Essentialism

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.

10 lessons learned in 2022

A 2022 calendar on a desk

They are:

1) Labels are limits.

We give ourselves disempowering labels and attributes all the time. Here are a few I heard from some of my coaching clients this year:

  • “I’m a chaotic person.”
  • “If I’m not certain I can do something, I can’t do it.
  • “All I need is more confidence…I’m just unconfident.”

None of these are true.

They’re just excuses meant to justify why we haven’t been living the life we truly want. If we’re chaotic, it makes sense that our physical and digital lives aren’t organized. If we’re uncertain, it makes sense that we haven’t put ourselves out there to try something new and scary. If we’re unconfident, it makes sense that we’re waiting and putting things off.

In my coaching experience, I’ve seen people of all ages and careers drastically change their personalities, habits, and values.

Nothing is fixed. Nothing is set in stone. The only thing keeping us from doing what we want is whatever fear, story, or label we tell ourselves to keep us from taking scary action.

2) Men and women are different.

Wooden cutouts of a man and a woman

And that’s okay. Actually, it’s necessary.

There are noticeable, meaningful, and beautiful differences between males and females. That is true of all animals. And what blows my mind most is that that is considered a controversial statement in 2022.

We can start with physicality and work our way down. Height. Weight. Muscle mass. Bone density. Fist size. Hip width. Fat distribution.

These are all averages, of course. I know women taller than most guys I know. And I know men who are more feminine than some women I know.

Which is a great segue from hardware to software.

Anyone who thinks gender is entirely a social construct has never taken testosterone or estrogen.

In Carole Hooven’s book T, she points to research done on men and women transitioning. Without fail, the women who began taking testosterone reported heightened levels of sex drive and decreased levels of empathy and emotionality. And men who started estrogen therapy reported increased compassion and emotional connection to others. I doubt society was telling these people to change in this way.

And no, that’s not to say women are too emotional or that it’s okay for men to be sexual deviants. It’s just useful to look at what makes us different from one another.

We can also observe the spectrum of masculinity and femininity:

Masculine energy: logical, assertive, resilient, seeking discomfort, conquering, direct.

Feminine energy: nurturing, intuitive, allowing, creative, gentle, accepting, indirect.

This can explain why men and women choose different professions, are often confused by the other sex, and are attracted to different characteristics. We’ll end #2 with that last point.

I’ve been single most of my life. So this year I became fascinated by what men and women are looking for on the dating market.

On dating apps, for example, men swipe right on (say yes to) 65% of women. Women swipe right on 3% of men.

That actually makes sense when we realize that women have way more to lose when pursuing a sexual relationship. They could get assaulted. They might get pregnant. They should be pickier than men.

Most women: “I want a guy who I connect with emotionally, who makes me feel safe, and who I can envision having a child and a ton of fun with.”

Most men: “See hot girl. Want hot girl.”

Moving on before I get canceled.

3) Porn is sexual junk food for the brain.

A man with glasses staring at his phone

For the vast majority of heterosexual men, porn is not a good thing.

It weakens sex drive, makes men ashamed of themselves, increases the risk of erectile dysfunction and premature ejaculation, raises our tolerance so we crave more intense porn, makes talking to women even more terrifying, devastates men’s body standards and sexual expectations for women, and decreases motivation and willpower in other areas of our lives.

Quitting porn has been one of the best things I’ve ever done for my sex life and health. But it’s hard. Reading Brett McKay’s How to Quit Porn was super helpful.

A 10-year-old boy with an iPhone will see more gorgeous naked women in five minutes than a man 100 years ago would see in his lifetime. Our brains are not evolved to handle that kind of stimulus.

On the flip side, I don’t think porn is empowering to women.

People say, “sex work is work.” Sure, I think if you’re a consenting adult, you should be able to choose whatever life path you want. But if the goal is to get men to stop objectifying women, making more porn seems like an odd approach.

Banning porn would be wildly impractical and downright impossible. But I don’t think it should be free. I dread the day my son gets internet access and can find whatever he wants at any time.

For anyone who wants to learn more, but doesn’t want to read a whole book, I’d suggest one of these resources explaining your brain on porn:

4) Anyone can, but most people won’t.

Can anyone get in great shape? Can anyone pack up and move to Australia? Could anyone really go downtown and ask out 20 people?

Yes.

But most people won’t. Most people (including myself) have a plethora of fears and stories stopping them from doing the things they’d actually love to do.

Different people have different starting lines, of course. It’s a lot easier for me to be moving to Argentina in a few months than it would be for my friend who has a one-year-old, two dogs, and a home to look after.

But if you live in the western world and are above the poverty line, you can really do anything you want.

One of my clients recently shared her fear of staying productive and healthy over the holidays. “I want to,” she said. “I really want to work out, eat well, and read over these next two weeks. But it’s impossible when you’re traveling and spending time with family.”

Then I asked, “If I said I’d give you a million dollars to have a super healthy and productive couple of weeks, what would you do?”

She smiled and told me working out, eating clean, and finding time to open a book would be effortless.

So again, we can do anything we want. The question is not: Are you able to do this thing? The question is really: How incentivized are you to make this thing happen?

One helpful model I like is asking myself, “If I knew I was going to die five years from today, what would I do?”

My answers to that question always lead me to do scary and fulfilling things. Flying to Vancouver to pursue a woman. Starting a coaching business from scratch with no experience. Moving to Buenos Aires. Spending quality time with the people I love.

In my experience, the people who do cool shit aren’t fearless; they’re courageous. Courage is being afraid but doing the thing anyway. Unfortunately, so many people wait until the fear goes away to live the lives they want. Then they wake up at 50 and wonder what they’ve been doing all this time.

5) Getting in great physical shape is the best thing you can do for yourself and your future family.

I got pretty cut this year. (Bragging? Maybe.)

And I’ve gotten to experience many short-term, superficial benefits.

First, I feel super confident with my shirt off. At the beach, on a summer run, changing in the locker room.

It’s not like women come sprinting out of the woodwork once I peel my v-neck off. But the internal peace I feel knowing that I’m good under the hood is hard to put into words. (The funny thing no one tells you is that when you start to get jacked, 95% of the compliments you get come from other guys.)

Second, I’m mentally sharper.

Many of us have experienced feeling like crap, then forcing ourselves to work out, and all of a sudden we feel awake and ready to go. Aside from the endorphins putting us in a better mood, we also know we just did something difficult and worthwhile. This makes us proud of ourselves and puts us in a more grateful headspace.

The actions needed to get in shape are actually pretty easy. It’s the patience and consistency that’s hard.

Here’s all I’ve done this past year to get a body I’m immensely proud of:

  • go to the gym 1 to 3 times per week
  • use the Fitbod app as a personal trainer to tell me what exercises to do when I’m there
  • eat well more often than not (avoiding sugar, refined carbs, and processed foods)
  • work out with my PT buddy twice a month
  • drink supplements like Creatine and Aminos (These are both legal, over-the-counter substances lol.)

That’s it. I just did these things almost every week.

None of them are difficult. It’s the “almost every week” part that’s difficult.

I hated going to the gym for an entire year. I needed my friend to go with me otherwise I’d leave after one set of one exercise. But once I started feeling and seeing real changes in my muscles and body fat…and once I got more familiar with all the machines and equipment and knew what I was doing, I was hooked.

The last superficial plus I’ll share is an example.

I had a lovely evening with a lady friend earlier this year. The morning after, she told me she really enjoyed grabbing my arms and feeling a good bit of muscle on them.

Is getting jacked necessary for being attractive? Absolutely not.

But in general, people are more sexually attracted to folks who are fit. We’re wired to think they’d make healthier offspring and it signals to us that they are disciplined enough to take care of themselves.

I’ll end this point with something more long-term. Here’s a quote from Dr. Peter Attia:

“If you’re over 40 and don’t smoke, there’s about a 70 to 80% chance you’ll die from one of four diseases: heart disease, cerebrovascular disease [stroke], cancer, or neurodegenerative disease [Alzheimer’s, dementia].”

As more of my friends have children, as I just spent two weeks in Virginia watching my grandpa die, and as another year comes to a close…I’m seeing more and more that my health isn’t just for me.

