A simple trick for learning things faster

A young boy at a laptop trying to learn something

I’ve been keeping a ‘Get Better’ list ever since I read Ultralearning by Scott H. Young.

While it’s wildly effective to hone in on our strengths, it’s good to balance that out by improving our weaknesses. If we only did the things we were naturally gifted at, our capacities to grow and experience life would be severely limited.

I sucked at chess when I first started playing. But after playing and studying consistently for almost two years, I can now play in tournaments and enjoy beating my friends.

Fortunately (or unfortunately) for me, I have a handful of hobbies and passions. Chess is one. But I also love rock climbing, writing, and Brazilian jiu-jitsu.

The goal is to get pretty damn good at each of these things I spend my time doing. And the main way I stay up to date on what to focus on is with my ‘Get Better’ list.

Simply put, it’s my list of weaknesses in each of my favorite activities. It includes my coaching business, friendships, and even my dating life.

Whatever makes the list, I know I need to find a way to drill it. Obviously, things like chess or jiu-jitsu are easier to practice because there are specific exercises or puzzles I can chip away at.

But there are more ambiguous weaknesses like: “Holding space for friends instead of giving advice.” How does one drill that?

Well, the next time one of my close friends is going through something, I can make an effort to listen twice as well and acknowledge that I see and hear them. No suggestions. No problem-solving.

It’s like working out a muscle that doesn’t get a ton of action. I did the same thing with curiosity.

Last year, in building my business, I had to reach out to a ton of people. This was super tough because I wasn’t naturally curious about others. But after five or ten connect calls with people from my past, I found myself genuinely wanting to learn more about whomever I was speaking with.

The muscle was getting stronger.

We can do this with anything. So if you made a ‘Get Better’ list, what would you want to improve specifically?

Do tell. I’d love to hear about it.

Solving vs. Managing

A solved Rubik's Cube

What’s the solution to overwhelm, poor health, and money problems?

I have no clue.

There are thousands of possible steps one could take to become more productive, more fit, and more financially stable. But these actions would depend on the person and their unique situation. What’s more, that person’s answers would change over time.

That’s because these challenges are infinite. They’re not problems to solve but instead areas to manage. They’re not games to win but instead fields to play on.

No workout would make us fit for the rest of our lives. No incredible conversation keeps a relationship strong forever. These things take upkeep.

I used to think if my business made over $10,000 in a month that I’d be set. I’ve had several $10k+ months over the past year and I’m still constantly money anxious. The stress hasn’t dissipated, it’s only leveled up as my bank account has. The fear used to be: Will I be able to afford rent next month? Now it’s: How long will I be able to keep this going before it all comes crashing down?

Making $10k was a problem to solve. It was finite. I either did it or I didn’t. The solution was to create enough value in my business that enough people paid me money in 30 days or less.

But the ambiguous feeling of “financial stability” is a battle that goes on forever. If I have a great month, I still have to show up to my sessions and I still have to type words on my keyboard. Then I do it all over again the next month.

We never arrive. But we often feel like we only need to check off a few more boxes in order to do so.

Even if we clean our room, we’ll either need to clean it again in the future or manage it in a way that it stays tidy.

In my coaching practice, I see a ton of people trying to find solutions to problems that actually need to be managed. Things like: finding a balance between work and personal life, practicing healthy habits, and making more money.

These things evolve as we evolve. What solves the problem now could get in our way in the future.

So when struggling with something, it can be helpful to ask: Is this a solving problem or a managing problem?

All my friends are getting married

^^Not the bride and groom.

In the past year, of my close friends: five got married, four got engaged, and two had a child.

As I inch closer to 30 years old, this all feels more and more normal. But it brings up a plethora of emotions as a guy who’s spent most of his life single.

This weekend, I saw one of my best friends marry the woman he’s been with for nearly a decade. The wedding was at a stunning art museum, I got to spend time with my favorite people on the planet, and I got seven hours of sleep in three days.

They’ve been one of those couples who have acted like husband and wife for years: living together, running a business together, and having more chemistry and compatibility than just about any other duo I’ve ever known. I’m not sure which brought more tears to my eyes: hearing them exchange vows or watching them mosh to Panic! At the Disco on the dancefloor.

My friends mean the world to me. My relationships with them are arguably my deepest held value. If I had it my way, every single one of them would do wildly fulfilling work, live long and healthy lives, and be with a partner who supports and cherishes them. So far, so good.

But naturally, there’s a murkier and more selfish side to all this.

I’m proud of the life I’ve created. I have my dream career, take excellent care of my health, and have a disgusting amount of meaningful connections.

But as a human being, I’m not free from the natural comparative thoughts.

When I look around and see 80 to 90 percent of my friends with a partner, when I see so many awesome people with other awesome people, the question is inescapable:

Is there something wrong with me?

Am I…

  • too picky?
  • unattractive?
  • not put together enough?

Logically, I’m aware that the answer to each of these questions is no. But logic rarely wins the battle.

One of my biggest fears in life is that there’s something (or multiple things) about me that makes me unlovable. Something with my personality, my looks, or both.

Again, it sounds like paranoia but it’s very much there. That stays between you, me, and the internet.

To be clear, none of these questions, doubts, or anxieties keep me from putting myself out there. I go on dates. I meet women. I even speak words to them.

But the point of this blog is to share my brain with ya’ll—not to gain sympathy but to articulate a hopefully relatable human experience.

I just deleted the dating apps from my phone after trying them for a month. I know people who’ve had success with them, but I found them to be utter garbage. Performing, ghosting, judging…not a fan.

So aside from continuing to build the life I want, the next step is to get better at talking to women out and about. There are two main challenges with this:

  1. I don’t go out much
  2. It’s pretty terrifying

Hence the “get better” part. But as always, I’ll keep you updated.

Seeing all my lovely couple friends this weekend didn’t make me sad. It fueled me. I’m even more energized to create and go after what I want.

And so I will.

Unsubscribe from this blog

How this thing began

In November 2019, I lost half of my subscribers in a single day.

That was because I only had two readers and one unsubscribed.

Still, it was devastating. How could one of my friends unfollow my poorly written and unoriginal thoughts on self-improvement?

794 blog posts later, I’ve become at least slightly better at writing—trying to share my stories and insights in a concise manner. People seem to dig it, as we’re now at 417 subscribers (thank you).

But after making the recent decision to email these directly to you, four people, two of which I know personally, have unsubscribed. And I couldn’t be more thrilled about that. Let me explain.

We’re starving for validation in the early days of creating something and sharing it with others. Do I suck? Is this good? Like and subscribe!

The problem is, we do suck. We haven’t found our voice, created any value, or developed enough skill yet. So why would people stick around?

Well, in my experience, it started with an early adopter: my friend Grace. She was so pumped that I was blogging and publishing something. She read every post.

For months, it was just the two of us reading my mediocre blogs on habits and mindset. I was basically just writing things I thought she would enjoy. But every now and then, I’d write about a personal story or an educational topic and other eyeballs would appear.

Slowly but surely, more and more people would visit the site. As I entered new communities, people from different realms would tune in: a new gym, an online coaching community, and past jobs.

For two years, I wrote a new blog every Monday through Saturday. Most of them were terrible. I cringe when I go back and read my old stuff. I was overly confident without any real-world experience to back my ideas up.

But I was getting in the reps. I showed up to practice almost every day. And as a result, I was accidentally becoming a clearer and more effective writer. It was quantity over quality.

I discovered that most people enjoyed it when I shared personal stories from my own life. I used to think that would make me sound self-important and boring. But it turned out that real-world experiences made people feel most connected. So I started telling more stories and giving fewer lectures.

