Friendly feedback

A bunch of people looking at graphs for feedback

One of my besties and I do an annual feedback review. The goal is to be as honest and exposing as possible. Crying is encouraged.

I try to use different questions each year. Here’s 2023’s:

1. What’re you hesitant to tell me for fear it might hurt my feelings?
2. How do you wish I was more like you?
3. How do you wish you were more like me?
4. What impresses you most about me?
5. What would you say at my funeral/eulogy?

These reviews always teach me something I didn’t know about myself. They also prove that openness and being candid don’t kill us but in fact, make us stronger.

I’ll report my lessons learned in a few weeks.

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.

Interviewing a “canceled” person

Meghan Murphy on The YouTuber's Guide to the Galaxy

On the latest episode of The YouTuber’s Guide to the Galaxy, I interviewed Meghan Murphy.

Meghan is a writer, journalist, and podcaster. She’s the editor-in-chief at Feminist Current, a website and podcast dedicated to protecting female spaces. She’s also the host of The Same Drugs, where she and her guests tackle sociopolitical topics like gender identity, race, censorship, and modern feminism. She’s also been on the Joe Rogan Experience a couple times to tell her story.

This is the first time I spoke with a “canceled” person. Meghan was banned from Twitter back in 2018, starting with this tweet:

She has since been let back on Twitter after Elon Musk bought the company. I should note that the Taliban has never been kicked off the platform.

Meghan was so fun to talk to. She has a bubbly sense of humor and is incredibly resilient when it comes to speaking her mind and maintaining her authenticity.

We dove into her criticisms of gender ideology, cancel culture, porn, hookup culture, and third-wave feminism. I’ve never really recorded myself talking about these things and must admit I was a little nervous. But it’s people like Meghan who inspire me to talk openly and honestly about potentially radioactive topics.

In our conversation, we discuss: the 3 tweets that got her originally banned from Twitter, what feminism really is, the overprescription of anti-depressants and ADHD medication, the pros and cons of being an independent creator, what it’s like to be “canceled” and lose friends because of that, and finally, Meghan tells me what a woman is.

Check out the episode here! It was a fun one.

I read 67 books in 2022—Why I’m never doing that again

A library full of books

I like to read. I’m a sucker for page-turning novels, self-improvement books, and fantasy comics.

Given that, it surprises people when I say I never read a book from start to finish until my sophomore year of college.

Up until that point, I had used Sparknotes or had bullshitted my way through book reports and assignments. I’m a role model to kids across the nation.

Cut to: today, where I read practically every day—morning and evening. I fly through audiobooks. I take pages of digital notes while making my way through nonfiction tomes.

In 2020, I read 63 books. In 2021, I read 70. And this past year, with a goal to read 80, I finished…67.

Why the decline? Because I realized toward the end of the year that my goal was kind of stupid.

Maybe stupid is too harsh a word. We’ll say the result I was aiming for was misguided.

Why did I want to read 80 books? To beat my previous record? To commit even more to my discipline and habits?


It was just to say I read 80 books.

It feels good to log what I read on GoodReads. And that’s the problem. I’ve been craving some sort of status. Deep down, I want to be seen as an intellectual who’s well-read. You know, the kind of guy who reads 80 books in a year.

But I can’t tell you what I got from 75% of the books I finished last year.

Finishing a book and understanding its insights are two separate things. I was just going for notches on my literary bedpost.

Sprinting through audiobooks at 3x speed. Whizzing through nonfiction without taking notes or stopping for any reflection. These are great ways to absorb nothing.

There’s an awful high school superlative: “Talks the most; says the least.” Well these past few years, I’ve been going for, “Reads the most; learns the least.”

I’ve obviously learned a lot. But only from a small amount of the things I’ve actually read. So it begs the question…

Would you rather read 50 books this year that give you little to nothing, or read 2 books this year that deeply impact your life?

I’m making some changes so I can lean into the latter option. From now on, I…

  1. must take digital notes for each nonfiction book I read
  2. have to keep a list of insights or changes I’ll make with each read (i.e. a ‘How Will I Use This’ list)
  3. lowered my goal to only read 52 books this year

A book a week. Still quite a lot for some people I imagine. The average for American men is 8.5 books read in a year (yes ladies, I’m single).

It’s time to slow down and focus on depth, not breadth.

If you want to learn how to read more books, check out my previous blog.

If you want to follow me on GoodReads, then go do so you silly, silly goose.

The subtle habit you need to stop doing

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

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

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

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


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

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

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

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

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

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

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

So that’s where it all started.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

It took me a year to get better at chess

My buddy and I started playing chess regularly during lockdown in 2020. We were both competitive and couldn’t leave the house, so we battled on the 64 squares online.

He was better than me. I hated it.

It became my life’s purpose to reliably beat him. That summer, we were both around 1000 ELO. Grandmasters are rated around 2500-2800 ELO.

Since then, I…

Played in tournaments with my friend, with both of us winning trophies and cash prizes.

Played in tournaments by myself, getting absolutely destroyed.

Went head-to-head against chess hustlers in Washington Square Park.

Bullied children.

Hired a chess coach. (In this lesson, he played me blindfolded…and won.)

Interviewed Eric Rosen, my favorite chess YouTuber. I’m writing a chapter about him in my book.

Studied chess puzzles and practiced almost every day.

Started a chess club.

Analyzed my games—looking for mistakes and checking out other possible lines.

Played whenever and wherever I could.

Got to 1300.

Got to 1400.

Got to 1500.

Climbed and climbed in 2021.

Got to 1600 before plateauing for the entire year of 2022.

And after being stuck at 1600 ELO for a year, I’ve finally broken through to the next level. On January 1st of 2023, I surpassed 1700 rating points.

Here’s the graph of my chess journey these past two and a half years. Notice the stagnation between December 2021 and December 2022.

They say it’s around 1600 ELO where a player can’t just increase his/her rating by playing more games. It takes study and game analysis. What got you here won’t get you there.

It was frustrating. I had to confront the humbling reality that much of my love for chess was my constant and visible improvement. When that improvement stopped, I had an identity crisis. I thought about quitting the game entirely more than once.

But cooler heads prevailed. I kept solving puzzles, seeing my tutor, and playing in tournaments despite the resistance.

I believe in cutting out draining and unfulfilling activities. But it’s wildly important to grit through something when it doesn’t feel exciting. We have to know if we can make it out to the other side.

Martial arts. Playing an instrument. Learning a language.

The image of being really good at these things is gorgeous. But the road to get there requires hours of mundane and tedious practice.

I don’t feel like going to most of my chess lessons, jiujitsu classes, or workouts. But the comfort level of a thing says nothing about our ability to do it. And more importantly, once we actually get going, much of that initial resistance fades away.

I’ve never regretted a workout or study session. But I almost always regret skipping one.

Anyway, let’s wrap this up.

My driving force in my early chess career was beating my buddy. That was all in good fun. I’m grateful for our rivalry because it kept me coming back.

But along the way, our games became just one of the many reasons I love the game. I see chess as a perfect cocktail of science and art. I love watching chess creators on YouTube explain games and play at high levels. I just signed up for my first international tournament in Argentina when I move there.

Maybe 1800 ELO will take me another year. Maybe two years.

It doesn’t matter. So long as I’m finding new ways to enjoy the journey. The only thing that matters is staying in the game.

A simple tip for better conversations

Two dialogue boxes showing a conversation

I’ve been connecting with strangers, coaching people, and staying in touch with friends for years. Here’s what I’ve learned about great conversations.

First and foremost, people love to feel important or interesting. It’s a basic human need—to feel like we matter and that people care about us.

That’s why we’d much rather talk to someone who asks us questions than someone who just talks about themselves. We all know people who only share their stories, their opinions, or their knowledge. Being asked zero questions can feel like we’re just being talked at. No matter how captivating or funny they are, eventually we want them to show some curiosity.

In coaching there are three types of listening: level 1, level 2, and level 3.

Level 1: listening through your lens

ex: “That reminds me of the time I did that. It was crazy!”

Level 2: listening through the other person’s lens

ex: “That’s crazy because you typically love doing stuff like that!”

Level 3: recognizing another person’s energy

ex: “You feel more excited than normal. What’s going on?”