It’s for my future wife, my future kids, and everyone else. If working out and eating well today means I get one more year with the people I love most, it’ll be worth it. I want to be a 60-year-old man who can pick up his grandkids and play with them.

Freak things happen, but an unfortunate number of early deaths are simply because someone didn’t take good care of themselves.

That wasn’t my grandpa, and it won’t be me.

6) When you start something, it never ends up being what you think it’s gonna be.

I started this blog in 2019. It was meant to teach people about habits and self-improvement.

I avoided talking about myself because I was certain nothing about me was interesting. There was also a fear that people would think, who the hell cares about you and your experiences?

The opposite turned out to be true. The most successful pieces I’ve written have reliably been about my own travels, anxieties, and insights. I go back and read my early stuff and it’s like reading a crappy A.I. who copied other personal development creators.

I’ve also tried my hand at several YouTube channels. Vlogging. Sketch comedy. Mindset tips.

None of them stuck.

I even had two podcasts. One with just my friends and me BSing and one where I’d interview guests on their specific passions.

They both faded out because I didn’t really know what my message was or who the shows were for. All these things combined made me feel like I was a guy who could never finish anything. I couldn’t see things through. I feared I lacked enough grit and resilience to create something worthwhile.

Then this year, as I was interviewing creators for my book, I got an idea.

What if I took my favorite medium, YouTube, and my favorite thing, interviewing awesome people, and combined them? Enter: The YouTuber’s Guide to the Galaxy.

Now, I get to learn from some of my favorite creators in the space—how they started, what their systems are, and everything in between.

Little did I know, I’ve been building all the skills needed to do this all along. Interviewing, editing, uploading, recording myself, listening to my own voice, working with designers and engineers, sharing my opinions…

The next job you take, the next business you start, the next door you open…It probably won’t be the thing you take to your grave. But it will get you closer to whatever the next door is.

You just have to choose.

When you do, one of two things happens.

  1. You love it, and now you know what you want to lean into.
  2. You hate it, and now you know what you want to avoid.

Sitting around and strategizing over the perfect podcast idea is the best way to never start a podcast. But sitting down, hitting the record button, and uploading shitty conversations is the first step to having the podcast of your dreams five years from now.

Don’t worry about what it could be. Just choose something that sounds fun and start. You’ll learn what it’s meant to be along the way.

7) We can double our quality of life by prioritizing our sleep.

Another health one.

I’ve doubled down on my sleep this year and I feel like a God. Late nights and partying are still fun from time to time. But the benefits I get from consistent 8 hours blows everything else out of the water.

Being well-rested makes us more creative, motivated, and happy. Being stricter about bedtime, getting right out of bed in the morning, drinking way less alcohol…These simple acts have a compounding effect.

(image from Deepstash)

Here are easy ways to get much better sleep:

  • go to bed and wake up at the same times as much as you can (including weekends)
  • track your sleep (I use the free app SleepCycle)
  • give yourself an extra hour in bed (if you want 8 hours of sleep, go to bed 9 hours before you wake up)
  • keep it dark before bed, and make it bright when you wake up
  • wear a sleep mask or use blackout curtains
  • avoid drinking anything before bed so as not to wake up to pee
  • keep your phone away during the first and last hours of the day
  • dial down caffeine and alcohol use

8) Dating apps suck.

I have several friends who have met awesome people on dating apps like Bumble and Hinge. I’m even going to be the best man at a bestie’s wedding this spring and they met on Tinder.

Whenever and however two people meet each other and fall in love, that makes me happy. But these are the exceptions, not the rule. And there’s a darker side to dating apps I wish more people would talk about.

Firstly, the experience is quite different for men and women.

Women get way more matches. This means they get more oddball dudes in their inboxes that they have to sift through. It also means they’re able to ghost several guys with ease.

I spent two months on the apps and it was terrible for my mental health.

I’m a fairly confident young lad. I like who I am. But after just a few days on one of these services, I felt as though I was an ugly and useless trash monster not fit for this world.

Above all, I’m afraid of what it’s doing for future generations. Dating apps, along with all other social media, are slowly destroying the need for a very important skill…

The ability to go out into the world and talk to people.

I mean really talk. Sit down face to face and have a conversation. Be able to debate, ask curious questions, look people in the eye, and share personalities and stories.

Teenagers today have higher levels of anxiety, depression, and anti-social behavior than we’ve ever seen. And I don’t think the remedy to that is to disincentivize them from going out and meeting people. Staying inside and staring at our phones just doesn’t seem to be the way.

Since the popularization of dating apps, fewer and fewer men are meeting women and having sex. That’s because we’ve created a “Facebook Marketplace” for dating. People scroll through, see if someone is hot or not, maybe get some idea of their hobbies or interests, and swipe yes or no.

Whereas meeting someone in person makes us much more likely to find them attractive. A picture tells us nothing about what it’s like to be in a room with them. I bet countless people have said no to a guy or gal on an app that they’d absolutely love if they met at a party.

I met some cool women on these apps. While it never blossomed into anything, I don’t regret my time with them. But the mental strain of the dating app rat race wasn’t worth it to me.

That’s why in 2023, I’ve set a goal to ask out 100 women. Face to face. Out and about.

The idea is to eliminate my fear of rejection through pure exposure. And obviously, it’d be great if I met someone awesome before getting to 100 invites.

9) Who’s in your hospital room?

Lake Gaston, 2009.

My grandpa died last week. Prior to, I spent a week down in Virginia with my family to be with them and be by his bedside during his final days.

I’ll write more about him and that time in another blog. But this part is actually about something I learned from Kevin Hart.

My company got to see him speak in Philadelphia right before COVID hit. It was more of a self-improvement talk than comedy.

He told the story of his brutal 2019 car accident.

“Man,” he said. “They told me I might be paralyzed for the rest of my life. When I couldn’t eat or go to the bathroom on my own…you know what I had in that room with me? It wasn’t my fame, my house, or my Instagram following. The only thing in that hospital room with me were all the relationships I built over the years. My team, my friends, my family…”

Since then, I’ve used this as a model for living my life.

If I got in a horrible car accident today who would be there in my hospital room when I woke up? Those people have to be prioritized now.

While it was quite an emotional time, I could smile looking around grandpa’s hospital room. Seeing my dad, my aunts, my grandma, my stepmom, my half-brother…This group of people was just a representation of the life this man created and the lives he touched. He made every single one of us feel special.

That’s what I want to do: make the people in my life feel special.

10) I have no choice but to live a fantastic life.

Manhattan, 2022.

Before my grandpa went, he told us all, one by one, what we meant to him and how much he loved us. He said he lived a great life and had no regrets.

And as I spent those days there, I would look at my grandpa while he was sleeping in that bed. My old man’s old man.

It didn’t take long for it to really sink in. That will be me one day.

A long long time from now, after Elon has taken us all to Mars…I’ll be an old man dying in a hospital bed. That inevitable fate is coming for me and every other person I’ve ever known, loved, and laughed with. I’ve known that and I write about it often. But seeing a physical manifestation of it was 10 times more powerful.

By truly understanding that certainty—that I will die one day, I felt only one thing.

I have no excuse.

Between now and whenever that day is, I have absolutely no excuse but to live a phenomenal life. How can I be rude to a friend, get pissed if a waiter gets my order wrong, or sit around wasting a day…knowing that it’s all going to end someday?

I feel so empowered to sit at this desk and work on projects I love, to charge more money in my business, to travel to other countries, to call my friends and family more, to stay in great shape, to learn more about the world and the people in it. There’s a fire under my ass.

This year, I’ve learned the importance of spending more time around birth and death. Playing with my friends’ kids brings an energy to the room that’s not possible otherwise. It makes me feel lighter and more joyful. It makes me imagine the kind of father I’m going to be.

Thinking and talking about death and dying makes me feel so present and appreciative of the people and opportunities I have at my disposal.

Some might think us all dying one day means none of this matters. I like to use that to my advantage.

Since none of this will really matter 500 years from now, why wouldn’t I go after what I want? Why shouldn’t I ask out a beautiful woman at a coffee shop? What’s stopping me from charging the kind of money I want to charge? Who cares?