At first I was afraid

Building an audience with the people already in my life: Facebook friends, coaching colleagues, high school acquaintances…It’s been a wildly rewarding thing to pursue.

I love when people comment or email me about their own thoughts or experiences based on something I’ve written about. It feels like a purer form of social media.

But the downside has been a deeper craving for approval. Since I have a personal connection with many of my readers, I have felt a heightened pressure to not upset them.

In the early stages of the blog—before I felt secure in my voice—whenever someone unsubscribed or criticized my ideas in a Facebook comment, it would eat away at me.

Any ounce of disapproval meant I wasn’t cut out for creating content or sharing my opinions. Then I would get twice as gloomy because I would recognize how strongly I needed people to like my work.

Pushing through

After these uncomfortable moments, I’d have to remind myself that I only had 20 subscribers and that it wasn’t even close to the end of the world. As it turns out, I’m still alive. Someone I went to high school with left a frowny face on my Facebook post and it didn’t end my life.

I kept posting and sharing. I continued to sharpen up my writing skills. And more people enjoyed it each month.

I don’t know when “getting over the hump” happens. But there came a time when I had gotten enough validation in the form of subscribers, praise, and my own security. This validation allowed me to simply let go of the fear of pissing people off. It made it easier for me to speak my mind.

It’s like having an incredible group of close friends nearby. With that community secured, it makes it easier to be yourself. But if you were to move to a new city where you knew no one, you might feel less loose with your words and actions. The need for approval would be more present.

That’s how I feel now.

So, when people unsubscribe or message me when they disagree or dislike what I say, I welcome it. I try to use these as opportunities to improve and gather perspectives outside of my own.

If someone finds these posts boring, how can I make my stories more captivating and my insights more relatable or usable? If the emails get annoying, how can I shorten these blogs?

Rejection is always a good thing. It weeds out the people who aren’t the right fit. Dates, clients, subscribers, etc.

Just like I would hate going on a date with a woman who didn’t actually like me, I’d feel awful if someone was subscribed to this blog just to be polite…these emails going unread in their inbox only to be deleted.

I want you to enjoy reading these and get value out of doing so. So if you don’t, I implore you to send me feedback or to unsubscribe!

I’ll be sending out a super short survey soon to learn more about what you guys want to read more of and less of moving forward.

Thanks so much for making it this far. You’ve allowed me to turn this side-project into a pillar of my life. I’m wildly grateful.


3 things I’ve learned after 1000 coaching sessions

A man and woman in a coaching session

The first coaching session I ever ran was on June 26, 2020. A friend agreed to be my first guinea pig.

I began coaching my buddies for free. Eventually, I charged $40 a call. Then $50. Then $80. Then I started offering 3-month packages instead of per-session prices.

In March of 2021, I joined the Insight Coaching Community (ICC). It was there that I would find my people, learn how to create clients, and build the career of my dreams.

Since then, I’ve:

  • been hired as an ICC team member to train other coaches
  • coached nearly 1000 hours
  • had intense conversations with 100+ people

Last week, a woman shared with me my favorite description of a coach I’ve ever heard. She said, “I thought a life coach was just an unqualified therapist?”

After a good laugh, I explained the difference. In oversimplified terms, therapy tends to uncover the past; coaching is meant to create change for a better future.

While I certainly don’t claim to have any kind of psychological expertise, I’ve learned a ton about the mindsets and behaviors of human beings over the last two years.

Here are my top three insights.

1) We protect ourselves with our identities.

Every person on the planet has certain proclivities, personalities, and tendencies that set them apart. But we tend to think these are fixed.

People say things like:

  • “I’m the kind of person who…”
  • “That’s just not me.”
  • “I could never…”

We craft these identities for ourselves. That way, when something undesirable happens to us we can simply blame our identity.

If our business isn’t doing well, we can point to the fact that we’re just not a pushy or organized person. That explains it. It’s not that we’re not doing the work; it’s our timid, non-masculine identity’s fault. It’s just who we are.

But these aren’t definitions; they’re stories.

“I’m not a go-getter,” is really: “The story I’ve lived in the past has not been one who follows through with what they want.”

This is good news. Because as cheesy as it sounds, we can change the story. How do I know?

Because I’ve seen people alter their stories right before my eyes. I’ve seen…

  • perfectionists become pragmatists
  • people pleasers set hard boundaries
  • go with the flow types create organized systems
  • impulsive actors become proactive
  • hyper-achievers embrace acceptance and gratitude

Most of the people I work with have turned into completely different humans in a matter of months. That’s not an advertisement for my services and it’s certainly not a guarantee. It just highlights a simple process that something like coaching can provide.

Step 1: Act and think a certain way.

Step 2: Open up about what you actually want and what you think is in the way of that. Notice how far your desires are from your current life.

Step 3: Pinpoint which obstacles are real and which are only in your head (most of them are just imagined—e.g. fears, doubts, uncertainties).

Step 4: Accept that if you keep doing exactly what you’re doing, you’ll keep getting exactly what you’ve been getting. Start taking action and making changes that make you feel uncomfortable and stretch you. Gather insights from failures and celebrate wins.

Step 5: Act and think in new ways.

Step 6: Repeat.

That sounds like every self-improvement book ever written. But that’s because it’s impossible not to improve oneself by following this stupidly-simplified formula.

Unfortunately, most people stop at step 1. They go through life without challenging their modes of operation. But all it takes is one person to ask one question for us to stop looking at the world through a toilet paper roll.

And in my experience, it’s those who are not invested in their identities who see the quickest results…because they have no excuses.

2) People want answers but need insight.

For context, Webster defines insight as: “gaining a more accurate or deeper understanding of something.”

My mentor shares two truths when it comes to the coaching world:

  • People don’t do well with solutions they’ve had little to no part in creating.
  • Our insights will never be as powerful as their insights, even if they’re the same.

Holding space for someone is one of the most powerful and valuable things we can do for them.

We often jump right into problem-solving and we miss what’s really going on. This usually shows up in three main ways:

  1. We believe them when they tell us what they’re struggling with when really there’s a much deeper problem.
  2. We offer advice and suggestions when all they want right now is to be heard and understood.
  3. We think our words are more useful than their thoughts and we limit their ability to gather insight on their own.

Here are some examples for each.

1. Not believing the first problem:

I coached a guy once who opened the call by saying, “I’ve done a lot this year already. I want to define what my next big projects and achievements are.”

“Great,” I said. “How much more doing and achieving would you need to feel satisfied?”

It was the fastest turn of events in a session I had ever seen. He started laughing.

“Wow,” he chuckled. “I have so much on my plate right now. I have no idea why I thought adding more to it would make me more fulfilled. It would crush me. I’m already overwhelmed.”

So we spent the rest of the call discussing his obsession with taking action at the expense of his mental sanity. That was the problem beneath the problem.

Notice how I slightly disregarded his original statement. He declared he wanted to brainstorm his next actions. If I just went along with that and we started spitballing, we never would’ve touched on the root of the issue.

2. On holding space:

At the end of each coaching session, I ask the client what they got out of our conversation. The most common response?

“I just feel ten times better saying all this stuff out loud.”

This is the same reason journaling is so therapeutic. When we take the thoughts out of our brains and put them into the world where they can be seen or heard, they become more real and less daunting.

In the coaching sphere, there’s a concept called the lamp post theory. It says that even talking to a lamp post about your fears and accomplishments would improve a person’s life.

Now imagine instead of a lamp post there’s another human being reflecting your words back to you, asking you thought-provoking questions, and challenging your answers.

3. Curiosity before solutions.

It’s the #1 principle in my business.

