Buenos Aires: day 2

My main goal in these blogs is to be completely transparent. Day 1 of my living in Argentina absolutely terrified me.

I spent hours with an American buddy who showed me the ropes and that was awesome. But once we parted ways, I felt like a child lost without his parents.

The sole reason for this fear: my Spanish isn’t good enough to carry on conversations yet.

I felt too timid to go to a restaurant or store on my own. What if someone tries to talk to me? What if they throw things at me? What if la policia take me away because my Spanish isn’t good enough?

I’m ashamed to say that my first night was spent in my apartment trying to figure out how to get food delivered. None of the apps would accept my debit card, so I just didn’t eat.

I know. It pains me to admit that. I was even telling myself at the time, “Dude. You came here to get uncomfortable. What the hell are you doing sitting here in this room?” I began questioning how I’d make it a week let alone several months.

On top of that, I live right next to a major nightlife hub—La Plaza Serrano. Every Thursday to Sunday, the nights are loud and long.

I barely slept.

If every night was like that, I certainly wouldn’t make it. But then day 2 began.

I woke up saying out loud, “Fuck this. You do scary things. Go outside.”

So I put on my finest pair of crocs and went grocery shopping. The simple act of walking around my neighborhood made me feel 100x better. These people aren’t here to kill me.

In fact, I’ve never been around so many openly kind and social people in my life. Anyone anywhere will stop and talk to you if you ask questions or spark conversation. They might even invite you to dinner.

I got lost on purpose so I had an excuse to walk the many cobblestoned streets. I met two backpackers from San Francisco while waiting in line to exchange cash. I walked past some of the most stunningly beautiful women I’ve ever seen.

Then I bought some groceries. This whole batch cost $6.50. I could get used to this.

I also found a jiujitsu gym and rock climbing gym, both within walking distance. The BJJ gym has plenty of weights and equipment too so that takes care of where I’ll work out during the weeks.

In the evening, I attended a “workout and meditation” meetup. The organizer’s plan was to exercise and chat goals every Monday to start the week off right. I had to walk through the heart of my neighborhood of Palermo to get there.

I was in awe. I tried to balance basking in my surroundings with not looking too much like a gringo tourist. Not trying to get robbed, ya know?

Palm trees. Botanical gardens. Zero honking cars.

This place is beautiful. The people. The buildings. The weather…

I got to the park where the meetup was. There I met Edward and Mili.

Edward is a Swedish web designer traveling the world with his golden retriever Louie. Mili is an Argentinian product manager who wants to quit her job and work on her own startup.

We got along instantly.

After 40 minutes of an intense HIIT workout, we sat and meditated and visualized our perfect week. Edward would ask guided questions like:

  • Who do you want to be this week?
  • What do your mornings look like?
  • What does the best version of yourself spend time doing (and not doing)?

I pictured myself going to more events, rock climbing, doing jiujitsu, meeting more people. I made an internal agreement that I wasn’t allowed to stay in my apartment simply because of fear. I had to be working or resting or something intentional. No avoidance.

After all that, the three of us just sat there chatting for another two hours. We talked entrepreneurship, they asked about my podcast, and I was picking their brains about things to do in Buenos Aires. It was sitting there, legs sore and mind 100% present, when all my anxieties and doubts simply faded and disappeared.

We eventually started walking back. Mili and I hugged and kissed each other on the cheek (a cultural greeting I’m still getting used to). Then Edward and I continued walking with Louie.

He and I discussed finding clients, hiring people, and self-improvement. We share a mutual love for Joe Rogan. We exchanged book recommendations. He told me he wanted to try Brazilian jiu-jitsu.

I made a friend.

I’m taking him to class with me tomorrow. Mili and I are getting dinner and beers this weekend.

I feel at peace typing these words on my balcony. It’s 23 degrees (73 degrees Fahrenheit for you uncultured swines).

Now I’m going to go get breakfast a few blocks away, walk to my new coworking space, and meet a dude for coffee I met online.

A lot can happen in 24 hours.

Want to hear the craziest travel story ever?

Too bad. I made it here safely and smoothly.

(My trip to Vancouver Island was more action-packed.)

I got into Buenos Aires this morning at 5:30. Zero hours of sleep on the plane. Anticipation and anxiety. Dropping my luggage and laying in the apartment bed was as blissful as I imagined.

