Dying, chess, and grapes

My cousin, shortly before I checkmated him.

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

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

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

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

How many visits left?

Lake Gaston, 2020.

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

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

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

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

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

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

Grapes and tuna fish sandwiches

A plate of grapes sitting on a dining table

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

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

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

We all burst into laughter.

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

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

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

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

Memento mori

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

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

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

Here are two reasons why.

1) It softens the blow.

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

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

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

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

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

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

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

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

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

Son, father, grandfather—2013.

What are you willing to sacrifice?

A woman trying to carry too many books

What is a strength of yours that is also a weakness?

My buddy asked me that last year and it led to a wild conversation. My answer?

“I obsess over the things I’m interested in.”

I’ve never dabbled. If I’m going to learn a new skill or embark on a new project, I commit to it 100%. Whether it’s a career path like building a coaching business or a personal hobby like chess or jiujitsu. If it stops being interesting to me, I quit and move on to something else.

How is this a strength?

Well, since I’m able to put my head down and stick with something consistently for months, I can learn things pretty quickly. I created a full-time coaching practice in nine months. I got cast as the protagonist in a play after my second audition ever. I became an advanced chess player in less than a year.

None of this is to brag. It’s just to emphasize the impact of commitment and consistency.

But how is this a weakness?

My hyper-obsession can get in the way simply because I get interested in too many things. This leads to suboptimal performance and occasional burnout.

We can do ten things to the first degree or one thing to the tenth degree. I also love this quote from Chris Williamson:

“You can have anything you want, but you can’t have everything you want.”

That’s a harsh truth for someone who wants a lot of things. But it’s true.

We can’t be an incredible parent and be in perfect shape and start a business from scratch and coach baseball and read tons of books and have a thriving social life and travel all the time and be a great musician and…you get the point.

Everything’s an opportunity cost. Time spent with our children is time not spent working on our side hustle. Time spent on our side hustle is time not spent with our children.

The question is: What are you willing to sacrifice?

Here’s an image to help illustrate this phenomenon—the Four Burners theory.

From jamesclear.com

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

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

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

That answer should be different for each of us.

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

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

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

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

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

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

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

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

Why I quit acting

Mike Mitch and Dillan Taylor acting on stage
Spring Awakening, 2016.

How I started acting

Since I was a kid, I had always wanted to be an actor.

I remember watching my favorites. Folks like Daniel Day-Lewis, Natalie Portman, and Christian Bale. I’d memorize scenes and perform them when I was alone. It was mesmerizing to me to be taken to a completely different world. What floored me most was knowing it was a set with actors, directors, and producers…yet finding it 100% authentic in the moment.

I wanted to do that for other people.

But when it came to taking opportunities, I wouldn’t. I avoided being a “theatre kid” in high school. I was too busy smoking weed and making fun of the theatre kids. I didn’t audition for anything during my first three years of college. I had a good reason not to.

I was terrified.

The semesters would pass by and I’d see flyers for the new shows being put on. Next semester, I’d tell myself.

Then, at the beginning of my senior year, I was walking through the liberal arts school. I happened to see a girl I knew who was in the theatre program. We chatted for a minute or two.

“What’s the play this semester,” I asked.

“To Kill a Mockingbird,” she replied. “The last day to audition is tonight at 6!”

Shit. I had nothing going on that night. Which meant I had no excuse to bail.

The day went on and I found myself back home watching the first season of True Detective. I wanted Matthew McConaughey’s swagger to inspire me. I sipped some whiskey to calm my nerves.

An hour or two before auditions, I convinced myself not to go. I wouldn’t know anybody. They’ve all been acting for years and I had no experience. The community and culture were probably already set in stone and I wouldn’t belong. I’d make a fool of myself.

Then I had an insight.

I wanted to be an actor. That was true. But how did I want to secure that for myself? I imagined the director knocking on my door.

“Hello,” he’d say. “I know you didn’t audition. But you strike me as someone who’d be really good at acting. Would you like to be in my play?”

I laughed because there was a 0% chance of that ever happening. No one was coming to hand me anything. I had to put myself out there and go for it.

I sighed and started walking to the campus. I tried to step fast enough to get there with plenty of time to settle in, but slow enough to not be covered in sweat.

As I panted through the building’s doors, I could already hear the cacophony of conversation coming from the theater. I followed the noise and to my horror, everyone was talking to everyone. I grabbed a script from the pile by the door and meekly took a seat toward the back of the stands.

I felt like the new kid in school who didn’t belong. I wanted to flee. Ten minutes passed and I thought, it actually makes sense for you to leave.

Then the director walked in. I expected the place to become silent.

It got twice as loud.

Students left their seats and walked up to start talking to him. I was screwed. But it was too late to weasel my way out. He took center stage and everyone sat down with their scripts.

At random, the director would pick scenes from the play and we would go up and cold read as any character. It didn’t matter who it was, guy or gal. The goal was to give him a sense of what we looked and sounded like.

I sat in my seat pretending to look at my script because I was too horrified to go up. Then I noticed too shiny brown dress shoes next to my feet. They were attached to the director. I looked up.

“We haven’t seen you yet,” he smiled. “Why don’t you read for Scout?”

My plan to remain invisible had failed. I crawled up there and did my best Matthew McConaughey I could muster. I was sweating profusely.

But I did it.

After the first round, I stayed up and read for another character. It got easier and easier. No one was laughing at how stupid I was. No one whipped their phone out to start filming me. As it would turn out, everyone else was just as nervous as I was.