I mentioned earlier that feeding someone an answer will never be as impactful as them finding that answer on their own. There is the rare case where someone asks us for our thoughts and actually uses our suggestions, but those instances are far and few between.

A few months ago, I was coaching a woman for the first time. She was having trouble setting boundaries with her hometown friends. She felt less connected to them and didn’t enjoy going out, drinking, and doing drugs all the time.

It would’ve been so easy for me to tell her what she was doing and why it wasn’t working. But I just asked her questions.

How is pleasing these people serving you? How is it hurting you? If nothing changed, what would you feel like a year from now? What are you responsible for? What’s outside of your control here?

After 50 minutes, she had an insight.

“Oh my God,” she laughed. “I don’t know why, but I feel responsible for their emotions. Like, how important do I think I am that their happiness starts and stops with me?” She started making fun of herself.

She asked me why it took her an hour to realize she wasn’t in charge of other people’s wellbeing. And that’s how insight works.

We can’t force anyone to think, do, or feel anything. It has to come from them first. And while there’s no guarantee, we can increase the likelihood of insight by being wildly curious and holding up a mirror for them.

I’ve had plenty of sessions where I ask piercing questions, reflect their words back to them, and challenge their thinking…and they feel nothing. That’s okay.

It’s not my job to ensure an insight. That’d be like a gym guaranteeing you a great body. You have to show up consistently and do the work.

We can only make changes when an insight is had. But most people want the change before the insight.

3) We’re all the same.

I’ve worked with: software engineers, CEOs, comedians, coaches, politicians, content creators, writers, doctors, athletes, marines, financial advisors, tutors, musicians, dog-walkers, yoga instructors, sales reps, and more.

And they’re all the same. Here why.

There’s a basic human trend I’ve noticed.

  1. We all want stuff—usually changes in our outcomes, mindsets, or situations.
  2. We feel like something’s in the way—usually fear, doubt, or uncertainty.
  3. We either work actively to maneuver through these challenges or we let them keep us where we are.

This trend is true of every single person I’ve coached regardless of how much money they make, what their personality is like, or how big or small their goals are. It’s true for me. It’s true for all of us.

I could ask you right now: What do you want most right now that you don’t have? What do you think is in the way?

A past client who was making $200k+/year had purchased her dream car and dream house. It didn’t bring her any of the fulfillment she was expecting, so we spent months diving into the things that did.

Another client wanted to get better at receiving criticism, so we did an exercise where he reached out to all his friends and coworkers and asked for open and honest feedback.

We’re all the same. We want things and we think something’s in the way. Then we either do something about it or we don’t.

Coaching helps those who do want to do something about it.

In summary

  1. We craft identities for ourselves to excuse the things that don’t go our way.
  2. We want people to give us answers when we really need to create our own.
  3. We all want things in life and think there are obstacles keeping us from getting them.

This is my dream job. I get paid to help others build the lives they truly want to live. It’s rewarding and fulfilling at the highest level.

It also holds up the mirror to me and my own ways of doing/thinking. I gather insights as I see my clients gather insights. I get inspired. Sometimes I get teary-eyed or get chills listening to what my clients are feeling and accomplishing.

These first 1000 sessions have been a tremendous learning experience. And this unqualified therapist couldn’t be more excited for the next 1000.

I thought I wanted to move to New York

What I’ve been doing

Two friends texted me today saying they missed the blog. One included a crying emoji.

Sometimes I go weeks posting every day. Sometimes I go a while without, especially if I’m away from home.

I just got back from living in Brooklyn for two weeks. The goal was to get an idea of what it’s like to live in the city before potentially moving there in October.

It was a lot.

I learned about the city and how to navigate it—both physically and emotionally. But I also learned a ton about myself—what I’m afraid of and what my values actually are.

And I’d like to reflect on both.

What I learned about New York City

Every day in Brooklyn felt like I was scribbling things down on an imaginary pros/cons list. I felt one of two emotions at any given time:

  1. “I can’t wait to get back home to Maryland.”
  2. “I never want to leave this place.”

There was no in-between. Let’s start with the negatives.


1) No established community

I had no clue how comfortable I was here in Annapolis until I went to a space where I didn’t know anybody. My mom and sister live 15 minutes away. Several best friends are within a 10-minute drive. I have an incredible roommate.

Throw this same man into a neighborhood of 150,000 people where he doesn’t know a soul…It’s daunting.

It took me three uncomfortable days to admit that I was lonely. My ego repressed the thought because I pride myself on being a social butterfly, someone who makes friends easily, and a guy who can strike up a conversation with just about anyone.

But I couldn’t hide from it. After a few phone calls with friends, I could physically feel how safe I felt talking with familiar voices. I tried to remind myself that any city that wasn’t Annapolis would make me feel that way.

I went out on my own a bunch. I got solo dinners a few times. I worked out and went rock climbing almost every day. I went to meetups.

But I didn’t feel at home. So I made it a mission to ask everyone I met in New York the same question: “How did you build community here?”

More on that later.

2) The cost

My buddy spent $450 in four days in Brooklyn. And he doesn’t even drink alcohol.

What the fuck.

I can’t speak for his spending habits, but I can confirm that if I went out all the time in New York, it’d only be a matter of time until I needed my mom to pick me up and drag me back to Maryland.

A beer that costs $3 elsewhere is $7 in New York. To guess the monthly rent of an apartment, simply take what you think it is and multiply it by two or three. I started laughing when a bartender told me my cocktail would be $21. She was not laughing.

3) The trash

It didn’t just stink. It also totally desensitized me to the sight of litter.

I was walking behind a kid and his mom. He opened his Dr. Pepper bottle and let the cap fall on the sidewalk. They both saw it and just kept walking.

Enraged, I extended my arm and prepared to bend down and pick it up. But then I looked to my right and saw ten times as much garbage scattered on the concrete. Regretfully, I just went about my day.

There was a sense of hopelessness. What would’ve picking up that bottle cap done to help?

(Sorry to my climate tech friends who read this blog.)

4) The homeless

It’s hard not to sound elitist here but this was quite the culture shock.

Someone asked for money on about half of my walks and subway rides. It wasn’t super bothersome. But what stung was having to deny empathy to so many people in such a short amount of time.

It hurt each time I declined a homeless man. But I looked around and everyone else seemed totally used to it.

“You have to deny your emotions in New York City,” my Brooklyn friend told me. “If you don’t, you’ll be drained every single day here.”

He was half kidding. But I thought about what it would be like if I gave change to every single person who asked for it. It’s a challenge that I have no answers for.

(I know, I know. How dare these homeless people make my life more difficult?)


1) The adventure

Every walk out of my apartment. Every subway ride. Every event. Every bar or restaurant. Every new connection.

My favorite thing about the city is the collective experience of living there. That may sound grandiose but let me explain.

Whenever I met someone new, I always had a conversation piece in my back pocket. All I had to do was ask three questions:

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

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

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

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

2) The food

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

And the fucking pizza. The hype is real.

3) No car

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

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

4) The discomfort

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

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

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

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

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

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

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

What I learned about myself

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

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

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

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

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

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

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

The next steps are:

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

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

Alone in the city

My makeshift travel work desk.

One week of my NYC test run down. One week to go.

I’m feeling one of two emotions at all times:

  1. I can’t wait to go home to Maryland
  2. I never want to leave this place

I’m in an entirely new space so my survival instincts are keeping me on guard and it feels like I should be on vacation. But I’m working full days of sessions and writing.

One of my best buds lives in Brooklyn. But last week, he was quite busy until Thursday, so I had to entertain myself each night prior. I’m quite good at that, but it’s scary.