When we converse with someone who only uses level 1 listening, we want to shoot ourselves. There’s no back and forth, no collaboration.

Want good conversations? Ask questions. Want great conversations? Ask follow-up questions.

Asking someone what they do for a living is common. Asking them why they chose that line of work, what they love and hate about it, and if they’d still be doing it if they had $1,000,000…most people don’t get asked those questions.

Follow-up questions make people explore and tell us more about their values, personalities, and decisions.

But all this doesn’t mean level 1 listening is bad. In fact, it’s necessary. Which brings me to the second principle of great conversations.

People want to feel a connection.

So while they’re powerful, don’t only ask questions. That turns a conversation into an interview. Some amount of self-sharing and inserting is needed.

What then, is the balance? Try this simple trick.

The 2-for-1 rule.

Ask two questions. Share one thing. Repeat.

If the conversation doesn’t seem to be flowing and they’re not asking any questions in return, take the lead. Ask a question. Then ask a follow-up question. Then share something about yourself.

This ensures that the other person knows we’re interested in them but also connects the dots between them and us.


  1. “How was your New Years?”
  2. “Sweet! How do you typically like to party or celebrate?”
  3. “Yeah, I feel the same. My ideal weekend is a cabin in the woods with a dog and a book.”

Obviously, this doesn’t have to be followed like a script. But the idea is to ask more questions and to connect with the person we’re talking to.


  1. Ask more follow-up questions.
  2. Still share your own experiences, ideas, and knowledge.
  3. Use the 2-for-1 rule: ask two questions, share one thing, repeat.

My 2023 Q1 goals

Happy New Year!

Like most people, I feel a surge of motivation and ambition when the dates change. And like most people, that intensity tends to fade come February.

So this year, I thought I’d try something new: quarterly goals.

What if there was a new year…every three months? Is it possible to keep things fresh and exciting more frequently? How can I balance repeatable systems with novelty? I don’t know if this is the answer but it’s an experiment I’d like to try.

It’s funny. Since starting my coaching practice I’ve made it a point to not be like any regular company. I got into entrepreneurship because I didn’t want a boss or entity telling me what to do or how to do it. I’ve rebelled against the traditional ways of doing things in business.

But as I become more experienced in my career, I’m realizing I’ve been throwing the baby out with the bathwater.

Not that I assault babies (for I do not do that anymore). But maybe if there are practices that companies do, it’s not because they’re all mindless drones who can’t think for themselves. Maybe common procedures are common because they work.

Anyway, let’s find out. I’ve broken down my quarterly goals into four categories: coaching, content, life/health, and people.

Between January 1st and March 31st, here are my major goals in 2023…


  • reach out to at least five people every Monday to connect
  • stay curious and ask follow-up questions
  • get to 40 Google Reviews
  • propose $20k/year


  • new morning writing schedule—Do The Thing! on MoWeFr, this blog on TuTh
  • finish the first draft of my book
  • get to 20 YouTuber’s Guide to the Galaxy episodes
  • get to 45 total YouTube videos uploaded


  • stretch every morning
  • teeth cleaned (dentist) and ears cleaned (ENT)
  • check testosterone levels
  • move to Buenos Aires
  • enroll in Spanish conversation course


  • work on best man speech with my comedian friend
  • ask out 25 women (in person, face-to-face)
  • create a CRM for my friends with their goals, projects, and wins

And finally, an affirmation…

“On April 1st, 2023, I will be in Argentina, drinking wine with new friends, with 500 YouTube subscribers.”

Have Q1 goals of your own? Email them to me.

Let’s do this!

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?


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.


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. 🥳

My 5 favorite books in 2022

Stacks of books in an old library

Here they are…

1) Models: Attract Women Through Honesty

By Mark Manson (Goodreads link).

This book represents the newer, more wholesome era of dating advice. A decade or two ago, men had pickup artistry: scripts and tactics to woo more women and have more sex.

But that’s all super narcissistic. Pickup artistry sees women as prizes and status symbols—not living, breathing human beings with lives and values of their own.

I’ve been a single guy most of my life. I’m confident, I’m extroverted, and I consider myself to be reasonably successful. And the act of putting myself out there with women is almost always a terrifying one.

In Models, Mark argues that the key to attracting more women has nothing to do with pickup lines or suave tricks. Instead, it’s all about becoming the best version of yourself as a man. Don’t pretend to be someone you’re not; lean into your strengths and create a life that fulfills you. That’s what people find attractive.

A simple example of this is not texting back right away. We shouldn’t wait hours to respond to pretend to be busy. We should have an active life so we’re genuinely not always available.

This all sounds like common sense now, but being more attractive can really be boiled down to:

  • working out
  • having hobbies outside of work
  • being excited by life
  • flirting with physical touch and teasing
  • never being needy
  • being willing to say no and stand up for your values
  • risking rejection
  • smiling and laughing more
  • asking curious questions

I’ve since used many of the principles in this book and have noticed way more fluidity in my flirting and conversations with women.

2) Becoming

By Michelle Obama (Goodreads link).

It’s really easy for me to see a well-known figure—an actor, athlete, or politician—and totally forget they’re human beings. They had a childhood. They have fears and insecurities. They want to raise healthy children. They want to be valuable.

Michelle’s storytelling abilities reminded me of Matthew McConaughey’s in his memoir Greenlights. Both of them make you feel like you’re at the dinner table or around a campfire listening to them talk about their lives.

Some of my friends know this, but I’m not a black woman who was raised in South Side Chicago. Despite that, I felt much more connected to Michelle’s story than Matthew’s.

Why? I love Matthew McConaughey but he has almost an unrelatable level of confidence.

My point is: Michelle spends every chapter being vulnerable. Sharing mistakes, frustrations, and anxieties. And being vulnerable is the only true way for others to relate.

When she and the Queen of England were complaining about their sore feet at an event. When she was trying to get Barack to quit smoking. When she was in her twenties and didn’t know what she wanted to be when she grew up. When her best friend died. When everything she wore made headlines. When she and her daughter tried to giddily sneak out of the White House.

I saw her. I saw these things happening. I laughed when she marveled at the little family moments. I cried when she was devastated.

One of the last sentences in this flawless memoir sums it up perfectly:

“I’m an ordinary person who found herself on an extraordinary journey.”

What a journey it was.

3) How to Quit Porn

By Brett McKay (Goodreads link).

Porn is wild. It’s something most people consume but don’t talk about.

I haven’t watched it in a long time because of the noticeable physical and psychological consequences. This book has been a huge help in breaking down the science of why we crave porn and how we can remove the habit from our lives.

(Since the vast majority of pornography is made for heterosexual males, it’s written for that audience; but it’s still an informative and fascinating read regardless of demographic.)

A teenager with an iPhone today will see more naked, beautiful women in 60 seconds than a man 100 years ago would see in his lifetime. Our brains aren’t evolved to handle that level of stimuli.

This dopamine hit from porn creates a plethora of issues:

  • It creates unrealistic body standards for women.
  • Watching a ton of it can make it difficult or impossible to get aroused without it.
  • Men often feel deep shame immediately after.
  • Watching porn reduces willpower, energy levels, and motivation.

The book describes porn as “sexual junk food.” It shouldn’t be seen as this shameful, disgusting addiction. That gives it too much power.

But on the whole, it is a net negative for most guys. Like any habit, this one can be broken. And since I broke it, I’ve experienced nothing but clear benefits.

(For anyone who wants to learn more about what porn does to the male brain, but doesn’t want to read this book, I’d recommend this short miniseries.)

4) Invincible

By Robert Kirkman (Goodreads link).

An action-packed comicbook series that they turned into a show. I tore through this one.

It’s like many other superhero comics but with murder, deep character development, and intricate world-building. It handles romance, betrayal, parenting, political corruption, friendship, teenage angst, and many other mature themes. All while being a funny and captivating page-turner.

5) Building a Second Brain: A Proven Method to Organize Your Digital Life and Unlock Your Creative Potential

By Tiago Forte (Goodreads link).

If this was the only book I read this year, it would be worth it.

Tied with Getting Things Done, Tiago’s Second Brain system has easily had the most impact on my productivity and workflow.

