by Greg Mckeown: got me to focus on what’s most important and ignore the rest.
Studying chess. Building a coaching business. Writing a book. Running this blog. Launching a new YouTube channel and podcast soon (more on that later this week).
Getting distracted can be quite the wrench in my day. So aside from a few of the popular tricks and tips—a Pomodoro timer, starting small, leaving my phone off and in the other room…there’s one rule I follow that makes everything else 10 times easier.
I stole it from Niel Gaiman, the prominent fiction writer.
When he’s writing a new book, he sits down and gives himself two options:
write
do nothing
That’s it. He can’t do anything else.
The freedom to not write removes any guilt associated with not getting work done. And it doesn’t take long until writing becomes less boring than just sitting there doing nothing.
I do the same.
When I’m not doing whatever deep work is needed from me, I’m sitting here daydreaming and talking to myself. Sometimes it lasts 60 seconds. Other times it lasts 20 minutes. But eventually, I always come back to the task at hand.
The impulse to check something is omnipresent. Email. Facebook. YouTube. Facebook again.
But those aren’t one of the options.
The rule must never be broken. Otherwise, it’ll be broken every day. So instead, I sit here and work…or do nothing.
I’ve tried my hand at many creative endeavors. I gave up on all of them except for this blog.
Here’s the timeline.
2010, high school: a punk rock band with my friends. 2015, summer: standup comedy. 2016, in college: theatre. 2018, winter: a podcast about people’s passions. 2019, fall: this blog and a YouTube channel about self-improvement. 2020, fall: a daily vlog. 2021, winter: sketch comedy videos
Clybourne Park, 2016.
Aside from acting, which I was deeply passionate about, each of these pursuits ended the same way. (I’ll tell the story of why I quit theatre in another blog.) The process went like this.
First, I would get inspired by other people whose skills I enjoyed. In high school, it was Blink 182. For standup, it was Louis CK. I started vlogging because of Casey Neistat.
I wanted to be as talented as these guys. I envisioned myself on stage captivating crowds or being recognized on the street by one of my million subscribers.
So I’d start the thing.
I learned every 2000s pop-punk song on guitar I could. I forced myself to sign up for an open mic. I bought a camera and microphone and started recording.
It was always exhilarating. For a week or two.
But each time, reality would quickly settle in. That reality was: If I want to get good at this thing and have other people enjoy it, it’s going to take a ton of time, consistency, and persistence through being mediocre.
Basically, I would suck at something and wouldn’t get the results I wanted fast enough. Then it would rapidly feel more like a chore than a passion project. Once the Resistance grew tall enough, I couldn’t justify continuing to work on it. I’d stop enjoying it or begin dreading it entirely.
The worst part about this cycle was it would make it difficult to trust myself. When I’d feel interested in a new venture, I’d think in the back of my mind, “But how long do you think this will actually last?” Then I’d hesitate to start.
Our Blink 182 cover band setting up, 2011.
So why does this happen?
I mentioned it above briefly, but the answer is quite simple: it’s due to unmet expectations.
We see the thing we want: fame, glory, high-quality entertainment. Then we go for that thing.
But as we start to put our heads down and do the work, we see that the things we wanted are hidden behind countless hours of grinding practice, boring or stressful tasks, and little to no recognition. It’s all the unsexy stuff we never see from those we admire.
When I wanted to be a standup comedian, I wasn’t fantasizing about all the empty clubs I’d bomb in at 2am. I just wanted a Netflix special.
When I started vlogging, I didn’t think about how many hours a day it would take to think of something interesting, film it, and edit it in a fun and captivating way. All I wanted was a following and ad revenue.
If our goals are the end results, we’ll never make it. It’s unsustainable to be driven by money, subscriber count, or viewership. Because when we start, we’re pretty bad at whatever it is we’re doing. So those incentives will naturally take a very long time to experience.
Let’s look at the only thing I’ve stuck with from that list above: this blog.
From day 1, I never cared about how many people were reading it. For the first several months, it was just me and one supportive friend. I still loved it.
Because I cherished the process. There was never a result in mind.