It feels like I’m the new kid at a school where everyone already knows each other.

Vital Climbing Gym. It’s hard to beat.

I’m staying in Williamsburg. It has a stereotype of being the yuppy, stuck-up part of Brooklyn.

While I can’t speak for the 150,000 people who live here, I can say that folks don’t seem too thrilled to start conversations with a stranger. There’s no silliness. People seem calculated and reserved. Everyone’s hot and everyone knows it.

I’ve sparked conversations with people at the climbing gym and with a few at coffee shops. The vibe is very much not, let’s be friends.

And that makes sense.

There are 8.2 million citizens in this city. If everyone stopped and opened up to every person who started talking to them, it would be unsustainable. People are doing their own thing.

But after a few nights in a row of this, I was beginning to doubt my social abilities. Maybe I’m not as extroverted and conversational as I thought. Maybe I’m not a master at making new friends in new environments.

Then I went to a chess meetup.

Meetup.com is great. You give it your location and the kinds of activities or groups you’re looking to take part in. Then you just RSVP and show up.

I just typed “chess” and 100+ meetups popped up. The closest one was Tuesday night at a brewery in Gowanus, an industrial neighborhood of Brooklyn.

After putting off getting on the subway (for fear of getting lost or stabbed), I geared up my Google Maps and headed south. Navigating through the different stops and line transfers made me feel like an adult who had a mortgage and could start a fire on his own.

I made it there with no stab marks and only mild disorientation. I walked into the brewery and was greeted by a jolly bartender with tattoo sleeves.

“Hey! Are you here for the chess? Can I get you a beer?” I wanted to hug her.

She pointed me to the back table. It consisted of six people who waved at me and called me over. It was the first time anyone had been excited to see me since coming to NYC.

I had met my people. They were chess nerds like me and we discussed our journeys in the game. I spoke about my tournaments, which made me sound way better than I actually am. After about five minutes of conversation, I realized I wasn’t this unlikable country boy.

What I have been understanding more and more, is that New Yorkers are quite willing to open up. They just need a context in which it makes sense to do so. Meetups, shared interests, groups.

We started playing.

I won a few games, then lost a few. But what I loved was that people just kept piling in. There were close to 30 who dropped in with their chess sets or their dogs. Everyone was friendly.

My new home.

My feeling was that if I lived here, I’d love to organize the event. Try different areas, hold tournaments, etc.

By the end of the night, I had added people on Facebook and even invited someone to a gifted coaching session with me. It was all I could’ve asked for.

Over the weekend, I spent each day with some of my best friends.

I’ll share those stories tomorrow.

I wanted to hate NYC—I don’t

The street of Williamsburg, Brooklyn

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

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

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

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

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

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

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

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

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

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

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

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

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

The rooftop of Vital, the climbing gym in Williamsburg Brooklyn

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

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

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

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

The journey continues.

Savage race

One of my fitness goals is to do at least one strenuous event each year.

2020 was a marathon. 2021 was a triathlon. And today, my buddy and I are doing a Savage Race.

Apparently, these races are pretty chill. We get to chug a beer after slogging through five miles and 30 obstacles. I was told we’d be covered in mud by the time we cross the finish line.

Despite today being a high of 95 degrees, I’m pretty excited. I love taking part in activities I’ve never done before, especially with my good friends.

I leave for NYC tomorrow. So I’ll post my results on Monday.



One of my besties showed me stickk.com. He used it to learn to draw in 30 days.

Here’s how it works.

You make a commitment. It’s usually an attempt to break a bad habit or build a good one. Examples could be: quitting smoking in 30 days, going to the gym three times a week, or reading every morning.

Then, you link your credit card. And with that, you can pick a charity you love (or hate). If you break your commitment, your card gets charged and that money gets sent to whatever charity you chose.

I started this week.

My commitment: Write any amount of words for my book, every weekday for two months.

If I miss even one day, that week is considered a loss and I’ll send $100 to Trump’s campaign. The same is true for all eight weeks. (Not a political statement. That’s just the organization I chose since I’m not a Trump supporter.) So in the end, I could possibly lose $800.

You can also recruit supporters. Friends and family can track your progress and you can even give them the power to say you didn’t stick to your commitment. (If you want to support me, here‘s the link!)

This is incentive, commitment, and accountability at the highest level.

Try telling me you don’t feel like working out when there’s $1000 at stake. We often feel like we can’t when really we just choose not to.

So many people say they struggle to remember names. It’s just because they don’t truly care to. If I told you I’d give you a million dollars to go remember 20 people’s names at the grocery store, it’d be easy for you. You’d have the incentive.

The problem is, when we choose not to exercise, say, there’s no immediate penalty. It’s just our future selves who suffer. But that’s impossible to grasp in the moment.

If you’re trying to stick to something, try stickk.com. It’s made writing consistently an easy task for me because it truly feels like I don’t have a choice.

What do you want to stick to?

The journey down south (pt. 6)

(Read parts 1 through 5 first.)

While I felt mostly chill about the whole car situation, not having a vehicle on a road trip leaves a person feeling quite insecure.

Not only did I not have the one thing I needed to get me from place to place. But I also was relying on my friends to take care of me. They were kind enough to house me and drive me around. But after a while, being so dependent made me feel like a child.

Day 6 (cont.)

So now that I picked up my car, I decided to go full send and got my own Airbnb for my last night in Asheville. I would spend the final evening driving my own car and sleeping in my own space.

I hugged my friends goodbye and did just that.

Day 7

I woke up that Thursday morning at 7am, showered, packed, and hit the road. It was 11 hours to the retreat near Tampa.

My favorite thing to do on long solo drives is to have deep phone calls with friends. I’m sure what it is, but something about being alone in a car makes me feel tens times more present with whomever I’m talking to.

But before I would do that, I spent the first two or three hours with my phone on airplane mode sitting in silence. Just thinking and listening to the sounds of the car as I sped down the highway.

Just like taking a walk with no phone, the mind will go to creative places if we allow it to. I thought about my friends, my business, my health. I came up with ideas that I voice-logged into my Apple Notes.

Eventually, my mind felt refreshed enough. I turned my phone back on and played “This is Drake” on Spotify. The world was right again.

My car doesn’t have a phone charger so when I go on road trips, I look at the next few directions on the GPS and commit them to memory. Not only does this save battery but it also makes me feel more old school—like I could take a wrong turn and have to ask for directions (i.e. look at my phone again).

When I crossed the state line into Florida, one of my best friends called.

We chatted about the podcast we’re making, about our separate vacations, and then he asked me a question.

“So what have been your biggest insights? What are you thinking about right now?”

He knows me well. He reads this blog (sometimes). He’s aware of my habit to take lessons from everything I do. I thought for a few seconds.

“You know what,” I said. “This may sound strange, but I honestly don’t really know what I’m thinking about right now. I’m not thinking about anything. I’m just talking to you.”

“Wow,” he replied. “I think that means you’re just present right now.”

I loved this realization. I truly wasn’t thinking about anything in my future or anything that happened in my past. I was just laughing and conversing with my good buddy.

I was so ready for this retreat. Ready to meet the man who taught me everything I know in my career. Ready to connect deeply with people I’ve only seen on Zoom in the past year. Ready to have nothing to do and nowhere to be.

We ended our call as I pulled into the neighborhood. Every house looked like a mansion. Then I got to the end of my GPS route and saw a van in the driveway. It was the van that would be taking us all around town.

I got out and heard laughter and shouting from the backyard. I walked around and saw all these people I’d known for a while but didn’t know at all.

“Dillan!!!!” was the first thing I heard.

