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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Oh yes.

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

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

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

I haven’t played any video games since 2018.

Here was my vicious cycle:

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

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

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

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

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

He was right.

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

3) “What’s your biggest fear?”

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

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

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

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

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

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

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

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.

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. 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.

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.

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.)

Back to the office, kind of

A cool office where young people are working

My friends and I spent the weekend in Brooklyn.

I have stories to tell from the trip but right now I’m feeling super foggy. I turn 28 tomorrow. At this age, all it takes is one night of drinking and poor sleep to throw me off for half a week.

I’m here, sitting in my chair. But it also feels like I’m not here.

Fun blogs to come this week.

Thanks, ya’ll

I got several messages about yesterday’s blog.

I commit to being open about everything that happens to me on here. But I sometimes fear that I seem like I’m craving attention.

My promise is that I’ll talk about what happens to me and what I learn from it.

Thank you for the support and the shares. It makes this whole life thing that much easier.

My internet went out

So I had to write this on my phone.

It’s the little things we don’t appreciate until they’re taken away from us.

Another trip to Brooklyn (pt. 3)

Yesterday, I gave a synopsis of my weekend in NYC. Give that a read before reading this blog.

Here are my takeaways:

1) Getting sexually harrassed is surprisingly not fun.

It’s kind of a funny story, and I’m willing to joke about it…but having a guy look over the urinal at me peeing was mildly traumatic.

I’ve thought about it every time I’ve used the restroom since it happened.

And I’m a tall, fairly in-shape guy who can defend himself. I can’t imagine what those situations are like for, say, women who don’t have these physical advantages.

2) More venues and events should prohibit cell phones.

They did this at the comedy show. But I would love to go to a restaurant where this was the rule as well.

When we don’t have anything to distract us, we’re forced to be present with the people we’re with. We can genuinely take in our surroundings.

On many occasions, I like to leave my phone in the car. That’s when I truly feel like I’m part of the world.

3) I don’t think I want to live in Williamsburg.

That’s the “wealthy, hip, and yuppy” neighborhood in Brooklyn.

My buddy and I walked through it and the vibe just didn’t land with me. Many people looked as though they had a stick up their asses. They seemed calculated.

This is all just a generalization. We stopped to talk with one dude who was super kind and helpful. But he was Australian so that doesn’t count.

We’ll see. I have ten months to narrow things down.

Another trip to Brooklyn (pt. 2)

Tomas Virgadula with Manhattan in the background over the East River
Said good buddy.

I spent the weekend in Brooklyn with my good buddy.

It was a much chiller few days than when I first visited back in September…So I’ll briefly go through what we did and tomorrow I’ll finish with my takeaways from the weekend.


I drove up to New Jersey to stay with a friend for the night. In typical 2021 fashion, this would be the first time meeting her in person.

She and her husband hosted me and took me out to dinner. I felt bad because I typically go to bed around 9pm and only got five hours of sleep the night before.

I almost fell asleep at the brewery we went to after the restaurant.


Since they live just outside the city, I took the NJ Transit into Manhattan. The train took about an hour.

From there, I hopped on the A and took it to Brooklyn. (Do I sound like a New Yorker?)

Since my friend was on a coaching call, I sat on his stoop and watched Game 6 of the World Chess Championship—where Magnus Carlson got his first win against Ian Nepomniachtchi.

He let me in, we hugged, then we drank seltzers and played chess.

That evening, we took the train into Manhattan to see a comedy show at The Comedy Cellar.

Beforehand, we got dinner and I had to use the restroom so we walked over to the public one in Washington Square Park.

At the urinal, a homeless guy looked over the divider to watch me pee.

My first thought was, No way. He’s definitely not doing that. I could feel him looking at me and my first fear was that I was about to get stabbed. I braced myself to grab his wrist or punch him in the face.

But then I realized what was happening. I turned and said, “What the fuck are you doing buddy?”

He apologized, then did it again after four seconds. I said, “Fuck off dude,” and walked to the sink to my confused friend. He didn’t know what happened.

Then another guy came in to use the urinal on the side. The homeless guy switched urinals to be closer to him, did the same thing, and the new guy also told him to piss off.

We walked out half-disgusted and half-laughing about the situation.

My buddy told me, “You get all the New York experiences! I’ve lived here for 12 years and nothing like that has ever happened to me.”