The idea is simple: we’re working with stone-age programming in a hyper-modern world. Our brains haven’t evolved much in the last 100,000 years. We still crave carbs, dopamine, and sex all the same.

But now that we have infinite access to all the information in the world, we expect our meat machines to catch up. But they can’t.

We’re not meant to remember every single thing that happens to us, every task we have to complete, or every idea we’ve ever had.

Enter: a Second Brain.

This simple personal knowledge management organizes anything you read, listen to, or think of. It categorizes things based on the projects you’re working on—whether it be finishing an essay, making a presentation, or redecorating the living room.

This book can be used as a step-by-step workbook. And I felt the result immediately: a feeling of decluttered peace. It’s also made writing blogs and making YouTube videos much easier.

I’d recommend this book to anyone who wants to take control of their digital lives—especially creatives or entrepreneurs.


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.


The curse of caveats

A woman arguing with her iPhone

I’ve been writing this blog and uploading podcasts since 2019. Since then, I’ve said a lot of things that pissed people off.

Perhaps not as many things as Kanye. But I’ve learned a lot about expressing oneself on the internet.

Back in the day, you had to be an author, politician, or activist to be able to spread your ideas to the masses. Now, you just need wifi. There are obvious pros and cons to this.

On the upside, more people have more freedom to exercise their basic human right to free speech. Individuals can go on social media or build a simple website, type out their thoughts, and criticize their own government if they want. That’s a beautiful thing. There are dozens of countries where this is unthinkable.

On the flip side, any shmuck can log on and build a community around the idea that the earth is flat. Anyone’s aunt can go on Facebook and start a comment war with her political opinions. With more access to ideas comes more energy needed to sift through the shitty and divisive ones.

Every single one of us has easy access to something that only a few people had 20 years ago: an audience.

Social media, algorithms, blogs…The internet is designed to spread ideas that get clicks and keep people on the platforms. What awesome power.

When I started writing this blog, it took months to get any sort of traction. I wanted badly to have a voice and share my philosophies and strategies for living a good life.

But once people started actually tuning in, I watered down my writing.

Since I’m a fairly agreeable person at heart, I tend to avoid rubbing people the wrong way (agreeable: wanting others to be safe and comfortable). That meant I was super hesitant to share any sociopolitical opinions, especially ones I knew my friends would disagree with. I also muzzled my more tough love and hardline approaches to self-improvement.

Even when I did write about these things, I would caveat and qualify every single point I tried to make. I read one of my old blogs a few days ago and counted five justifications.

At the time, I thought this made me a strong thinker and arguer. I believed it would broaden my scope and allow me to reach more people.

But it just made my writing stale and lifeless.

There’s a great quote I try to remind myself when I type these blogs and produce my podcasts: “When you create for everyone, you create for no one.”

Thus is the curse of caveats. If you walk on eggshells to avoid anyone’s disapproval or disagreement, your perspective has no meat to its bones.

Let’s look at two examples.

1) “Cats are terrible pets.”

2) “A lot of people think cats are terrible pets. Obviously, not everybody thinks this. And it must be said that even those who prefer dogs can enjoy petting a cat from time to time. I’m not trying to insult any cat owners. I just want to get to the truth.”

(Genuine caveat: I love cats. It was just an example lol.)

#2 will reach no one. It reads like a boring academic essay and makes no one feel anything. It proves I don’t have any conviction in what I’m saying.

#1 on the other hand is bound to be polarizing. It’s guaranteed to invoke emotion.

Readers who have a cat will likely get pissed and baffled by my making an objective statement from a subjective feeling. Readers who hate cats might bask in the mutual humor of benign hatred.

In summary, I’m looking for one of two possible results. The first is someone reading my stuff and it really resonating. They see their own thoughts and experiences in my words. The second is someone challenging what I say and offering their own perspective.

I’ve had countless emails where people send me one of these two reactions. And I love it every time. It leads to deeper connections and fruitful conversations. I always come away with a clearer picture once I’m forced to think even more about whatever it is I wrote.

That said, I encourage any of you to reply to any of these emails. I respond to all of them.

Almost every topic is nuanced and complex. But that doesn’t mean we have to caveat and qualify every minute point. When someone calls that stuff out, we can just continue to explain our meaning or begin to have our minds changed.

That’s called conversation.

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.

These four words have changed my life

My jiujitsu coach, Carlos Catania.

I’ve been going hard in the self-improvement paint for about five years now. Between books, blogs, and YouTube, I’ve consumed thousands of hours of content. The Kool-Aid tastes oh so sweet.

After a while, you start to realize all these gurus and audiobooks are saying the same things:

  • take action
  • make small, consistent changes over a long period of time
  • remove distractions
  • define where you want to go
  • exercise and eat well
  • get 8 hours of sleep
  • surround yourself with supportive and healthy people
  • focus on one important thing at a time
  • make lots of mistakes and get feedback on them

That’s really it. Please Venmo me @Dillan-Taylor for changing your life.

Jokes aside, I spent these last several years finding books and leaders whose messages really resonated with me. And there genuinely are books that have changed my life (Atomic Habits, Essentialism, The War of Art).

But one trap I’ve experienced and seen other people experience in the self-help world is that of endless searching. Seeking the perfect formula or concept to make the rest of our lives easy or effortless.

I would read a book about focus and, armed with new tools, feel super motivated to sit at my desk for hours each day to build a business or edit a podcast. Then when I sat down, it would be difficult, confusing, or boring. Then I’d think, “Huh, I thought this was supposed to be easy now?”

Shockingly, my business wasn’t building itself, my checking account wasn’t going up in my sleep, and my YouTube channel wasn’t flooding with subscribers. It’s like I thought the motivation I gathered from consuming content was all I needed.

Then reality would set in. “Wait, you mean I actually have to do this shit…like, all the time?”

After all this searching, and after coaching people for years, I’ve come to a harsh conclusion:

No matter how skilled or how wise we become, life will often feel challenging, confusing, and boring…and that’s okay.

There’s no place to arrive at. No enlightenment. No point where we’re just “good” from now on. It’s a never-ending mountain to climb. We’re never “done.”

So how then do we measure our success? If it never ends then how do we know we’re where we’re supposed to be?

For me, it’s these four words:

More often than not.

It’s not about choosing great habits and practices and never breaking them. If I want to get fit, it’s not about working out every single day. But it’s also never going to happen if I can skip and cheat whenever I want. So it has to be somewhere in the middle.

More often than not is that middle.

More often than not, am I doing the things I need to do to get in better shape? Am I eating well, exercising, and getting good sleep more often than I’m choosing not to do those things?

We can apply this to studying for school, growing a YouTube channel, or learning a new skill.

So let me ask you.

More often than not, are you doing the things you need to do?

I’m moving (not to NYC)

A sign in the middle of the desert pointing to different South American cities

My roommate just announced she’ll be moving out in March. This sparked three emotions.

  1. I’m super excited and proud of her for leveling up her life—starting a bigger and better job and moving in with her boyfriend.
  2. I’m sad to end the best living situation I’ve ever experienced.
  3. I can’t ignore the anxiety that comes from figuring out where to pack up and go next.

As you might’ve guessed from the title, I’ll address #3 in this post.

My immediate thoughts were on staying in this apartment, finding a replacement roommate, or getting a one-bedroom nearby. But hidden underneath was the reminder that I was supposed to move to New York City this fall.

Not only do I feel like I’ve given all my readers blue balls by not actually going. I also just have an itch for adventure that hasn’t been scratched. The last time I went somewhere totally new and had to rebuild myself, my community, and my skills, was when I studied in Germany at 20 years old.

Oktoberfest, 2014.

That was eight years ago. Now, I’m (hopefully) much wiser, more competent, and more secure. If the immature boy that was Dill can live in another country, make life-long friends, and learn a foreign language…what’s stopping me now?

The obvious answer is nothing. Well, nothing but fear and excuses.

Cut to the chase

After the teaser email a few days ago, I got bombarded with texts asking where the hell I was off to. I must say making people wait for it brought me sadistic pleasure.

I’m moving to Buenos Aires, Argentina. 🇦🇷

Just for a few months. One of my besties has really helped me along with all of this.