I’m off coffee

A woman holding a coffee mug under the setting sun

Yesterday was a big day for me.

Two months ago, I embarked, for the second time, on a journey to quit drinking coffee. I went cold turkey for attempt #1 and nearly died. So this time, I took a much slower approach.

Step 1: Drink either half cups or use fewer grounds to make weaker coffee.

Step 2: When the bag of grounds is out, switch to Four Sigmatic‘s mushroom coffee—which contains less than half the amount of caffeine as a regular cup of coffee.

Step 3: When the mushroom coffee is depleted, switch to tea.

I did step three yesterday. It was a bag of black tea I stole from my roommate and it had about 10% the caffeine as a normal cup of Joe.

I worked a full day of sessions and writing and felt incredibly fulfilled. The reason why may sound silly to most.

In the past, I’ve gone through bouts of physical addiction to things like Adderall, nicotine gum, and alcohol. I’m sensitive to relying on chemicals to live my life (i.e. be funny, be productive, or take action).

I don’t mean this in a hippy-dippy sense, but I want to be pure—all-natural. I want to connect with others, take risks, and work hard entirely on my own. People in sobriety are probably rolling their eyes as they read this.

I’ll still have a cup of coffee, drink beer, and experiment with substances. But for the same reason I take months off of drinking, I never want to come close to feeling like I need a chemical.

The next step will be moving to green tea which is weaker than the kind I’m sipping now. Eventually, I’ll just be drinking cold water in the morning.

It’s only been a day without coffee, so I don’t have a ton of data. But I can say this much…

Dillan Taylor's sleep data

I slept through the entire night—something I never do. Waking up felt like a time machine. I also didn’t crash or slow down at all yesterday afternoon. I could get used to this.

When I first wrote about wanting to quit coffee again, I got several messages. Some assured me I didn’t need to. But many sent me products and suggestions on how to best go about weaning myself off it.

Thank you for reaching out. Cheers.

The journey down south (pt. 5)

I was either chewing a granola bar or was terrified to cross the rickety bridge.

(First, check out parts 1 through 4.)

Day 3

After a magical night of mushrooms, chess, and beer, the four of us got up for some Sunday hiking. The original plan was to wake up around 6am to get to this gorgeous waterfall two hours away.

That was hilarious.

So instead, we woke up at 9 and went to one of their go-to parks about 40 minutes from Asheville. We brought our hiking gear and a cooler with a few beers. We also stopped at a cafe for some road sandwiches.

The green mountains around Asheville have some of the best hiking I’ve ever experienced. It was with these same friends that I ate shit while hiking next to a waterfall a few years prior. They saw me slip and fall a good 10 feet down the steep hill. About five feet in, I thought, This is how I die.

This hike was much chiller (flatter). We parked, found a trail, and let Nanny off the leash. They were taking me to the creek. Or to my death…I’d find out soon.

After I snapped this Nanny said, “delete it.”

We found the water and stepped in up to our knees. It was freezing. I resisted the urge to cannonball into the deeper end. The rocks were slimy and slippery and I didn’t want to sprain my ankle in the Appalachian wasteland.

Similar to the night before, I felt like a kid again.

We skipped rocks, played fetch with Nanny, and basked in the sun. I felt envious of my friends that they had such frequent access to stunning nature. That’s my biggest qualm with moving to New York City.

I love green. And while I’m wildly extroverted, I crave quiet and isolated places…So I thought I’d move to one of the most populated cities on the planet.

Anyway, we finished a lovely hike and made it back to the car. The passengers cracked some beer and we headed back to the apartment.

I had been in communication with one of my coaching friends who was getting into Asheville that night. We met in our online coaching community and bonded over the topics of entrepreneurship, money-making, and dating.

She got into town and we met up for dinner. It was our first time meeting in real life.

I’ve done that now a handful of times. So be the times. Here’s the process:

  1. Build a strong relationship with someone over Zoom/over the phone.
  2. Make a plan to meet them in real life.
  3. Travel to execute that plan.
  4. Experience the surreal feeling of seeing what they look like in real life—how tall they are, what the side of their head looks like, how they walk.
  5. Feel two conflicting emotions at the same time: 1) It’s my good friend! 2) I have to get to know this person.

All that happened as we ate at this delicious Hawaiian restaurant. Half of me was chilling with my buddy and the other half was on a job interview.

Regardless, we had a fun evening. She met my friends and got recommendations for how to spend her remaining few days in the city. She was going with the flow and I shared that sentiment.

But I did need to get my car back at some point.

Day 4

On Monday morning, I called the repair shop to make sure I could pick up my 2009 Nissan Tesla (one of the lesser-known models).

They told me they were down a mechanic and would have to get to it tomorrow.

My thought was: All good. I have plenty of time. The retreat isn’t until Thursday.

While the adults were off at work, I used their cabinet desk to get some writing done and to respond to emails.

I texted my friend and updated him. When he got home, we started watching Lil Dicky’s show, Dave. He loved it.

Day 5

On Tuesday morning, I called the shop to confirm. They told me they needed to order a part and that I’d have to wait until tomorrow.

My thought was: What the God damn fuck, I need my car.

I was starting to get nervous. It felt like my car was being held hostage.

When they got home that day, we watched a few more episodes of Dave and then went out to a brewery for dinner.

Day 6

On Wednesday morning, I called the shop to confirm. My heart was racing.

I went for the assumed close: “Hey. So you guys are repairing my car today and I just wanted to make sure I could pick it up after working hours.”

He asked for my name and the make/model of my car. When I gave it to him, he put me on hold to check and see if they’d be able to fix it that day.

My thought: This.

After five minutes, he came back and said we were good to go for today. I could pick it up whenever I wanted and could pay for the repair over the phone. The dark clouds vanished.

“Thank you,” I said. I shared the good news with my friends and we left as soon as they were done working.

You never really appreciate something until you experience life without it.

Florida, here I come.

Following my dreams

Dillan and Emma Taylor at an amusement park
Here’s a pic of my little sis and me at an amusement park. It has absolutely nothing to do with this blog.

Where are you?

I’m aware that these blogs have been a bit scattered for the past two weeks. Here are my excuses.

  1. Most of my writing lately has been for my book, which I’ll discuss more today.
  2. While slowly recapping my road trip, it’s becoming harder to remember the sequential details of each day. But fear not, I will finish the story.
  3. I’m building a group for founders/entrepreneurs. In other words, my creative energy has been kind of diluted.
  4. I’ve been actively trying to get off nicotine gum for the last seven days. What started as a stimulant for writing became a physical necessity. I’ve never even smoked a cigarette; who would’ve thought? (I’m also almost entirely off coffee.)

So I’ve fallen off the wagon. This is me getting back on it.

I want to share a few changes I’m making to this blog and give an update on the book.


Many of you subscribe to my once-weekly, then biweekly, now monthly newsletter.

That is no more.

It started as a fun little email I would make for my friends. But in recent months, as I spend more time on money-making projects and things that are reaching way more people, the newsletter has steadily become a chore rather than something I look forward to.

Lynne Tye, a badass entrepreneur I interviewed for my book, told me about the difference between giving up and quitting.

Here’s my rule for quitting: If the Resistance of the thing is greater than the value I get from it, I move on.

That’s what happened with my first podcast Fancy, my YouTube channel, and my daily vlog. I was wildly committed to each of them…until I wasn’t. And creating something out of obligation simply isn’t sustainable. Lack of passion is tough to hide.

So what now?

Starting June 1st, you’ll be able to subscribe to this blog.