After a two-hour power nap, I met up with a dude I connected with on Zoom. He showed me around my neighborhood, bought me lunch, and helped me get a public transit card and exchange cash.

He was basically my guardian angel. I thanked him profusely for helping me land on my feet in this foreign city. He told me he was just paying forward all the guidance he got from people before him.

Now I’m sitting on my balcony typing away as I listen to pedestrians walk by saying things I can’t understand. Three men are playing hang drums and accordion. My space is small and peaceful.

I feel far away, which is exactly what I wanted. My two main goals in being here were:

  1. to give my life a cold shower, and
  2. to remove access to my friends and family so I could focus on my work and health.

Here are the first things I noticed today…

  • The women are gorgeous here.
  • Life is quite different when you’re the foreigner (when you don’t speak the language and when most people don’t look like you).
  • I haven’t felt this adventurous since I lived in Germany when I was 20.

I’m off tomorrow. The to-dos are: jiujitsu class in the morning, finding a coworking space, and getting a membership at a rock climbing gym.


Tomorrow’s the day

Tomorrow is my flight to Argentina. It’s also my grandpa’s birthday who passed away in December.

Last night, I had a travel nightmare. I tend to get those before big excursions.

I was sitting at my gate waiting to board the plane. There were about 30 minutes to go before I realized I had forgotten to get my boarding pass and check my bag.

Panic ensued. How did I make it through the terminal without accomplishing those essential tasks?

And that’s really at the heart of why travel makes me so stressed out: the fear of being incompetent.

My friend put it perfectly. She told me the story of immediately losing her backpack and passport when she went to Poland. She laughingly told me, “At that moment I felt like I was too stupid to be traveling alone.”

That’s exactly right. If I miss a flight, if I get confused by foreign public transportation, if I can’t find my way…my deep fear is that other people could figure it out but I’m too stupid to.

Yesterday was emotionally taxing. I said goodbye to some close friends, hung out with my family, and came home and crashed at 9pm. Today I’m armed with my first full night’s sleep in a week. Some work to do. Rock climbing with a buddy. Packing. Hanging with besties.

The next time you get an email from me will be from my apartment in Buenos Aires. All I have to do is make it there alive.

See you then.

This book is taking longer than I thought

Woman typing away on a typewriter

I set out to write a book in July 2021. The plan was to interview creators: people who built something cool, shared it with others, and made money doing so.

Since then, I’ve sat down and had conversations with people I’ve looked up to for years. I interviewed the woman who wrote the article that inspired me to run my own online business. I spoke with my favorite YouTuber who’s the reason I love chess. I’ll also be including my chats with my favorite author and my biggest inspiration in the entrepreneurship space.

My harshest lesson: it’s so incredibly easy to not write a book.

If you’re ever looking to procrastinate more, just tell people you’re writing a book. It sounds amazing. Hearing the praise from friends and family about your new venture. Setting up Zoom calls with people you never thought you’d meet. It’s been exciting and wildly rewarding.

But hidden underneath all these rosy scenes is the most boring and painful activity: sitting down and actually writing the damn thing.

Here’s a list of tasks I’ve done instead of fighting the resistance to writing:

  • color code each sublabel in my Gmail accounts
  • buy Christmas gifts in March
  • outline ideas for my next book

One of the most common questions asked when creating something is, “Why is it so hard to do my work?”

While there are hundreds of factors at play, I think the answer is simple: Because when we actually try to do something, it’s possible to fail. Planning is simple. Executing is messy and uncomfortable.

NBA players never miss shots in practice. It’s stunning how accurate they are. Then in games, their percentages go way down. Things are tougher on the main stage when the stakes are higher and everyone’s watching.

For me, sitting here and writing these blogs each week is basically effortless. I get up between 5am-7am, make a cup of coffee, then black out for 45 minutes until I’ve crafted a masterpiece for you all. That’s my basketball practice.

Chipping away at this book feels like game day.

It takes longer to write the same amount of words because I feel like there’s so much more on the line. A mediocre blog will be forgotten in a day. But the difference between an excellent and crappy book could change the trajectory of my career.

Not entirely logical but that’s certainly how it feels.

That’s why people get so caught up in prepping: business plans, roadmaps, and outlines. That stuff is useful to a point, but most people just use them as ways to avoid doing the real work: reaching out to people, building something people can use, getting feedback and iterating on it…

There were periods when I didn’t write anything for months. So I had to create a weekly system that ensured I put at least something down every other day.