Now, this blog has way more subscribers. So I obviously feel more inclined to make it good and worth reading. But at the end of the day, I just get joy from typing my thoughts out a few times each week.
The first podcast I ever recorded, 2018.
So when we’re thinking about pursuing something new and creative, I’ve learned it’s crucial to ask this simple question: Do I actually want to do this work, or am I just craving the end result?
In other words: Am I okay if no one cares about this for the first year of doing it?
If the answer is no, it might be worth reconsidering.
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.
Freshman year 2012, my roommate after 9 shots of fireball.
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?
We don’t.
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.
Setting up regular phone calls. Going out of our way to visit them. Asking them about their world.
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.
May 2022, after a Savage Race.
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.
This is typically reserved for the people we’re closest to. Again, we’re looking for high-quality perspectives on how we’re doing in the eyes of those around us.
Here are the questions my friends and I dive into:
When have I hurt you?
What do you think would be most beneficial for me to improve?
What’s something you’d like me to know?
When have you been impressed by me?
What do you think I do better than most people?
We’re guaranteed to hear things we weren’t expecting. And if we do this with multiple people, it’s useful to connect the dots from similar responses.
In summary:
As much as we’d like to see them as organic entities, our friendships don’t simply take care of themselves.
There are two parties involved. They are likely to morph as the years tick by. And there’s no telling what those evolutions will look like or result in.
I have friends I get closer to each year. I got asked to be the best man by someone I’ve only known for two years. I got completely ghosted by one of the closest friends I’ve ever had.
It’s hard to predict what happens in our friendships. But if we continue to live for our values, we’ll probably cut out those who aren’t right for us anymore and attract those who are.
To my friends who are reading this, I love you all. ❤️
Last week, I took my friend to her first jiujitsu class. She’s athletic and open-minded so I thought I’d show her the misery I put myself through on weeknights.
While she enjoyed it, she said it was…a lot.
I remember when I first started in 2020. For about three months, I reluctantly went to class only to flail around and have someone control my every move. It was demoralizing.
But slowly, I began to defend myself. I got submitted less and less. Eventually, I even beat a few teammates.
The learning curve was steep. Going from total noob to slightly less of a noob was quite a journey.
My face just about every class.
So while learning a move in class last week, I looked over at my friend choking her partner. Her eyes were as wide as they could stretch. Most people aren’t used to bending and suffocating other people for fun. It can be overwhelming.
She took it easy and only sparred with a few people. They took it slow with her and talked her through everything. I’m lucky to be at a super welcoming and friendly gym.
Afterward, she wasn’t entirely sure if it was something she’d want to commit to. I completely understood. It’s hard to market.
“Hey, would you like to try something really really uncomfortable and grueling, that will take you a pretty long time to get even remotely good at, while you roll around in a puddle of other people’s sweat night after night?”
Jiujitsu, everybody.
Whatever she chooses to do, I was quite proud of my friend for giving it a go. It made me realize that we really only have two choices when learning, pursuing, or attempting something new.
Option 1: “One day…”
Option 2: Day 1.
Getting in shape. Learning an instrument or foreign language. Starting a business. We can either start these things or wait.
Starting is exhilarating, ungraceful, and often discouraging. When we begin to climb the mountain, we see how tall it actually is. We can also imagine the downsides pretty easily. It’ll be scary. We could fail. We might look stupid.
But waiting can be an unfulfilling trap. When we create all these conditions that have to be met before diving into something, years can go by and we realize we’re standing in the same (or in a worse) spot. These downsides are usually more long-term and therefore are harder to anticipate until a ton of time has gone by. It’s tough to imagine the regret you’ll feel ten years from now.
An example of this difference is building an exercise habit.
The cons of going to the gym are simple. You don’t know how to use certain equipment. You’re out of shape. You’re not sure which exercises to do. It’ll be unfamiliar and tricky before any results are had.
But the cons of not exercising regularly are cloudier and easier to ignore. It’s hard to motivate ourselves with the possibility of being deeply disappointed by our bodies years down the line. But that’s exactly what happens to many of us. We look at ourselves and wished we started working out a while ago.
