29 life tips on my 29th birthday

No, I don’t feel older. But I do feel wiser.

Here are some things I’ve learned in these 29 years. Hope you find one of them valuable.

1) Learn the names of employees at restaurants you frequent.

Find great servers, build relationships with them, and ask for them every time. It makes them feel validated to have a regular who prefers them, you can tip them well, and you know you’ll always be taken care of.

Ask them about their life. No one does that. 99% of customers don’t even know their name or they forget it after a night.

I went to the Chipotle near my apartment one to three times per week for two years. There was this quiet dude who was always working. His name is Mike and he was taking on extra shifts to take care of his mother who was sick.

Every time I went in there, I said, “What’s up Mike! How are you man? How’s your mom doing?” He’d give me updates and then pile two enormous piles of steak onto my burrito bowl, free of charge.

All it takes is spending five seconds to treat someone like a human being for them to want to go out of their way for you.

2) Ask 3 questions before stating your opinion.

When someone says something you disagree with, hold off on your counterarguments and rebuttals. It’s more important to ensure you know exactly where they’re coming from and why they believe what they believe.

Steelman their argument. Articulate their opinion so that they’re pleased with your summary.

This has three useful effects:

  1. It makes them less combative and defensive.
  2. You avoid arguing with things they don’t believe.
  3. It slows things down and gives you time to decide whether or not you even want to pursue a disagreement.

A simple rule to build this habit is to force yourself to ask three clarifying questions before giving your thoughts. So you believe x because y?

3) In a group of friends, ask: “What impresses you most about every other person?”

When you’re hanging out with two to five people, this is a fun and wholesome game to play. Everyone takes a turn going from person to person and saying what they most admire about them.

No matter how close you are to these people, you’re bound to hear and say things you’ve never heard or said before.

Everyone feels more connected and heartwarming conversation ensues.

4) When you feel the urge to send an emotional text, wait 24 hours.

No one’s ever been told to “stay awake on it.” Get a night’s sleep and see if you want to send that same text tomorrow. You probably won’t.

I’ve saved myself from sending countless passive-aggressive or annoyed one-liners and paragraphs. These kinds of messages never lead to fruitful solutions. They never make the recipient go, “Oh you’re frustrated? I’m so sorry. Here’s why I was wrong and I’ll never do it again.”

All context is lost over text. If it’s that important and the feelings are still there the next day, call the person.

Don’t hit “send” when you’re in a state. That state will pass, but the message can’t be unsent.

5) Have your phone out of sight when watching movies or TV.

Two screens are too many. Just sit and enjoy the story.

Especially if you’re watching with someone else. It’s meant to be a shared experience.

Too much dopamine-searching weakens attention span and makes us less present. Do what you’re doing. If you’re watching a film, watch the damn film.

6) Know what success actually is.

What we think it is: Someone who is really good at something, doing things we could never figure out.

What it actually is: Someone who worked on something for years and years until we all see their polished results.

Just keep at your thing and eventually you’ll be amazing at it.

7) Buy expensive noise-canceling headphones.

Use them for work, to listen to music or podcasts while you cook, or just to quiet the world around you.

It’s one of the best purchases you can make. I suggest Bose.

8) If a book is bringing you zero value or entertainment, just put it down.

I used to have this rule that I had to finish every book I started. Slogging through boring pages was torture. All that rule did was take weeks (sometimes months) away from me reading something I might’ve actually enjoyed.

If it felt like a chore or a battle to get through the last three chapters, stop reading it. There are too many phenomenal books out there for you to be wasting your time on one that sucks to you.

You might hate a book but love it five years from now. But do your present self a favor and spend time diving into writing that fills you up.

9) Status is fun, but it’s a mirage.

Money. Clout. Reputation.

These things aren’t meaningless. I love making great money. I love building relationships with people who have wealth and power.

But these things will never complete us.

How many times do we have to hear rich and famous celebrities tell us being rich and famous does nothing for our happiness and fulfillment? Status can be fun but it will never be the final piece of the puzzle.

If your basic needs are met, if you’re healthy, and if you have loving relationships…and you’re still waiting on more status or success to be fulfilled, you will remain empty.

There’s nothing wrong with wanting to make more money or wanting a more interesting life. But real fulfillment comes from spending quality time with great friends and family, learning hard and rewarding skills, and being a grateful and healthy human being.

10) If you hate cooking, pick an easy and healthy meal to make every day.

It doesn’t have to be every day. Most days will do.

I love cooking…for other people. But when I’m home alone, I feel zero motivation to experiment or spend more than 20 minutes preparing a meal for myself. I just don’t care.

So, rather than wishing for more invisible willpower, I just choose a simple and nutritious meal I could make basically every day.

For a while, it was scrambled eggs with black beans and salsa. Protein. Carbs. Tasty.

Sometimes I’d use peri sauce instead of salsa. Sometimes I’d cook sausage instead of beans. Make it flexible and repeatable. This removes the headache of figuring out what to eat for at least one meal per day.

11) Frequently ask, “If I knew I’d die 10 years from now, how would I be living my life differently?”

Then do those things.

12) Set up regular hangouts centered around activities.

An easy way to consistently spend quality time with people and get out of the house.

Love knitting, board games, or walking? Find a friend or a group of people who enjoy it too. Then pick a day to regularly meet with them and do that thing.

Some examples from my life:

Thursday morning swims with a bestie.
Tuesday night chess club.
Sunday rock climbing with the bros.
Biweekly phone calls with my friend living in Rwanda.

We expect our relationships to take care of themselves. Proactively scheduling things is a lovely and efficient way to ensure we actually tend to them.

13) Run errands without your phone.

When was the last time you left the house without your phone?

Next time you have stuff to do out and about, leave the black rectangle at home. You won’t be on-call. You’ll have no choice but to be present and engaged with your surroundings. You’re more likely to spark conversation with strangers.

Feel the peace that comes from spending an hour or two completely unreachable and offline. Nothing to compulsively check. Nothing to experience other than the world around you.

14) Write letters, not cards, as gifts.

Giving a $5 card with a sentence on it is such a common tradition and it has always seemed odd to me.

People do it for “the thought.” But there are so many other, more personal and meaningful ways, to express that sentiment. Namely, taking 5-10 minutes to write a letter.

Outline plainly what this person means to you, what you love and appreciate about them, and how they’ve helped you and made your life better. Then read it to them.

It doesn’t matter if this is on printer paper or on a notecard. It’ll mean so much more to them than a funny card with your signature on it. They’ll remember how it made them feel for years.

15) No one is thinking about you as much as you are.

From your perspective, you’re the main character in the movie. But for everyone else, you’re a supporting character at best and a background extra to most.