There are about 45 of you who regularly check this site to see the latest post. Then when I post some on Facebook, depending on the topic, that brings anywhere from 20 to 700 extra eyes to the page. That system is a bit up in the air and it asks you guys to do most of the work.

So at the start of next month, readers can subscribe and get each blog sent directly to their email. Eventually, you’ll be able to choose the specific categories you want. (e.g. blogs about business, personal stories, writing, dating, habits, etc.)

Stay tuned.

Latest book update

I cried last Friday. Let me explain.

Eric Rosen is my favorite YouTuber. Here’s his channel.

He’s one of the biggest chess content creators in the game. His Twitch channel has 219k+ followers. He has close to 600k YouTuber subscribers. His videos have played an enormous role in my improvement and love for the game of chess.

Dillan Taylor interviewing Eric Rosen

I interviewed him for my book on Friday.

It was the most nervous I’ve ever been to meet someone. I logged into Zoom 20 minutes early. When the clock reached 3pm on the dot and I read the banner, “Eric Rosen is in your Waiting Room,” it genuinely didn’t feel real.

We spoke for an hour and a half and it’s one of my favorite conversations I’ve had to date. He was such an authentically kind and giving person. He took me through his entire journey in making it as a professional content creator—from 0 followers to hundreds of thousands, from tutoring chess to beating top 10 players, from learning how to set up a camera to getting tens of millions of views a month.

When we concluded and I closed the Zoom, I sat in this chair and watched the recorded file download to my computer. I couldn’t help but have a big dumb smile on my face and get teary-eyed. So many emotions.

Extremely grateful to spend time with people who are creating cool things. Proud of myself for putting myself out there. Inspired to do great work.

Anyway, hope that clears a few things up. I’m feeling jazzed about the future.

I’ll continue to share updates from behind the curtain of my book. I’ll finish recapping the road trip this week. And finally, in six days, I’ll be living in NYC for two weeks as a trial run before moving there.

Much to come in the near future.

See you tomorrow.

The journey down south (pt. 4)

Part 1

Part 2

Part 3

(^^Read those first.)

Day 2

Getting into Asheville did not go as expected. But didn’t care at all.

I was grateful to be with my friends. We got up that Saturday morning and got breakfast tacos and mimosas. I asked my buddy a few thought experiments as we munched on our spicy chorizo.

“If you got $100 billion tomorrow, tax-free, what would you do with the money?”

He fired back the best response I’ve ever heard to the question. After a few typical answers—properties, investments, cocaine—he smiled and said…

“But then I’d probably spiral into a crippling depression as I realize that money wouldn’t make me happier.”

“Whoa,” I nodded. “You want another mimosa?”

“Yeah, dude.”

We walked back to the house. A thought occurred to me as I was laughing with my bud.

I’m quite lucky that all of my best friends have partners I get along with and consider good friends of my own. I love hanging out with them. But nothing beats one-on-one time with someone you’ve been close with for decades, especially if you only get to experience it once a year.

With the whole day ahead of us, we walked their dog and drove downtown. I wanted to do something I’ve been really getting into lately.

Slam poetry.

Just kidding—rock climbing.

We parked and walked to this tiny gym. It was so small we sped right past it the first time around. One guy ran the whole thing—the register, instruction, he even climbed with us.

My buddy had never climbed and I was a total novice. “We’ll suck, but we’ll suck together,” I told him. We started with the beginner-level problems.

I could see that his technique was off, but I had no idea how to correct him. Not wanting to give him damaging advice, I said nothing. This was mainly because I had terrible technique myself.

We lasted about an hour until our forearms and hands couldn’t take it anymore. But it was such a treat to do something active and challenging with a friend.

We also met the guy who ran the gym, Sam. He was chill.

After a lovely Japanese dinner, we bought some shrooms from one of his work friends. Apparently, mushrooms are easier to get in Asheville than anything else. It’s common for people to grow them in their own backyards.

When we got back, my buddy’s girlfriend had returned from work (on a Saturday, damn Communists). We cooked up some food, ate a small portion of mushrooms, and my buddy and I played a few games of chess.

I don’t really like doing drugs, especially psychedelics. When I trip, I tend to lose my social skills. And whenever I lose the ability to articulate my thoughts and feelings, I get wildly insecure. It makes me feel like a baby. Like…an actual infant.

So I only took one that was about an inch long, skinny, and with a tiny cap. Taking such a small amount usually leads to a giggly energy boost. I have no interest in hallucinating or entering the baby state.

After brutally destroying my friend in one or two games of chess, we cracked some beers and waited to go out for the night. They lived two blocks from the main street with a bunch of bars and restaurants.

One of my buddy’s coworkers walked by the house and shouted to him. They started chatting it up. Meanwhile, his partner and I started talking about…something.

I have no idea what the topic was, but I loved it. It seemed we couldn’t finish a sentence without laughing. What were we laughing at? I have no idea.

I felt pure joy. Everything seemed to be flowing as she and I were chuckling and sharing insights. The windows were open to let the breeze in. Then I looked around and noticed that every color around me was twice as vivid.

“I think these mushrooms are stronger than we thought,” I suggested.

“I was just about to say the same thing,” she replied.

We kept chatting, picked a spot to go eat, and drank another beer. Eventually, my buddy came inside from the balcony and said, “Yo, I think these shrooms are stronger than we thought.”

We burst into laughter.

Once we gathered ourselves we started walking to the first bar. I felt like a kid, but in the best way possible. It was as though everything was funny and we had nothing to worry about. Everything someone said led to laughter.

We sat down at the restaurant, ordered food, and I asked the bartender to make me his favorite cocktail. It was hands down the worst drink I’ve ever had. My friends agreed.

It was getting later (which is how time works) and we went to one more bar down the street. When we walked in, I saw people playing chess toward the front. My people.

My friends and I ordered some beers and they got some more food. I walked right over to the chess table and made friends with the group of five immediately.

The main guy asked me if I played. Not wanting to reveal my hand, I gave my usual answer: “I love to play!” When I asked him how good he was, he told me he was venomous. Uh oh.

My buddy’s girlfriend went home to go to sleep but he stayed with me to watch me play. I introduced him to the chess peeps, he joked with them, and then he sat down in one of the nearby high chairs. His eyes were only half-open so I knew I was running against the clock.

Five moves into the game with Mr. Venom, and I realized he was not nearly as good as he spouted. He hung a piece and I improved my position. Eventually, I got cocky and stopped paying close attention. Then I hung a piece. We got into an endgame where I forced a trade of Queens to ensure a pawn promotion.

In other words, I won and he resigned.

He was a great sport. We shook hands and he bought my friend and me another beer each. Though I wasn’t sure how much more my friend could handle before he fell asleep in his chair—something I’ve witnessed more than once when we were in college.

We finished the fun. I paid the tab. And we stumbled home.

The journey down south (pt. 3)

Nanny the dog
Look at that smile.

(Here’s part 1 and part 2.)

Day 1 (cont.)

After two hours of sitting out front of the car repair shop, my friends pulled up in their white Suburu. It was like they rode in on a white stallion to come and save me.

We hugged. They helped me with my stuff. And then I treated them to Waffle House—only the finest.

I had never been before. We each scarfed down our waffles and eggs. I started chatting with our waitress. She was working the graveyard shift and she told us her ex was on the run from the federal police.

“Wow,” I said. “Well…I sure hope they find him!”

“Thanks,” she replied. “I’ve always had great taste in men.” We chuckled and felt that was the right time to leave.

We took Nanny, their dog, for one last walk around the grass. Then we got in the car and finished the night-time drive.

It went by quickly. We hadn’t seen each other in person for many months so the conversation flowed. They told me about their plan to move back to Maryland this summer. I shared my events for the rest of 2022. They brought a small cooler of beer so the other passenger and I cheersed and sipped them.