That’s because we’re so afraid of Day 1. But it all starts there.
What are you avoiding? What’s Day 1 look like for you?
My 10-year high school reunion is tonight. I’m thrilled.
I can’t believe it’s already been a decade. I remember wearing the tye die tank top in the photo above, walking through the neighborhood near our freshman dorm, and smoking a joint with my roommate.
“Dude,” I coughed. “When my sister is a freshman in college, we’ll be 30.”
“Whoa,” he retorted.
At the time, that idea seemed so far away that it would never actually come true. But now it’s less than two years away.
Before I take tequila shots with a bunch of people who didn’t know my name in high school, I’d like to reflect on who I was when I graduated. In the moment, I’m sure I felt like I had finally grown up. In reality, I was just an insecure teenager with a driver’s license.
If I had an hour with that 18-year-old doofus, what would we talk about? Would he be impressed by me? Would he judge my mustache? What would I say to him?
Probably these things…
1) You’re supposed to feel confused, self-conscious, and clueless.
No one has their shit figured out, especially at 18. We’re all just dumpster fires hiding behind beautiful Instagram photos and Facebook posts.
It felt like you were the only insecure kid in high school. But you’ll soon realize that everyone else was just really good at hiding it. I didn’t start feeling truly confident in life until I was 23. And that was after failing college and trying to kill myself.
As a life coach, I work with people of all age brackets. I know 50-year-olds who are still figuring out what they want to be when they grow up. You’ve got plenty of time.
You’ll never “arrive.” There is no solution or formula to life that makes the rest of it smooth sailing.
So just keep putting yourself out there and trying new things. Your values and interests will change as you do. But you have to take action and go out and explore.
2) Don’t go to college until you can specifically state what you want to work on and why school is the best choice for that.
You were a trash student, dude. A 2.2 GPA in high school.
Why do you think putting tens of thousands of fake future dollars on the line would make things easier for you? On top of that, you’d have no supervision and access to all the booze, drugs, and women you could imagine. Does that sound like it would produce high levels of commitment and productivity?
Swallow your pride and stay home for now. Get a job at a restaurant, start saving money, and build creative skills. It will suck to see your friends go off to four-year universities. But you’ll be grateful in four years when you’re not paying $1000 a month for a piece of paper you’re not using.
3) You’re not really valuable right now, but you absolutely will be.
I don’t mean you’re useless as a human being. But at this time, in both the dating market and the general economy, you don’t have much to offer.
It sucks to hear, but if you start slowly building your skills, you’ll be super attractive years from now. That goes for women, businesses, and collaborators.
Right now, girls tend to be attracted to fun. You’ll see that when you go out drinking.
But as you go deeper into your 20s, they tend to be attracted to confidence, drive, and security.
So, if you start working out, developing skills you can sell, and treating yourself and others with respect…you’ll be unstoppable.
4) Be as kind as you can as quickly as you can.
The phrase “Nice guys finish last” is bullshit.
What it actually means is don’t sacrifice your values to make others happy. But do care about the happiness of others.
The more you make people feel welcomed, heard, and cared for…the more they will want to be around you and take care of you too. The most important thing in life (aside from your physical health) will be the relationships you build over the years.
Stop talking shit about people. Stop complaining about things you can’t control. Always seek the lesson and value in every situation.
That is the ultimate kindness: seeing life as something happening for you and not to you.
5) Don’t listen to me.
I can talk for hours about all the things I wish I did more of and less of.
I could tell you to take great care of your body, become financially literate, ask out more women, start playing chess or doing jiujitsu, build a writing habit, and never make a Twitter or Instagram…
But you’ll figure all of these things out from sheer necessity.
The best way to learn how to do something is to learn how not to do it. I can give you all these insights because I’ve done so many things poorly.
And to deprive you of mistakes and regrets you’ll experience would be to limit your ability to grow and learn.
Go out and do stupid stuff. Create cringe memories. Overdraft your checking account.
The people who know the most are typically the ones who have been through the most. Put yourself through the wringer and you’ll have no choice but to be the best version of yourself.
Now go, my son. Smoke a bowl and play guitar for four hours.