Stop obsessing over everything you do and say. Not a single person is thinking about you even 1/10th as much as you are. They’re just worried about being the main characters in their movies.

Go to the gym. Share your opinions. Apologize and improve when you make mistakes and get feedback.

Because no one cares as much as you do.

16) Take month-long breaks from booze and sugar.

Pick a month. I typically do January and October.

You’ll get excellent sleep, eat better, and have more energy and willpower.

Can’t do this? You might have a problem.

It’s crucial to prove to yourself you don’t need something like alcohol to have fun, be fun, or live an interesting life.

17) Keep a list of your friends’ goals.

What they’re working on. What they want most. Their latest wins.

Check in on them and see how these things are going. It takes minimal time on your end and they’ll feel seen and supported.

18) When you’re feeling stuck, answer these 3 questions:

  1. What do you want most right now?
  2. What’s in the way of that?
  3. What’s step 1?

19) No one has ever been rejected into a coma or black hole.

The fear of being rejected is 100x worse than actually being rejected.

Ask that person out. Give that sales pitch. Ask for help.

The absolute worst thing that can happen is they say no. Now you’ve gone from not having that thing to not having that thing. You’ve lost nothing.

20) They’re not texting you back because…

They don’t want to.

People who are excited to converse and engage with us will prove it by continuing to converse and engage with us.

Short texts. No response. Never calling back.

These don’t necessarily mean this person hates you. You’re just not a priority to them right now. That’s okay. It doesn’t make them bad people. It just means you shouldn’t keep exhausting yourself to keep the conversation alive.

The number of times in high school and college I kept texting a girl who clearly wasn’t interested in me…I thought, Maybe if I just send the right text, if I just send the perfect joke…she’ll want to get with me.

Never happened. People who want to talk to you will talk to you. If they put in zero effort, stop being needy and move on.

21) The 10/80/10 rule.

10% of people will dislike you no matter what.

10% of people will love you no matter what.

The other 80% will decide based on how skilled you are, how fun you are, and how delightful you are to talk to.

22) Be an ESPN sportscaster.

Bring up the accomplishments and highlights of your friends and partners. Hype them up. Show them off. Congratulate them in front of other people and on your own.

“Look at this! Let’s see that again! Isn’t that incredible?”

They may seem embarrassed but underneath that, they’ll feel super supported and respected.

23) Never set a secret expectation for someone.

If you want something from someone, tell them. No matter how overt or passive-aggressive you are, they can’t read your mind.

Quiet expectations are a one-way road to resentment, disappointment, and unspoken tension.

Be clear and direct about what you want.

24) Be on time.

It’s the easiest way to show respect for others and yourself. It also relieves the constant burden of feeling rushed and frantic.

Being the person who’s always late to things is a childish reputation to have.

25) Download ‘News Feed Eradicator.’

Hate scrolling on Facebook but don’t want to delete it?

Download this browser extension. It hides your Facebook news feed. No more being hypnotized by the algorithm.

26) Keep a list of your biggest insights.

Realizations, discoveries, mindset shifts. What have you changed your mind about lately?

It’s like finding old photos of who you were and what you were working on in the past.

27) Tell your friends “I love you.”

Especially guys. You’ll wish you said it more when you die.

28) Under 50 and don’t like what you look like shirtless? Prioritize exercise and diet.

It’ll only get harder. Now’s the time.

Hire a trainer. Get someone to help you figure out what to eat.

Give yourself more energy, confidence, and brain power by taking care of your body. If you were responsible for taking care of someone else’s body, would you fill it with sugar, simple carbs, and processed foods? Would you make sure that that body was never active?

Be kind to your future self and take care of your present self.

29) The quickest way to earn someone’s respect is to be able to take a joke.

There’s a difference between bullying and poking fun.

If someone is messing around with you, laugh. Join in on the joke.

This shows people you don’t take yourself so seriously and that you’re secure with yourself. I struggled to take jokes when I was younger because I was wildly insecure. Every jab felt like a missile.

Now, I make fun of myself more than anyone else. Life’s short. Be less serious and more silly. You’re no God.

Final thoughts:

Hope you enjoyed some of these. Hope you disagreed with some of them. Email me and let me know what you think.

See you next year for my 30th!

I should care about this thing, but I don’t—What do I do?

Dillan Taylor with his family standing on a cliff.
West Virginia, 2022.

For all of my 20s, I would list family as one of my top priorities. But there was a problem.

It wasn’t.

From 18-23, I was a lost soul trying to find his way at college. My priorities were getting drunk, acting in plays, and scrounging endlessly to find ways to eat and pay my late bills. Then I failed school and didn’t know who I was, what I wanted, or what skills I could offer the world.

And from 23-26, I was reborn and dove headfirst into self-improvement. I started making money, working out, and building the habits for a strong and capable life. I did all the things I wanted to do and weeded out the things I didn’t. I pushed myself to new and scary heights. I crawled out of the hole of a life I dug for myself in my early 20s. I learned sales, started podcasting and making videos, and became mindful and stoic.

But something was missing.

In all those formative adult years, I never once felt like a good son, brother, or nephew. I would say I valued family, but my actions told a different story.

I called and visited when it was convenient or fun for me. I avoided helping my mom out with simple things around the house. I would say I was going to do things and not do them.

The strange part was that I knew this wasn’t the way. I felt slimy every time I told my mom I’d help clean out the attic, and then would stay at a friend’s house and show up hungover in the middle of the afternoon. It was draining and deeply disappointing to everyone involved. And she would say so.

This all tugged on one of my deepest-held fears: Am I going to be a neglectful dad? Will I be incapable of sacrificing my own desires for the sake of my family?

Then three huge things happened that changed everything:

  1. I moved out of my mom’s house.
  2. I started a life coaching business.
  3. My grandpa started to decline.

In the summer of 2020, my friend from middle school reached out and asked if I wanted to get an apartment with her. She was also living with her mom at the time.

Dillan Taylor and his roommate when they were in middle school
Me and my roommate in 8th grade lol, 2008.

We moved into the apartment where I’m currently typing this blog in October of that year. I felt closer to my mom and sister almost immediately.

The place is only 16 minutes away from their house. But the space between us created room for us to miss each other.

But I still didn’t genuinely feel like I wanted to make quality time with family a priority. And that scared me. What was wrong with me?

My mom has done more for me than any other human being. Why didn’t I jump at every opportunity to help her with whatever she needed? Why didn’t I actually care?

Cut to April 2021. As part of my life coaching certification, we each got paired with a coaching partner. My partner, who is one of my closest friends today, was coaching me.

I came prepared with a question: How do I change how I feel about my family?

I was sick of my actions not matching up with my words. If I didn’t change my habits, I knew I’d regret it forever.