Blog writing two mornings a week. Book writing three mornings a week. Even if it’s just 30 minutes of deep work. That absolutely crushes the alternative of zero minutes of deep work, which was my default state for a while.

Anyway, here are my biggest updates to prove writing this book hasn’t just been one big scam…

  1. I’ve finished all my interviews.
  2. I’ve transcribed each interview and completed round 1.
  3. I have a list of every individual chapter I want to write (one to three pages each).
  4. The first draft should be completed in the next two months.
  5. I’ve decided to self-publish and market it with the help of all of you and by partnering with the folks I interviewed.

To those of you who ordered pre-sale copies for half off, sorry for the wait. I promise it’ll be worth it.

This project has been more fun and fulfilling than I ever imagined when I started this journey. I get to WhatsApp with some of my favorite creators and entrepreneurs. I bond with other friends who are in the midst of writing their first books.

It’s funny. The book is called Do The Thing! That’s the simplest advice. It’s also the hardest thing to do.

If you want to order your own copy before it comes out, here’s the link. I’ll sign it and write a personal note to you.

Now please stop distracting me so I can write.

About my flight…

Dillan Taylor's delayed passport webpage
What I’ve been staring at every day for the last two weeks.

I shared a few days ago that my passport got delayed, along with thousands of other Americans.

The problem? I’m supposed to get on a plane today at 2:40pm and fly to Buenos Aires, Argentina.

For weeks, my passport application status just said, “In Process.” I tried calling their toll-free number to set up an appointment at an in-person passport office. The closest ones to me are in DC, Philly, and the northeast.

95% of the time, my calls didn’t go through. It either went straight to a dead line, or the automated messaging system spewed these words that are ingrained in my head: “Thank you for calling the US Passport’s Automated System. Your call is very important to us. Due to high call volumes, we are unable to take your call at this time. We recommend you call back at a different time. Goodbye…*click*”

But every now and then, my call would go through. And it felt like I won a prize. Bursting with glee, I’d have to calm myself down and remind myself that the war was far from over.

Monday was the first time I got to speak to a human being. Her name was Lori. “That’s my mom’s name,” I said, hoping that would create a cosmic bond between us and force her to send me a new passport that day.

“I don’t give a shit,” Lori replied. Just kidding.

But she told me my only option was to make an appointment. If I showed up to an office without one, they wouldn’t even let me in the building.

“There aren’t any appointments available in DC between now and Thursday,” she sighed.

“I’m willing to drive,” I said. “Are there any openings in nearby states?”

After clicking away at her keyboard, she said the closest one was in…Buffalo, New York. Wednesday afternoon. Seven hours away.

“Book it,” I said without hesitation. She entered my unique code and phone number. I would’ve driven 15 hours. I just wanted a God damn passport.

“Oh shoot,” Lori whispered.

Oh shoot? Oh shoot??? Clearly she means, ‘Oh shoot,’ looks like we’ve actually made a huge mistake and your passport is being hand-delivered to you by Joe Biden along with a new MacBook Pro and free Chipotle for life.

Unfortunately, that’s not what she meant. “Someone just grabbed that appointment,” she explained. “They come and go pretty quick.”

Then immediately, “Oh wait! One just opened up in DC for Wednesday morning,” she cheered.

“Jesus Mary and Joseph, Lori book it!! Do it now! Send it!!!” I was elated.

“…It went away,” Lori said dejectedly.

My emotional state was being kicked around like a hacky sack. It felt like Lori was my only ally and at the same time trying to sabotage me.

“O..okay,” I muttered. Like a defeated and confused child who just wants more waffles but there aren’t any left in the freezer. Lori apologized and I thanked her for her efforts.

That day and the day after were two of the most stressful and anxiety-ridden days I’ve experienced in years. It was kind of a wake-up call.

I never really get stressed. My life is quite simple and highly rewarding. I mean, the thing that has brought me the most mental suffering in years is not being able to fly to a beautiful foreign country on time. What a glorious problem to have.

But I was still feeling it. There was sluggishness in my eyes. It was harder to laugh. I was tired when there was no reason to be.

This whole government passport system is slow and inefficient. But this whole ordeal was my fault.

I knew when my passport expired last year. I had all the time in the world to be proactive and just get a new one. But I waited until I actually had an international flight planned. I take full responsibility. Poor Lori was just doing her job and answering the thousandth phone call from some flustered American trying to leave the country.