I went home and despite doubting I’d get a part, I was proud of myself. After years of thinking about going for it, at least now I could say I actually tried.

My actor friend messaged me a few days later while I was at work. I got a role. My first role in a play.

It was a small part. A side character with ten lines. I was elated. Ten lines? It’ll be impossible to forget them!!

That semester was my first experience being in a theatre company. I became familiar with the rehearsal process, learned my way around the back of house, and made new theatre friends. I also started taking acting classes.

It was a perfect timeline:

  1. Got that first role in the fall of 2015.
  2. Got cast as a protagonist in the following spring production.
  3. Became convinced that I wanted a career in theatre after college.
  4. Got cast in the more intimate play that following fall with a different director. He taught me how to tell a story and helped me drastically sharpen my skills.

But there was a problem.

Here’s the thing…

Clybourne Park, 2016.

As my years at university drudged on, I was doing worse and worse in school. I was skipping classes, not handing in essays, and using that time to sit in on acting classes. I was too deep into my major to switch to a theatre degree, so I had to improvise.

Obviously, this was unsustainable.

My girlfriend at the time was an actor too. That winter, we took a bus up to NYC and auditioned for grad schools. We had spent months preparing our monologues and resumes.

It was a thrilling and anxiety-inducing experience.

Hundreds of actors from around the country would wait to be called into a room. It was a small banquet hall where 50 people with clipboards were facing a small stage with a chair on it. We’d walk in, head to that stage, arrange it how we wanted, then introduce ourselves and perform two monologues.

We had two minutes starting when we spoke our first word. At the two-minute mark, the time-keeper in the back would raise his/her hand and say, “thank you!” Then the gods would decide our fate.

She and I both got several callbacks. It was an exhilarating way to spend a day: running around a giant Broadway hotel to different masters program scouts from around the globe.

Here’s the punchline to this drawn-out story: I got accepted into three different schools. One in Long Island, one in San Francisco, and one in Birmingham, England.

I couldn’t go to any of them because I flunked out of college that spring.

Emailing each of them back was one of the most depressing things I’ve ever had to do. But things got worse.

After an unsuccessful “college try,” I moved back in with my mom with my tail between my legs. I’m all for people living with their parents to save money and figure something out, but this wasn’t my choice. I was back to square one. No job. No real skills besides acting. A ton of debt.

A few weeks into that summer, that same girlfriend broke up with me. She had graduated and wanted to explore the world and herself. I was in a hole with no idea how to start digging myself out. It made total sense. But it crushed me.

Unfortunately, none of those events motivated me to begin climbing that mountain. In fact, in June of 2017, after stealing a bunch of prescription pain pills and anti-depressants from various people, I tried to kill myself.

That sounds awful. And it was. But it wasn’t out of intense depression. It was almost out of laziness.

I had so many things to figure out and repair. The second I thought about the first few steps, I’d get overwhelmed and would avoid anything and everything. It seemed truly insurmountable. So I tried to bypass it.

I’ve shared that story before and can go into more detail in a future blog. But all you need to know for this one is that it was my breaking point. My rock bottom.

My decision

To Kill a Mockingbird dressing room, 2015.

Waking up from that, everything clicked.

Whatever I had been doing up until that point clearly wasn’t working. Something had to change. Many things had to change. So I started at the beginning.

I began applying for jobs—bigger restaurants in my area. I opened a new checking account since my old one was closed due to prolonged overdrafting. I got a gym membership and started working out 2-3 times per week.

But the question remained: When would I have time to audition and perform in plays? There were numerous theatre companies in my area. How could I make it work?

I wouldn’t.

It was both one of the easiest and most difficult decisions I had ever made. I wasn’t ready.

I wasn’t prepared to pursue arguably the most grinding, unforgiving, and least lucrative careers in the world. I could barely take care of myself. I needed to grow up.

Many of the successful paid actors I know today have one or two (sometimes three) side jobs. They’re scraping by.

I didn’t want that. I don’t ever want to live anything close to paycheck to paycheck ever again. I didn’t know what I would pursue instead, but I knew it would be something much more likely to make a great living. I had an inkling it would be in the world of business.

So I haven’t done any sort of acting since failing school in the spring of 2017.

Will I ever be on stage again? Maybe.

Theatre will always be a love of mine. Going to shows is one of my favorite ways to spend a night out. I’ll always have a deep respect for the craft of acting and storytelling. I still act out my favorite movie/television scenes when no one is around.

But if I never act in another play again, I wouldn’t regret it.

I have so many other things I’m passionate about. My business. Creating content. Writing. Chess. Jiujitsu. Connecting with others.

I’m not the lost 23-year-old I was when I was…23 (that’s math). For now, I’m content with going to see as many performances as I can. I also have a bunch of old theatre friends creating their own shows and doing incredible work. Seeing them do their thing makes me smile every time.

For me, acting was like the perfect guy or gal you meet at the worst possible time in your life. It brought me tremendous joy, fulfillment, and friendships. But wasn’t the right time. I had to learn how to live first.

It wasn’t you; it was me. We had our time. Maybe I’ll see you again. 🎭

July Q&A

1) “What’s a question you wish someone would ask you?”

With all the time I spend being curious about other people, it’s so refreshing to have anyone ask me questions about myself and what I’m working on.