I wanted my mom to tell people that I made her life easier, more fun, and less heavy. I wanted my sister to see me as someone she could come to for anything. I wanted my dad’s side of the family to view me as an active and present member of the family.

So I asked my coaching buddy, “How do I change my mindset? Is it possible to alter how I feel emotionally? Can you force yourself to be motivated to do something you don’t feel compelled to do?”

He held space for me. He asked me incredibly powerful and thought-provoking questions. He helped me find the answers I already knew that were hidden beneath the surface.

By the end, everything was clear.

“I’ve been going at this all wrong,” I said. “You can’t just force your mindset to change. I have to change my behaviors first and let the beliefs come afterward.”

My emotions and motivations were out of my control. What I did, how engaging I was, how often I showed up…These were completely within my control.

So I added family time to my weekly system. When planning my week on Mondays, I couldn’t finish without having some form of quality time or conversation. Phone calls. Lunches or dinners. Visits at my mom’s.

What felt like a chore at first quickly became activities I thoroughly enjoyed. I wanted to do things with my mom. Our conversations were more fun. We laughed more. I was curious about how I could help her.

That’s been my journey these past two years. I’m about to turn 29, the age my parents were when I was born.

All those years I blew my mother off. I can’t get those back. While I’ve forgiven myself, it’s still my deepest regret. But I can do everything within my power to be a great family member now and from here on out.

When my grandpa started to noticeably decline in 2021, I changed my habits around driving down and visiting my grandparents. Once every two or three months. Because of that, I got way more hours in with them before my grandpa passed away last month.

Dillan Taylor and his grandpa sitting on a boat in Lake Gaston
Lake Gaston, 2010.

If I didn’t do that, I’m positive I’d be thinking, I should’ve spent more time with him. I should’ve shown more appreciation while I had access to him.

But I didn’t. While I was down there with my dad, grandma, and aunts, all I felt was, I’m so glad I’m here. I’m so grateful I prioritized seeing him more this past year.

And I feel the same about my mom and sister.

Something heavy just happened with that side of my family—a story I’ll share in the coming weeks. But I was thrilled to see that my immediate responses have been: How can I be there for my mom? How can I make things easier for her? How can I show up for my sister?

These aren’t things I felt in my early 20s.

I got coached last week. She asked me, “Do you think your mom would say all the things you want her to say about you…today?”

With watery eyes, I replied, “Yes. I think she would.”

I hope that’s true.

Key takeaways:

  • Words are lovely, but you are what you do consistently.
  • You can change your values and motivations by changing your behaviors first.
  • Live in a way that would make the people you love say great things about you when you’re not around.

The subtle habit you need to stop doing

I’m Dillan, and I’m a recovering shit-talker.

When I failed college in 2017, I got a job at the Cheesecake Factory. There I started making money, building strong habits, and getting my life together.

The first change to make? I wanted to be a kinder person.

That’s great. But how does one begin practicing that? Well, it wasn’t something I started doing more of; it was something I put an end to…

Gossiping.

In other words, saying something about someone who isn’t in the room—something that would make me uncomfortable if he/she heard it come out of my mouth. In other words: shit-talking.

It’s one of the easiest ways to bond with people: over mutual hatred or frustration of other people like bosses or fellow coworkers. It’s fun. When we know they’ll never hear what we have to say, we feel brave enough to say whatever we want. This person is an idiot. That person is an asshole.

I bring up the Cheesecake Factory because that’s where I started my experiment. I swore to never say anything about anyone I wouldn’t say to their face. And, when I felt the urge to talk shit, I had to instead share something I respected about that person.

This was hard. At times, it felt impossible. Why would I force myself to say something wholesome about someone who brought me nothing but headache or anguish?

Well, it only took a few weeks for me to notice a shift in my thinking. In fact, I was beginning to see the world differently.

I know that sounds a bit fantastical, but it genuinely felt as though I was reprogramming my brain. I was in a better mood at work. Annoying things didn’t make me as mad for as long as they used to. I liked people more.

The biggest thing? I saw just how frequently everyone around me gossiped about others. It’s like trying to stop using the word “like” as a filler word, then recognizing how often other people say it.

So that’s where it all started.

Cut to: today. I have absolutely zero interest in engaging in gossip or any conversation where we’re just badmouthing someone who’s not in the room.

I was at a party a few months ago and a raging shit-talk fest erupted. I left the room.

When my friends start criticizing somebody, I’ll go as far as to say something like: “Hey, thank you so much for trusting me and being open and vulnerable. But if we’re going to talk about someone else in this way, let’s set an intention. Let’s make sure we leave this conversation with a change or an action to take so we’re not just gossiping.”

You might be reading all this and thinking, Dillan…isn’t this all a bit overdramatic?

Well, I did theatre in college. So drama is in my blood.

Jokes aside, here’s why I think this is important.

I think gossiping is a slippery and cowardly slope to other deeper and darker habits. Comparison. Resentment. Insecurity.

That last one is massive. I’ve never known someone who is hugely secure, confident, and fulfilled by their life…who talks shit about other people. Gossip almost always comes from a place of insecurity.

Alex Hormozi said something in a 12-second video a few months ago that really stuck with me:

“People who are ahead of you in life are not talking shit about you. They’re not even thinking about you.”

The healthiest, most successful people I hang out with spend zero time gossiping. Instead, they congratulate people behind their backs. They highlight areas of admiration and respect, and any judgment spoken comes from them pointing out their own flaws.

No one who’s crushing it in life is leaving a mean comment online.

So I’ll leave you with two questions to ponder:

  1. How much time do you spend talking about people who aren’t in the room?
  2. How much of what you say about those people would you be comfortable with if they heard you say it?

Praise people behind their backs. Criticize people to their faces.

10 tricks to living a shittier life

An ostrich with its mouth wide open

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.

What are you willing to sacrifice?

A woman trying to carry too many books

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.

From jamesclear.com

We have four areas we can add flame to. Friends, family, work, and health.

When we turn up the heat on one, we reduce the heat from the others. And vice versa.

So another way to word the question from earlier is: How much heat do we want to give each burner? They can’t all be at 100%.

That answer should be different for each of us.

For example, I’m a single entrepreneur with no kids. It makes sense that my family burner isn’t as turned up as my friends who have a one-year-old.

Right now, I’m trying to hone three areas of business to provide me financial freedom in the next year:

  1. One-on-one coaching.
  2. Writing—this blog and books.
  3. My podcast/YouTube channel.

That’s a lot. And maneuvering through all of these without burning out can be difficult at times. But that’s the definition of sacrifice.

What am I willing to give up (temporarily) to accomplish my goals?

  • Tons of family/friend time.
  • My morning routine.
  • Connect calls with people.

A year from now, my burners will look completely different.

What do your burners look like? What do you want them to look like?