New plan: I was just going to take the next open appointment within the next two weeks, then move my flight to whatever day came after that.

On Wednesday morning, I came down to this temporary office space in my friends’ basement. Coffee in hand, I opened up the travel.gov page I’d been visiting every day. I typed in my info to check the status of my passport and get my unique locator number to give to the eventual person I’d speak with.


Big bold letters. My passport was approved, completed, and shipped.

A wave of peace flushed over my body. All was right in the world.

I called the airline to reschedule my flight. Her name was Sandra. She was super professional and had a lovely Hispanic accent. She told me that since I got the cheapest option, I’d have to just cancel it and buy an entirely new flight.

“Is that the absolute best option for me,” I asked like a sad puppy.

“Let me see what I can do,” Sandra replied. She put me on hold for 10 minutes.

When she returned, she told me she would break the rules and just move my flight. I’ve never felt more grateful for a stranger’s kindness.

My new flight is next Saturday. Nine days from now.

Thank you, Lori. Thank you, Sandra. My guardian angels.

Until then, my close friends are kind enough to let me continue living with them. So long as I scrub the mold and vacuum the ceilings.

I’ll let you know when I get to my destination. ✌️

Buenos Aires, we have a problem

I’m flying down to Argentina this Thursday afternoon. Or so I thought.

I renewed my passport in January and paid for expedited shipping. My new one was supposed to come in the mail last week.

It didn’t.

Apparently, passports are a hot commodity right now. The state department is getting slammed with requests and the nation is experiencing massive delays.

I spent hours on the phone last week trying to get through to someone. The calls either didn’t go through or they would go through and then the automated system would hang up after 30 seconds.

First world problem? Yes.

Incredibly stressful and unsettling? Very much so.

My sole mission today is to figure out how to get this stupid little blue book before Thursday. I’m going to the DC passport office. Even though my passport is being processed by the LA office. And you can’t just show up to an office without making an appointment. But you can only make an appointment over the phone. But there’s no way to get through on the phone.

So I’m going to take a shot in the dark and explain my situation. Maybe they’ll throw me in jail. Maybe I’ll get put on the No Fly List.

Whatever it takes. Stay tuned.

29 life tips on my 29th birthday

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

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

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

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

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

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

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

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

2) Ask 3 questions before stating your opinion.

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

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

This has three useful effects:

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

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

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

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

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

Everyone feels more connected and heartwarming conversation ensues.

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

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

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

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

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

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

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

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

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

6) Know what success actually is.

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

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

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

7) Buy expensive noise-canceling headphones.

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

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

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

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

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

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

9) Status is fun, but it’s a mirage.

Money. Clout. Reputation.

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

But these things will never complete us.

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

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

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

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

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

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

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

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

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

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

Then do those things.

12) Set up regular hangouts centered around activities.

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

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

Some examples from my life:

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

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

13) Run errands without your phone.

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

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

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

14) Write letters, not cards, as gifts.

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

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

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

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

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

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

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

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

Because no one cares as much as you do.

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

Pick a month. I typically do January and October.

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

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

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

17) Keep a list of your friends’ goals.

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

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

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

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

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

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

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

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

20) They’re not texting you back because…

They don’t want to.

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

Short texts. No response. Never calling back.

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

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

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

21) The 10/80/10 rule.

10% of people will dislike you no matter what.

10% of people will love you no matter what.

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

22) Be an ESPN sportscaster.

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

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

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

23) Never set a secret expectation for someone.

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

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

Be clear and direct about what you want.

24) Be on time.

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

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

25) Download ‘News Feed Eradicator.’

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

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

26) Keep a list of your biggest insights.

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

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

27) Tell your friends “I love you.”

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

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

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

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

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

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

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

There’s a difference between bullying and poking fun.

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

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

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

Final thoughts:

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

See you next year for my 30th!

What are we getting wrong about masculinity?

My guest on the podcast this week is Jake from Rattlesnake TV.

He analyzes interviews and debates with well-known political figures and celebrities like Jordan Peterson, Russell Brand, and Ben Shapiro, just to name a few. His channel breaks down their charisma, debate tactics, and conversational skills so we can learn from them, have better disagreements, and build better arguments.

In just five months, Jake’s channel is rapidly approaching 100k subscribers. We dive into how he blew up so quickly in the episode as well.