“Do I go here for a year,” I asked. “Or do I stay put for another 12 months until I figure something else out?”

“Dill,” she replied. “You’re thinking in terms of one-year leases. Why don’t you lower the bar and just go somewhere for one to three months?”


She lived in Rwanda for years and met her husband there. Needless to say, this is someone I’m glad to have in my corner when it comes to living in another country.

When I confirmed my interest she started blasting me with articles and how-tos. I read every single one. Best South American cities for foreigners. Cheap Spanish classes online. How to secure health insurance and visas abroad.

What seemed like a nice little fantasy quickly became a set of clear-cut action steps. I renewed my passport and bought my plane ticket.

Why Buenos Aires?

I’ve been wanting to travel to Argentina’s capital city for years. It’s gorgeous, clean, and safe (especially relative to other South American cities).

But on top of that, it’s reliably rated as the #1 spot in the continent for digital nomads: people who can work anywhere in the world so long as they have a laptop and internet connection. As an online coach, a podcaster, and a writer…this is perfect for me.

For anyone interested, here’s a breakdown of the city from NomadList.

As with any place, there are tradeoffs. Let’s go through the cons first.


1) It’s a 10-12-hour travel day away from my friends and family.

You might be asking, “But Dillan, didn’t you say a few months ago your #1 value was close proximity to the people you love?”

Nothing gets by you, dear reader.

Yes, quality time with my peoples is something I cherish. That’s what the two-month excursion is for. 60 days will fly by I’m guessing.

Two friends have already shared ideas of coming down to visit. My birthday is right before my departure and my community’s annual coaching retreat is just after my return. There will be no shortage of friend time in these coming months.

Plus, Buenos Aires has a thriving and organized entrepreneurial community. Meetups, events, coworking spaces…It will be hard for me not to befriend like-minded individuals who also speak English.

I plan on taking a weekly Spanish conversation course. But with only two months, I’ll be leaning into my English-speaking compadres.

2) Uh, I think that’s it.

Some sites claim the internet is slow in South America. But others have said it’s no problem. So we’ll see.

A market street in Argentina


Okay, the fun part.

1) As stated above, BA is a clean, safe, and beautiful city. It has beaches, high-quality nightlife and restaurants, and quaint and quiet suburbs.

Aside from the dirt-cheap public transportation, the city is incredibly walkable. I plan on living in the neighborhood of Palermo Soho, which at most would be a 10-minute walk to my gym and coworking space.

BA is said to feel more European than South American. It’s super organized and stylish. I’m certainly one of those things.

2) Same timezone.

Simple as that. I wouldn’t need to change anything about my schedule. Sessions, calls, sleep cycle…None of it shall be touched.

3) It’s ridiculously cheap.

The average cost of living (including rent, utilities, food, and fun)…is around $1000/month.


I pay more than that in rent alone.

A nice bottle of wine in BA is $3. A nice dinner? $9. The luxury one-bedroom apartment I’m looking at booking is $700 per month. It’s nicer than my current two-bedroom and costs $400 less.

The big reason I didn’t move to NYC was the disgusting cost of living. But now I feel like I’m being financially irresponsible for not moving to Argentina.


There are hundreds of reasons I could rattle off as to why I’m excited to sell all my belongings and fly to South America. The feelings of accomplishment, the new relationships, the skills I’ll develop.

But underneath it all, I’m just pumped to inject some novelty into my life.

I’ve grown into an entirely different human being these past five years. From attempting suicide, to starting to build my life, to working at a restaurant, to starting a blog, podcasts, and YouTube channels, to working in sales, to quitting that sales job to start my own business, to playing chess and doing jiujitsu, to making my business profitable and sustainable, to writing a book.

It’s been a wild ride. I’ve tried a plethora of new things and have been lucky that much of it has stuck.

But I’m still craving something to drastically take me out of my comfort zone. I thought it was New York. It wasn’t (not yet, at least).

So for now, I’ll be enjoying these holidays and the last few months with the best roommate I’ll ever have. I’ll sell or donate all my furniture, books, and clothes. I’ll continue to live frugally to save and invest my money.

And of course, I’ll keep writing about all of it.

Stay tuned. ✌️

Add accountability to your life

A coach looking at his clipboard and holding his team accountable

Grindset: a funny term for one’s ability to work their ass off every day without anyone telling them to do so.

Some people are able to build on their own, get lost in deep work, and grind away using only their passion and discipline. I am not one of these people.

Let me explain.

When I interviewed Courtland Allen, founder of Indie Hackers, he mentioned the accountability problem.

“It’s crazy how most people don’t do the things they know they should,” he said. “Exercise, spend time with friends, eat well, create things…We know this stuff makes our lives way better but we don’t do them. But we’ll easily show up on time to a nine-to-five job we don’t really like every single day. That’s crazy to me.”

Why is that so much easier? Because we have people holding us accountable to do so.

If we show up late to a job, we experience some sort of damage. It’s embarrassing. We could get written up. Our bosses and coworkers are watching.

But when it comes to writing a blog, recording a podcast, or building a solo business…it’s just you. There’s no one over your shoulder telling you what to do and when to do it. If you take a day off to watch TV, no one will reprimand you.

Earlier this week, I wrote about how my creative projects burnt me out. Aside from reorganizing and reigniting myself, I did something else to help with the problem mentioned above.

I got an accountability partner. Actually, I got two.

They’re both fellow life coaches and dear friends. With one, we log our working hours using Toggl and send the other person our weekly summary every Monday. With the other, I got a bit creative.

I made a shared document between the two of us with a weekly list of my creative goals:

  • 2-3 YouTube clips
  • 2 TikToks
  • 2 blogs
  • 1 podcast episode every other Thursday
  • a reflection of how it went

As I work on these goals, he can see which ones I get done. If they’re not all completed by the following Monday, he gets to grill me. A la accountability.

I can already feel the power of having to report to someone. I love the freedom of not having a boss but accountability keeps me at this desk until the job is done.

If you’re having trouble exercising, for example. If you hired a personal trainer and bet $3000 you’d never be late to a session, it would become super easy all of a sudden.

We often don’t do things because we don’t feel incentivized to do things. We say things like, “I can never remember people’s names,” or, “I can’t wake up early.” But if I told you I’d give you $1m to remember the next 20 names you meet and wake up at 5 am every day for the next month…you’d have no problem.

So what do you want to do more of or less of? Who can you ask to help hold you accountable?

Reply to this email and let me know.

Do these 2 things when you’re overwhelmed

Many of you may have noticed I took a hiatus from this blog for several weeks. Between the coaching business, the podcast, and finishing the first draft of my book…I’ve felt creatively burnt out.

For the first time since starting this blog in October 2019, I opened up WordPress, began typing, and stopped after writing a couple sentences. Anything I posted would’ve been forced and inauthentic.

So I took a week off.

One week turned into two. Then two became three. Just like working out, the more we skip something, the easier it is to continue skipping it.

Even after revamping the workflow of my podcast, I still felt overwhelmed and unclear as to how I was going to get everything organized. I took entire days off. I procrastinated and avoided all my creative work.

In other words, anything that required me to sit alone in my office and push through resistance…didn’t get done.

Coaching and getting on calls were non-negotiable. The accountability of another human being waiting for us is a powerful thing.

So what to do?

Well, after getting coached on it, I did two things.

1) Check your health-trio.

Diet, exercise, and sleep.

What are you putting into your body? Is it a lot of processed foods, sugar, and empty carbs? You don’t have to be a nutritionist to know you’re not feeding your body well.

I try to go 80/20—80% of what I eat is well-sourced protein and produce, nutrient-dense, and optimized for health rather than pleasure. The other 20% is for me to enjoy life. Pizza, burgers, cheesecake…

When it comes to working out, you don’t have to be a model or an athlete. But you have to do something that gets you sweating every week. 15-minute workouts, going for walks or runs, playing a sport you love…There are simple and enjoyable ways to move your body. You’ll feel better and will eventually start looking better.

I highly recommend the app FitBod; it’s the reason I’m in shape. Hiring a personal trainer is also great. But if you want to start small you can just find a friend who you can go on walks or runs with.

Finally, how many hours of sleep do you get each night?