Most of us go around waiting for permission to live the lives we truly want. But sometimes certain events can wake us up.

Thanks for waking me up, gramps.

Fin.

Hope you got something out of that!

Please, dear reader, do me a favor. I’d love to know the biggest lesson you learned this year. Please email it to me.

Thanks for your support. Here’s to another year. 🥳

A difficult and lovely week

Lake Gaston, 2013.

This photo is of me, my dad, and my grandpa. We’ve been told that each generation is brighter and more handsome than the last. (Not by many, though.)

I spent this weekend in Manhattan with a friend and his girlfriend. On Saturday, I got the call I’d been anticipating for the past year.

Grandpa was admitted to the hospital on Thursday (his fifth time since the summer). On Saturday morning, he decided he wanted to be taken off life support. He wanted to go.

I packed my stuff, canceled my Saturday plans in the city, and drove straight to Virginia. My aunt flew in from Wisconsin and my dad drove down from Pittsburg.

Since taking him off his heart medication Saturday night, we’ve all been taking shifts at the hospital as we wait for it to happen.

It’s all quite fresh, so I’ll save the whole story for another time. I feel guilty even writing about it now. It feels as though I’m using a dramatic moment for content. But this blog is about my experiences and what I learn from those experiences.

And that’s what I’d like to share today.

I’ve gotten thoughtful calls and texts from several friends and family members. One thing I’ve heard a handful of times is, “I know this is a really hard time for you.”

And I can’t help but think, well, it is and it isn’t.

I’ve spent a good amount of time crying this past week. In the car, with my family, on the phone…Realizing I’ll never have another conversation with him or hear another one of his jokes breaks me every single time. This is a wildly emotional time and when it finally happens I’ll feel a level of devastation no amount of stoicism can prepare me for.

But I won’t remember this as a depressing or hopeless time. Not even close.

I’ll remember being with my family. I don’t often get to be in a room with my dad and both aunts. But whenever I am, we’re all laughing and telling stories. It’s been a treat to smile with them, to hug them, and to cry with them.

I’ll remember the blog I wrote when I realized every visit counted with my gramps. That was the starting point for me to prioritize seeing him. Since then, I’ve tried to go down once every two months. I’m so so glad I did.

I’ll remember the last joke he told me. Sunday morning, my aunt put his glasses on him. I was at the foot of his bed. Once he focused his eyes, he said, “You’re telling me I gotta look at Dillan? Take these off.”

I’ll remember how awesome my dad and aunts are. Being there for him at his bedside, taking care of the logistics, and working as an effective and loving team.

I’ll remember the last real conversation I had with him. I stopped by right after he had his mini-stroke. We sat on his balcony, ate grapes, and talked about geography and travel. He asked me about my business and the book I’m writing.

I’ll remember getting pho with my aunt and talking about her dreams for the future.

I’ll remember laughing in the hospital room as my dad cracked jokes and my grandma and aunts told stories about gramps. We all went through our favorite photos, videos, and voicemails of the old man.

I’ll remember feeding him Dots like he was an insatiable kid in a candy store.

I’ll remember my revitalized appreciation for family. And how easy it is to forget what really matters until something like this happens.

And among many other things, I’ll remember the last thing he ever said to me as he lay in his hospital bed:

“Dillan, how you doin’ buddy? You’ve been an excellent grandson. I’m proud of the man you’ve become and of the success you’ve built for yourself. Your mom did an amazing job raising you. Give my best to her and your sister.”

These are the things that will stay with me forever. I’m grateful.

At some point, I’ll return home and continue writing these posts and making YouTube videos. That’ll be a strange time. It feels like everything should stop for a while. But I know that’s not how it works.

For those who’ve made it this far, thank you. If there’s anyone you’ve been meaning to call or spend time with, do it now.

You’ll never remember that weekend you stayed home because it was more convenient. But you’ll always remember sitting down and laughing with the people you love.

❤️

I started tracking my working hours—Here’s what I’ve learned

Dillan Taylor's Toggl-tracked working hours

A month ago, I started logging how I spent my time each week. This was inspired by my good friends who run a design studio and do the same.

Toggl is a free service often used by freelancers who get paid by the hour. But I’ve been using it as an accountability tool.

Every Monday, my coaching friend and I email each other our weekly Toggl report. It shows how many hours we logged, what we worked on, and how long we worked each day.

A few blogs ago, I wrote about how easy it is to add accountability to our lives. But I still think I’ve underestimated how much more motivation I would feel knowing I’d have someone looking over my shoulder.

Quick caveat: In order for this to work, it’s essential to have well-defined projects and tasks. Anyone can “work” for eight hours and not get anything done.

I’ve always hated the phrase “work hard.”

Like, work hard…at what? If I carry a 100-pound rock from one town to another, that’s backbreaking work. But what did I accomplish? If I did that every day, I will have worked insanely hard. And I would lose all my clients and eventually get evicted from my apartment.

Anyway, with clear actions at my desk, I set the ground rules. I would log any time spent that took creative and undistracted brainpower. That includes:

  • writing
  • editing
  • organizing digital notes
  • coaching sessions
  • courses
  • recording
  • life-planning
  • responding to emails and voice notes
  • outreach
  • chess study
  • connect calls

(To those who think including chess and chores on this list is cheating, I’d direct you to this page.)

Dillan Taylor's Toggl-tracked working hours

Now that this has become a habit, I’ve gained a few insights I didn’t have one month ago. Here they are…

1) Things take way longer than we think.

I’ll sit down to answer two or three emails thinking it’ll take five minutes. Then when I hit stop on my tracker I realize I’ve been at it for 35 minutes.

I had nothing to do this Saturday. So I decided to edit the next podcast episode and put some finishing touches on it.

Five hours later, I thought, Holy shit, what time is it?

Getting lost in a flow state and uncovering all that needed to be done made the hours tick by. As you can see from the image above, Saturday’s “finishing touches” turned into a seven-hour workday.

(I don’t usually work on weekends, but sometimes it’s all I want to do.)

2) We can’t actually work for that long.

Seven hours of work on a Saturday might seem like I’ve fallen victim to the hustle-culture cult. But you might also notice that that was my longest day by far.

I wrote for two hours on Thanksgiving. But if we look at the other four weekdays (my actual work days), my average time spent working was 4 hours and 52 minutes.

And last week kicked my ass. It was the most I’ve worked since quitting my full-time sales job in 2020.

34 hours.

When I punched out on Sunday and saw “33:49:54,” I thought…That’s it??

I felt like I had one of those 80-hour workweeks I hear about from Instagram entrepreneurs. I gave it my all. I got so much done.

34 hours? Not even a standard American workweek.

My takeaway: 80-hour weeks, 12-hour days, seven days a week…it’s all bullshit. For the vast majority of people, that’s just not possible.

I don’t even think an eight-hour day is sustainable every single day. Not of actual work—creating, problem-solving, deep learning. People might spend 8-10 hours in their work environment, but most of us only have three to five hours of genuine deep work capacity in us each day.

There are certainly folks with much more in their gas tanks than me. But it’s important to dispel this rumor that the only thing keeping people from intense work schedules is their discipline levels.

I worked 34 hours and wanted to go on holiday for a month. Still waiting to hear back from Elon about my Twitter application.

3) Given #1 and #2, it makes sense to not do too much.

That doesn’t mean not putting in effort or having low standards. But if things take longer than we think and if we have a finite amount of bandwidth…it makes sense to keep our task list to a minimum.

Instead of doing five things at 20%, what if we did one thing at 100%?

This obviously isn’t possible for everyone. People have kids, demanding jobs, and hundreds of things to get done at any given week.

But willingly putting more things on your plate than you have working hours in a day is a recipe for burnout and anxiety.

My advice: Do less, but better. Cut things down to the bare essentials. Minimize.

It’s counterintuitive, but we can get more done and have more impact by doing fewer things. And tracking how we spend our time makes that process a whole lot easier.

I burnt out (again)

A tired woman staying up late at night and looking at her phone

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:

  1. What are the three most important things that demand your focus right now?
  2. What are you doing too much of that’s getting in the way of these things?
  3. 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.