Toward the end of the conversation, we discuss masculinity—a topic I’ve been fascinated by this past year. How far does it have to go before it’s considered “toxic?” And what are we getting wrong about masculinity in the west?

I thoroughly enjoyed the conversation. Jake and I have become buds and have been WhatsApping back and forth about content creation and martial arts.

If you’d like to listen to the episode, you can find it here!

Moving out and moving on

First morning in my Annapolis apartment—October 31, 2020.

This is the last time I’ll sit in this chair, at this desk, typing on this keyboard.

In a few hours, my friend will be here to help me pack everything I own into a U-Haul and then a tiny storage unit. I’ll squat at his house for the next week and a half. Then I’ll get on a plane and fly to Buenos Aires.

Packing up the office.

I got sad and nostalgic for a few seconds yesterday when I was taking everything down. But it quickly turned to excitement for the next chapter.

A new question has come to mind when it comes to change: “Did I think I would die with this thing?”

When my roomy told me she was moving out, I couldn’t stay glum for long because I knew I wasn’t going to die with her as my roommate. Just two 57-year-olds drinking Bud Light seltzers and playing Uno.

I sold my dresser and bookshelf yesterday—furniture I had as a child. Did I think I was going to die with those things? No.

That means between now and the day I die, I got rid of them at some point. This is that point.

I built my career in this office. I learned how to make money, create content, and play chess in this office. Now it’s time for me to get to whatever the next level is in another office.

It’s funny. Humans are so good at turning empty boxes into homes. But I was really just borrowing this room. By next week, it’ll be filled with someone else’s life and they’ll have no idea who I was or what I did at this desk.

Anyway, it’s time to move on. My priorities for the next month are simple:

  1. transition smoothly to Argentina
  2. finish the first draft of Do The Thing!
  3. post consistently on the podcast

Onward and upward!

2023 feedback review: my results (part 2)

Connor Russo's bachelor party in the mountains with the bros
Connor’s bachelor party in the mountains, April 2022.

Earlier this week I shared the biggest criticisms I took away from my annual feedback review with my buddy. I’ve already been utilizing the changes I wanted to make and it’s been cathartic.

I didn’t want to do this but I feel it’s only natural I share the more tender and positive stuff. One of my biggest insecurities is coming off as arrogant or self-important…but here goes.

Biggest positives:

1) I practice a growth mindset.

Growth mindset: understanding that skill and talent come from consistent time, effort, and repetition.

Fixed mindset: the false belief that skill and talent are innate and unmovable—you either have it, or you don’t.

It’s the difference between, “I’m just not a musical person,” and “If I sit down and practice piano for 10 minutes a day, I could get pretty good.”

Connor, the guy I do this feedback exercise with, has commented on my lack of perfectionism before. I love to just dive into new projects or crafts, know I’ll be garbage at them, then break through that initial brick wall until I’m actually kind of good.

Theatre, chess, jiujitsu, rock climbing, coaching, content creation…

All these things were pretty painful at the start. I was either cringing at my lack of ability or getting humiliated in one way or another.

In those moments, our 100,000-year-old survival systems kick in. We feel anxious and want to give up. But that’s just a wall to get over.

And once we crawl up and over to the other side (after a few weeks or a few months), that awkwardness and clunkiness turns to fluidity. The problem is that a lot of people simply give up before getting over the wall.

2) I’ve built a life around only doing the things I want to do.

This one really hit when he said it. It’s my central operating system: creating the life I want by helping others do the same.

Joe Rogan is undoubtedly my biggest inspiration in how to live. Let me explain.

Love him or hate him, he lives an incredible life. He was pivotal in me taking control of my life back in 2017. For two reasons…

  1. He was the first real masculine male figure who made being disciplined look really cool to me. Listening to his podcasts and YouTube clips gave an energy of, “Hey man. I love you, but you have got to get your shit together! You could be so much better than you are, and you owe it to yourself to start moving in that direction.”
  2. His career was the first crystal clear example I’d seen of only doing the things you love and making great money from that. He’s a podcaster, comedian, and UFC commentator…and he has worked at these for decades and figured out a way to become rich from each passion.

In short, Joe’s work ethic and results made me think I could get good enough at the stuff I enjoy to make a decent living. I particularly loved his career trio: three different pursuits which offer tons of overlap and variety at the same time.

I’m actively trying to model that myself. My trio is:

  1. life coaching
  2. writing
  3. podcasting

If I just do these things for the next 30+ years, that would be my dream career.