The 2 options for learning something

A girl in a kimono karate kicking in mid air

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?

Solving vs. Managing

A solved Rubik's Cube

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?

I thought I wanted to move to New York

What I’ve been doing

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:

  1. “I can’t wait to get back home to Maryland.”
  2. “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:

  1. “How long have you lived in New York?”
  2. “Why’d you move here?”
  3. “How’d you build community?”

And voilà. Those three simple prompts would show me a person’s story, values, and personality. Once I told them I was planning on moving there, they couldn’t add me on Facebook fast enough.

Casey Neistat said, “People don’t live in New York City. They survive.”

If I were to ask those same three questions in any other American city, it would just sound like boring small talk.

2) The food

Some of the best meals I’ve ever had were in these 14 days. Israeli. Greek. Indian. Jamaican. Cantonese. All within a few blocks of one another.

And the fucking pizza. The hype is real.

3) No car

Not having to drive or park anywhere was the bliss I didn’t know I needed.

Sometimes you don’t know what’s nice to let go of until it’s gone. That’s why I deleted my Instagram a few years ago.

4) The discomfort

I’m sure that sounds weird. I was just complaining about that in the cons section above. Let me explain.

I put off using the subway in Brooklyn for days until I had no choice but to jump on it. It was nerve-wracking. Between my travel anxiety and fear of getting stabbed, I was quite shaken up.

But then I just got to my destination and everything was fine. After doing that a few times, not only did I become comfortable on the train but I really began to know my way around. The synapses were connecting. I was, as they say, learning.

It felt like I had conquered something. As though I had a duel with fear and I came out on top.

That’s exactly how I felt when I climbed my first rock wall last month. And when I built my coaching business last year. And when I placed in chess tournaments.

We’re scared of something. Then we do it. We don’t die. Then we decide if we want to continue doing it. If we do, we get better and eventually comfortable with it. If we don’t, we stay scared of whatever it is.

I choose the former. If I spent a year in New York and had a community and a plethora of new skills by the end of it, I’d feel like I conquered something vast.

What I learned about myself

I really thought I wanted to move to New York City. And this trip only confirmed that.

I have friendships I can strengthen in Brooklyn. My friend in Philadelphia is an hour and a half train ride away. Maryland is not far. I have so much growing and stretching to do.

On that note, it would actually be pretty hypocritical of me to not move there. I help people do things they’re scared of for a living. If I didn’t practice the same, I’d be like a doctor who refuses to see a doctor.

The first week was lonely, yes. But then I got to spend time with my peoples. A best friend came to visit. I chilled with my Brooklyn buddies. I got invited to a rooftop party. I met people. I went on a date and had a lovely time.

Packing up to leave on Saturday was a sad couple of hours. That’s how I knew. I didn’t want to leave. But I had my time there and it served its purpose perfectly.

I’m energized to set myself up for a colorful life there. I want to put myself out there. I have four months.

Coming back to my suburban apartment…it felt like I was coming home to a little country town. It was so quiet. I had to go somewhere and was pissed to realize I had to get in my car and drive there.

The next steps are:

  • find a place in Brooklyn
  • sell all my stuff besides the bed, clothes, and tech
  • make as much money as possible
  • spend as much time with friends and family as I can
  • enjoy the end of this chapter

And of course, I’ll keep you updated along the way.

I wanted to hate NYC—I don’t

The street of Williamsburg, Brooklyn

Sunday was the first night of my two-week trial run living in Brooklyn. It was heavenly.

I get anxious every time I see the Manhattan skyline. Coming into New York City always feels like I’m entering a foreign warzone. My survival instincts kick in and I feel awake and on guard.

Last month, I talked with a friend who’s planning to move out of state and away from where she grew up—just like me. She’s continued to push the date back, so I lovingly called her out.

“It sounds like you’re creating reasons to not do it,” I said. Luckily for me, this landed well.

This is an unfortunate human tendency: constantly building conditions that must be met before doing the scary things we know will make us grow. We think: once I…

  • have more money
  • feel more confident
  • get a new job

Then I’ll be ready. But conditions will never be perfect. Any meaningful life decision will come with 1000 logical-sounding reasons for not doing it.

And yet, this is what my brain has been going through. As much as I rebel against this, it turns out I’m human too. I’ve been contemplating all the reasons I shouldn’t move to New York. (This video didn’t help.)

  1. I’d be leaving my well-established community—my mom, sister, and several best friends
  2. It’s ridiculously expensive
  3. Eventhough I’m a social extrovert, it’s scary to have to make new friends

Aside from creating as much income as I sustainably can in the coming months, the remedy for these fears seems obvious. I have to put myself out there.

It sounds simple (it is), but that tends to be the solution to most things.

I have a phobia of heights, so I put myself out there and tried top roping (rock climbing) with my friends. Last year, I had to build a coaching business from scratch, so I put myself out there and reached out to as many people as I could and offered to coach them. New York intimidates me, so I’m putting myself out there and am going to meetups and events by myself.

Tonight, I’m going to a chess gathering at a brewery. It’s called Chess & a Beer, two of my favorite things. For the last two nights, I’ve gone to dinner by myself. I also joined the local climbing gym.

The rooftop of Vital, the climbing gym in Williamsburg Brooklyn

Anyway, it’s hard not to jump back and forth between all the pros and cons of living here.

I walked through the local park and experienced more in 10 minutes than I do in one night in Annapolis. I heard at least six different languages spoken, saw a men’s league soccer game, got a free margarita from a cute bartender, ate excellent Mexican food, toured a gorgeous rooftop gym, and walked alongside the East River overlooking the lit up city of Manhattan.

This was all within a 20-minute walk of one another.

It’s been one full day. It feels like it’s been an entire week.

The journey continues.

Time doesn’t fly; you’re just not paying attention

People say: “When you’re 10 years old, a year is 10% of your life. But when you’re 50 years old, a year is only 2%. That’s why time speeds up when we get older.”

I think that’s bullshit.

When we’re young, everything is a novelty. We’re learning about the world, about our environments, and about ourselves. We try new things: activities, styles, hobbies. We know very little.

Then as we get older, for better or worse, most of what we do becomes routine. We pick the things we like and we do them over and over again. Or, unfortunately, some of us become akin to factory workers; we wake up, go to work, come home, watch TV, wait until the weekend to have fun, and repeat. Our lives become familiar.

I do the same thing. Although I have the freedom of running my own business and creating my own schedule, I still have my own version of clocking in during the week.

So what’s wrong with this?

Well, nothing’s wrong with it per se. But it does allow our minds to shut off. Let me explain.

Habits are great because they let us go on autopilot for things we want to do (or don’t want to do). I’ve gone to the gym so consistently that sometimes it feels like I just wake up there.