(Here’s a short and fun video on the term “sellout.”)
What I’ve done
I don’t actually think I’ve sold out. But I’ve just done something I thought I’d never do: I created a Patreon.
For those who don’t know, Patreon is a service where people can support creators they enjoy—YouTubers, artists, bloggers, etc. Oftentimes, those creators offer bonuses and exclusive content for those who help at different degrees.
This seemed silly to me for the longest time. But then I started interviewing creators for my book.
James and Anthony Deveney took me through their journey of quitting their full-time jobs to run their podcast, Raiders of the Lost Podcast. (If you like movies and television, I highly recommend their show.) They were able to do so because of the level of support their patrons provided.
Eric Rosen, my favorite YouTuber, broke down all of his revenue streams when we spoke. Merch, ad revenue, Twitch subscribers. But in the early days, he said it was mostly from people donating on his streams.
It’s never been easier for one person to reach (dare I say…influence?) a large number of people. Steph Smith made a great point. She said, “Britney Spears was a content creator. She wrote songs and shared them with millions of people. Today, some bro can film himself in his apartment and have a million followers on TikTok.”
I’m not some bro and I don’t have a TikTok. But it’s been wild to type my thoughts out and have a bunch of friends, family, and strangers read them.
And with the popularity of things like podcasts and YouTube, free content has never been more prevalent. It’s expected, actually. Anyone else get triggered when they click on a NY Times article and get asked to pay for a subscription?
I do every time. But then I think, There’s a team behind this…It’s someone’s job to produce this.
Why I did it
To be clear, this blog will always be free.
The site has a simple system:
I live my life
I reflect on all my insights, mistakes, and fears
I write about them here
You either enjoy them or go, “meh.” 🤷🏼♂️
Repeat
I don’t see that ever having a price tag. Making a subscription service like Substack doesn’t interest me.
But there is a dream life I’m working toward. It’s pretty simple.
I want to be a full-time writer and coach. I’ve got the coaching thing down. But in the future, I’d like to be publishing a new book every 2-5 years, write 2 or 3 blogs on here each week, and have 5-10 coaching clients. In between would be plenty of time to travel, work on other projects or programs, and do all the non-work things I love (chess, friends/family time, jiujitsu).
With all that said…if any of you get value out of these posts and want to support the blog, you now have an avenue to do so. Only if you really want to. If not, you’re dead to me.
Whoops. I mean, *if not, that’s totally fine! Nothing will change on here.
But for those who do, you’ll get some bonus stuff. Extra blogs, video updates from me, access to a Q&A, monthly Zoom calls, the running draft of my bookDo The Thing, and polls for what you’d like me to write about next. I’m even working on setting up an advice column.
Whether they’ve chipped in financially or not, I’m forever indebted to anyone who has taken two minutes to read anything I’ve written. I wasn’t even planning on having ten readers. Now this blog has hundreds. Onward!
If you’d like to become a patron, you can do so here.
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?
My favorite bar in NYC—The Gutter. (Subtly crushing my friends in bowling.)
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.
Logical reason:
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.
My God.
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.
Emotional reason:
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.
Just a couple’a cool dudes.
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.
TLDR:
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.
2) Care.
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:
“Hey 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! 😎
I’m about halfway done and have a few interviews left to do. It comes out this summer and I’d love to write a chapter on you. Would you like to contribute?
It would be no more than an hour of your time for a video call. Plus, I can send you the questions beforehand to speed things along. What do you say?
No worries if you don’t have the time or interest. I’m sure you have to say no to most things!
Dillan ✌️😇”
That’s it. She got back to me a few days ago and we’re in talks of setting something up next month.
If you want to reach out to someone you dig, do it. You have nothing to lose. Just know that you most likely won’t get a response and that’s totally fine.
But the answer’s always no when you don’t ask for what you want.
Doing so has allowed me to talk to some incredible people. It can help you do the same.
I’ve been keeping a ‘Get Better’ list ever since I read Ultralearning by Scott H. Young.
While it’s wildly effective to hone in on our strengths, it’s good to balance that out by improving our weaknesses. If we only did the things we were naturally gifted at, our capacities to grow and experience life would be severely limited.