Anyway, it sounds almost childish. I just want to do the things I want to do, get better at those things, and repeat that process until I die.

I don’t really set goals. I don’t care about getting a certain amount of money or subscribers or clients. I just want to keep podcasting, writing, and coaching.

If something changes, I’ll pivot. But until then, the train keeps moving.

3) I’m an active listener.

Connor said, “When you listen to people, you make them feel seen and understood, never judged…which is sadly super rare in people today.”

I make a lot of eye contact and often reflect people’s words back to them. What’s funny is I don’t really notice any of that in myself. It must be programmed into me from 1300+ coaching sessions and hundreds of hours of interviewing people.

The biggest gift we can give people is curiosity. Asking people questions and follow-up questions is one of the best ways to make them feel good when they speak with you. It’s a heart-warming way to connect with other human beings.

Connor had a lot of other insanely kind things to say. But these were the three that meant the most to me.

We do this kind of feedback review each year. I’d highly recommend you do something similar with your friends. It can be as simple as two questions:

  1. What’s something I can improve?
  2. What impresses you about me?

What do you want feedback on? What answers are you scared to hear?

Let me know your thoughts.

2023 feedback review: my results (part 1)

Bro love. ❤️

This is Connor. He hated me in middle school, is the reason I run my own business, and has been one of my best friends for 15 years. He and his wife run a kick-ass climate tech studio and startup.

Each year, we do a feedback review where we answer deep and critical questions about one another. (Here were my biggest takeaways from last year’s review.)

2023’s questions:

  1. What’s something you haven’t told 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?

No feedback is complete without an action item. So for each critique, I came up with ways to change. Here’s how it went…

Biggest criticisms:

1) I’m ugly.

Just kidding.

*1) I send people sociopolitical links they’re not interested in.

I don’t feel identified with the conservative label. But most of my close friends are more liberal or left-leaning than I am, so it makes me feel like I stick out a bit.

And since I rarely seek confrontation and am rather agreeable, I tend to avoid potentially tense or divisive discussions.

But sometimes I let my opinions peep through. And when Connor brought up the fact that I have sent some podcasts and clips or made some brief comments, I realized something about myself.

I have a habit of sending people links. I tell myself and the person I’m sending them to, “Hey, I think you’d find this fascinating.”

But I discovered what I really meant was, “Hey, here’s something I wish you understood and internalized. Hope ya like it!”

It’s been my cowardly way of indirectly debating and making arguments. As though watching a 40-second YouTube short and avoiding any sort of long-form conversation would bring insight to my friends.

Worse yet, I’ve been coming to conclusions about what I think my friends’ opinions are. I thought, I have liberal friends. They must be blue-haired, mega-woke granola people.

But I have zero evidence to even begin to back that claim.

Change #1:

I called a few friends to apologize for hiding behind links, promising that if I had anything to say I’d just say it myself. I don’t have to have someone else make an argument for me in a podcast or YouTube video. I can construct my own opinions.

Furthermore, I realized I crave two contradictory things at the same time:

  1. I want to have open and honest discussions and debates with my close friends about divisive topics.
  2. I absolutely don’t want to have those conversations. I just want to chill with my friends.

One friend made a great suggestion while I was on my apology phone tour. I can pursue conversations like those by simply stating, “Here’s something I’ve been thinking about lately. Can I get your thoughts on it? I’d love to workshop it because it’s something I feel super passionate about.”

Respectful. Light. Welcoming…Instead of, Hey watch this clip, it’ll expose how stupid you are! Lmk what ya think. 😉

2) I hold people to the high standards I hold myself to.

In terms of honesty, communication, and discourse. And well, they don’t feel like high standards to me. They just feel normal and reasonable.

Firstly, I refuse to lie in any way.

I was basically a compulsive liar when I was younger—lying even about small and insignificant things—and it created a world of chaos for me. I had to remember what I said to each person in my life. And worse yet, when you lie all the time, you slowly begin to believe the lies you tell others, building a false world for yourself.

On top of that, one of my most significant life principles is open and candid truth-telling.

I will always tell my friends, family, and colleagues what is on my mind—so long as I can do so in a respectful and valuable way. I don’t just blurt out every thought that pops into my head.

I tell my close friends what they’ve done to make me feel hurt. I tell my family what they mean to me. I give brutally honest feedback to my fellow coaches (with their permission).