I run a life coaching business where I spend hours going deep into the minds and lives of others. I’m writing a book where I pry at people’s habits and insights. And I love it. I find people—specifically people who are doing things—fascinating.

But it can burn me out if I go a long time without anyone returning the favor. It’s a basic human need to feel important and seen.

So did I start this Q&A to fill a void? You be the judge.

My favorite question to ask and be asked is: What’s on your heart and mind right now?

It’s so broad and yet pointed and specific at the same time. It’s practical, emotional, and allows the answerer to be vulnerable immediately if they so choose.

So what’s on my heart and mind right now?

  • launching my new YouTube channel/podcast next week
  • sending my book proposal to Stripe Press today
  • the fact that I interviewed Courtland Allen, one of my favorite creators, yesterday
  • being pissed that I ordered a new car for delivery and it’s been delayed twice
  • getting in excellent shape and burning away my love handles

2) “How did you get into rock climbing and what level climbs do you do? #v1gang”

This made me lol.

Two of my besties took me climbing earlier this year and I didn’t love it immediately. I found it quite challenging, which pissed me off because they made it look so easy. So I kept coming back out of competition and ego.

As I improved and could enjoy it more, I thought it would actually be a great way to irradicate my phobia of heights. So I tried rope climbing.

This was a huge milestone for me. Climbing up that wall and being attached to a rope connected to my friend at the bottom was one of the most terrifying experiences of my life. My head was flooded with images of me falling and breaking my limbs.

But I made it to the top.

Coming back down, out of breath and coated in sweat…I felt triumphant.

When I lived in NYC for two weeks, I was an eight-minute walk from a gorgeous climbing gym. I went nearly every day, which would prove to be awful for my muscles and ligaments.

Although I got injured after those 14 days, I got way better at bouldering (shorter climbs without a rope). It was there that I did my first and only V4. So I would say V3s are my sweet spot between challenging and doable.

3) “What are some non-technical/intangible areas you’re thinking about and/or working on these days (e.g. attitudes or skills such as patience, listening, being more present)?”

The biggest thing I’ve tried to actively practice and improve this year has been empowering and praising people.

When someone impresses me. When they are clearly working hard at something. If they’re putting effort into things that matter to them.

I tell them.

It can be as simple as saying, “Hey, I want to acknowledge you for x, y, or z.”

Sometimes they just say thank you. Other times it makes their entire week. And on rare occasions, they tell me it’s exactly what they needed to hear. We never know where a person is at mentally.

A few months ago, at the end of a session, one of my clients took two minutes to do that to me.

“I just wanted to say,” she started. “That I know we’re here to focus on me and my dreams. But I’m so proud of you for pursuing yours. Building a business where you can help people and make money doing it. Creating stuff and only doing what you want to do without working for anyone else. It’s inspiring.”

My eyes teared up. No one had said anything like that to me before. And the last person I would expect that from was one of my coaching clients. I’ll never forget it.

We have the power to do that at scale for those around us. It could change their world.

4) “What are some of your favorite books and why?”

Here are five I love in no particular order. Follow me on GoodReads!

  1. Essentialism by Greg Mckeown: got me to focus on what’s most important and ignore the rest.
  2. The House in the Cerulean Sea by T.J. Klune: the most delightful story I’ve ever enjoyed.
  3. Anything You Want by Derek Sivers: one of the reasons I started my own business.
  4. The Madness of Crowds by Douglas Murray: changed my perspective on some of today’s most radioactive topics.
  5. Becoming by Michelle Obama: a truly vulnerable and inspirational memoir I couldn’t put down.

Thanks for all your questions! To keep this short, I didn’t get to all of them. Please keep sending me stuff you’d like me to dive into more.

The simple rule that helps me get work done

A typewriter on a desk

I tend to work on a ton of things at one time.

Studying chess. Building a coaching business. Writing a book. Running this blog. Launching a new YouTube channel and podcast soon (more on that later this week).

Getting distracted can be quite the wrench in my day. So aside from a few of the popular tricks and tips—a Pomodoro timer, starting small, leaving my phone off and in the other room…there’s one rule I follow that makes everything else 10 times easier.

I stole it from Niel Gaiman, the prominent fiction writer.

When he’s writing a new book, he sits down and gives himself two options:

  1. write
  2. do nothing

That’s it. He can’t do anything else.

The freedom to not write removes any guilt associated with not getting work done. And it doesn’t take long until writing becomes less boring than just sitting there doing nothing.

I do the same.

When I’m not doing whatever deep work is needed from me, I’m sitting here daydreaming and talking to myself. Sometimes it lasts 60 seconds. Other times it lasts 20 minutes. But eventually, I always come back to the task at hand.

The impulse to check something is omnipresent. Email. Facebook. YouTube. Facebook again.

But those aren’t one of the options.

The rule must never be broken. Otherwise, it’ll be broken every day. So instead, I sit here and work…or do nothing.

I’ve quit nearly everything I’ve started—Here’s why

I’ve tried my hand at many creative endeavors. I gave up on all of them except for this blog.

Here’s the timeline.

2010, high school: a punk rock band with my friends.
2015, summer: standup comedy.
2016, in college: theatre.
2018, winter: a podcast about people’s passions.
2019, fall: this blog and a YouTube channel about self-improvement.
2020, fall: a daily vlog.
2021, winter: sketch comedy videos

Clybourne Park, 2016.

Aside from acting, which I was deeply passionate about, each of these pursuits ended the same way.
(I’ll tell the story of why I quit theatre in another blog.) The process went like this.