Sleep is often the first thing people sacrifice and it’s arguably the most important medicine we can take. The good news is there are minimal side effects and it’s free.

97% of adults need seven to nine hours of sleep each night. Not consistently doing so leads to increases in anxiety, cravings, and avoidance. It also decreases motivation, focus, and happiness levels.

Sleep trackers are incredibly useful. I recommend the app SleepCycle or the Whoop strap.

If you’re putting garbage into your body, sitting still every day, and sleeping poorly…you’re obviously going to be struggling to get organized. That’s like driving a car with all the warning lights on. Take care of the machine that is your body.

2) Break everything down.

Take all your personal and professional projects, and chunk them into their simplest, easiest, clearest steps. This is something we should do every week.

James Clear said, “Most people think they lack discipline when they really lack clarity.”

The most common reason we procrastinate is that our tasks are unclear. When things are ambiguous they seem much more difficult than they actually are. We have to really flex our problem-solving muscles.

Or we could just take the time to make things clearer.

Last week, I wrote out all my “projects.”

  • car stuff
  • start posting podcast clips again
  • declutter office and room
  • finish first draft of book

Nice and simple, eh? Nein.

For weeks, I would put things like “take care of car stuff” on my calendar. Then when it came time to do it, my brain would go, “What the hell does that even mean? What’s step one?”

And that’s the key. Can you break down whatever you need to do into the next three actionable steps?

For me, “car stuff” became “call the title office, go get the emissions tested, and go to Home Depot for screws to put on the front license plate.”

Ah, much clearer. That all seems manageable.

When our brains need to take more steps to sift through the fog, they become much more likely to throw in the towel.

So this morning, with my health trio in check, and with my projects broken down, I feel much more prepared to get things done this week.

How do you combat overwhelm? Email me and let me know.

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.

Why I ate Mcdonald’s last night

I ordered McDonald’s last night. Why?

Because I wanted to.

One Big Mac. One Spicy McChicken. One Large Fry. Delicious.

For the whole month of September, I consumed zero:

  • alcohol
  • sugar
  • pasta
  • bread
  • processed food

Doing 30-day challenges like this always enlightens me about portion control and cravings. I ate McDonald’s and didn’t feel ashamed because 80 to 90 percent of my diet is nutritious.

I eat primarily home-cooked meals, farm-raised meats, and organic produce. Fancy boy, right?

But the truth is I’m not well-versed at all when it comes to nutrition. The same goes for fitness.

I go to the gym three times per week, do jiujitsu two or three nights a week, and see a personal trainer twice a month. To someone who doesn’t exercise, that may seem like a lot. But I’m not doing intricate or complicated workouts. It’s all simple yet consistent.

And that’s the key word here: consistency. You are what you do consistently.

One fast food meal won’t make you overweight or out of shape. Consistently eating junk and never exercising will.

Just like one great workout won’t make you an athlete. Consistently making yourself sweat and eating mostly well will.

So, what are you doing (or not doing) consistently? What results are you getting?

The science of friendship

A group of friends sitting and laughing around a coffee table

A good friend sent me a podcast yesterday. It was a panel of academics sharing research on the relationships of friends.

I thought I’d go for a short walk and listen to 10-15 minutes of it. But it was so insightful and entertaining, I spent an entire hour just walking laps around my apartment complex in the cold and rain.

It’s called, “Time for a Friendship Reset?” by Aspen Ideas to Go. For anyone who wants to listen to it, it’s available on Apple Podcasts and Spotify.

They discuss how limited the research on friendships is. In doing so, they share relatable and digestible experiences we’ve all gone through in our friendships.

Here are a few of my biggest takeaways:

  • Men tend to bond with each other through activities and often avoid maintaining friendships with openness, vulnerability, and communication.
  • There’s a powerful script when trying to save an eroding friendship: Here’s why I loved our friendship in the past—you made me feel this way. Then it seemed like this happened and now I feel this way. I’m sorry I didn’t have to courage to say anything until now. How have things happened from your perspective? What can we both change moving forward?
  • It’s totally natural to feel jealous of our friends. The same is true of those who take up time with our closest friends.
  • Friendships are often more powerful than family relationships. While you can’t choose your family, friends are close bonds that are entirely based on two people choosing to spend their time, love, and attention with one another. There’s no contract like there is with a spouse or a blood relative. That’s also why it hurts so bad when someone chooses to let the friendship die.

If you check it out, reply to this email and let me know what you got out of it!

The 5 traits of the most successful people I’ve coached

A hiker at the top of a mountain cliff

This week, I hit my 1000th coaching hour. That means I’m a certified Master Insight Coach. It took me one year, six months, and four days.

I’ve coached nearly 100 different people these last few years. This has given me a pretty good look at how we make decisions, what we’re afraid of, and our capacity for growth.

I’m lucky to have been able to coach some amazing people. Some of them I see myself working with for years and years to come.

Humans are infinitely complex and quite simple at the same time. We all have different personalities, strengths, and limiting beliefs. But we all want stuff, feel there’s stuff in the way of that stuff, and then either do something or nothing about it.

There are five major traits I’ve seen in the people who crush life. I see these folks as genuinely successful.

By “successful,” I’m not factoring in their income. I measure success by how fulfilled a person is by the life they’re creating.

Here we go.

1) Ownership

The top characteristic I’ve seen in people who move in the direction they want.

They don’t blame things outside of their control for their situation. They might mention them, but they quickly dive into what’s in their control to do something about it.

“Not everything is my fault, but it is my responsibility.”

The people who actually get what they want in life understand that if they want to experience change, they have to change.

2) Doubt, fear, and anxiety

“You’ve got to be fearless” is bullshit advice.

Humans are wired to stress about things. Only now, we don’t worry about getting attacked by animals; we ponder our purpose in life.

No matter how well a client is doing, they tend to still be afraid and doubtful as they level up.

  • “I don’t know what I’m doing.”
  • “Maybe I’m not cut out for this.”
  • “What if I screw up now that the stakes are higher?”

I’ve heard this all a thousand times. But they always get through it.

Which brings me to #3…

3) Doing the scary thing anyway

Successful people realize that they’re allowed to feel how they feel. Emotions come and go naturally.

But they don’t let these feelings stop them from doing what they want. They experience the growing pains of improvement.

It goes like this:

Step 1: I want this new thing
Step 2: I’m going to take action to get it
Step 3: This isn’t as easy as I was hoping
Step 4: I don’t know if I can do it
Step 5: I’m kind of doing it and it’s actually not that hard
Step 6: I can do anything I set my mind to
Step 7: Repeat

4) Committed and focused

The people who are most serious about improving their lives play full out.

They show up on time, are ready to take notes, and are eager to take action.

They are also prepared to invest in themselves. Not just with money, but time and effort as well. They make their well-being a priority.

5) Growth mindset

Those who climb the mountain know the only thing between where they are and where they want to go is time and effort.

They stay away from fixed phrases like “I can’t” or “I’m not the kind of person who…”

Deep and meaningful change is possible for every single one of us. The only way it wouldn’t happen is if we choose for it not to happen.

Take a person who is convinced they couldn’t run a marathon. They’re unlikely to start training for one. They won’t register for one to give them the incentive. They won’t find a training partner to hold them accountable. Six months will go by and they’ll be in the exact same place…thus proving themselves right.

Successful people realize the journey will be more difficult, uncomfortable, and complex than they originally thought. But they keep practicing and doing.

The hard becomes easy. Then they look to new challenges.

Which of these traits do you feel you have? Which do you think you need to work on? Reply to this email and let me know.

10 tricks to living a shittier life

An ostrich with its mouth wide open

Since attempting suicide in 2017, I’ve been obsessed with living a better life. I’ve even made a career out of helping people improve theirs.

But for those of you who have it too good, are too fulfilled, and are looking to downgrade…here are 10 easy tricks to help you start living a shittier life today.

1. Talk shit about people when they’re not around.

By saying things about others you would never say to their face, it makes you more resentful and cowardly. Also, when you gossip and badmouth around friends, they’ll subconsciously wonder if you do the same to them when they’re not around.

People get drained by toxicity. This is a great way to decrease people’s energy when they’re with you.

2. Laugh at exercise.

67% of Americans are overweight. That’s totally fine. The number should be higher.