5 things I’d tell my 18-year-old self

Dillan Taylor at Kings Dominion in 2012
Kings Dominion, fall 2012.

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.

You’ll find your way eventually.

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.

To Florida and back

This morning, I leave for a two-week road trip. The longest vacation I’ll have since starting my own business.

The end goal is my coaching community‘s five-day retreat. But rather than fly down, I’m taking my car to make a few stops.

Stop 1: Asheville—to stay the weekend with some of my best friends.

Stop 2: Savannah—a gorgeous place on the river for some much-needed solo time.

Stop 3: Tampa—to spend a few nights at my coaching mentor’s house.

Then the retreat just south of there.

I feel a sense of bliss. Here’s why.

I love my job. It’s genuinely my dream career. It fulfills me, pays my bills, and allows me to connect with humanity at the highest level.

But we all need breaks.

Regardless of how much we enjoy something—an activity, a place, a person—we need space away from whatever that thing is. It’s in taking this room to breathe that we recharge our respect for it.

Americans work too much. We have the fewest vacation days in the western world and aren’t even close to being the most productive.

But time off relaxes us. It clears our minds, making us more energized to live. It only makes sense that someone who’s thrilled with their life would be a better worker.

Anyway, I’m excited about this time off. I won’t be posting any blogs. I won’t be on at all. (Maybe I will, but probably won’t.)

The main reason I’m excited? It’s because I don’t specifically know what I’m excited for. I feel empty, void of expectation. I’m just going to enjoy each individual day as it comes.

No hard structure or plans. Just friends, driving, reading, and thinking.

See you in two weeks. ✌️

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.

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?

✌️

Anyone can talk

A man talking through a cup phone

For years, I said that family was one of the most important things to me. But that was a lie.

How do I know?

Because my actions tell the whole story. I never went out of my way to help my mom. I rarely spent quality time with my sister, aunts, or uncles. I visited my other half of the family when it was convenient.

Billionaire industrialist and vigilante Bruce Wayne once said, “It’s not who I am underneath, but what I do that defines me.”

The cliche states that actions speak louder than words. Basically, anyone can talk. Talking is easy. It feels good. Sometimes, people are so good at talking, they trick themselves into thinking they’ve already done something.

That’s why ideas, plans, and roadmaps bore me. It’s all just words.

That’s not to say we shouldn’t prep for the future. I’m just far more interested in what a person is doing than what they say they’d like to do.

(Keep in mind, I’m criticizing myself here.)

Here’s a pretty personal example.

One of my close friends has basically been radio silent for the past year. He doesn’t answer my calls or texts. I worry about his health and wellbeing. I get no answers.

He sent me a super long text on my birthday a few weeks ago. He apologized profusely. He told me how much he loved and respected me. Reading it made me cry at my dining room table.

When I responded to try to set up a call…nothing. I haven’t heard from him since.

Anyone can talk. It’s through our consistent actions that we prove who we really are (thanks, Batman).

If we want to be kind and loving friends, we have to show our friends we support them and are curious about them. If we want to care about our health, we have to exercise regularly and eat mostly well. If we want to be productive, we have to sit down and do the work every week.

So what can we do with all this?

Try this exercise: Take five minutes and write out all the things you value most. Then, take another five minutes and write about the actions you take on a regular basis for those things.

Notice where things are lacking. What can you do more or less of? What needs to change?

As always, let me know how it goes. 😎

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?

Up late with no regrets

Jorge Masvidal and Colby Covington fighting in UFC 272

This Sunday was the first Sunday in a year where I intentionally scheduled nothing.

Coming into the weekend, I realized that meant I could do something I haven’t done since January 2021.

Watch the UFC fights.

It’s the only sport I care to pay for and make time to watch. When people start talking to me about football, I usually stop them in their tracks. (Is Brett Favre still playing?)

Since the fights are almost exclusively on Saturday nights, I’ve had to skip out on them. They run late, usually ending around 2am.

That’s not conducive to waking up at 6am to prep for morning and afternoon sessions. I didn’t have to worry about that this weekend.

On Saturday, my buddy and I competed in a chess tournament. He did great, going 4-1 and securing third place in his section. I did okay, with two wins and three losses.

We got a late dinner and some beers. He asked if I wanted to hang with him and his roommates at their place to watch the fight. No, in fact, I did not want to do that.

Instead, he dropped me off, I made a vodka drink (not a whiskey drink), and bought the fights.

They were incredible. It felt like an old piece of me I loved was awakened. I was standing up and cheering in my living room.

On paper, it sounds quite lonely to pay for a UFC card, drink a cocktail, and stay up late all by oneself. But it was me-time I’ve been craving for months.

I woke up Sunday morning much later than normal—around 9am. I was groggy and slightly hungover (from three drinks, thanks 28 years of age).

And I was happy.

There was nothing on my calendar. I had nothing to do. I drove back to Baltimore to pick up my jacket and sunglasses I left at the tournament the day before. It was a gorgeous day. A best buddy called me and we chatted for two hours. I read a comic book. I listened to a podcast.

I got nothing done. And it was a productive day.

Productive for my mind and soul (whatever that means). It was peaceful. I could get used to this.

Today, I feel well-rested and ready to jump into the week. I’m a fan of taking weekly vacations—which I think normal people just call “weekends.”

A weekend of nothing

“Take a picture of us taking a picture of us.”

Readers of this blog know last week was an impactful one for me.

An intense level of burnout led me to change my entire workflow moving forward. That began this weekend.

Minus any trips, vacations, or special events…this Saturday and Sunday mark the first weekend in a year I didn’t work at all. No sessions, no planning, no creating.

I hiked with my buddy. We played chess. My friends took me rock climbing. Two besties are in town from Rwanda and Philadelphia (two equally foreign and exotic lands). We all got brunch in DC Sunday morning.

It was lovely, to say the least. There was no optimization, no brainstorming, no building. Just stories, laughter, and quality time with close peeps.

I love worky-type stuff. But space away from anything (and anyone) is essential. I forget that sometimes.

To “regular” people who enjoy their weekends, this may sound odd. But these past two days have quite literally felt like a vacation to me. I have to learn how to do nothing once or twice a week. Like anything, I’m assuming it’ll come with practice.

Days one and two are checked off. I’ve already begun the process of maneuvering my time slots with my weekend clients.

It turns out most people are accommodating when we simply ask for what we want.

I could get used to this.

I ran away

The sun shining through the woods

Last week, I joked about running away from everything and spending time off the grid. This weekend, I did just that…sort of.

I’m pretty sure I had a mental breakdown from Tuesday to Sunday.

I’ve never experienced anything like it. I’m still sorting things out so I’ll try to make sense of much of it today. In this blog, I’ll go through:

  1. What happened
  2. What I learned
  3. What changes I’ll make moving forward

Let’s dive in.

1) What the hell happened to me?

I woke up exhausted on Tuesday. But not a typical exhausted.

I’ve gotten bad sleep before. This was different. This wasn’t sluggishness or fog. I was awake. It was strange.

I felt no excitement or joy…None.

Whoa. I ran an experiment. I wrote out all of my favorite things and imagined myself doing them at the highest level. Spending time with friends and family laughing hysterically. Growing a business I love. Living in my new NYC apartment. Playing in chess tournaments…I felt nothing.

I wasn’t looking forward to any of it. In fact, I resented and was angered by anything I had to do last week. Client sessions, admin work, plans with a friend. I didn’t want to do any of it.

This was a shock to my system. I’m always excited. I love projects. I love talking to people and spending time with those I love.

But the only thing I truly wanted to do was run away to a cabin in the woods and not talk to a soul. Unfortunately, that wouldn’t fly.

I had a week of calls. Much to do, like any week. My next vacation is Brooklyn at the end of the month. My first thought was, Just make it until then. Not a chance.

The problem-solver that I am, I worked hard to find the source of all this.

I went through every interaction, every experience, everything I did and said in the past two weeks. Is this a trauma thing? Am I nervous about something? Did I do something I feel guilty about?

No. No. And no.

Then what the fuck is wrong??

Mindfulness told me that nothing was wrong. There was nothing to fix. But that’s much easier to say when I’m not in the thick of it.