I sucked at chess when I first started playing. But after playing and studying consistently for almost two years, I can now play in tournaments and enjoy beating my friends.
Fortunately (or unfortunately) for me, I have a handful of hobbies and passions. Chess is one. But I also love rock climbing, writing, and Brazilian jiu-jitsu.
The goal is to get pretty damn good at each of these things I spend my time doing. And the main way I stay up to date on what to focus on is with my ‘Get Better’ list.
Simply put, it’s my list of weaknesses in each of my favorite activities. It includes my coaching business, friendships, and even my dating life.
Whatever makes the list, I know I need to find a way to drill it. Obviously, things like chess or jiu-jitsu are easier to practice because there are specific exercises or puzzles I can chip away at.
But there are more ambiguous weaknesses like: “Holding space for friends instead of giving advice.” How does one drill that?
Well, the next time one of my close friends is going through something, I can make an effort to listen twice as well and acknowledge that I see and hear them. No suggestions. No problem-solving.
It’s like working out a muscle that doesn’t get a ton of action. I did the same thing with curiosity.
Last year, in building my business, I had to reach out to a ton of people. This was super tough because I wasn’t naturally curious about others. But after five or ten connect calls with people from my past, I found myself genuinely wanting to learn more about whomever I was speaking with.
The muscle was getting stronger.
We can do this with anything. So if you made a ‘Get Better’ list, what would you want to improve specifically?
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?
In the past year, of my close friends: five got married, four got engaged, and two had a child.
As I inch closer to 30 years old, this all feels more and more normal. But it brings up a plethora of emotions as a guy who’s spent most of his life single.
This weekend, I saw one of my best friends marry the woman he’s been with for nearly a decade. The wedding was at a stunning art museum, I got to spend time with my favorite people on the planet, and I got seven hours of sleep in three days.
They’ve been one of those couples who have acted like husband and wife for years: living together, running a business together, and having more chemistry and compatibility than just about any other duo I’ve ever known. I’m not sure which brought more tears to my eyes: hearing them exchange vows or watching them mosh to Panic! At the Disco on the dancefloor.
My friends mean the world to me. My relationships with them are arguably my deepest held value. If I had it my way, every single one of them would do wildly fulfilling work, live long and healthy lives, and be with a partner who supports and cherishes them. So far, so good.
But naturally, there’s a murkier and more selfish side to all this.
I’m proud of the life I’ve created. I have my dream career, take excellent care of my health, and have a disgusting amount of meaningful connections.
But as a human being, I’m not free from the natural comparative thoughts.
When I look around and see 80 to 90 percent of my friends with a partner, when I see so many awesome people with other awesome people, the question is inescapable:
Is there something wrong with me?
Am I…
too picky?
unattractive?
not put together enough?
Logically, I’m aware that the answer to each of these questions is no. But logic rarely wins the battle.
One of my biggest fears in life is that there’s something (or multiple things) about me that makes me unlovable. Something with my personality, my looks, or both.
Again, it sounds like paranoia but it’s very much there. That stays between you, me, and the internet.
To be clear, none of these questions, doubts, or anxieties keep me from putting myself out there. I go on dates. I meet women. I even speak words to them.
But the point of this blog is to share my brain with ya’ll—not to gain sympathy but to articulate a hopefully relatable human experience.
I just deleted the dating apps from my phone after trying them for a month. I know people who’ve had success with them, but I found them to be utter garbage. Performing, ghosting, judging…not a fan.
So aside from continuing to build the life I want, the next step is to get better at talking to women out and about. There are two main challenges with this:
I don’t go out much
It’s pretty terrifying
Hence the “get better” part. But as always, I’ll keep you updated.
Seeing all my lovely couple friends this weekend didn’t make me sad. It fueled me. I’m even more energized to create and go after what I want.
In November 2019, I lost half of my subscribers in a single day.
That was because I only had two readers and one unsubscribed.
Still, it was devastating. How could one of my friends unfollow my poorly written and unoriginal thoughts on self-improvement?