Exercise has a plethora of benefits: increased confidence and energy levels, mental clarity, heightened motivation and willpower, increased general attractiveness, lower risk of disease later in life, and more strength overall.

So it should be avoided at all costs. Try viewing it as this uncomfortable, sweaty activity only meant for athletes. Be confused as to why anyone would put themselves through physical strain. Making fun of it will make you feel better for not doing it. Tell people you love your body by doing nothing to protect or improve it.

This is a great way to feel worse physically and mentally throughout your day.

3. When in conversation, focus on being right.

99% of people know something you don’t. But they must never know that.

Act as though you are enlightened and have all the answers. This will make conversations with you boring and non-collaborative. Be the teacher, never the student. Don’t ask questions. Constantly preach your knowledge to others, especially when they don’t ask for it.

When someone disagrees with you, the goal should not be to understand where they’re coming from and find common ground. The goal is to explain why they’re wrong and you’re right. Shame them into believing this if you have to. That will guarantee they never will and it will disconnect you both entirely.

This is a great way to keep people from feeling safe to explore their thoughts around you.

4. Drink more coffee, soda, and booze than you do water.

75% of Americans are chronically dehydrated. Again, those are rookie numbers.

Consuming a lot of caffeine and sugar can increase anxiety and stress levels. Downing alcohol frequently weakens the immune system and lowers sleep quality. This is all a perfect cocktail (pun intended) for a shittier life.

Drinking water protects organs and tissues, carries nutrients to cells, and flushes bacteria from your bladder. Sounds awful.

Skip a cold glass of water and reach for coffee first thing in the morning. This is a great way to start the day in a manic state.

5. Avoid doing the things you think would be cool to do.

We all have things we’ve been talking or thinking about but have taken zero action on. Learning Spanish. Dance classes. Starting a business, blog, or podcast. Painting. Piano. Pickleball.

The more we avoid actually doing any of these things, the more regret we’ll feel when we’re older. The pain of longing is guaranteed to feel shitty.

There will always be 1001 reasons why it’s inconvenient to start something. Let those excuses keep you from having more fun, improving your skills, and being more fulfilled.

This is a great way to wake up at 60 and question why you didn’t actually pursue your dreams.

6. Start and end your day by looking at your phone.

If you’re looking to add compulsion and anxiety to your life, this is one of the simplest ways.

Rather than giving your mind space to wake up or wind down, feed it with notifications, news, and chaos. Reading, stretching, or meditating would make the rest of your day more peaceful and present.

Fuck that. Keep your brain spinning every waking hour.

This is a great way to never feel done and to be addicted to a screen.

7. Give in to most of your cravings.

We all indulge. But try to avoid moderation. Make indulgence a lifestyle. Give in to temptations several times a week.

Junk food. Porn. Entertainment. Booze.

Doing this over and over again will supplant this story that you’re addicted to your cravings. When really it’s just a habit you currently have that can be broken or replaced. But don’t let your mind know that.

Treat yourself to whatever meal you want. Skip exercises or difficult things. You’ve earned it. Your body doesn’t care that you’ve earned it but hey…you’ve earned it.

This is a great way to be less fit and powerless against your compulsions.

8. When talking to others, talk more about yourself than about them.

Being interested in others is the best way to make them interested in you. They’ll feel seen and heard. People will enjoy your company more. They’ll feel connected to you.

Steer clear of that. Avoid asking curious questions. Definitely don’t ask follow-up questions to prove you’ve been listening. Try to stick to your stories and your opinions. Keep it one-sided.

This is a great way to weaken rapport and have worse conversations.

9. Take responsibility for the emotions of other people.

There are 7.98 billion people on the planet. If you do or say anything that could offend, frighten, or rub someone the wrong way…you should be arrested.

You’ll never agree with anyone 100% of the time. So it’s best to walk on eggshells and muzzle yourself to avoid any confrontation or misalignment. Don’t be yourself. Definitely don’t ask for what you want. If there’s even a slight chance of someone else being uncomfortable, stay silent.

It’d be easy enough to apologize or have a conversation if you ever do hurt anyone. But it’s best to avoid it entirely.

This is a great way to remain a shell of yourself.

10. Stay soft.

View discomfort as the worst-case scenario. Challenging moments will strengthen you. They’ll sharpen your communication and problem-solving skills. Avoid that.

You should be triggered easily. We all care about things. But you should get unhinged whenever you see or hear something you don’t like or agree with.

Shun people who have differing opinions from you. Judge them. Question their morality and humanity. Try to shame others into believing what you believe. It’ll never work. But you’ll feel superior and enlightened.

This is a great way to stay mentally weak and to keep your head in the sand.

Hope that helps! Let me know if these 10 tips help you decrease your quality of life.

One question: the best feedback you’ve ever gotten

Two men giving feedback to one another at a conference table

Receiving feedback from our friends, family, and colleagues is one of the quickest ways we can improve ourselves.

It can also be extremely painful.

Our egos can get hurt. Not everyone’s opinions are valid. We see what people really think about us.

But building thicker skin and understanding we’re far from perfect are some of the most valuable things we can do. I ask for suggestions for this blog. I do regular improvement sessions with my closest friends. It can be uncomfortable but it always leads to something better.

If none of that interests you but you want to make improvements in your relationships, health, or work…ask this question to the people closest to you.

What’s something you’re afraid to tell me because you think it would hurt my feelings?

The answers you hear may sting in the short term. But you’ll start being more mindful, improving skills, and seeing reality for what it is.

Try it out. Let me know how it goes.

I got paid to play chess

Photo from:

Yesterday was the quarterly Baltimore Charm City Chess Tournament. I played in the U1400 section.

Typically, I compete with my buddy. But he was on a work trip so I was left to my own devices.

I got to the hotel early, as I always do. After signing in and dropping off my bags (my chess set and food), I took my usual stroll around the Johns Hopkins campus.

It always gives me anxiety walking on a college campus. It brings me back to my days of skipping class and feeling low status. Sometimes I feel insecure pacing by students as a 28-year-old man with a mustache.

But it was a lovely day. The air was crisper as fall approaches.

When it got closer to 10:30 I headed back to the hotel to see the first pairings. My first of five opponents was a teenager with a lisp.


In the first game in my last tournament, I played against a four-year-old and nearly lost. I’m not proud of it, but losing to a kid has a particular sting to it.

But this teen was good. He slowly squeezed me until I blundered a piece and resigned. After losing, my mind flooded with excuses.

I’m tired. It’s not as fun without my friend here. I might leave early and enjoy my Sunday.

Fear of failure leads our minds to hilarious places. I texted my buddy, “Never again will I do a tournament by myself.” I was so salty!

If you’ve ever climbed a mountain or worked on a difficult project, you know this feeling.

Starting or launching a pursuit is exciting and novel. We have these shiny images of what it’s going to be like. Then we get going.

Nine times out of ten, it gets hard or boring or both. We have to push through resistance. We need to improvise and solve problems we didn’t account for.

At some point, we even question why we wanted to do this thing in the first place. That’s where I was at. All I could think about was losing my remaining four games.

But I stayed.

In game two, I demolished the poor guy and he resigned after 13 moves. Chess was fun again.

I texted that same friend, “Nvm just beat a guy in 13 moves my spirits have lifted.”

It’s wild how easily our states can change. It makes me question reality. How much of our perceptions of what is going on are painted or tainted by how we feel at that moment? I went from genuinely hating chess to being eternally grateful for spending a day playing my favorite game.

With my newly-found momentum, I won the rest of my games—tying for second place and winning $100.

The winner and I played in my first-ever tournament last winter. We drew. I saw him and congratulated his performance.

These events always pump me up to improve my game and play more. If you’d like to see my actual games, here’s a link to a study I made. I even annotated some of them so you can see my thought process.

Having hobbies and activities that have nothing to do with work or money is rewarding and therapeutic.

What are your favorite things to do outside of work? Let me know.

(PS—Here’s my favorite final position from round 5. It’s rare to have the enemy king so deep in your own territory.)

4 questions to avoid repeating mistakes

A table full of writing utensils

It’s been a while since I emailed you guys a blog. 11 days to be exact.