First, I would get inspired by other people whose skills I enjoyed. In high school, it was Blink 182. For standup, it was Louis CK. I started vlogging because of Casey Neistat.

I wanted to be as talented as these guys. I envisioned myself on stage captivating crowds or being recognized on the street by one of my million subscribers.

So I’d start the thing.

I learned every 2000s pop-punk song on guitar I could. I forced myself to sign up for an open mic. I bought a camera and microphone and started recording.

It was always exhilarating. For a week or two.

But each time, reality would quickly settle in. That reality was: If I want to get good at this thing and have other people enjoy it, it’s going to take a ton of time, consistency, and persistence through being mediocre.

Basically, I would suck at something and wouldn’t get the results I wanted fast enough. Then it would rapidly feel more like a chore than a passion project. Once the Resistance grew tall enough, I couldn’t justify continuing to work on it. I’d stop enjoying it or begin dreading it entirely.

The worst part about this cycle was it would make it difficult to trust myself. When I’d feel interested in a new venture, I’d think in the back of my mind, “But how long do you think this will actually last?” Then I’d hesitate to start.

Our Blink 182 cover band setting up, 2011.

So why does this happen?

I mentioned it above briefly, but the answer is quite simple: it’s due to unmet expectations.

We see the thing we want: fame, glory, high-quality entertainment. Then we go for that thing.

But as we start to put our heads down and do the work, we see that the things we wanted are hidden behind countless hours of grinding practice, boring or stressful tasks, and little to no recognition. It’s all the unsexy stuff we never see from those we admire.

When I wanted to be a standup comedian, I wasn’t fantasizing about all the empty clubs I’d bomb in at 2am. I just wanted a Netflix special.

When I started vlogging, I didn’t think about how many hours a day it would take to think of something interesting, film it, and edit it in a fun and captivating way. All I wanted was a following and ad revenue.

If our goals are the end results, we’ll never make it. It’s unsustainable to be driven by money, subscriber count, or viewership. Because when we start, we’re pretty bad at whatever it is we’re doing. So those incentives will naturally take a very long time to experience.

Let’s look at the only thing I’ve stuck with from that list above: this blog.

From day 1, I never cared about how many people were reading it. For the first several months, it was just me and one supportive friend. I still loved it.

Because I cherished the process. There was never a result in mind.

Now, this blog has way more subscribers. So I obviously feel more inclined to make it good and worth reading. But at the end of the day, I just get joy from typing my thoughts out a few times each week.

The first podcast I ever recorded, 2018.

So when we’re thinking about pursuing something new and creative, I’ve learned it’s crucial to ask this simple question: Do I actually want to do this work, or am I just craving the end result?

In other words: Am I okay if no one cares about this for the first year of doing it?

If the answer is no, it might be worth reconsidering.

Being ghosted by my best friend—What I learned

A few years ago, one of my best friends—the guy I thought would be my best man—cut me out of his life entirely.

He stopped returning my texts and calls and never responded when I told him I wasn’t upset and only wanted to talk. To this day, I don’t know the reasoning behind it. I can only imagine there was something about me he felt would be better if removed from his life.

But I’m still in the dark.

It took me about a year of coaching, reflecting, and overthinking before I found closure. But I’d be lying if I said there wasn’t some sort of trauma as a result.

Despite that, it’s taught me a ton about friendships and all that goes into them. Here are two things I’ve learned.

1) A friendship is just another relationship.

Freshman year 2012, my roommate after 9 shots of fireball.

A friendship takes a consistent effort to remain strong and healthy—just like a romantic partner.

In fact, friends are much stranger than significant others when you think about it. With a partner, sex is involved (hopefully), families are shared, and you may even reproduce together.

With friends, you’re basically saying, “Hey. I enjoy talking and doing activities with you. Let’s keep meeting up to do those things. We’ll never do anything romantic together, but we’ll still support one another as we live our lives.”

When we’re younger, it can be easy to take having friends for granted. In school, we’re physically forced to be surrounded by people our age with similar goals—be they playing the same sport, having similar hobbies, or smoking the same weed.

But as we get older, we go off to college. We move to different parts of the country or planet. Some people leave their previous lives behind. Others start families.

My 10-year high school reunion was this weekend. I absolutely love reconnecting with people from my past. It fires me up to see people grow and better themselves as the years go by.

One guy who was a bit overweight in high school lost all of it, is totally jacked now, and looks like a Calvin Klein model. I found myself teary-eyed as he took me through his journey. I told him I was proud of him.

Anyway, as we inch through our 20s our values and priorities evolve. When we add another human to that mix, a plethora of things can happen.

We’re almost guaranteed to change. Our friends are almost guaranteed to change. How do we know that these changes will align and harmonize with one another?

We don’t.

It’s out of our control. But what we can control is how present we are with the people we care about and how well we communicate what we want.

Setting up regular phone calls. Going out of our way to visit them. Asking them about their world.

I have a number of friends I used to party with. But now that I don’t care for getting wasted and doing drugs, a huge chunk of my shared values with those people is gone. So naturally, we don’t spend time together.

The friends I used to go out with aren’t the same ones I talk to about my business ideas. Likewise, the folks I bond with over goals and growth aren’t the same ones I party with now.

Each relationship has its own role. And those roles change as we change. Keeping a friendship thriving takes effort, luck, and communication.

Speaking of communication…

2) It’s important to regularly check in with your friends.