We got into Asheville around 9pm. We were all tired from a day of driving. I thanked them profusely several times.

I unloaded my stuff and they prepared their pullout couch for me. Little did I know I’d have to fight for my spot.

Nanny the dog lying on a pullout couch
She’s a fierce beast.

It felt like my vacation had started. I was finally in Asheville. I was with my friends. We were laughing. I laid down for bed.

Now I just needed my car.

(Here’s part 4.)

The journey down south (pt. 2)

Phil Cocchiaro petting his dog Nanny

(Go read part 1 if you haven’t already.)

Day 1 (cont.)

Jerry lugged my broken-down car onto the bed of his tow truck. We hopped in and sparked light-hearted conversation.

His middle-of-nowhere-Virginia accent only allowed me to catch every other sentence. But similar to learning Spanish in high school, I was able to fill in the blanks. He was a jolly dude.

“Where ya headin’,” he asked me.

“Florida’s the end goal,” I replied. “I’m going to a retreat with my life coaching community. Do you know what a life coach is?”

He had no clue. He said he was just in Florida, though.

“Me and the wife flew into Miami for a cruise. First time on a plane. 64 years old.”

“Wow,” I said. “What made you decide to try it after so long?”

“Wife roped me into it,” he chuckled. “Didn’t have a good reason not to. Got a Budweiser at the airport. Sat down in my seat. Wasn’t scared at all.”

We continued chatting for the rest of the 20-minute drive back to his shop. He told me about his family and asked me about Maryland.

We were in Pulaski, Virginia. I scoped the farmlands and shopping centers to see if maybe moving to Brooklyn was the wrong choice. Alas, Pulaski didn’t grip me.

A map of Maryland, Virginia, West Virginia, and North Carolina
Heart: where I live.
Pin: where my car broke down.

We got to the repair shop and I gathered the luggage I’d need over the weekend. They were closed on Saturdays and Sundays so I’d have to pick my car up on Monday.

“You gone be good out here by yerself?” Jerry asked me.

“Do I have any other options?” I joked timidly. “What is there to worry about—coyotes, murderers?”

He laughed. “Well, if ya get hungry, there’s a McDonalds that a way, and a KFC that a way. There’s also some hikin’ trails down the road a bit. I know ya said ya like hikin’.”

I did say that. Thanks for remembering, Jer. But I looked down at my two heavy suitcases and my backpack.

“I think I’ll just sit in this chair and wait for my friends to come pick me up,” I said. “They’ll be here in about two hours.”

“Okee dokes,” Jerry smiled. We shook hands, I thanked him for the ride, and he got on his Harley Davidson and zoomed down the road and out of sight.

I wanted to feel productive before the coyotes came for me. So I opened up my laptop and wrote a few pages for my book. I also did something I haven’t done in years.

I drank a soda.

It felt amazing…for 10 minutes. Then I got dizzy.

My friends texted me saying they were only an hour away. Until then, I’d sit in a chair that reeked of cigarettes, sipping my Mountain Dew, calmly typing away on my Macbook.

What struck me most was how unfazed I was.

This was a huge inconvenience. I was on a road trip, and the device I needed to keep me on the road was out of commission. If I get travel anxiety 100% of the time, why wasn’t I freaking out?

This was insight #1: I had nowhere to be and nothing to do.

I can’t remember the last time I had days in a row where I truly had no deadlines. As cheesy as it sounds, my shoulders were completely relaxed because I knew everything would be totally fine.

My friends were coming to pick me up. I’d get to have fun with them. My car would get fixed. I’d make it to Florida.

All was good.

I took another sip of my sugary death liquid and wrote another paragraph. The sun was going down and I was smiling.

(Here’s part 3.)

The journey down south (pt. 1)

Dillan Taylor, Phil Cocchiaro, Jess Molnar, and Nanny the dog in a car

I just got back from my two-week road trip—Asheville, Tampa, Savannah, and back to Annapolis.

In these next few days, I’ll share the events that occurred, the characters I met along the way, and all the lessons learned.

Day 1

I left on a Friday morning after waking up early to pack and go to the gym. I felt great.

No clouds. Bright sun. Windows down kind of weather.

It’s an eight-hour drive from Maryland to Asheville. My first stop was to visit one of my best friends of 16 years—since 7th grade. Him, his partner (another dear friend), and their dog, Nanny.

I was thrilled to do what we usually do: hike, laugh, drink beer, do mushrooms, romp around.

The drive was seamless. After a few phone calls and one or two Drake albums, I noticed about five hours had flown by. I also hid the clock on my car radio so I wouldn’t be looking at it every three minutes.

It felt like a perfect day. I was elated. I texted my friends my ETA and they sent me their new address.

Then something happened.

I was doing my usual 90 mph in the left lane on highway 81. Out of nowhere, I felt a pop from the hood of my car. My “SERVICE ENGINE SOON” light came on immediately. And despite pressing down harder on the gas pedal, my car started slowing to a halt.

On top of that, white smoke began pouring out from under the hood and through my AC vents. It didn’t smell great. I used my detective skills to deduce that something was in fact wrong.

I pulled over to the side of the busy highway. My car wouldn’t accelerate and my AC stopped working. So I decided to sunbathe while I troubleshot.

Dillan Taylor sunbathing in his broken-down car
Notice the florescent tint of my European skin.

I did what any man would do in this situation. I called my mom.

She sent me the number for our Verizon roadside assistance. The service was shotty so each page took about 60 seconds to load. When I made it to the end of the tow request, the app wouldn’t recognize my location.

Not pictured: the thousands of semi-trucks making my car shake as they passed.

“You are not in a real location,” it told me.

Fuck, I thought. I’ve never felt so invalidated. I looked around at the surrounding farmland and hilltops to confirm that my location was actually a part of reality.

The app disagreed. So I called.

The dude who answered was super kind. He said his name was Tim but his accent suggested otherwise. I gave him all my information and then he asked exactly where I was.

“Excellent question, Tim,” I replied. “Let me go check this mile marker and let you know.”

I muted myself so Tim didn’t have to listen to the death trap that was 81 South. Then I sprinted to the next mile marker. 90.6. I made it back to my car, dodging traffic along the way.

When I gave him the rest of what he needed, he told me my tow truck would be there within the hour.

“No worries, Tim. I’ll just stay here while I wait.” He didn’t laugh. He just told me for a fifth time how happy he was to serve me and hung up the phone.

I called my friends to share the great news. They offered to come pick me up—two and a half hours out of the way. I felt bad about this but didn’t have any other option. I texted them the address of the repair shop my car would be sent to.

When the service came, I met Jerry, my tow.

Dillan Taylor's car being towed by Jerry
A gorgeous day for a car repair.

Jerry looked under my hood and said my radiator blew out. I took his word for it, knowing absolutely nothing about cars. I was bummed by inconveniencing my friends but pleased to get my car fixed in the next 24 hours.

Little did I know, it would take a lot longer than that to get my car back.

(Here’s part 2.)

To Florida and back

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

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

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

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

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

Then the retreat just south of there.

I feel a sense of bliss. Here’s why.

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

But we all need breaks.

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

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

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

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

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

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

See you in two weeks. ✌️

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

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

I think that’s bullshit.

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

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

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

So what’s wrong with this?

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

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

And that’s my point.

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

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

“Where the hell did four months go?”

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

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

  1. Newness
  2. Gratitude

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

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

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

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

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

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

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

It only takes a sentence.