I used my Ph.D. in Bro Science to dissect things. It felt as though my brain wasn’t producing dopamine. It was hard to laugh. I had zero motivation to do anything. I dreaded waking up and attacking the day.

Anyone who knows me knows I’m always laughing, I’m always motivated, and I love waking up and getting moving.

I cried a few times.

Here’s why:

  • I felt awful
  • I had no idea why I felt so awful
  • I both wanted to be consoled by my friends and not talk to anyone
  • I felt guilty for showing up to calls as (barely) half a person
  • With my limited knowledge of mental health, I thought about how many people experience way worse than what I did

Not fun.

This continued each day. I went to bed hoping I’d wake up refreshed and back to normal. Then I’d get up disappointed and reluctantly head into my office.

On Thursday, I had a session with my coach. When I laid out everything I was going through, we dove in. Without recounting the entire session, here were my major takeaways:

  1. I need more support.
  2. I work every day and didn’t even realize it.
  3. I’ve built an accidental brand of someone who’s unstoppable and has it all figured out (lol).
  4. In the 10 days of February, I had given myself to (held space, helped, served) 53 people for 36 hours.
  5. I’m working on too many things.

Holy shit. I was totally burnt out.

With this blog, with becoming a leader in my coaching community, with building more and more relationships in life and business…

People have been asking for my time and attention more than ever before. My output—the amount of value I’ve been trying to give—has been blowing up like a balloon. That balloon popped last week.

As I’ve reminded myself countless times in the past: It doesn’t matter how good we are at time management—there are only 24 hours in a day. We can’t trick Father Time.

I was giving 100 things 1% of me. As opposed to giving one thing 100% of me.

That session gave me a ton of clarity on what was going on. But it didn’t make me feel any better.

The next day on Friday, I was in a session with someone and I realized I hadn’t been listening to them for about 60 seconds. My eyes started watering.

I felt terrible. It was unprofessional of me to try to power through this. I finally understood the merit of taking a mental health day.

So I took a mental health weekend.

I reached out to the seven people I had sessions/plans with, told them I needed to escape for a few days, and then asked to borrow my friends’ dog, Hank.

I got an Airbnb an hour away. Seven of seven people responded with nothing but well-wishes and heart emojis. ❤️

I packed some clothes and a book, picked Hank up, and we headed off the grid.

So…

2) What the hell did I learn?

When we got to the place, I dropped my bag and phone off. Hank and I left immediately to explore the local hiking trails.

When we got to the first one, I let Hank off the leash and he galloped around the trees with glee. Hiking with a well-trained dog should be an American pastime.

He found a stick and handed it to me. I thanked him for the gift and we walked aimlessly.

A few things hit me in those first few minutes in the woods:

  1. I don’t do this enough.
  2. Intention is a beautiful thing, but so is doing something without a goal or purpose.
  3. Life is 40 times more enjoyable outside without a phone.

The sun was going down so we went back to the Airbnb. I fed him and ordered dinner for myself.

The evening was spent reading, playing with Hank, and thinking.

When we woke up, I gave him breakfast and we went straight back out to the trails. It was snowing. He looked even more graceful sprinting through piles of white.

Back at the place, I made a cup of coffee and started reading a novel. A few minutes in, I realized I was enjoying it more than I had in the past. 90 pages in and it felt like I was soaking it in for the first time.

What was different?

Then the insight struck me. This was the first time in months I had picked up a book simply because I wanted to read it. It wasn’t for my routine. It wasn’t my 30 minutes of morning reading. I was just reading a good book on a snowy morning with some coffee and a dog lying at my feet.

“I need more mornings where I don’t care what time it is,” I said out loud.

“Quiet, I’m trying to sleep,” muttered Hank.

I stopped reading when I wanted to stop, not because it was time to stop. I could get used to this whole “not scheduling every hour” thing.

We played more tug-of-war, cleaned the place up, and checked out. Before returning home, we hit a nature park and wandered around for an hour or two. Every ten minutes that passed was like a percentage increase in my life battery.

I discovered that this stuff…time in nature, electronic-free walks, mornings without a clock…these were no longer self-care luxuries. At the level I’m at now, they’re necessities.

With that said…

3) What the hell am I going to do with all this?

I brought Hank back home and chilled with my two friends for an hour. I told them about my mental state. They listened with care.

When they asked how the Airbnb was, I said, “Necessary, not enough, and expensive.”

While it was helpful, it didn’t remove the physical sensation in my eyes and throat. But it did show me what I needed to change.

First, I need to stop working on Sundays.

I’ve been willing to do sessions on weekends because several of my clients have 9 to 5s and I don’t do evening calls. But that means when I’m not taking a trip, my week looks like this:

Mon—write book, organize week
Tue—sessions, chess lesson
Wed—sessions, group calls
Thu—sessions, newsletter
Fri—sessions, creative work
Sat—sessions, maybe fun
Sun—sessions, chill before week starts

No days off. Literally. That’s stupid.

My brain has no time to shut off or unplug. I’m always on.

Last night, I turned my phone on airplane mode and watched six episodes of Avatar: The Last Airbender (I have no idea who played in the Super Bowl).

Even that felt like a rarity. How often do we watch something on TV while on our phones? How many God damn screens do we need at one time?

So, here are my to-dos:

  1. Get back to everyone I’ve been blowing off.
  2. Reschedule my sessions/calls.
  3. Tell my clients I can’t work Sundays anymore.
  4. Spend more time without my phone and not looking at the clock.

I’ve already halted two projects I was working on. Taking those off my shoulders gave me an immediate wave of relief.

Moving forward, I’m going to be doing less. Less but better. Less but with more time, love, and attention. I’ll do more by doing less. Yes. Less.

Conclusion

I’m immensely grateful to have people in my life I can be vulnerable with.

Even this blog. I’m lucky to have an outlet where I can share stuff like this.

I also think about my mom.

I work for myself and have no one to worry about other than me. What if I was a single parent with a full-time job? I couldn’t just cancel everything and escape. Again, I’m lucky to be able to do what I do.

Please, if you’ve been through anything similar, share it with me. I’d love to learn more about the scope and scale of mental health.

Thanks for making it this far. I’m back and feeling pumped to do much, much less! 😘

Getting away

Hank the dog

Today, I’m borrowing my friends’ dog and staying in an Airbnb in the woods.

I canceled all my calls and obligations. Here’s what I sent seven people.

“Hey…! I’m so sorry. I know this is last minute but I’m experiencing some crazy burnout and need to get away. I’m rescheduling everything this weekend and running away to a cabin in the woods. Hope this lands well!”

I can already see I got back four responses from people with nothing but support and well-wishes.

This has never happened to me before. I don’t know the source of this anxiety and overwhelm. It came out of nowhere.

This is new territory for me so I’m learning how to manage it. I dare say there are several learning and growth opportunities here.

I’ll let you all know what those are when I return from playing with this dog off the grid. No phone. No wifi.

Just me, Hank, and a book.

Roadblock?

A chessboard sitting on a bed

I’ve been in a chess slump for the past month.

My rating climbed and climbed over 2021. But now I feel I’m stuck around 1650. It feels like I’ve reached a plateau.

This has made me jaded while playing online. I even felt resentful at my last tournament.

The lesson? I’ve learned that my main satisfaction in the game has been my growth in it. It’s time to change that.

But now I’m approaching an advanced skill level. To continue improving, I’m going to have to really start studying and treating it less as a small side hobby.

The other day, one of my favorite chess streamers Eric Rosen said something which hit me hard.

“A lot of players obsess over their win rate or their rating. I think too many players forget about the goal of having fun with the game.”

It’s so cliche. So simple. I was one of these players.

This could easily be applied to any other area in our lives: career, relationships, health. We focus so heavily on improving or pursuing a thing. It can be wildly helpful to pause from time to time and ask ourselves the question.

How can I make this more fun?

Core principles

Every individual or business should run on a small set of core principles.

I just updated mine:

1) Curiosity before solutions.
2) Make people feel loved and heard.
3) Serve; don’t please.
4) Do the things I love all the time and get better at them.
5) Take nothing personally.

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.