May 2022, after a Savage Race.

By “check in,” I don’t simply mean reaching out. I mean reflecting on how the relationship is doing.

This can seem a bit dramatic to people who aren’t as willing to be open and vulnerable. But it’s one of the healthiest and most productive things my friends and I do.

It can be done in many ways.

On a small scale, simply telling our friends how much we appreciate them can make an enormous impact. Praising them behind their back. Letting them change our minds and inspire us, and telling them when that happens.

I tell my guy friends I love them. At first, they don’t know what to say but it quickly becomes a natural part of the conversation.

At the mid-level, it’s important to vocalize what’s working and not working with our buddies. This is where setting clear boundaries comes into play.

I talked with one of my close friends last year about how she made me feel belittled and patronized in conversation. We talked compassionately and respectfully about it for four hours. Last summer, I asked a best friend I’ve had since 7th grade to put in more effort. He went from doing practically nothing to calling me much more frequently.

It’s not about demanding our friends meet our expectations. It’s about creating agreements with them that allow the friendship to flourish.

At the highest level, I’d recommend a yearly feedback exercise.

This is typically reserved for the people we’re closest to. Again, we’re looking for high-quality perspectives on how we’re doing in the eyes of those around us.

Here are the questions my friends and I dive into:

  1. When have I hurt you?
  2. What do you think would be most beneficial for me to improve?
  3. What’s something you’d like me to know?
  4. When have you been impressed by me?
  5. What do you think I do better than most people?

We’re guaranteed to hear things we weren’t expecting. And if we do this with multiple people, it’s useful to connect the dots from similar responses.

In summary:

As much as we’d like to see them as organic entities, our friendships don’t simply take care of themselves.

There are two parties involved. They are likely to morph as the years tick by. And there’s no telling what those evolutions will look like or result in.

I have friends I get closer to each year. I got asked to be the best man by someone I’ve only known for two years. I got completely ghosted by one of the closest friends I’ve ever had.

It’s hard to predict what happens in our friendships. But if we continue to live for our values, we’ll probably cut out those who aren’t right for us anymore and attract those who are.

To my friends who are reading this, I love you all. ❤️

The 2 options for learning something

A girl in a kimono karate kicking in mid air

Last week, I took my friend to her first jiujitsu class. She’s athletic and open-minded so I thought I’d show her the misery I put myself through on weeknights.

While she enjoyed it, she said it was…a lot.

I remember when I first started in 2020. For about three months, I reluctantly went to class only to flail around and have someone control my every move. It was demoralizing.

But slowly, I began to defend myself. I got submitted less and less. Eventually, I even beat a few teammates.

The learning curve was steep. Going from total noob to slightly less of a noob was quite a journey.

My face just about every class.

So while learning a move in class last week, I looked over at my friend choking her partner. Her eyes were as wide as they could stretch. Most people aren’t used to bending and suffocating other people for fun. It can be overwhelming.

She took it easy and only sparred with a few people. They took it slow with her and talked her through everything. I’m lucky to be at a super welcoming and friendly gym.

Afterward, she wasn’t entirely sure if it was something she’d want to commit to. I completely understood. It’s hard to market.

“Hey, would you like to try something really really uncomfortable and grueling, that will take you a pretty long time to get even remotely good at, while you roll around in a puddle of other people’s sweat night after night?”

Jiujitsu, everybody.

Whatever she chooses to do, I was quite proud of my friend for giving it a go. It made me realize that we really only have two choices when learning, pursuing, or attempting something new.

Option 1: “One day…”

Option 2: Day 1.

Getting in shape. Learning an instrument or foreign language. Starting a business. We can either start these things or wait.

Starting is exhilarating, ungraceful, and often discouraging. When we begin to climb the mountain, we see how tall it actually is. We can also imagine the downsides pretty easily. It’ll be scary. We could fail. We might look stupid.

But waiting can be an unfulfilling trap. When we create all these conditions that have to be met before diving into something, years can go by and we realize we’re standing in the same (or in a worse) spot. These downsides are usually more long-term and therefore are harder to anticipate until a ton of time has gone by. It’s tough to imagine the regret you’ll feel ten years from now.

An example of this difference is building an exercise habit.

The cons of going to the gym are simple. You don’t know how to use certain equipment. You’re out of shape. You’re not sure which exercises to do. It’ll be unfamiliar and tricky before any results are had.

But the cons of not exercising regularly are cloudier and easier to ignore. It’s hard to motivate ourselves with the possibility of being deeply disappointed by our bodies years down the line. But that’s exactly what happens to many of us. We look at ourselves and wished we started working out a while ago.

That’s because we’re so afraid of Day 1. But it all starts there.

What are you avoiding? What’s Day 1 look like for you?

5 things I’d tell my 18-year-old self

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

My 10-year high school reunion is tonight. I’m thrilled.

I can’t believe it’s already been a decade. I remember wearing the tye die tank top in the photo above, walking through the neighborhood near our freshman dorm, and smoking a joint with my roommate.

“Dude,” I coughed. “When my sister is a freshman in college, we’ll be 30.”

“Whoa,” he retorted.

At the time, that idea seemed so far away that it would never actually come true. But now it’s less than two years away.

Before I take tequila shots with a bunch of people who didn’t know my name in high school, I’d like to reflect on who I was when I graduated. In the moment, I’m sure I felt like I had finally grown up. In reality, I was just an insecure teenager with a driver’s license.