And that’s my point.

You ever drive to work (or somewhere you go often), and when you get there you realize you don’t remember the journey? It’s because you’ve done it so many times your brain doesn’t have to be on guard. Meanwhile, if you took a different route to that same place, you’d be much more alert and mindful because you’d have to make new decisions.

That’s what happens to us in our week-to-week lives. When there’s no newness, when we’re doing the same things over and over again, we wake up one morning and realize it’s already May.

“Where the hell did four months go?”

Nowhere. Time moves at the same rate for each of us. Some just pay attention better than others.

So how can we be more mindful? How can we slow down time? Two ways.

  1. Newness
  2. Gratitude

We’ve covered newness a bit. In this lies adventure, spontaneity, and curiosity.

This is something I could use way more of. I’m a super scheduled person. So I’ve been trying to leave more unstructured time in my calendar.

Trips also help—especially last-minute trips. Surprise your partner. Surprise yourself. Take a weekend off, go to the airport, and take the cheapest flight to somewhere random.

Constantly change things. Keep doing the things you love but find different ways to do them. Do them with different people. Try activities that scare you.

I have a phobia of heights. Right now, I’m slowly using rock climbing to squash that fear through exposure.

As for gratitude, this is a habit that can be built quickly.

Not only can we begin our day by writing or saying three things we’re grateful for. But we can also just start telling the people in our lives why we love them and what they mean to us.

It only takes a sentence.

I try to do this frequently. They don’t always respond with the same sentiment. But that’s not because they don’t feel the same way. It’s because they haven’t built that habit yet.

Want to make a good friend uncomfortable? Tell them how they’ve positively impacted your life. Watch them scramble for words. It’s lovely.

Anyway, my two questions for you are:

  1. How can you add more newness to your weekly life?
  2. Where can you express more appreciation?

Answering these questions will help you create your own time machine.

What we don’t see

When we look at famous actors, we don’t see all their failed auditions.

When we look at pro athletes, we don’t see the other 99% who didn’t make it to the big leagues.

When we look at a successful person, we see their highlight reel; we don’t see their embarrassing moments, their doubts, or their anxieties.

We often compare our insides to other people’s outsides. But we’re all terrified one way or another.

We want to live fulfilling lives and feel we’re spending our time well. We want to feel loved, feel important, and feel supported. This is true regardless of our occupation, geographical location, or income.

For years, I thought everyone around me had their shit figured out and I was the only person on the planet who was clueless. Then I got curious about people.

All it takes is asking someone a few questions to realize: None of us have figured out life. We’re all just winging it and are doing our best.

Don’t look to a person’s social media page to see how they’re doing. Look at their current fears and stresses. That will paint the real picture.

The gift of suffering

We were not suffering in this photo.

My friend and I saw a play at the Kennedy Center last night. It was lovely.

Things shutting down for a year made us appreciate being able to go out and do things. Since things have gone relatively back to normal, I’ve been treasuring every activity.

Jiujitsu. Climbing. Dinners. We never truly relish things until they’re taken away from us.

My coaching friend and I had a call yesterday before I left for DC. He was telling me about this five-day meditation retreat he experienced last week—just a month after his dad passed.

His biggest insight was the ability to lean into suffering. He told me, “You can’t have a lotus without mud.”

In other words, we can’t fully respect the highs unless we’ve felt the lows. We can’t bask in connection with others unless we’ve been lonely. Love means more to us when we’ve been heartbroken.

Despite my incredible tribe of friends and family, I’ve felt wildly alone in the past—like I had no one to talk to or share with. What a gift that was.

Now, when I have a conversation with a close friend, it’s almost like I enter a flow state. True present awareness. I feel nothing but gratitude and groundedness. But that’s only because I know what it’s like to long for that state.

Who appreciates a plate of food more: the rich kid who wants for nothing or the kid who almost starved to death?

✌️

Grow a mustache—Why you should be more polarizing

A man with a mustache and sunglasses looking into the distance

(Yes, ladies. Even you.)

The idea

I want to alienate more people. Let me explain.

The goal is not to go out of my way to piss people off. I don’t want to do or say anything controversial just for the sake of being controversial.

But I noticed recently that most (if not all) of my writing has been curated for anyone and everyone. I’ve been painting with a broad brush in the hopes that any kind of person could sit down and enjoy my stories and lessons.

The consequence of that has been me avoiding certain topics I thought would be lost on most of my readers: the ins and outs of my business, hot takes, possibly-arrogant stories…

Then everything changed when the fire nation attacked.

Whoops. I mean, everything changed when I grew a mustache. Here’s what I mean.

The stache

Dillan Taylor and Hank the dog sitting in his bed
There are more pics of Hank in this blog than there are of me.

I shaved my beard and left my mustache about a month ago. Since then, I’ve gone to a wedding, a bachelor party, and have gone out drinking.

The thing I noticed immediately? Mustaches are polarizing.

Some people (women) wanted nothing to do with it. Others went out of their way to say how attractive they thought it was.

Prior to that, no woman had ever mentioned to me in casual conversation how sexy she thought my face was. I realized that was because I was trying to have a face anyone could get down with.

I went from attempting to reach everyone to only spending time and energy with mustachers. They were bought in. They were my people.

Then I thought about other areas I could apply this.

The meaning

When we polarize people, some folks naturally get alienated. Some hate mustaches. Some don’t care about business tactics.

But for the ones who stick around…the connection with them is 10 times stronger. It’s not about trying to get people to buy in; it’s about investing in the ones who are already bought in.

Lower quantity. Higher quality.

So what does this mean for us?

I’m guessing half of my readership cannot actually grow a mustache (ladies…and some dudes [sorry, gents]). But we can think about this as we create things and as we connect with others.

Do you hold any opinions you’d be uncomfortable sharing with the people around you? If not, that’s a problem. It could be a sign that you just go along with what everyone else thinks and that you have few values of your own.

When creating something, are you trying to make it so everyone can enjoy it (like I did)? When we build something for everyone, we build something for no one. Find your people.

In my coaching business, I have high standards for the people I work with. I want committed action-takers who show up on time and do what they say they want to do. That’s not most people.

And that’s the point. Most people shouldn’t work with me.

It’s not about the ones left behind. It’s about finding our people and giving them the world.

Grow a mustache.

You can do it (actually)

A group of athletes running a marathon

Here’s a self-improvement cliche: You are capable of so much more than you think.

I check in with my coaching clients every two months or so. The most common statement I’ve heard over the last year when I do so is, “I never actually thought I’d be able to do this stuff.”

To be clear, it’s not because I have some mystical or magical coaching technique. It’s because the average person doesn’t consistently reflect on what they want, what they think is in the way, and what they can do to get further.