No one cares where I went to school

Two students sitting down on the grass at university while doing their homework

In early 2020, I wrote a shitty blog ranting about college.

I still hold all the same opinions. But today I’d like to briefly discuss one aspect.

The fact that I run a profitable business that sustains my life and fulfills me at the highest level. I help people create the lives they want, get organized, and even grow their own businesses.

And in the last four years, not a single person has asked if I went to school.

Not where I went to school. If.

I’m not saying any of this to brag. I’m a college dropout who spent most of those four years living with his mom because he couldn’t afford anything else. (To which I’m incredibly grateful. Thanks, mom!)

The point is this.

In the past, people cared about where we got our credentials. Today, most people just want to know if we’re useful.

“Where did you graduate?” is now “Can you help us?”

I have friends making six figures because they taught themselves how to code. I know folks with great jobs because they’re great people who learn well and have strong interpersonal skills. I do well because I’ve developed the skill of coaching and curiosity.

All of which is possible without paying $80,000.

The caveat here is that of course there are professions where schooling is entirely necessary. I don’t want a surgeon who taught herself how to cut people open.

I don’t think college is a bad idea. It’s just not the only idea. There are many other ways to do interesting things and make money.

Many companies would ask me: What are your credentials?
“Alcoholism,” I would say. “Bankruptcy and divorce.”

Steve Chandler

Fuck Off Day

A woman waving goodbye to her toddler son as he runs out with his backpack

Last night, I went over to my best friend’s house for dinner.

He and his partner were telling me about the move to intentionally add alone time into their relationship. Now every Tuesday around 4pm, they take turns leaving to go do something and give the other person the house to themselves. Tongue in cheek, they’ve been calling it “Fuck Off Day.”

It’s funny because a person could hear this and think, Oh, you’re trying to spend more time separated...sounds unhealthy.

When in fact, it’s one of the healthiest things I’ve ever heard a couple do.

They have an incredible relationship. And this practice is intended to maintain that strength.

I’m not an expert in love…but this truth can be applied to everything else in our lives:

Space from people, environments, and activities (especially ones we love) is essential.

Let’s go through some examples in order.

People:

We all need alone time. We need to know what it’s like to simply sit with our thoughts and emotions.

I used to think I was just a wildly extroverted guy. Then I realized I was just surrounding myself with people so I never had to confront my anxieties. When we’re alone, there’s nowhere to hide.

Aside from that, time away from those we care about creates room for us to miss them.

It’s in someone’s absence that we truly notice what they bring to our lives. Until they return. We can’t fully appreciate something until it’s taken away from us.

Since I moved out of my mom’s house, we’ve grown ten times closer. She’s not my roommate anymore. She’s my amazing mother.

When I visit friends from other cities, I cherish every hour of conversation I have with them. I know that when the weekend is over, we’ll go back to our lives hundreds of miles apart.

In breakups, we can logically know that it’s for the best…yet we still feel the agonizing pangs of loss not having this person to laugh or be romantic with.

All this to say: We need space from people to solidify how much we love and appreciate them.

Environments:

Why do we take vacations?

For the Gram, yes. But also to just fucking get away.

Away from our routines, our neighborhoods, our kitchens.

There’s something liberating about being in a totally new place. We’re often not even sure what the place is going to look like or what it has to offer. We just know we’d like a change of scenery.

I take one trip every month. Sometimes to another state. Sometimes out of the country. Why?

Because I work on weekends. Several of my clients work nine-to-fives and I don’t do calls on weeknights. That means I often work seven days a week. And that means I can only take so much before I have to get the fuck out of here.

I love this office but after a certain amount of time, any room can feel like a prison cell.

So I go somewhere. I visit a buddy. I see my family. I go hiking. Sometimes I just take the weekend off and host a friend here at my apartment.

It’s actually nice to not do my morning routine for a few days. But then, after taking that space, I quickly crave my old environment. I miss my desk, my roommate, my bed.

Then when I return home, I feel refreshed. I get back into my habits and rituals feeling reignited.

All because I took some time away from them.

Activities:

I love chess.

But there’s a reason I don’t play it for eight hours a day. It’s the same reason I don’t do anything for that long.

I’d get sick of it.

I had a session yesterday with a super ambitious salesman. He loves his job and is always eager to do well and help his team.

But the job is so time-consuming that he feels he doesn’t have any time for himself. So we created some boundaries for him to set and build that time (i.e. space).

I asked him: “What would you be able to do with the free time you create?”

He responded immediately: “I’d do my job better.“

He wants space from his job so he can be more present and capable when he’s in it. That’s how I feel about chess, coaching, and everything else. That’s why we need rest days from the gym—to allow our muscles to rebuild themselves and recover.

TL; DR:

Intentional time away from the people and things we love strengthens our relationships with them.

THINGS I’m grateful for

Luigi, Yoshi, and Mario standing next to one another

Yesterday, on the CREATE Program calls, we talked about expressing gratitude.

We separated the things we’re grateful for and the people we’re grateful for.

One woman laughed because of how hard it was to not go straight to the people in our lives. It felt counterintuitive. There’s usually a negative connotation in focusing on the stuff we have instead of the relationships we enjoy.

But my prompt was this:

What are the things—both tangible and intangible—you are so incredibly grateful to have in your life?

Awesome answers included:

• “My sobriety”
• “How much time I have left on Earth”
• “My past—for all its valuable lessons”
• “Having a computer which connects me to so many people”
• “My growth”

It was difficult to have this conversation without a big dumb smile on my face.

Here’s my answer to the question:

I’m grateful for the infinitely small probability of getting the life I have.

I didn’t choose my parents or my environment. Which means I didn’t choose to not be a Syrian refugee. I didn’t choose to not have a shitty mom. I popped out in a hospital in Virginia Beach in 1994 and they happened to hand me back to two capable, loving adults. Then those adults raised me in middle-class America.

That’s some good shit.

There are so many factors that could’ve drastically altered my life. A few strands of DNA. One of my best friends not attending my high school. A childhood injury.

But so far, everything has happened how it happened and I look how I look and live how I live.

I’m grateful for the brain I was born with. It has given me the skills to connect with others and create a lovely life for myself. It allows me to read and write every day. It keeps me from being mean to people.

Tomorrow, I’ll talk about the people I’m grateful for. Stay tuned.

(**If you would like to join wholesome conversations like this one, ask me about the CREATE Program!)

Why I never lie

A child with painted hands

Until I was about 23 years old, I’m pretty sure I was a compulsive liar.

I lied about: my sex life, my skills, and stories which may or may not have happened to me. The goal was to create a Dillan who was way cooler, more impressive, and more capable than the Dillan I was.

The effect?

Not only was I keeping reality away from my friends and family. I was also muddying my own lens of the world around me. I began believing the lies I was telling.

I also trusted people less. If I wasn’t being honest, how easy was it for others to be dishonest too?

Studies show that people who are carrying a gun suspect way more people to also be carrying a gun. So too with lying.

One of the heaviest burdens a liar carries is having to remember all that they said.

In my junior year of college, I got caught in a lie. I told one person something that contradicted what I told another person. The memory still makes me cringe. I felt like a child who got caught lying about stealing a cookie.

After that moment of disgust, I set out to intentionally break my habit of lying. It was fucking hard and took me about three years.

Even to an honest person, setting out to not tell a single lie is quite the challenge. It’s almost ingrained in our culture to spare the feelings of others and tell white lies to be polite.

I just finished a book—Lying by Sam Harris—which debunks every reasonable-sounding argument for telling a lie.

My two biggest takeaways are:

1) Lying erodes trust in the people we care about (both consciously and unconsciously).

I have a friend who’s one of the kindest and most compassionate people I’ve ever known. But one time, we were hanging out and someone texted her seeing what she was up to.

Not wanting this person to know she was choosing other friends over her, my friend lied. She said she was just chilling for the night to get ready for an early morning.

We laughed it off, but I remember thinking, Has she ever done this to me?

Now I’ve seen that she’s willing to lie to a friend. Whether we like it or not, I’ll never trust her 100% when I invite her to something and she says she can’t go.

2) Fake praise or encouragement is not kind; it’s disrespectful. It wastes a person’s time and morphs their grip on reality.