And I want others to do the same for me. Hence this entire feedback review.

Lastly, I try to remain kind and compassionate toward people even when they’re not in the room.

One thing I pick up on quickly is how often someone talks about others who aren’t currently present. Gossip is an enormous turnoff for me. It drains me and it makes me question how often the gossiper talks about me when I’m not around.

My goal is to praise others when they aren’t in the room. I’m not naive, but I try to remain positive and grateful basically 100% of the time.

All this is to say…I often expect these same values and practices from other people.

When one of my friends suggests I lie, I’m shocked. When I learn someone feels a certain way about me, I get frustrated that they haven’t brought it up to me yet. When I hear someone gossip, I think less about them.

I’m proud of these values but I don’t want them to make me feel disgusted toward the people in my life.

Change #2:

First, be mindful. Remind myself that my principles are mine and I’m not in charge of other people.

Second, continue being the change I want to see in the world. When someone lies, ghosts, or gossips…don’t judge or shame them in any way. But instead advertise what you would prefer: uncomfortable honesty, candid conversation, and praise. Lead by example.

In other words: make these boring and wholesome alternatives sexy again. It won’t guarantee people will become more like you, but it will continue to create a more positive atmosphere.

3) I don’t collaborate enough in disagreements.

This last one combines #1 and #2.

Not completely understanding the other person’s beliefs + feeling my way of thinking is supreme = subpar debates and discussions.

I love diving into potentially divisive and radioactive topics: race, gender ideology, sexism, etc.

But I have only been able to do so consistently with friends I already agree with. That makes me sad because I want to be able to talk about anything with anyone. It also means I stay in my bubble: not having my ideas challenged enough and not considering opposing opinions.

Part of this is due to the naturally uncomfortable nature of having these conversations…especially with friends. If you’re at a dinner party with four buddies, would you rather play CatchPhrase or debate police brutality in America?

But a huge component is my own lack of collaboration and questioning. I want to dive headfirst into my thoughts and point out other people’s errors. Folks love that.

When someone says something I disagree with, my internal emotional reaction is, That’s ridiculous, let me set this person straight. Turns out no one is interested in being “set straight” or educated.

People just want to be heard and understood. So…

Change #3:

First and foremost, I need to make it clear to people that they are completely free to share their thoughts and opinions without my judgment or condescension.

I can ask way more questions before I share any of my own ideas or counterarguments. Above all, I can find common ground.

Where do we completely agree? Where do our perspectives divert? What values and desires do we share?

I need to address these things before turning into a professor. No one wants to be lectured at. No one wants to attend a TED Talk against their will.

Finally, I have to get better at steelmanning.

Strawman fallacy: attacking a weak or incorrect version of someone’s argument, often straying from the actual points the person is making.


  • “You care about climate change? So you just want us to stop driving cars and having babies?”
  • “You’re pro-law enforcement? So you think cops should just be able to do and say what they want to innocent civilians?”
  • “You think pornography is bad for society? So you think we should shame women in the industry?”

Steelman argument: debating with the best possible interpretation of someone’s argument.

When you steelman someone, you articulate their opinions to the point that they agree with you. “Yes, that’s exactly what I’m saying.”

It’s hard to do this, especially when we vehemently disagree with someone. But it’s the best way to have a fruitful conversation.

I’m going to practice doing this. I can’t unload my thoughts before steelmanning the person I’m speaking with.

It took a few days for these criticisms to really sink in and for my defensive nature to fade. But I’m excited to put these changes into practice.

Later this week, I’ll share the positive feedback I received in part 2.

Here Be Barr | The Ultimate Guide to New York City

Jon Barr on The YouTuber's Guide to the Galaxy podcast

On this week’s episode of The YouTuber’s Guide to the Galaxy, I interviewed Jon Barr.

He’s a NYC vlogger and travel creator. I discovered his channel when I was considering moving to Brooklyn. To anyone looking to learn more about the culture and variety of New York, Jon’s your guy.

His channel currently has 340k subscribers. We dove into how he went from a burnt-out sportscaster to a full-time traveling filmmaker.

We cover: what it’s like to be a full-time content creator with a newborn baby, how Jon started his channel, how Casey Neistat changed the YouTube space, Jon’s protocol for when homeless people approach him, what stereotypes of New Yorkers are untrue, how long it can take for a video to go viral, and much more.