If I had an hour with that 18-year-old doofus, what would we talk about? Would he be impressed by me? Would he judge my mustache? What would I say to him?

Probably these things…

1) You’re supposed to feel confused, self-conscious, and clueless.

No one has their shit figured out, especially at 18. We’re all just dumpster fires hiding behind beautiful Instagram photos and Facebook posts.

It felt like you were the only insecure kid in high school. But you’ll soon realize that everyone else was just really good at hiding it. I didn’t start feeling truly confident in life until I was 23. And that was after failing college and trying to kill myself.

As a life coach, I work with people of all age brackets. I know 50-year-olds who are still figuring out what they want to be when they grow up. You’ve got plenty of time.

You’ll never “arrive.” There is no solution or formula to life that makes the rest of it smooth sailing.

So just keep putting yourself out there and trying new things. Your values and interests will change as you do. But you have to take action and go out and explore.

2) Don’t go to college until you can specifically state what you want to work on and why school is the best choice for that.

You were a trash student, dude. A 2.2 GPA in high school.

Why do you think putting tens of thousands of fake future dollars on the line would make things easier for you? On top of that, you’d have no supervision and access to all the booze, drugs, and women you could imagine. Does that sound like it would produce high levels of commitment and productivity?

Swallow your pride and stay home for now. Get a job at a restaurant, start saving money, and build creative skills. It will suck to see your friends go off to four-year universities. But you’ll be grateful in four years when you’re not paying $1000 a month for a piece of paper you’re not using.

3) You’re not really valuable right now, but you absolutely will be.

I don’t mean you’re useless as a human being. But at this time, in both the dating market and the general economy, you don’t have much to offer.

It sucks to hear, but if you start slowly building your skills, you’ll be super attractive years from now. That goes for women, businesses, and collaborators.

Right now, girls tend to be attracted to fun. You’ll see that when you go out drinking.

But as you go deeper into your 20s, they tend to be attracted to confidence, drive, and security.

So, if you start working out, developing skills you can sell, and treating yourself and others with respect…you’ll be unstoppable.

4) Be as kind as you can as quickly as you can.

The phrase “Nice guys finish last” is bullshit.

What it actually means is don’t sacrifice your values to make others happy. But do care about the happiness of others.

The more you make people feel welcomed, heard, and cared for…the more they will want to be around you and take care of you too. The most important thing in life (aside from your physical health) will be the relationships you build over the years.

Stop talking shit about people. Stop complaining about things you can’t control. Always seek the lesson and value in every situation.

That is the ultimate kindness: seeing life as something happening for you and not to you.

5) Don’t listen to me.

I can talk for hours about all the things I wish I did more of and less of.

I could tell you to take great care of your body, become financially literate, ask out more women, start playing chess or doing jiujitsu, build a writing habit, and never make a Twitter or Instagram…

But you’ll figure all of these things out from sheer necessity.

The best way to learn how to do something is to learn how not to do it. I can give you all these insights because I’ve done so many things poorly.

And to deprive you of mistakes and regrets you’ll experience would be to limit your ability to grow and learn.

Go out and do stupid stuff. Create cringe memories. Overdraft your checking account.

The people who know the most are typically the ones who have been through the most. Put yourself through the wringer and you’ll have no choice but to be the best version of yourself.

Now go, my son. Smoke a bowl and play guitar for four hours.

You’ll find your way eventually.

I sold out and got a Patreon

Voted World’s Okayest Blogger 2022.

(Here’s a short and fun video on the term “sellout.”)

What I’ve done

I don’t actually think I’ve sold out. But I’ve just done something I thought I’d never do: I created a Patreon.

For those who don’t know, Patreon is a service where people can support creators they enjoy—YouTubers, artists, bloggers, etc. Oftentimes, those creators offer bonuses and exclusive content for those who help at different degrees.

This seemed silly to me for the longest time. But then I started interviewing creators for my book.

James and Anthony Deveney took me through their journey of quitting their full-time jobs to run their podcast, Raiders of the Lost Podcast. (If you like movies and television, I highly recommend their show.) They were able to do so because of the level of support their patrons provided.

Eric Rosen, my favorite YouTuber, broke down all of his revenue streams when we spoke. Merch, ad revenue, Twitch subscribers. But in the early days, he said it was mostly from people donating on his streams.

It’s never been easier for one person to reach (dare I say…influence?) a large number of people. Steph Smith made a great point. She said, “Britney Spears was a content creator. She wrote songs and shared them with millions of people. Today, some bro can film himself in his apartment and have a million followers on TikTok.”

I’m not some bro and I don’t have a TikTok. But it’s been wild to type my thoughts out and have a bunch of friends, family, and strangers read them.

And with the popularity of things like podcasts and YouTube, free content has never been more prevalent. It’s expected, actually. Anyone else get triggered when they click on a NY Times article and get asked to pay for a subscription?

I do every time. But then I think, There’s a team behind this…It’s someone’s job to produce this.

Why I did it

To be clear, this blog will always be free.

The site has a simple system:

  1. I live my life
  2. I reflect on all my insights, mistakes, and fears
  3. I write about them here
  4. You either enjoy them or go, “meh.” 🤷🏼‍♂️
  5. Repeat

I don’t see that ever having a price tag. Making a subscription service like Substack doesn’t interest me.

But there is a dream life I’m working toward. It’s pretty simple.