794 blog posts later, I’ve become at least slightly better at writing—trying to share my stories and insights in a concise manner. People seem to dig it, as we’re now at 417 subscribers (thank you).
But after making the recent decision to email these directly to you, four people, two of which I know personally, have unsubscribed. And I couldn’t be more thrilled about that. Let me explain.
We’re starving for validation in the early days of creating something and sharing it with others. Do I suck? Is this good? Like and subscribe!
The problem is, we do suck. We haven’t found our voice, created any value, or developed enough skill yet. So why would people stick around?
Well, in my experience, it started with an early adopter: my friend Grace. She was so pumped that I was blogging and publishing something. She read every post.
For months, it was just the two of us reading my mediocre blogs on habits and mindset. I was basically just writing things I thought she would enjoy. But every now and then, I’d write about a personal story or an educational topic and other eyeballs would appear.
Slowly but surely, more and more people would visit the site. As I entered new communities, people from different realms would tune in: a new gym, an online coaching community, and past jobs.
For two years, I wrote a new blog every Monday through Saturday. Most of them were terrible. I cringe when I go back and read my old stuff. I was overly confident without any real-world experience to back my ideas up.
But I was getting in the reps. I showed up to practice almost every day. And as a result, I was accidentally becoming a clearer and more effective writer. It was quantity over quality.
I discovered that most people enjoyed it when I shared personal stories from my own life. I used to think that would make me sound self-important and boring. But it turned out that real-world experiences made people feel most connected. So I started telling more stories and giving fewer lectures.
At first I was afraid
Building an audience with the people already in my life: Facebook friends, coaching colleagues, high school acquaintances…It’s been a wildly rewarding thing to pursue.
I love when people comment or email me about their own thoughts or experiences based on something I’ve written about. It feels like a purer form of social media.
But the downside has been a deeper craving for approval. Since I have a personal connection with many of my readers, I have felt a heightened pressure to not upset them.
In the early stages of the blog—before I felt secure in my voice—whenever someone unsubscribed or criticized my ideas in a Facebook comment, it would eat away at me.
Any ounce of disapproval meant I wasn’t cut out for creating content or sharing my opinions. Then I would get twice as gloomy because I would recognize how strongly I needed people to like my work.
Pushing through
After these uncomfortable moments, I’d have to remind myself that I only had 20 subscribers and that it wasn’t even close to the end of the world. As it turns out, I’m still alive. Someone I went to high school with left a frowny face on my Facebook post and it didn’t end my life.
I kept posting and sharing. I continued to sharpen up my writing skills. And more people enjoyed it each month.
I don’t know when “getting over the hump” happens. But there came a time when I had gotten enough validation in the form of subscribers, praise, and my own security. This validation allowed me to simply let go of the fear of pissing people off. It made it easier for me to speak my mind.
It’s like having an incredible group of close friends nearby. With that community secured, it makes it easier to be yourself. But if you were to move to a new city where you knew no one, you might feel less loose with your words and actions. The need for approval would be more present.
That’s how I feel now.
So, when people unsubscribe or message me when they disagree or dislike what I say, I welcome it. I try to use these as opportunities to improve and gather perspectives outside of my own.
If someone finds these posts boring, how can I make my stories more captivating and my insights more relatable or usable? If the emails get annoying, how can I shorten these blogs?
Rejection is always a good thing. It weeds out the people who aren’t the right fit. Dates, clients, subscribers, etc.
Just like I would hate going on a date with a woman who didn’t actually like me, I’d feel awful if someone was subscribed to this blog just to be polite…these emails going unread in their inbox only to be deleted.
I want you to enjoy reading these and get value out of doing so. So if you don’t, I implore you to send me feedback or to unsubscribe!
I’ll be sending out a super short survey soon to learn more about what you guys want to read more of and less of moving forward.
Thanks so much for making it this far. You’ve allowed me to turn this side-project into a pillar of my life. I’m wildly grateful.
The first coaching session I ever ran was on June 26, 2020. A friend agreed to be my first guinea pig.
I began coaching my buddies for free. Eventually, I charged $40 a call. Then $50. Then $80. Then I started offering 3-month packages instead of per-session prices.