Side note: The more I do these interviews, the more I realize how insignificant superficial metrics like subscriber count are.

What I mean is…I keep reaching out to people who have tens or hundreds of thousands of subscribers and thinking they’re higher-quality human beings than me. Then, we hop on a call and have a conversation and I realize they’re all just kind, humble, and humorous people.

When they treat me respectfully, I think, Wait, but I only have 134 subscribers. I’m scum compared to you. Why are you treating me like your equal?

Even though that’s exactly how I’ll treat newer creators when I have hundreds of thousands of subs.

More and more YouTubers are agreeing to be on the podcast, which I think will make it easier for more and more YouTubers to agree to be on the podcast. I’m having so much fun.

If you want to listen to my conversation with Jon, here’s the link.

Email me any and all feedback you have. 🫶

How to Not Die Alone (book review)

Logan Ury's book How to Not Die Alone
(from loganury.com)

“Dating is harder today than ever before. We define our own identities, unlike our ancestors whose lives were defined by their communities. We have thousands of options at our fingertips, which makes us question our decisions. We’re uncomfortable making big decisions. Social media makes us believe that everyone else is in happier, healthier relationships than we are. We don’t have relationship role models. We’re bombarded with messaging that we have to get this right, and that the ‘right’ answer exists at all.”

Logan Ury is a data scientist at Hinge and this book is her Magnum Opus. It’s designed as an actionable and practical guidebook for dating better and dating often.

With years of data research and personal stories from her dating coaching clients, Logan breaks down how single people often get in their own way…starting with the three dating tendencies:

1. Romanticizer: You want the soul mate, the happily ever after—the whole fairytale. You love love. You believe you are single because you haven’t met the right person yet. Your motto: It’ll happen when it’s meant to happen.

2. Maximizer: You love doing research, exploring all of your options, turning over every stone until you’re confident you’ve found the right one. You make decisions carefully. And you want to be 100 percent certain about something before you make your choice. Your motto: Why settle?

3. Hesitater: You don’t think you’re ready for dating because you’re not the person you want to be yet. You hold yourself to a high standard. You want to feel completely ready before you start a new project; the same goes for dating. Your motto: I’ll wait until I’m a catch.

Here are some of my biggest takeaways…

• seek Life Partners: people trustworthy and reliable, and who will stay with you for the long haul; avoid Prom Dates: individuals fun in the short term, but who ultimately let you down

• superficial qualities like looks or money matter less in long-term relationship success than people think they do—lust fades and people adapt to their circumstances, the same is true for shared hobbies and similar personalities; what to look for in a Life Partner: emotional stability and kindness, loyalty, growth mindset, personality that brings out the best of you, skills to fight well, ability to make hard decisions with you

• in the end, a relationship is about what happens when you two are together—focus on who you’re being when this person is around, you can even ask your close friends, “What am I like when you see me with my partner?”

• the Monet Effect: when we see only a rough sketch of someone, our brains (hoping for a great outcome), fill in the gaps with flattering details—then when we discover their inevitable flaws they seem worse than they actually are…then we look for something better, feeling like the grass is always greener just over the horizon

• dating apps cause us to focus on the wrong things—we value what gets measured and apps can only measure superficial traits, so they exacerbate our shallowness; apps overwhelm us with choices and make us indecisive, they create a habit of relation-shopping: comparing and contrasting people as if they’re potential purchases

• to meet more people in real life: go to more events, get set up by friends and family, and build the habit of connecting with strangers out and about

• 10 steps to better dates:

  1. shift your mindset with a pre-date ritual
  2. choose the time/date of the date thoughtfully
  3. opt for a creative activity
  4. show your work, let your date know how much effort you put into the date
  5. play
  6. skip the small talk
  7. be interested, not interesting
  8. limit phone use, keep it out of sight
  9. end on a high note
  10. use the post-date 8 to shift to the experimental mindset

• the post-date 8 questions:

  1. what side of me did they bring out?
  2. how did my body feel during the date?
  3. do I feel more energized or drained than before the date?
  4. is there something about them I’m curious about?
  5. did they make me laugh?
  6. did I feel heard?
  7. did I feel attractive in their presence?
  8. did I feel captivated, bored, or something in between?

• f*ck the spark—instant fireworks is not a sign that this relationship will be happy and healthy, it could actually distract you from red flags

Every single person should read this book. Every person in a relationship should read this book so they can gift it to their single friends. ❤️

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.