I want to be a full-time writer and coach. I’ve got the coaching thing down. But in the future, I’d like to be publishing a new book every 2-5 years, write 2 or 3 blogs on here each week, and have 5-10 coaching clients. In between would be plenty of time to travel, work on other projects or programs, and do all the non-work things I love (chess, friends/family time, jiujitsu).

With all that said…if any of you get value out of these posts and want to support the blog, you now have an avenue to do so. Only if you really want to. If not, you’re dead to me.

Whoops. I mean, *if not, that’s totally fine! Nothing will change on here.

But for those who do, you’ll get some bonus stuff. Extra blogs, video updates from me, access to a Q&A, monthly Zoom calls, the running draft of my book Do The Thing, and polls for what you’d like me to write about next. I’m even working on setting up an advice column.

Whether they’ve chipped in financially or not, I’m forever indebted to anyone who has taken two minutes to read anything I’ve written. I wasn’t even planning on having ten readers. Now this blog has hundreds. Onward!

If you’d like to become a patron, you can do so here.

Thanks, thanks, and ever thanks. 😎

About New York…

Dillan Taylor and Tomas Virgadula walking the streets on New York City

My friends and readers of this blog know that I’ve been preparing to move to Brooklyn later this year. Mostly because I won’t shut up about it.

I did a two-week trial run in the city to see if I would actually enjoy the hustle and bustle of New York. Turns out, I love it.

Coming home from that, I felt elated, motivated, and driven to get myself ready for the transition. I was dead set.

Last week, I decided not to move. Let me explain.

Wait, but why?

Bowling in New York City
My favorite bar in NYC—The Gutter. (Subtly crushing my friends in bowling.)

For people who’ve been following this saga, I’m sure this seems anticlimactic. I mean, I’ve been writing about this since November of last year. The first blog I wrote about wanting to make the trek is still my most viewed piece, with 1000+ unique readers.

So what happened? Did I chicken out? Was I using people’s love for adventure as click bate? Am I a sleazy fraud?

Well, yes and no.

I can break it down into two main reasons for not packing up and moving my life to New York this October. There’s a logical reason and a more emotional one. Let’s hit them in order.

Logical reason:

As soon as I got back from my NYC beta test, I felt it was finally time to stop procrastinating and crunch the numbers.

I put everything I could think of into a Google Sheet. All the purchases and fees. All the housing payments. Loads of furniture I’d have to buy. The U-Haul. I did my best to estimate what the first three months would look like for my bank account.

My God.

It’s been so easy to joke about the cost of living in New York, but seeing it all laid out in front of you is a completely different beast.

For what I want, rent would be $2.5k-$4k per month (not including utilities). Moving in would require the first and last month’s payment. Depending on the quality of furniture I got—couch, desk, chairs—it would all cost somewhere between $2k-$5k.

Sitting in this seat and looking at all the numbers quickly adding up, I got anxious. I know enough about myself and my business to know that I could continue to create income that would allow me to do this. I could figure it out.

But not comfortably.

When I told one of my buddies, he put it well.

“It sounds like you’d be in survival mode the first few months.”

He was exactly right. I doubt I’d become homeless. But during the first three to six months in Brooklyn, my main goal would be to figure out how to pay my bills.

For obvious reasons, I don’t want to do that. I want to go somewhere new and live my life. I want to go out and have fun. I’m looking to adventure. Counting every dollar doesn’t appeal to me.

After filling out the sheet, the thought occurred to me: What if I didn’t move this year? With that came a rush of relief.

Then I thought, Damn…my readers are going to roll their eyes.

Emotional reason:

I went to a best friend’s wedding a few weekends ago. The week prior, another best friend moved back to the area after living in Rwanda for years.

She brought back her husband, who she met there, and will be going to grad school in the fall. That week preceding the wedding, they came over and I met her husband for the first time.

Just a couple’a cool dudes.

I liked him immediately.

What I expected to be a quick hello turned into hours of sitting at my dining table and talking. My friend even used my office to take a call with her soon-to-be fellow students. Meanwhile, I sat and chatted with her husband and picked his brain on what he thought about the states. It was his first time leaving the continent of Africa.

Hugging them goodbye brought joy to my heart. There’s a huge difference between, “When will you be in town next,” and, “See you next weekend?” And that difference means the world to me.

My deepest-held value is spending quality time with those I care about.

I often think of the ‘hospital room’ scenario. If I got into a horrible car accident today, who would be in that hospital room with me when I woke up? It sounds dark but it’s a useful mental model for measuring how strong our relationships are at any given time.

Anyway, not only did this friend just move back here after years of adventure across the ocean. But another one of my best friends will be returning to the area at the end of the summer.

That means that in a one hour radius, I’ll have 14 close friends, my mom and sister, aunts and uncles, and my jiujitsu team.

I told my buddy all this on the phone the other day. What he said reassured me.

“You know, man,” he said. “There’s that statistic. 80% of people die within 100 miles from where they were born. I used to think that was depressing. But now as I get older, I realize…it’s really fucking hard to leave your friends and family.”

Ain’t that the truth.

Call me a chicken, but I’m finding it hard to justify leaving all of my favorite people on the planet. I’m under no illusion that we’ll spend the rest of our lives living 10 minutes away from one another. But at the very least, I feel the need to take advantage of this opportunity while I have it.

TLDR:

NYC is expensive and I love my friends and family. Maybe next year.

How to send a cold email to someone you respect

An iPhone with email apps on the home screen

I’m writing a book on creating. Over the past six months, I’ve been interviewing creators and entrepreneurs of all shapes and sizes.