In March of 2021, I joined the Insight Coaching Community (ICC). It was there that I would find my people, learn how to create clients, and build the career of my dreams.
Since then, I’ve:
been hired as an ICC team member to train other coaches
coached nearly 1000 hours
had intense conversations with 100+ people
Last week, a woman shared with me my favorite description of a coach I’ve ever heard. She said, “I thought a life coach was just an unqualified therapist?”
After a good laugh, I explained the difference. In oversimplified terms, therapy tends to uncover the past; coaching is meant to create change for a better future.
While I certainly don’t claim to have any kind of psychological expertise, I’ve learned a ton about the mindsets and behaviors of human beings over the last two years.
Here are my top three insights.
1) We protect ourselves with our identities.
Every person on the planet has certain proclivities, personalities, and tendencies that set them apart. But we tend to think these are fixed.
People say things like:
“I’m the kind of person who…”
“That’s just not me.”
“I could never…”
We craft these identities for ourselves. That way, when something undesirable happens to us we can simply blame our identity.
If our business isn’t doing well, we can point to the fact that we’re just not a pushy or organized person. That explains it. It’s not that we’re not doing the work; it’s our timid, non-masculine identity’s fault. It’s just who we are.
But these aren’t definitions; they’re stories.
“I’m not a go-getter,” is really: “The story I’ve lived in the past has not been one who follows through with what they want.”
This is good news. Because as cheesy as it sounds, we can change the story. How do I know?
Because I’ve seen people alter their stories right before my eyes. I’ve seen…
perfectionists become pragmatists
people pleasers set hard boundaries
go with the flow types create organized systems
impulsive actors become proactive
hyper-achievers embrace acceptance and gratitude
Most of the people I work with have turned into completely different humans in a matter of months. That’s not an advertisement for my services and it’s certainly not a guarantee. It just highlights a simple process that something like coaching can provide.
Step 1: Act and think a certain way.
Step 2: Open up about what you actually want and what you think is in the way of that. Notice how far your desires are from your current life.
Step 3: Pinpoint which obstacles are real and which are only in your head (most of them are just imagined—e.g. fears, doubts, uncertainties).
Step 4: Accept that if you keep doing exactly what you’re doing, you’ll keep getting exactly what you’ve been getting. Start taking action and making changes that make you feel uncomfortable and stretch you. Gather insights from failures and celebrate wins.
Step 5: Act and think in new ways.
Step 6: Repeat.
That sounds like every self-improvement book ever written. But that’s because it’s impossible not to improve oneself by following this stupidly-simplified formula.
Unfortunately, most people stop at step 1. They go through life without challenging their modes of operation. But all it takes is one person to ask one question for us to stop looking at the world through a toilet paper roll.
And in my experience, it’s those who are not invested in their identities who see the quickest results…because they have no excuses.
2) People want answers but need insight.
For context, Webster defines insight as: “gaining a more accurate or deeper understanding of something.”
My mentor shares two truths when it comes to the coaching world:
People don’t do well with solutions they’ve had little to no part in creating.
Our insights will never be as powerful as their insights, even if they’re the same.
Holding space for someone is one of the most powerful and valuable things we can do for them.
We often jump right into problem-solving and we miss what’s really going on. This usually shows up in three main ways:
We believe them when they tell us what they’re struggling with when really there’s a much deeper problem.
We offer advice and suggestions when all they want right now is to be heard and understood.
We think our words are more useful than their thoughts and we limit their ability to gather insight on their own.
Here are some examples for each.
1. Not believing the first problem:
I coached a guy once who opened the call by saying, “I’ve done a lot this year already. I want to define what my next big projects and achievements are.”
“Great,” I said. “How much more doing and achieving would you need to feel satisfied?”
It was the fastest turn of events in a session I had ever seen. He started laughing.
“Wow,” he chuckled. “I have so much on my plate right now. I have no idea why I thought adding more to it would make me more fulfilled. It would crush me. I’m already overwhelmed.”
So we spent the rest of the call discussing his obsession with taking action at the expense of his mental sanity. That was the problem beneath the problem.