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

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

Anyway, my two questions for you are:

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

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

What we don’t see

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

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

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

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

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

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

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

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

I’m reading 80 books this year—Why I don’t recommend it

A bookshelf stacked with books of all kinds

I read 64 books in 2020. Last year, I read 70.

So naturally, I stretched the goal this year and set my GoodReads challenge to 80 books.

I’m hitting a point of diminishing returns. Let me explain.

I love reading. It calms me down and makes me feel like I’m entering another person’s mind while applying lessons to my own life. I also keep an extensive collection of notes with each book I read.

But 80 books is a lot. For the first time in my life, it feels like I’m reading to meet a quota instead of reading because I’m feeling pulled to. (I never read a single book in school.)

Not that that’s always a bad thing. I don’t always want to go to the gym but I force myself to go three times a week. That’s a number I have to hit because I know it’s good for me.

But the difference with reading books has been my lack of retention. I looked through my 2022 GoodReads list the other day. There were at least three books I didn’t remember reading at all.

I’ve been flying through audiobooks. If I don’t take notes, then within a week or two, all that I learn has left my mind. And even when I do take notes, it’s not like I’m reviewing what I capture every week.

Would you rather read 50 books you forget about or 5 books that change your life?

My point is: “I read 80 books this year” sounds sexy. It sounds impressive. It sounds like something you tell your friend who doesn’t read to make yourself feel big.

But I won’t be doing it again. I’m sacrificing enjoyment for quantity. It looks cool on the outside and feels grey on the inside. It’s like a gorgeous Instagram influencer who’s severely depressed. (Does that make sense? I’m not depressed.)

Goals can be great. But we have to know why we’re pursuing them. “Because it sounds impressive” is a terrible reason.

Quitting vs. giving up

A woman in a red shirt banging her head against her keyboard and wanting to quit

A few weeks ago, I interviewed Lynne Tye for my book. She’s a badass entrepreneur who wrote the article which inspired me to launch my business.

The conversation flew by as we laughed and vibed over building stuff. Our discussion was full of gold but I wanted to share a simple framework that I found super useful.

The difference between quitting and giving up.

According to Lynne, giving up is when we still want the result.

“I gave up the other day,” she said. “I was running and stopped halfway through and walked the rest…which is trash. I still wanted the result of getting in a good run, but I stopped putting in the work needed to get that result.”

Quitting, on the other hand, is a strategic choice. It’s when we decide to put our time and energy elsewhere because we no longer crave the result.

In 2020, I was certain I wanted to become a YouTuber. I started posting a vlog a day. After two months, I realized I absolutely hated it and didn’t care about filmmaking. So I stopped.

Did that mean I gave up on my dream? No. It meant I stopped wasting valuable mental and creative energy so I could channel it into something I did care about.

“Quitting is such a valuable thing,” Lynne told me. “Like quitting cigarettes. What we want is constantly changing so we need to keep taking stock of that. More people should quit more often.”

So the next time you want to stop something, ask yourself: Do I still want the result of this?

Then you’ll know if you’re choosing to quit or if you’re simply giving up.

The gift of suffering

We were not suffering in this photo.

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

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

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

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

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

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

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

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

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


Grow a mustache—Why you should be more polarizing

A man with a mustache and sunglasses looking into the distance

(Yes, ladies. Even you.)

The idea

I want to alienate more people. Let me explain.

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

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

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

Then everything changed when the fire nation attacked.

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

The stache

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

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

The thing I noticed immediately? Mustaches are polarizing.

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

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

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

Then I thought about other areas I could apply this.

The meaning

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

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

Lower quantity. Higher quality.

So what does this mean for us?

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

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

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

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

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

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

Grow a mustache.

You can do it (actually)

A group of athletes running a marathon

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Keep running.

2am nightmare

Every month or two, something shitty happens.

I wake up in the middle of the night—usually around 2 or 3 o clock—and I’m wide awake. Each time, I think it’s like 30 minutes before my alarm is supposed to go off. Then I check the time and panic.

I’ll walk out of my bedroom and read or listen to a podcast. Something light until I get sleepy.

Eventually, I get tired again. But that tends to take another two to five hours. If I fall back asleep, it’s for another hour at most. Then I have to get up and start my day.

That happened today. I feel like a zombie. And I never know what to do.

I canceled my last call just to take a nap.

Anyone else experience this?

I’m scared to talk to women

A guy with flowers behind his back as he picks up a woman for a date

I’ve never been able to go up to an attractive woman and just start flirting with her. I used to think there was something wrong with me—that I was weak or a coward.

But that’s 95% of dudes.

For many years, I thought having “game” was just one thing: being able to court someone and get them interested in spending time with me.

But that’s wrong. I think having game (a term I hate) is more universal.

Here’s how I define it now: building a connection with another person, making them feel interesting, and looking forward to the next conversation.

The cool thing is, we can do this with anyone, not just a potential romantic partner. All it takes is vulnerability, genuine values, and curiosity. Meta skills like storytelling, humor, and adventure are helpful as well.

My point is: I don’t think I’ll ever be the guy who walks up to a group of women at the bar for no other reason than to hit on them. That’s where I’m uncomfortable.

But when there’s a reason for communicating, that’s where I thrive. Example: My buddy and I spent hours talking to and hanging with this group of women in NYC.

How did we start talking to these ladies? Bowling.

They were in the lane next to us. So it only made sense that we joked and laughed with them as we watched each other throw gutter balls. We had a reason to start building that connection.

So, yes. While I find it terrifying to randomly go up and start flirting with a woman, if there’s a reason for it, I’m confident in my ability to get the ball rolling.

I’ve never written about my dating life in this blog. If you don’t hate it, let me know and I’ll keep spilling the tea. ❤️

Writing is still hard

A person sitting at their desk and writing with pen and paper

I’m day 69,420 into writing my book. It feels that way at least.

When I decided to embark on this journey last August, I thought I could finish it by December…Silly, silly man.

I’ve pushed back the publish date several times now. Partly out of procrastination, but mostly out of necessity. Here’s what I mean.

When I started, I did what I tell others to do when they’re creating something. I reached out to my network. I asked everybody if they knew someone I should talk to. It was easy to find people to interview.

So I did. It was fun and super low pressure.

Then, I interviewed the hosts of my favorite movie podcast. Then, I email-interviewed my favorite author and speaker. And then, I interviewed an entrepreneur I look up to who wrote the article that inspired me to launch my business. And then, my favorite chess streamer and YouTuber responded to my email and asked to set up a call in May.

This thing is getting bigger. What a lovely problem to have.

I call it a “problem” for two reasons:

  1. I’m still setting up calls with people which means more time is needed to write this thing.
  2. To keep the book short and minimal, I’m choosing to cut out certain people I’ve interviewed. That makes me feel bad.

But on the upside, my confidence has soared as I’m getting people who are huge in my eyes to hop on a call and talk to me about what they’ve created. That lights me up.

Also, here’s the good thing about not being all big a famous with an enormous audience: there’s not a ton of people I can disappoint. Many people bought pre-sale copies of the book. But I doubt they’re checking their calendar and stressing over when they’ll get their $10 back (soon, my friends).

Anyway, here have been my biggest lessons so far:

  • Reach out to people. You can’t get what you want if you don’t ask for it. If they don’t respond, you’ve lost nothing because you already weren’t talking to them.
  • People LOVE being asked thought-provoking questions they’ve never been asked before.
  • Writing is easy. Sitting down to start writing feels impossible.

Stay tuned. ✌️

What I learned from Will Smith’s slap

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

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

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

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

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

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

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

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

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

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

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

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

Was I disgusted by what he did?

Of course.

Will I go see the next movie he stars in?

Of course.