It’s the difference between someone who practices piano for 10 minutes a day and someone who doesn’t think they’ll ever be a good piano player and therefore never practices once.

One is guaranteed to improve. The other is guaranteed to change nothing.

The people I see creating fulfilling lives for themselves are not the ones making the most money. They don’t have above-average IQs. They don’t have the perfect morning routines or meditation practices.

They just take consistent, small steps in the direction they want to head.

I ran a marathon in 2020 without training for it once. That was one of the stupidest things I’ve ever done. Don’t do that.

My legs stopped working about 19 miles in. After that point, the only thing that kept me going was my mind (and the encouragement of my friend).

My brain told me I had to stop. I had to walk the rest. But I just kept hobbling.

I knew there were only so many steps between where I was and the finish line. Once I made it there, my first thought was, WTF, brain. Why’d you lie to me like that?

Running 27 miles with rubber legs is different than living our day-to-day lives. But the mentality is all the same.

We want something. We think there’s something in the way. Then most of us choose not to pursue it. We often think, I can’t bear this. But you can. You already have.

I knew I could keep running in pain because, well, I was already running in pain. I had proof I could handle it.

Unfortunately, most people stop before they get that proof. Don’t stop.

Keep running.

What I learned from Will Smith’s slap

I never thought I’d use this blog to respond to pop culture, but here we are.

Anyone with eyes knows about what happened at the Academy Awards. People seem strangely divided on their opinions. I’m not going to dive into mine here.

I just want to share an insight I had when I first read about it and watched the uncensored video.

My emotional reaction was something like: Oh my God, that’s not the Will I know!

Once I felt that, I started laughing. I don’t know this man even a little bit. In fact, I know more about the characters he’s played in movies and on television than I do about him.

For some reason, when someone is famous or in the public eye, we get a false sense of familiarization. We build internal relationships with them. We say things like, “I adore her,” or, “I can’t fucking stand that guy.”

Either way, we truly have no idea what it’d be like to sit down with this person and have coffee with them. Maybe they’re as outgoing and humble as they seem. Maybe they’re an asshole. We. Don’t. Know.

And we’re not supposed to know. Actors used to have a mystique about them. You know, back in the good old days before I was born. Here’s an entertaining video explaining why modern actors just don’t shine the same.

My point is: We should judge a person’s work, not the person themselves.

Having millions of dollars and being known by millions of people doesn’t make someone more ethical, more intelligent, or more rational. Those things become harder with more money and power.

They’re just as smart and as stupid as we are. They’re not Gods. They get jealous and cranky. They make mistakes.

The difference is that when we slip up, a few people at most will hear about it. When Will Smith does something idiotic, billions of people to come will see it unfold.

Was I disgusted by what he did?

Of course.

Will I go see the next movie he stars in?

Of course.

On confidence

Confidence is not a necessity. It’s a reward.

I’ve had nearly a thousand coaching conversations with people. I’ve heard it every week for over a year.

“I just need more confidence.”

In other words: “I must first have this internal emotional change. Then and only then will I be physically able to do what I want to do.”

It’s totally understandable. But it’s nonsense.

If confidence is the belief in oneself, how can we have such faith when we’re unskilled and inexperienced in a thing? Unless we’re full of ourselves, we’ll naturally be nervous and unclear. That’s okay.

Being scared has nothing to do with us being able to do something. We do scary stuff all the time. If we don’t, it’s not because of inability; it’s because we choose not to.

Running a business. Talking to people we’re attracted to. Improving a skill.

We often think: “I need to learn X so I can do Y.”

When in reality, it’s: “I need to do Y and then I’ll learn X.”

Do first. Then feel confident as a reward for doing.

Don’t wait for it to fall into your lap.

Startups suck

The whiteboard of a startup business with planning and sticky notes

That sounds harsh. Here’s what I mean.

When I visited my friends in Philly this January, I walked one of them to the train station. We were chatting in the freezing cold about the next steps for my business.

I mentioned I wanted to help startups. I had always been fascinated by them from afar but have had no interest in creating one myself.

What she said struck me.

“I mean, you do run a startup,” she said. “You manage a profitable business. You provide a service that other people pay for all on your own.”

Whoa, I thought. “I suppose that’s true,” I replied.

She reminded me that we seem to have unhealthy images of what startups actually are. Millions of dollars of venture capital. Software as a service. Founders who work 10-hour days and neglect their health.

I don’t want to do any of that. And I don’t have to.

I’m rereading Rework by Jason Fried. It’s a business book on how to optimize for fulfillment, not profit or growth.

In it, he argues that when starting a business, we don’t need business plans, we don’t need to grow if we don’t want, and we don’t need a big team. All we need is to sell a product or service to people willing to pay for it. Then, we need to make sure our revenue is higher than our expenses.

That’s it.

Jason also suggests not using the word “startup.” Just say business.

Before starting my coaching practice, I saw the “world of business” as this intimidating, unwelcoming entity. But there really isn’t a “business world.”

There’s just the world. It’s made up of human beings. They make decisions. They buy stuff. I had this idea in my head that startups were these mystical and magical creatures. They’re not.

In starting a business, all we need are three things:

  1. A product/service
  2. People willing to buy it
  3. A way to take their payments

If we can’t define these three things first, there’s no business. There’s just an idea.

That conversation with my friend a few months ago was short and simple. And it uplifted my spirits moving forward. As I continue to meet startup founders and learn about what they do, I’m not thinking, OMG I’m talking to a startup founder right now. I’m thinking, Wow, this person is really interesting. I’d love to learn more about what they’re going through.

As always, things are much simpler than we think.

Success?

Is success a number or a feeling?

Is it a dollar amount in our bank account…or not being stressed about bills?

Is it how many followers, subscribers, or connections we have…or the level of connection we feel with the people we’re in the same room with.

Is it our weight…or the refreshing and limber sensations of a healthy and active body?

Fight back

Two people fighting in a field

I’ve heard some helpful models when it comes to making decisions:

  • If it’s not a hell yes, it’s a no.
  • Listen to your body.
  • Trust your intuition.

These are lovely and quite useful. But they can also be utter nonsense.

Last night, I returned to my jiujitsu class after sitting out for a year. Everything in my body was telling me not to go.

You clearly don’t love it anymore. Everyone is going to be miles ahead of you by now. You’re tired and trying to slow down, just rest.

This is what my intuition was telling me. It was not a hell yes. Resistance was miles high.

But I went anyway.

Right when I got there and saw my old friends, my energy came back. We hugged, we laughed, and I got my ass kicked.

A lot of people tell me they’re intuitively led. Our intuition is a powerful thing.