While I’m sure some of you are delighted by this, it’s left me feeling guilty. When you subscribe to something, you do so because you expect value from it.

Some of you support the blog financially. Some of you neglect your children and careers just to read what I write. I’m so grateful.

The truth is, I put too much creative work on my plate at once. Here’s my to-do list from the last 30 days:

  • finish rough draft of Do The Thing!
  • restructure my community’s website
  • write 2-3 blogs per week
  • edit YouTube videos, podcasts, and TikToks for YGG
  • manage new clients in my coaching business
  • go on three vacations with my friends and family

Too much.

But now that I’ve crossed off a few of these items, I’m ready to clean up, reflect, and make sure this doesn’t happen again. I thought today’s post would be a good time to do an exercise I found on Instagram.

It’s called the AAR Method (after-action review) and it’s used by the Navy Seals. It’s a four-question framework. In sharing the model with you all, I’ll give my answers for each step.

1. What did I intend to accomplish?

I tried to move in the direction of what I want my work life to look like.

It’s threefold:

  1. writing blogs and books
  2. running a podcast/YouTube channel
  3. having my one-on-one coaching business

To me, it’s a fulfilling cocktail of conversations and deep work.

2. What happened?

I started sprinting in this direction with no real plan and with little help. My schedule and timelines were up in the air. I got to things when I could get to them.

Problem was, I often felt creatively empty after spending hours of bandwidth on one or two things. I also felt the effects of task-switching. After hours of writing in the morning, coaching in the afternoon, and editing in the early evening, I’d be absolutely drained by 5pm.

3. Why did it happen that way?

I didn’t create any organized systems for keeping everything on track. With everything left to chance, my days were cluttered and sporadic.

I also just expected myself to be able to handle all this. There are these sexy Instagram-worthy archetypes of entrepreneurs doing a thousand things and working 12-hour days.

In reality, most of us have about four to five hours of deep, undistracted work in us each day. So putting eight hours of writing and editing on the calendar was destined to fail.

In summary: unrealistic expectations and a lack of organization.

4. What will I do next time for a better outcome?

Give each day of the week a theme. On these days, I write. On those days, I edit.

Some sort of digital system would also be useful for deadlines. I’m working on that with services like Evernote and Trello.

Finally, next time new projects present themselves, I’ll ask myself: “How much harder will this make things for me?”

I usually go to great lengths to keep from being busy or overloaded. I’d like to never get there again.

I think these questions will help.

Don’t let the result be the goal

A bullseye dartboard with a dart near the middle

My favorite thing about interviewing creators is hearing the same philosophies or mindsets for different crafts.

I’ve sat down with YouTubers, founders, comedians, doctors, athletes, musicians, authors, and more. Here’s something they’ve all said.

“You have to enjoy what you’re doing. It’s okay to set goals and to want to make money. But if status, wealth, and success are your only driving factors, you won’t make it.”

Benjy Himmelfarb, a DC standup, said a comic’s first two years are just about getting comfortable on stage. As I’ve been interviewing YouTubers for my podcast, they’ve said the exact same thing.

When we start a new venture—a business, a new job, creating content—the beginning is mostly about figuring out how to get good and how to find our voice and styles. Nine times out of ten, the people who are doing the best are just the ones who’ve been doing the thing consistently and committedly.

Occasionally we see young phenoms who start crushing it immediately. But those are rare. We just think they’re everywhere because they get a ton of exposure.

Eric Rosen is one of the biggest names in the chess world and has 575k subscribers on YouTube. It took him a year of consistently streaming and posting to start to experience success.

Courtland Allen sold Indie Hackers—a community for online business owners—to Stripe for millions of dollars. But this was after 10 years of him starting companies that failed, coding every day, and being uncomfortable in Silicon Valley.

Courtney Maginnis has spent over a decade doing comedy in New York City. She’s worked with College Humor and Comedy Central and still works a nine to five to support herself.

Point is, building true skill and leverage takes time.

If the result is the goal, we’re just suffering while looking at the clock. As cliche as it sounds, we have to enjoy the process.

Right now, my YouTube channel isn’t that great. The first few interviews I used were for my book so they’re just grainy Zoom calls. I don’t know how to make good thumbnails. I have to refine my interviewing and editing skills.

But I’m loving the conversations I’m having and working on the show is the most fun I’ve had of any of my creations. So if I stick with it, I have no doubt it’ll be great. But what metrics are keeping me going?

The idea of 100k subscribers sounds amazing. But that will probably take years. That can’t be my compass.

So my one and only goal right now is to make it to 100 episodes. Once I get there, we’ll see how I’m feeling.

To end, I’m not suggesting we don’t set financial goals or look at metrics. I just don’t think doing something unfulfilling in the hopes for success is sustainable.

We don’t necessarily have to do what we love. But we should at least like what we do.

I interviewed a hero of mine

The YouTuber's Guide to the Galaxy episode 2

The second episode of my podcast is out now. It was the most nervous I’ve ever been for a conversation.

Eric Rosen is one of the biggest names in the chess space. He has…

  • 575k subscribers on YouTube
  • 225k followers on Twitch
  • an International Master title in competitive chess (there are only 4000 of these in the world)

This conversation was recorded for my book back in May. It took me about 30 minutes of talking to understand that it was real.

That may sound silly to most, but I’ve been enjoying this guy’s content ever since I got into chess back in 2020. I’ve seen well over 500 of his videos and I’ve taken all his online chess courses. Meeting him was wild.

He was so kind and so generous with the details of his journey and business. He took me through all his revenue streams, his processes, and his goals for the future.

I loved the conversation and I think you will too if you enjoy creating.

Watch it on YouTube:

You can also listen to it on Spotify or Apple Podcasts.

Send me any feedback you have! If you like the show, please rate and review it on your podcasting platform. That’s super helpful for bringing it to more people.

Thanks, everyone. 😇

August Q&A—Roe v. Wade, addiction, biggest fear

1) “What’re your thoughts on Roe v. Wade being overturned?”

If you’ve been reading this blog for more than a few months, you probably noticed I don’t touch on anything sociopolitical.

That has less to do with fear and more to do with the fact that it just doesn’t interest me. I’ll talk about anything in person. But when it comes to what I write and publish, this is a space for me to type about what I love.

Major insights. Business. Mistakes I’ve made. Doubts and anxieties I’m having. The things I’m creating. Building better relationships. How to live a fuller life.

These are the things that keep bringing me back to the keyboard. I’m sure this list will change but for now, the system is: sit down and write about what you know.

I don’t know much about politics or anything in that realm.

For me, that means I wouldn’t enjoy writing about it. And for you, that would be a disservice because you’d be hearing my half-baked thoughts on meaningful and often radioactive topics.

Lastly, I get a lot of emails and messages now. People send me their thoughts and criticisms after certain blogs.

I love every single one of them. I even save my favorites.

Last week, I got an email with feedback on my last piece on dying. In the article, I said that since we all kick it one day, we have no choice but to be present and appreciative in the here and now.

But in this guy’s feedback, he asked why that was the only choice. He correctly posed that someone could also choose the path of nihilism and hopelessness, which I didn’t consider. How cool!

Someone read something I wrote, gave mental energy to think about it, and then articulated thoughts to send me to challenge me and improve my delivery. It’s quite rewarding.

But I don’t have the interest or bandwidth to do this several times a week with people who disagree with me politically. I love responding to reader emails. But I don’t want to start Facebook comment wars with people. I simply don’t have the space for it.

So for now, I’m happy to keep that stuff closer to my chest.

2) “Have you ever felt addicted to anything?”

Oh yes.

Some roll their eyes when they hear this. But for about a decade, I was severely addicted to video games.

I don’t mean I played them a lot. I mean, when I was into a game, it would consume my entire life.

In high school, I’d hide under my bed so my mom would think I left for school only to stay home and play Skyrim or Call of Duty. I skipped and failed college classes to stay in and play Xbox. I’ve racked up thousands of hours of Runescape.

I haven’t played any video games since 2018.

Here was my vicious cycle:

  1. Discover a game I loved
  2. Take Adderall so I could play that game better and longer
  3. Come down from that Adderall around 4 or 5pm
  4. Drink alcohol—the only way to combat the crash
  5. Be wasted by 8pm
  6. Wake up hungover
  7. Repeat

I’ve gone through a few periods in my life where I’d live this cycle for months on end. It was terrible.