False encouragement is a kind of theft: It steals time, energy, and motivation that a person could put toward some other purpose.

Sam Harris, Lying

This has to do with short-term vs. long-term thinking.

If we give open and honest feedback (with grace and permission, of course), in the short term we may risk hurting a person’s feelings.

But in the long term, we accomplish a number of things. We…

• become a trusted confidante
• genuinely help this person improve
• cultivate a deeper relationship with this person

Giving and handling feedback well is its own separate conversation. But when I create something, I don’t want people to tell me why it’s awesome. That may feel good for four seconds, but what I really want is to build something valuable.

As uncomfortable as it can be, I can only accomplish that by having people I trust point out my blind spots and mistakes.

An essay is always improved after a round of edits.

On the other hand, if I’ve only been told that my thing is perfect…when I share it with the world and no one likes it, I’m left confused and heartbroken.

We can avoid that by simply being honest.

Conclusion

Where do you tell lies—even white lies?

How difficult would it be to not tell a single lie for the next seven days? I encourage you to try it. It’s more liberating than you may think.

My 10 Commandments

The front lawn of a courthouse

I’m not the least bit religious, but I do advocate for living a principled and value-driven life.

Here are my 10 Commandments.

Thou shalt…

  1. Pursue a Growth Mindset—seeing everything as a lesson and a chance to improve.
  2. Never be uncomfortable with your shirt off—remaining fit and active.
  3. Treat every human being with the same amount of humor and respect—be they a CEO or a gardner.
  4. Pick your battles, but be confident when expressing your ideas and opinions.
  5. Cherish every minute of quality time you get with close friends and family.
  6. Never order food or watch a show unless with another person.
  7. Never take anything personally—especially rejection.
  8. Go to the gym at least three times per week.
  9. Never text while driving a car—even at a red light.
  10. Spend more time in a day reading or having a conversation than staring at a screen.

Being human, I don’t stick to these perfectly. But having these guidelines has moved me drastically closer to the person I aim to be.

What are your commandments?

I asked my doctor friends about vaccines

Three doctors looking at

This is NOT a post trying to convince someone to get vaccinated. It’s a blog about humility.

How it started

A few months ago, I had a warm debate with a friend about the COVID vaccine. I found her arguments to be shaky and without much reassuring evidence to support them.

But it wasn’t what we were arguing about that struck me. It was the level of certainty she had about her opinions while clearly being nothing close to an expert herself.

Certainty that the counter-evidence was likely bullshit. Certainty that the 1% of medical doctors against vaccines are in the right. Certainty that the virus is being propped up so the government and big pharma may gain control over citizens.

In general, I’m less interested in what a person thinks and care way more about how they think.

The conversation with my friend eventually fizzled out, but I couldn’t help but think: Have you had this debate with any real medical experts?

This was my first dose of humility…because I hadn’t spoken to anyone in that field either. So I decided to change that.

I’m lucky to have friends and folks in my life who are either medical doctors or are surrounded by them. I reached out to each of them and asked for their expert opinions in a neutral way.

I didn’t state my thoughts and then ask for validation. I simply said: “I’m trying to get a clearer picture here. As a medical professional, would you be willing to share your thoughts on the COVID vaccine?”

Every single doctor I reached out to sent me paragraphs in response.

Here are the notable takeaways:

• “I’m extremely confident in my ability to read and dissect medical literature surrounding this topic. I think a lot of people who “do their own research” don’t know the first thing about how to conduct, analyze, or determine the relevancy of medical studies. A Google search is not even remotely the same thing.”

• “One of the reasons mankind is still alive is the existence of vaccines. Polio, Measles, Mumps, Varicella, Meningitis, Influenza, and more…would ravage us if we didn’t have vaccines. I think people have become more skeptical in the world today compared to 20 years ago about nearly everything and essentially with this first new vaccine coming in that time, it’s a perfect target for controversy.”

• “As far as reasons I support it? It’s literally the answer to this problem we are all dealing with. It is safe, it’s well researched, the studies are all massively in favor of it, and it’s the fastest and likely the only way to go back to our normal lives.”

• “After these years of education and practical training, I think vaccines are one those things that have received unnecessary negativity towards.”

• “I know there are people who can’t get it, and that is okay. I also know that people who chose not to get it aren’t necessarily selfish people, they are normally just extremely uninformed or misinformed. Everybody acts in a way that they think is best. But just because you think you’re right, doesn’t mean you are. And in this case, it is causing harm to other people. It’s everyone else’s job to protect those of us who are more vulnerable. It’s part of our societal duties.”

• “I understand people want to be wary about side effects which is absolutely fine, but everything we do in medicine is evidence-based practice. We all take the Hippocratic Oath and essentially we try to do no harm while doing what is right for patients.”

• “I would understand the resistance to the vaccine if there was legitimate cause for concern, but there isn’t. Every single time I see a new BS conspiracy theory pop up, I take a week or two to look at the research and listen to the various experts that I know personally or follow on various forms of media. Without fail, every concern has been comprehensively debunked.”

• “It baffles and frustrates me that people are so resistant to entertaining the possibility that they may be wrong. It’s led to so much vaccine resistance and done so much harm. It’s the reason we are still in this mess, the reason the delta variant is such a problem, and the reason so many people are dying unnecessarily.”

What to do with all this?

To be clear, if any of these doctors said something like: “I actually warn people against the vaccine because of x, y, and z…” I would’ve included that too.

These just happen to be all the major points made by the five people I reached out to. I’m also aware that five people isn’t a great sample size.

The point of all of this is highlighted in the first takeaway I listed: I don’t have the slightest clue of how to read and dissect medical studies. Likewise, my friends who think they can in a matter of minutes seem foolish to me.

I think in the world of the internet—where we can find anyone articulating any opinion—it behooves us to practice more humility.

When did experts become morons? Corruption is real and people make mistakes, yes. But what allows someone to feel certain they know more than someone who’s been studying that thing for decades?

We’re experiencing a strange death of expertise.

Which makes me eternally grateful to have people in my life I can turn to who know way more than I do.

If I were thinking of getting spinal surgery, and I had a friend—who’s a server in a restaurant, say—tell me they actually did some research and thought I shouldn’t because it could damage my vertebrae…my response would be: “What the fuck do you know about spinal surgery??”

Vaccines and spinal surgeries are obviously different things in scope and scale. But what I’m trying to hammer home is the ridiculous nature of listening to people who certainly don’t know what they’re talking about.

This goes for my friends who are for the vaccines as well.

In summary:

1) I don’t know shit. Neither do most of us…so we should turn to the people who do know shit before cementing our own ideas.

2) Skepticism is healthy, but the point of expertise is to have people we can trust to take care of the wildly complex things which keep our lives going.

3) The next time we feel certain about an opinion, we must ask: How much time have I spent challenging this opinion? Who can I talk to in order to challenge these thoughts?

3 rules for disagreeing with someone

In the past four years, I’ve had debates, discourse, and disagreements about politics, feminism, religion, race, transgenderism, vaccines, and more.

Some were heated and aggressive. Some were fun and fruitful.

I handled myself quite well during some. I sounded like an ass during others.

It doesn’t matter how much we connect or get along with someone else. We’ll never agree with 100% of what they believe. Disagreeing is a natural part of the human experience.

Through my conversational struggles and from the many mistakes I’ve made, I’ve learned three helpful (yet difficult) rules for having more productive disagreements.

Feel free to disagree with them (get it?).

1) Come to terms with this truth: We can never force someone to think, feel, or believe something. They have to get there on their own.

We are not creatures of logic. We make decisions based on emotion and then justify those decisions with logic.

In countless disagreements, I foolishly thought that if I just brought up another point of juicy rationale, I’d crack the other person and they’d see things the way I saw them.

Confirmation bias plagues us all. It will always be easy for us to pick and choose the (supposed) evidence which fits our narrative. We decide what we want to be true and identify with that belief. Then, if someone disagrees with that belief, it feels like they’re disagreeing with who we are as a person.

Yesterday, my friend told me about a heated debate between his two friends regarding the COVID vaccine.

One friend was arguing that the vaccines are probably not safe. He sent a screenshot of a well-sourced article listing the possible negative side effects.