“Yeah, I feel so lucky,” I replied. Then we headed to the show.

We sat in the front row.

They took our phones so no one could record or take pictures during the performances. I loved that.

Ensuring people stay present and keeping an up-and-coming comedian from being canceled by a blogger…I’m a fan.

The show was fantastic. We got out around 10pm, walked to the closest street corner, and I heard, “Dillan?”

I turned around and saw one of my friends from high school. “What are the fucking odds?!” I replied.

A group of friends taking a selfie on a Manhattan street corner


The purpose of this weekend was to walk around neighborhoods I would possibly move to.

We trotted around Williamsburg and Bushwick, got lunch, met up with another buddy, and hung out at his place for a couple hours.

A super low-key day. We stayed in, got sandwiches from a bodega, and watched movies.

This was a “And then this happened” blog. Tomorrow will be the “And here’s what I got out of it” blog.

See you then.

Sober hangover

I got back from my NYC weekend late last night.

My first session today is at 7am—in 30 minutes.

I feel truly hungover from lack of sleep.

So much to tell the readers. But not today.


A day in the life of a Life Coach

Kinda creepy, eh?

I don’t find myself to be some high-performing productivity God.

But I do manage my time well and seem to get everything that I want to get done, done. Always productive; never busy.

People often say to me, “I’m sure you’re so busy…” But that’s not true. To me, busy implies a sense of being out of control—too many things to do and barely enough time to do them.

I have a ton of free time because I make sure that I do. I spend time with my friends and family. I take at least one trip each month. I play chess every day. I get plenty of sleep. (*The caveat here is that I’m 27, single, and I don’t have children.)

This is all on purpose. Whenever I feel any of these things begin to slip, I know it’s time to readjust my work and task load.

So today I thought I’d give a peek behind the curtain and run through an average workday for me. I hope it’s not as boring as I imagine it will be.

But here goes…

Between 5-6am: Wake up.

This was 6-7am before the time change this week. I’ve just kept the same circadian rhythm so now I can sound like one of those guys from an entrepreneur inspirational video.

I turn my SleepCycle alarm off. My phone is on airplane mode from the night before and I can’t take it off until I finish my morning routine.

I put my glasses on, make my bed, and go out to the kitchen to drink my fluids. In the fridge are my water bottles, ice-cold from the night before.

If I worked out the day prior, I chug a bottle of Athletic Greens. Then I drink half of my Nalgene of regular water.

I do this before any caffeine to make sure the first thing I do each day is hydrate after 8-10 hours of no water. Then I make a cup of coffee, usually Bulletproof.

6-8am: Morning routine.

I bring my coffee into my office, turn the lights and my computer on, and scratch off the day before on my giant wall calendar. Then I begin the morning routine I’ve basically had for the last two years.

  1. Look at my Google Calendar and block out my day in my notebook.
30-minute chunks.

2. Write my three affirmations:

I, Dillan Taylor, support myself as a prosperous coach.
I make $10K/mo.
I love doing scary things.

3. Read for 20-45 minutes.

Usually nonfiction to get the brain moving and pondering at the start of the day.

4. Write this blog.

Depending on the content and on my level of motivation, this can take anywhere from five minutes to an hour. If I love it, I post it to Facebook.

5. Solve 15 chess puzzles on

I get 15 each day with my membership. So I go until they run out.

6. Stretch for 3-5 minutes.

Usually to a personal development or educational YouTube video.

These are mostly leg, back, and hip stretches…to prepare for a day of mostly sitting.

7. Meditate for 10 minutes.

I use the Waking Up app.

Meditation is the most important step of all…and it’s the easiest to skip.

8. Take my phone off airplane mode, maybe shower, and start my day.

The first two hours of the day are mine. Nothing to respond to. Nothing to solve or fix.

8-11am: Coaching sessions.

I try to get my sessions done earlier in the day when I have the most brainpower.

Active listening, reflecting, and challenging people and their thoughts can be mentally draining. If I can avoid sessions later in the day, I do.

11am-12pm: Eat and shower (if I haven’t already).

This is my breakfast, so to speak (type?). Usually eggs, sausage or bacon, and fruit (with peanut butter).

12-3pm: Other calls and miscellanous work.

These could be coaching sessions, connect calls, and admin stuff I didn’t finish on Monday.