But it’s not so impressive when it keeps us from doing the things we know are good for us. I’m not a fan of relying on willpower and discipline to get things done. But sometimes it really is as simple as sitting down, forcing ourselves to do something that isn’t super fun, and doing the work.

If I listened to my body every day, I’d spend those days on my couch watching YouTube on my phone.

It’s important to ask oneself: Is this intuition or is this Resistance?

The perfect morning

It is my birthday. And I couldn’t be happier with how I’m spending the morning.

Phone is off. Coffee is hot. I just read my favorite book for 20 minutes and am now writing in my fourth favorite blog.

I got too fucked up this weekend in NYC. No alcohol for a while.

After slowing way down, I’m ready to use the new boundaries I set to put my head down and build something special. The fire is rekindled. I’m in the mood to show up as a professional.

Resistance can’t win. It doesn’t stand a chance.

I’m 28. And time is only continuing to tick.

Here’s to another year!

New principles

A man in a suit sitting and working at his desk

Last week, I watched this video on non-negotiable principles.

The dude in the video—Alex Hormozi—is super bro-y but he provides a ton of gold. The video made me consider my business’s principles.

I’ve had them written down on my whiteboard since the start of the new year. I realized five was too many. I couldn’t even name them off the top of my head if someone asked. That means they were just sentences that sounded nice.

So I trimmed them down to three.

1) Curiosity before solutions.
2) Help people so much, they don’t need me.
3) Take nothing personally.

It’s not like customers and clients are going to start flooding through my door now that I have three principles. But even seeing this refined list on my whiteboard makes me feel clear and established as to what I stand for.

If I hire people in the future, I now have a set of must-haves. My favorite line from the video is:

“Most people shouldn’t work for your company.”

Because most people won’t embody all three of these principles. That’s okay. It’s about finding the ones who do.

We don’t need to run a business to have two or three core principles, though. What are yours?

I’d love to hear them.

Stupid games

Dice and pieces on top of the board of a game

Naval Ravikant said, “Play stupid games, win stupid prizes.”

This sounded a bit harsh and over-dramatic when I first heard it. It took me a while to actually get it.

We often play “stupid” games:

  • trying to be the smartest person in the room
  • looking really cool on social media
  • making as much money as humanly possible
  • being on our phone for hours each day

I have coaching clients who have played tons of these games. I’ve played tons of these games.

The question is: What does it look like to win the game you’re playing?

If you climb your way to being the absolute coolest person on Instagram (whatever that means), what would you be able to do with that? What would that mean for your life? What would that fulfill?

If you feed your phone addiction and make sure you never miss a notification, or respond to every email as quickly as possible, what would winning that game look like?

In my experience, the prizes of these games often include being kind of happy for a short time…then going right back to whatever our normal state is. After that, it’s feeling disappointed that this thing didn’t bring us enlightenment.

An even darker example is texting and driving, one of the stupidest games out there. 400 fatal crashes happen each year from driving while using our phones.

But what is ‘winning’ texting and driving? Not having to wait 10 minutes to see what our friend texted us?

In 2020, my mom was completely stopped at a red light waiting for it to change. A young man hit and totaled her car at 50 mph. He was texting.

I always think, I wonder what he was doing on his phone and I wonder if it was worth it? He played a stupid game and won a stupid prize.

So which games bring us awesome prizes?

For me—and I would argue for most of us—it’s all the cliche stuff:

  • being a great friend/son/daughter/etc
  • getting physically/mentally fit
  • improving skills
  • being kind and curious

So, what games are you playing?

If you were to win that game, what would that look like? Would it be worth it?

It turns out I’m not perfect

I no-call no-showed a connect call yesterday.

It was with a fellow coach. I accidentally stood her up.

I saw her message saying something like, “Hey! Ready for our call?” My heart sank into my chest. I had completely forgotten to put it in my calendar. Therefore, it didn’t exist.

One of my values is timeliness. When people are late to things with me, I tend to get heated.

But when stuff like this happens, I get humbled and it becomes much easier to practice patience and compassion.

When I get annoyed with something, it begs the question:

Have I ever done this thing that I’m so upset at? Have I been perfect in this regard?

Getting a raise vs. having a kid

I got dinner with my old boss last night.

He recently got promoted to VP in his company. He’s also the recent father of two.

When I asked him about the new VP position, he calmly said, “Yeah man. It’s cool.”

When I asked him about his partner and kids, he lit up. He raised his volume. He smiled as he spoke. He talked with his hands. “I love it,” he said. “It’s my favorite job I didn’t know I wanted.”

I pointed out how much more excited he seemed about his role as a dad than his role as a VP. He told me that one influenced the other.

When he detached himself from wanting a promotion and focused his love and attention on his family and wellbeing…he got the promotion.

We so often chase something only to see it evade us. Like magnets repelling from one another.

Fulfillment. Friendship. Opportunites.

These come readily to us when we just stay present, provide as much value as we can to those we care about, and continue to do the things we want to do.

We work on ourselves. We sharpen our axes.

We get what we want when we don’t care about getting what we want.

It’s never enough

Pizza crusts on a plate

Yesterday, my best buddy and I won $1,000…each.

It was a raffle for subscribing to The Hustle, an extraordinary newsletter on the worlds of tech and business. I’m a sucker for those things…

“For each person you refer, you both could win a billion free socks!” Or something like that. My friends often roll their eyes. But look who’s laughing now.

The $1K comes in the form of an Airbnb gift card. This is phenomenal because it feels like I’ve won free experiences, as opposed to the less-sexy prize of $1K in my savings account.

I’d be grateful either way. And this blog is about that ‘g’ word.

God.

Lol jk. It’s about being grateful.

Something happened five minutes after I saw we won. Something I’m embarrassed to share.

I started thinking about all the trips I have planned in 2022 and about how nice it would be to have my lodging paid for. Brooklyn in February, road trip to Florida in April, NYC again in May, European road trip in July…

Then I thought, Ah man…There’s no way $1K is going to cover all of that. If only it were $5K…

I actually thought that. It took five minutes for me to feel like a free $1K wasn’t enough! Am I insane??

I immediately laughed at myself. “Yeah Dill, some people really have it awful. What ever are you going to do?” Silliness.

Unless I’m a sociopath, the point of sharing that is to highlight the human tendency to always want more. That’s why conditional happiness (or the hedonic treadmill) is a dead end.

Conditional happiness: “I will be happy/fulfilled/satisfied once I have or do this thing.”

Then we get whatever that thing is and we are happy…for five minutes. Then we go right back to our default state.

One of my clients got his dream job, his dream car, and is financially set for life. He told me that none of that brings him sustainable fulfillment. Robin Williams was loved by the world, made millions of dollars, and pursued his dreams successfully. And he hung himself. I got free God damn money and got upset it wasn’t more.

It’s up to us to build a default state of gratitude and appreciation.