The other friend then went to that same article and screenshotted a paragraph that was conveniently left out: the conclusion which said that the vaccine was ultimately proven to be safe.

I heard this part and thought that would be the shutting of the door to their argument. But the friend merely brushed it off and continued with his disputes.

With the power of the internet, we can find millions of people who agree with every possible opinion known to man. There are people with PhDs who believe the earth is flat. There are intelligent people who think the planet is 6000 years old.

Whether it’s opinions about vaccines or about our favorite athletes…our default is to cling to evidence that supports how we already feel and to shy away from evidence that challenges our beliefs.

Since that’s the case, we cannot ‘logic’ our way through a disagreement.

2) Ask way more questions.

There are several reasons for this.

Firstly, it’s crucial to understand fully what we’re arguing against. The last thing we want to do is misrepresent someone and challenge ideas they don’t actually hold.

We ask questions to paint a crystal clear picture of what they’re actually thinking.

A strawman is a fallacy in which we argue against the worst possible representation of someone’s point.

Example: “Oh, we need to do something about climate change? So you just want us to stop driving cars and stop having kids, huh?”

No…that’s not what they’re saying. That’s a strawman.

By asking curious and clarifying questions (not leading questions meant to achieve a ‘gotcha’ moment), we’re able to steelman. This is the opposite of a strawman, in which we’re able to articulate someone’s opinions perfectly.

A steelman would have us say: “So just to be clear, you believe…” Then they would say: “Yes.”

That has to be our starting point.

The second reason asking questions is so effective is it demonstrates to the other person that we’re not here to attack them. The more curious we are, the more we show we just want to understand them, the more their guard will drop.

This isn’t a trick. We want everyone involved to lower their guard and feel safe to express themselves without reacting in a defensive manner.

Curious questions make it a conversation, not a debate. This is ideal. Debates have winners and losers. But in great conversations, everybody wins.

The final benefit of asking questions is it adds scrutiny to the conversation, exposing the true strength of the person’s argument.

While this should never be the goal of asking questions, it’s possible that the person “defeats” themselves with their own words. It’s a great way to see if this person has given thought and research into this thing they believe or if they just want to believe this thing.

I recently had a disagreement over the COVID vaccines myself. (To be clear, I’m not super passionate about vaccines. It’s just come up a ton in recent months so it’s fresh on my mind.)

My friend who was super wary of the vaccines was sharing his opinions. I did my best to just ask questions. As I did, I felt that their answers were on shaky ground and I found many holes in their arguments.

There were a lot of “I don’t know’s” and “I don’t remember’s.”

Again, I wasn’t trying to slam dunk this person I have a ton of love for. I just wanted to get a clear picture of their beliefs.

Asking questions is hard, especially when we don’t feel curious at all. Curiosity is tough to fake. But it’s the only way to ensure nothing gets lost in translation.

3) Separate the person from the argument.

We’re not arguing with people; we’re arguing with ideas.

I could go on for hours about how much I hated having Donald Trump as our president. But I’m also super close with people who absolutely loved him.

That doesn’t mean I actually hate these people. It just means I don’t connect with their ideas. We don’t need to agree with someone to hug them or to have a beer with them.

So in a disagreement, it’s powerful to avoid saying things like:

• “Where you’re wrong is…”
• “What you don’t see is…”
• “I disagree with you on…”

With phrases like these, it sounds again like we’re disagreeing with them as a person.

It’s better to say things like:

• “My problem with that perspective is…”
• “That argument to me is…”
• “The way I see things is…”

With phrases like these, we make it apparent that we’re just discussing ideas. It’s not a battle over who’s more righteous, more intelligent, or more sophisticated.

Conclusion

We have to pick our battles. I’ve ruined social events because I thought it was the perfect time to argue against Catholicism.

But we should also feel safe and free enough to express ourselves. This can best be done if we change our goals for disagreement.

Instead of wanting to win, we should want to collaborate and learn.

“Seek out people, books or ideas that contradict your current beliefs and one of two things will happen…A) you will discover that you are wrong or B) you will improve your arguments for your own ideas.”

-Mark Manson

Talk to your friends

Two friends laughing together while sitting on a bench

I had an incredible phone conversation with one of my best friends yesterday.

They’re usually great, but this one really hit all the nails: a ton of laughter, business updates, and vulnerability.

One of the silver linings of the pandemic has been the multiplication of how much I value my friendships. I find it vital to go out of our way to visit and maintain communication with the people we share our lives with.

We all have those friends with whom we can go a year without talking to and then just pick right back up where we left off. That’s lovely…but if it’s a close friend, I see that as an utter waste.

Let me explain.

I’m 27. I started my own business this year, am single, and have no kids. I’ve never been more career-focused than I am right now.

All this to say I’m hyper-aware that we’re all living our own lives. We’re stressed. Many of us are still figuring out who we are and what we want. Some of us have families. It’s not like high school where we can spend every weeknight and weekend having fun with our buddies.

However, since that’s the case, there’s never been a better time than right now to sustain healthy and fulfilling friendships.

I’ve had…

• one of my best friends ghost me out of his life with no explanation to this day
• friends get arrested
• friends have quarter-life crises

It’s when we’re the most anxious, the busiest, and most overwhelmed that we need our friends the most.

If we let a year go by without any communication…yes, maybe we can pick right back up. That’s fine. But how many total hours of laughter, connection, and memories did we miss out on?

I love knowing what my friends are working on, are afraid of, and are thinking about on a consistent basis. I’m not saying I need to talk to them every single week, but more than twice a year is preferable.

We can start small. That friend we see once a year…we can bump that up to twice a year. We can set up a monthly call with our busy friends with kids.

It feels like work. Because it fucking is.

Let’s assume the major facets of life are health, wealth, and relationships (broadly speaking). I’ve noticed we put a ton of effort into working on our physical health, our mental health, and our careers, but we sort of expect our relationships to just take care of themselves.

When really they’re just like anything else important to us. They require effort, practice, and collaboration to figure out what works and what doesn’t.

When I’m an old ass man, I want to look back and think I’m glad I did…as opposed to I wish I had…

Right now, I’m so glad I had that phone call with my buddy. And I’m looking forward to visiting him in two weekends.

Dammit, our parents were right

Parents helping their daughter learn to ride a bike

I’m almost the same age my mom was when she had me.

As my friends and I approach the ripe age of 30, I’m realizing more and more that the cliches of getting older are cliches for a reason.

There are the funnier ones, like:

• hangovers get worse
• it’s easier to build fat
• we enjoy quiet alone time more

But in this blog, I’d like to briefly discuss a recent shift in my perspective. Let me explain.

Until now, I’ve relished a fairly obligation-free life. I’ve been single most years. I have no kids or pets. I’ve never owned any real estate.

But something struck me the other day as I was laying on the couch with Hank—my friends’ dog I’m pet-sitting.

Hank the dog laying on the couch
Sorry for the crouch-shot.

I’ve spent the last two weeks walking, feeding, and playing with this other living creature. Here’s what I’ve realized.

We may begrudge adding more responsibility to our plates, but it makes our lives more fulfilling and purposeful.

When I wake up at 6:30 and can’t see straight, I hear a rhythmic thumping as Hank’s tail wags and slams against my wall. It doesn’t matter how many times we do it; he’s elated to get up, eat breakfast, and go for a stroll around my apartment complex.

Every morning.

If that doesn’t motivate someone to get their day started I don’t know what would.

Parents might roll their eyes reading this. I’m aware I’m just watching a dog here.

But this is my first true experience of another living being depending on me to survive and live an enjoyable life. It’s been a real jolt of energy to add some responsibility to my life.

One of my best friends, for example, just had a baby. Even being ‘Crazy Uncle Dill’ has added some meaning to my days.

Her first words were: “Dillan is hilarious.”

I’m not saying I’m trying to have kids tomorrow. I’m saying I’ll remember this as a pivotal mindset shift as I become…dare I say it…an adult.

Simple lesson (pt. 3)

A simple lesson I learned this year:

It’s lovely to craft a successful career for ourselves. But what is twenty times more important is sustaining fulfilling relationships with other people—friends, family, and colleagues.