Many of my friends have asked me how I got into contact with some of these big names—folks like Eric Rosen, Derek Sivers, Courtland Allen, and Steph Smith.

The answer is intricate and complex…

I emailed them.

Around 30% of those I reached out to, all of whom I genuinely adore, responded to my message. Then, shockingly, they agreed to share their time and energy with me. But why?

Well, there are a few basic principles every cold email should have. There’s also a simple formula to make structuring this outreach fun and easy. I’ll share both in this post. Then, I’ll share the exact email I sent to Steph Smith, a badass content writer.

Caveat: There is no way to guarantee that someone will respond. Most people simply won’t and that’s okay! You’ve gone from not talking to them at all…to not talking to them at all.

Let’s start with the step-by-step formula.

Cold Email Must-Haves

1) A personal and human intro.

Anyone can tell when they’ve been spammed a copy and pasted message. It’s impersonal and robotic. It invokes zero motivation in the recipient because they know the sender doesn’t actually care—they’re clearly just sending that same message to the masses.

So right out the gate, it’s vital to convey that you genuinely know who this person is, that you’re familiar with their work, and that you respect them for it.

That way, they know they’ve just been emailed by a human being who is actually interested in their time or resources.

2) Why you’re writing to them.

Cut to the chase.

Who are you and why are you sending them this email?

3) A clear and simple call to action.

What specifically are you asking for?

Would you like their time? Their feedback? A reference?

Make the ask so understandable that they’ll have to say either yes or no. A great finisher question is: Is that something you’d like to do?

Highlight the value they’d be getting out of it. They need to know what’s in it or them.

Also, paint the full picture of exactly what it is they’d be saying yes to. How long would it take? How much effort would be required on their end?

Answer any possible questions or objections before they think of them themselves. Not only does this put them at ease and make it more likely that they’ll agree to the thing, but it also shows them they’re dealing with a professional who is prepared and organized.

4) Give them an out.

Most people, especially those of higher status or prestige, will have no problem saying no to a stranger. Again, they’ll likely just not respond. Which makes sense; they’re busy!

But, a subtle yet impactful thing to end on is something that gives them permission to say no. It can be as simple as: It’s totally okay if you don’t have the time or interest for this right now. Just thought I’d shoot my shot!

Never, ever say something assumptive like: Looking forward to speaking with you soon.

That comes off as passive-aggressive. The person will think, “Huh? I haven’t agreed to speak with you soon.”

Keep it light. It takes the pressure off them and shows them you’re not some needy person begging for their time.

Now that we have the structure, let’s move on to the most important concepts to keep in mind.

Key Principles of a Cold Email

1) Keep it short.

Less is more. No one wants to read a bunch of long paragraphs with no spaces in between. Would you be pumped to read a poorly-typed novel from a stranger when you have a million other things to do?

If a word, sentence, or paragraph can be deleted and have the email still make sense, scrap it.

If reading your message feels like a chore, they’ll likely just chuck it in the Trash bin.

2) Care.

While there’s a ton of psychology involved here, I’m not advocating for manipulating people.

Everything in your email should come from the heart. Remember, these are for people we genuinely respect and value. That also makes it easier when they don’t reply. It’s probably because they’re doing the work that we cherish. And if they do reply, it’s just an unexpected bonus.

3) Be persistent but not annoying.

Most of the time (but not always), I’ll send a follow-up.

I call it being “lovingly persistent.” Not pushy. Not needy. But staying true to asking for what I want.

At some point last year, Lynne Tye—founder of Key Values, stopped responding to my emails. I sent her a follow-up because I really wanted to talk with her. Not only did she respond and set up an interview, but she told me she massively respected my “persistence and hustle.”

To drive this home, here’s a real-life example.

Steph Smith wrote the book Doing Content Right. It’s helped me tremendously with the structuring and planning of my blog and book.

Here’s the word-for-word message I sent Steph:

“Hey Steph!

Got introduced to your book/Gumroad course and I’ve been tearing through it. I’m stunned by the level of detail you put into everything you do. Thanks for helping me grow my blog! 😎

In short: I’m writing a book on creating. 

I’m about halfway done and have a few interviews left to do. It comes out this summer and I’d love to write a chapter on you. Would you like to contribute?

It would be no more than an hour of your time for a video call. Plus, I can send you the questions beforehand to speed things along. What do you say?

No worries if you don’t have the time or interest. I’m sure you have to say no to most things!

Dillan ✌️😇”

That’s it. She got back to me a few days ago and we’re in talks of setting something up next month.

If you want to reach out to someone you dig, do it. You have nothing to lose. Just know that you most likely won’t get a response and that’s totally fine.

But the answer’s always no when you don’t ask for what you want.

Doing so has allowed me to talk to some incredible people. It can help you do the same.

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.

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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.

Cheers.

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.

Cons:

1) No established community

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

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

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

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

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

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

More on that later.

2) The cost

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

What the fuck.

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

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

3) The trash

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

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

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

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

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

4) The homeless

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

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

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

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

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

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

Pros:

1) The adventure

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

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

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

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

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

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

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

2) The food

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

And the fucking pizza. The hype is real.

3) No car

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

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

4) The discomfort

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

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

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

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

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

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

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

What I learned about myself

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

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

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

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

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

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

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

The next steps are:

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

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

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.

stickk.com

Writer-Dill.

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.

Changes

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.)