I’ve decided to forgive The Hustle for only sending me $1K. Please send your condolences directly to my email.

Football is scary

An American football on the grass of a field

Yesterday, my mom took me and my uncle to a Washington Football game.

The only sports I care for are MMA and soccer, but I always say yes to a live sporting event for three reasons:

  1. I’ll enjoy any event if I’m with people I care about.
  2. It’s always fascinating to see people who are at the highest level perform (in this case, NFL players).
  3. The people-watching is golden.

Today, I want to talk about that third one.

Growing up, football was my favorite sport (sorry, Bow Wow). Then around high school or college, I noticed something that turned me away from it.

People truly treat it like a religion.

Don’t get me wrong, I love how a sport can bring people together and evoke powerful emotion in millions of people. I enjoy listening to folks passionate about a sport discuss the business and inner workings of what makes the game tick. I enjoy the roars of crowds at games like the one I went to yesterday. Depending on the UFC bout, you can find me standing and screaming at the TV.

But what leaves a sour taste in my mouth is hatred—disgust for other players or fans (i.e. human beings) because of the jersey they’re wearing.

I’m not saying every single football fan is filled with rage, but it’s not uncommon.

When I was in high school, I would go see my team play against our rivals. I despised them. I wanted them to lose every game. I was convinced I didn’t like them as people without ever speaking to a single player.

Why?

For no other reason than the arbitrary fact that I attended my school. If circumstance led me to attend the rival school, I would’ve felt the same about my school. If I grew up in another state, I wouldn’t have even known either of these high schools existed.

Thus the religious context comes into play. When I see babies or toddlers with Steelers jerseys on, I doubt those kids chose to be Steelers fans. Likewise, if we’re born into a Muslim or Hindu family, we’re unlikely to be raised as Christians.

At the game yesterday, I saw fans flipping other fans off, telling them to “stop fucking talking,” and ironically clapping in their direction when their team did something good. There was an essence of mob mentality, meaning I saw people do things they would never do if they were in a living room with just one opposing fan.

There was no genocide, but in what other contexts do we act this aggressively toward other people?

I’m probably being overly dramatic. I just think it’s odd to see people feel so identified with a group of people they’ve never met. And it’s not even that group of people; it’s the shirts they’re wearing.

This blog likely triggered a few football fans. Apologies.

But maybe that proves my point?

The R word

Every now and then I talk about Resistance.

The concept comes from The War of Art by Steven Pressfield—a book I read once a year.

Resistance is the invisible force that keeps us from doing the things we want to do and living the lives we want to live.

It takes many shapes: fear, procrastination, justification, anger, shame…

It says: “You don’t have to do this right now. Do it later. It’ll be easier and more enjoyable if you do this in the future.”

Most of the time, Resistance sounds reasonable. We can’t start until we do this thing, until we have more knowledge, until we have more confidence.

I’m writing a book. Each and every time I sit down to start typing, without fail, I find reasons to wait. I set out to begin writing at 9am, but won’t start until about 9:45.

Readers of this blog know I’m not a big grind-hustle-discipline guy. I don’t think we have to torture ourselves to live a life worth living.

But the simple truth is we don’t get something from nothing.

There are plenty of things worth doing that we won’t feel like doing. Whether it’s something small like reading or working out, or something with higher stakes like starting a company.

We can just start. It’s time.

I’m sad and I don’t know why

A gorgeous winter landscape with the Sun going down

Maybe sad is the wrong word.

Last week, one of my clients said the same thing happens every winter: From December to February, he just wants to quit his job, not talk to anyone, and smoke weed by a campfire.

I feel that.

Not that I really want to do any of those things, but I do feel a twinge of sadness or dissatisfaction and I can’t pinpoint the source.

Yesterday, I called my best friend to tell him that and see what his thoughts were. But after ten minutes of just chatting and laughing, my state had completely changed.

I had energy. Things felt light again. What happened?

Aside from being a social creature who gets filled up by human conversation…I was reminded of an inconvenient truth.

Our states and conditions are constantly changing.

Happiness is an emotion. Just like rage or sadness. I don’t think we can genuinely “be” happy; I think we can feel happy. Being assumes it’s ongoing and everlasting.

This is why I don’t strive for happiness. My goal is fulfillment.

We can be fulfilled and still be sad, stressed, or uncomfortable. So during times like these—when it’s colder and darker than usual—I stick to my fulfillment system:

Every day, every week, I do the things I love and try to get better at them: Quality time with friends/family, coaching, chess, exercise, reading…

Yesterday, after work I wanted to:

• cancel a run with my buddy
• skip the gym
• watch YouTube and porn until midnight

I didn’t do any of that. Despite my mind telling me what was good for me, I stuck with what I knew: You won’t be happy to do these things, but you’ll be glad you DID them.

It’s true every time.

Likewise, when I choose not to do the things I know I regret after—watching porn, staying up on my phone, ordering $40 of DoorDash—I’m thankful 100% of the time.

How the hell do I conclude this blog?

Basically, I’m feeling grey at this point in time, and that’s okay. Nothing’s wrong. There’s nothing to fix.

I’m confident that if I just keep living with my values and doing the things I know make me a fulfilled person, the grey will subside.

Meow.

Am I an asshole?

Here’s one of my favorite parables (I’m not actually certain it’s a parable, technically):

If you go out into the world and happen to run into an asshole, you just met an asshole.

If during your travels, you run into 30 assholes, you’re the asshole.

I used to work with this woman who thought the world was out to get her on a daily basis. She complained about people, judged others, and gossiped constantly.

Each week, it seemed like something wildly unfortunate and unfair would happen to her. This confused me until I realized an odd, almost spiritual truth:

The world is what we think it is.

Whether we see life as a gift or as a burden, it all comes from within.

I used to think people sucked. And lo and behold, they did.

But once I started working on myself, improving my life, and seeing people as fascinating…they became much more lovely.

It’s all one big self-fulfilling prophecy.

First time at chess club

Last night.

I found out there’s a chess club in my city. They meet every Tuesday night in the Whole Foods cafe.

I showed up with my chess set and clock to a bunch of old men sitting and playing casual games.

For some reason, I was nervous on my way.

Not that I would get my ass beat (in chess). Something about hopping into a new community of people.

I guess at 27, I’m still giddy about making new friends.

They were some of the kindest people I’ve ever met. The youngest guy (he was in his forties) welcomed me to his board for my first game.

I played two gentlemen, two games each. I absolutely destroyed them.

We played for two hours until the grocery store closed. I told them about my first tournament coming up this month and they were super supportive…as if we’ve been teammates for years.

Needless to say, the nerves were gone.

Things are never as bad as the possibilities our minds make up.

I’ll see them next Tuesday.