Notice how I slightly disregarded his original statement. He declared he wanted to brainstorm his next actions. If I just went along with that and we started spitballing, we never would’ve touched on the root of the issue.
2. On holding space:
At the end of each coaching session, I ask the client what they got out of our conversation. The most common response?
“I just feel ten times better saying all this stuff out loud.”
This is the same reason journaling is so therapeutic. When we take the thoughts out of our brains and put them into the world where they can be seen or heard, they become more real and less daunting.
In the coaching sphere, there’s a concept called the lamp post theory. It says that even talking to a lamp post about your fears and accomplishments would improve a person’s life.
Now imagine instead of a lamp post there’s another human being reflecting your words back to you, asking you thought-provoking questions, and challenging your answers.
3. Curiosity before solutions.
It’s the #1 principle in my business.
I mentioned earlier that feeding someone an answer will never be as impactful as them finding that answer on their own. There is the rare case where someone asks us for our thoughts and actually uses our suggestions, but those instances are far and few between.
A few months ago, I was coaching a woman for the first time. She was having trouble setting boundaries with her hometown friends. She felt less connected to them and didn’t enjoy going out, drinking, and doing drugs all the time.
It would’ve been so easy for me to tell her what she was doing and why it wasn’t working. But I just asked her questions.
How is pleasing these people serving you? How is it hurting you? If nothing changed, what would you feel like a year from now? What are you responsible for? What’s outside of your control here?
After 50 minutes, she had an insight.
“Oh my God,” she laughed. “I don’t know why, but I feel responsible for their emotions. Like, how important do I think I am that their happiness starts and stops with me?” She started making fun of herself.
She asked me why it took her an hour to realize she wasn’t in charge of other people’s wellbeing. And that’s how insight works.
We can’t force anyone to think, do, or feel anything. It has to come from them first. And while there’s no guarantee, we can increase the likelihood of insight by being wildly curious and holding up a mirror for them.
I’ve had plenty of sessions where I ask piercing questions, reflect their words back to them, and challenge their thinking…and they feel nothing. That’s okay.
It’s not my job to ensure an insight. That’d be like a gym guaranteeing you a great body. You have to show up consistently and do the work.
We can only make changes when an insight is had. But most people want the change before the insight.
3) We’re all the same.
I’ve worked with: software engineers, CEOs, comedians, coaches, politicians, content creators, writers, doctors, athletes, marines, financial advisors, tutors, musicians, dog-walkers, yoga instructors, sales reps, and more.
And they’re all the same. Here why.
There’s a basic human trend I’ve noticed.
We all want stuff—usually changes in our outcomes, mindsets, or situations.
We feel like something’s in the way—usually fear, doubt, or uncertainty.
We either work actively to maneuver through these challenges or we let them keep us where we are.
This trend is true of every single person I’ve coached regardless of how much money they make, what their personality is like, or how big or small their goals are. It’s true for me. It’s true for all of us.
I could ask you right now: What do you want most right now that you don’t have? What do you think is in the way?
A past client who was making $200k+/year had purchased her dream car and dream house. It didn’t bring her any of the fulfillment she was expecting, so we spent months diving into the things that did.
Another client wanted to get better at receiving criticism, so we did an exercise where he reached out to all his friends and coworkers and asked for open and honest feedback.
We’re all the same. We want things and we think something’s in the way. Then we either do something about it or we don’t.
Coaching helps those who do want to do something about it.
In summary
We craft identities for ourselves to excuse the things that don’t go our way.
We want people to give us answers when we really need to create our own.
We all want things in life and think there are obstacles keeping us from getting them.
This is my dream job. I get paid to help others build the lives they truly want to live. It’s rewarding and fulfilling at the highest level.
It also holds up the mirror to me and my own ways of doing/thinking. I gather insights as I see my clients gather insights. I get inspired. Sometimes I get teary-eyed or get chills listening to what my clients are feeling and accomplishing.
These first 1000 sessions have been a tremendous learning experience. And this unqualified therapist couldn’t be more excited for the next 1000.
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.
Cons:
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?)
Pros:
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.