I would feel my physical and mental health slip. Daily drinking. Poor sleep. Avoiding friends. Barely eating.

And it would all start with a stupid video game. Once I threw away my Xbox and deleted my Runescape account, the cycle stopped. There hasn’t been a day where I’ve been interested in going back.

Last year, I was teaching my buddy from high school how to play chess. Seeing how into it I was, he said, “You know what chess is for you, right? You replaced your video game addiction with chess.”

He was right.

I don’t think we ever delete our addictions. We simply shift the ways in which we exert that energy. Now, I’m addicted to creating a great life, spending time with the people I love, and helping others do the same.

3) “What’s your biggest fear?”

It’s always been some version of: I’m a fraud.

All the success I’ve had and am having is just a fluke and people will eventually catch on that I have no idea what I’m doing. That’s the fear.

I’m afraid I’ll be 37 years old and on the verge of eviction. I have no evidence that that would ever happen, but that’s the root of my underlying anxiety. Anything to do with money. When I see my friends getting married and having kids.

While I know it’s not true, deep down I think: You’ll never have the skills to do that. You’re a manchild.

It’s strange how we can have worries that we know logically don’t make any sense. But emotionally, it’s a completely different story.

I’m doing great and I’ve never been more fulfilled by my life—my friends, family, health, and work. But buried deep in the vault, that fear still lingers.

Thanks for all your questions! Please keep sending me stuff you’d like me to dive into next month.

I tried to skip a vacation but my friend wouldn’t let me

A gorgeous lake and a partly cloudy sky

For the first time since starting my business in 2020, I’m busy.

It’s something I never want to be. Many Americans use the word “busy” as a fake complaint. They’ll groan about it while flaunting it like a badge of honor. How am I? Good! Busy. Super busy.

But to me, busy just means a person isn’t in control of their time. The number of tasks outweighs the available hours for those tasks. It implies a feeling of rushing from one thing to another.

So when people tell me something like, “You must be so busy,” I correct them.

“No,” I reply. “Just productive.”

This lands well with some people. With others, I sound like a douche.

Anyway, this month has been different. I have genuinely been busy and it’s been a shock to my nervous system. It’s the fullest my plate has been all year.

Coaching. Restructuring my community’s website. Chess tutoring. Jiujitsu class. My new podcast. Writing my book and these blogs.

You can have anything you want, but you can’t have everything you want. And this month, I’ve felt the quality of my attention and production slip. My bandwidth is being allocated to too many different things.

To add fire to flame, this is the most vacation I’ve taken in a single month.

I know that’s a terrible thing to complain about. But deadlines can make it difficult to be 100% present when you’re trying to get away. There’s guilt involved. The story that replays says, “I could and should be getting work done right now.”

Two weeks ago, I spent the weekend at my family’s lake house. Yesterday, I got back from a four-day stay in West Virginia with my mom and sister. This weekend is a trip to Deep Creek Lake with close friends.

It was the last night in West Virginia. Flooded with anxiety about getting everything done, I texted the group and pulled out of Deep Creek.

I woke up to a few responses saying they totally understood and they hoped to see me soon. That felt nice.

Then my buddy called me.

“What’s up man,” I asked.

“Yo dude,” he started. “Saw you weren’t coming to the lake this weekend. What’s going on?”

I shared about my workload and my fear of not being fun. He listened respectfully, told me he understood, then challenged me.

“I totally know how stressful deadlines can be, man,” he offered. “But I think now’s a great time to lean on your people. We got your back. And I think there are steps we can take to make this happen.”

He came up with a few ideas. They involved carving out specific times for me to tinker on my laptop while they took care of other things. He told me I could work in their van while they got the boat ready and could come pick me up.

“Fine dude,” I chuckled. “You win.”

I decided to go. But it had way less to do with his proposed solutions and more to do with the fact that he called me in the first place to get me to come. It felt like a slap in the face.

It said, Hey dummy, don’t skip out on memories with your friends. The workload will eventually end, but you won’t be able to get those memories back if you miss out on them.

His language was much lighter and kinder than that, but it had the same effect.

I’m lucky to have friends who push me to live a better life. It’s not something everyone has access to.

20 years from now, we’ll tell stories about drinking beer on a boat. Because no one ever tells a story that starts, “Dude! This one weekend, I stayed home and got a bunch of work done…”

Put first things first.

Dying, chess, and grapes

My cousin, shortly before I checkmated him.

I spent this weekend at the lake house. My grandparents were supposed to be there, but my grandpa was in the hospital.

He had a mini-stroke two weekends ago, got let out the next afternoon, then had to go back the following day because something was wrong with his liver.

Him being 81, none of this was shocking. But it was deeply troubling.

Since they couldn’t come to the lake, I left early Sunday morning to stop by Norfolk and see them on my way home. I’m so glad I did.

How many visits left?

Lake Gaston, 2020.

Almost exactly a year ago, I wrote a blog about the finite amount of time we have with people. The example I used was my grandfather.

Assuming someone lives to be 90, and assuming we maintain a relationship with them, how much time left do we have left with that person?

Well, we simply subtract their age from 90. Then, we multiply that by the average number of times we see them a year.

I see my mom once or twice each week. She’s 58. So that’s about 2496 more dinners and walks with her.

My family in Wisconsin and I see each other once a year or so. They’re in their late forties. So that’s roughly 42 more weekends at the lake with them.

I see my gramps about three times a year. He’s 81. So I have about 26 visits left.

Grapes and tuna fish sandwiches

A plate of grapes sitting on a dining table

When I got to my grandparents’ place yesterday, my grandpa was in the shower after just getting home from the hospital. Grandma made me lunch and we sat chatting at their dining table.

When my grandpa came out, he sat down next to me and held out his left hand. The stroke made him unable to use his right. I focused intently on him. He was visibly frustrated. Who wouldn’t be after losing their functionality?

“Dotty,” he signaled to my grandma. “Help me put in my hearing aids, just in case Dillan says anything worth listening to.”

We all burst into laughter.

It was a gorgeous day outside, so we set up the balcony chairs and sat overlooking the bay next to their apartment. Grandma made tuna fish sandwiches and got us a big bowl of grapes.

For 30 minutes, it was just me and grandpa out there talking about business, travel, and science. I always try to ask him questions about his past, his experiences around the world, and his fondest memories. It’s always a hoot to hear him tell stories about my dad and aunts when they were growing up.

Grandma eventually joined us and we just sat out there talking. I don’t even remember what we were discussing. It didn’t matter.

The only thing that mattered was I was there and we were happy.

Memento mori

That’s Latin for “remember that you’ll die one day.” It’s a reminder we could all use on a daily basis.

Many people shy away from any conversation about death and dying. Depending on peoples’ experiences, this can be a rigorous topic. It can come off as morbid and depressing.

But I think burying our heads in the sand when it comes to death is one of the most damaging and unhealthy things we could do. Meanwhile, shedding light on it and speaking about it openly brings with it so much opportunity.

Here are two reasons why.

1) It softens the blow.

My grandpa will pass one day. It’s possible that that happens before I get all 26 of my remaining visits with him. When that happens, I’ll be devastated.

But I won’t be crippled by it. I won’t collapse. I’ll look back with gratitude that I got to have conversations with him about Brooklyn on his balcony while eating grapes.

2) It makes it easier to be present and grateful.

When someone truly understands the simple fact that none of this will last forever…the only option is to be mindful and appreciative of all that they have.

How can I get into a comment war with someone…How can I get pissed at a server…How can I ghost a friend who’s texting me…when I know that I and everyone I’ve ever known will be dead one day?

It’s things like my grandpa being in the hospital that really wake me up. They remind me. Hey, don’t forget.

I’ve returned from this trip with renewed energy. I feel so lucky that I’m young and that all my friends and family members are alive and healthy. I get to do work that fulfills me. I get to meet beautiful women. I get to travel. I get to.

Every phone call. Every bit of quality time with people I love. They feel ten times as impactful.

I’m paying attention. I’ve been reminded. Thanks, gramps.

Son, father, grandfather—2013.