If there’s space between tasks, I’ll read, go for a walk, or watch a few YouTube videos.

3-5pm: Gym.

At least three times per week. I use Fitbod to pick and track my workouts.

My weightlifting cycle is: push (chest/triceps), core (abs), pull (back and biceps), legs.

5-9pm: Dinner, maybe chill with friends.

If I’m in by myself for the night, I’ll cook something simple—usually a protein, veggie, and starch.

If I hang with friends, we may order food—usually Chipotle—or one of us will cook for the group. Wine or beer may be included.

In a perfect world, I wind down around 8:30pm. I use Freedom to block internet on my phone so I can’t stay up watching YouTube. I turn airplane mode on and stretch before getting into bed.

9pm: In bed.

If I’m still fairly awake, I read my Kindle until my body tells me it’s time to shut down.

I set my alarm for the morning, put my sleep mask on, and try to fall asleep.

10pm: Asleep.



I’m moving to New York City

Two women hugging and looking out over the New York City skyline

In September, I spent a weekend in Brooklyn. It was one of the best weekends of my life.

I was meeting one of my good friends in real life for the first time. (2021, am I right?)

For years, I’ve been one of those folks who says, “New York is a great place to visit, but I could never live there.” That weekend proved me wrong. And now, when my current lease is up in October, I’ll be moving there.

Here’s why.

1) The opportunity.

In 24 hours in NYC, I…

• scheduled two coaching sessions with strangers (one of whom became a client)
• played chess hustlers in Washington Square Park
• saw Seth Meyers walking with his son (his calves are tremendous)
• declined cocaine from the CFO of a major magazine company
• bowled with one of my new best buds
• ate mushroom chocolate in the apartment of someone I had only met that night

All that to say…there’s plenty to do.

After connecting and setting up my second coaching session, I thought, Wow, my business would thrive here.

Everyone in NYC is pursuing something. They’re looking to create exciting and rewarding lives. My kind of people.

They also probably have money. After three minutes of research, I can confidently confirm the expensive stereotype of New York City.

Aside from the professional aspects, I saw more culture and diversity in two hours than I have in any of my previous travels or books read.

People of all shapes, sizes, and colors. Any type of cuisine. Parents yelling at their children in languages I’ve never heard. I have no idea what country that mom was from but holy fuck was she giving it to that kid.

On top of that, there are a zillion comedy clubs and venues to drop into for a night of entertainment.

Being hosted by an actual New Yorker made all this more enjoyable. I wasn’t a tourist traveling with other tourists. I was immersed.

2) The adventure.

I don’t think there’s anything wrong with sticking around one’s hometown. I’ve been in Maryland practically my whole life.

But there are certain things we can only achieve by exploring somewhere else—away from the comfort of what we’re familiar with.

We learn what we’re made of. We learn how to make friends and build a community from scratch. We experience a different way of being.

I learned more about myself in my one year in Germany than I did in the previous 20 in the states.

It’s also hard to deny the comparison game. We see friends moving to cool cities or foreign countries and it can feel like we’re doing something wrong by staying put. I’ve certainly felt this.

Anyway, I’ve been down to try out a new place for years, but never felt I had the life skills or stability to make it happen the way I wanted.

Until now.

I thought about moving a few years ago. But, working in a restaurant, I didn’t want to move to Colorado just to work at a different restaurant. I wanted things to change internally first. (Not judging anyone who has done this. It’s just not what I wanted to do.)

Now, I have a career I’m skilled in and proud of that I can take anywhere. I have a good friend I can be neighbors with in Brooklyn. And most importantly, I know what my values are and I know how to take good care of my physical and mental health.

I’m ready.

3) It scares me.

I’m also actually NOT ready. And that’s the point.

Walking around the city, I was in awe. It was like I was in a museum, staring at the buildings and the crowds of people.

I was also anxious.

Everywhere I went, I felt like I was going to be late for something. It was exhilarating. I both loved and resented the fast-paced nature of the city. Stillness didn’t seem to be the prevailing vibe. It was unfamiliar and uncomfortable to me…and I loved that.

Even after I got home from that weekend, I could feel the go-getter nature still pulsating through my veins. I wanted to work. I wanted to do things.

Every single morning in 2021, I’ve written the affirmation: “I love doing scary things.”

One of the biggest areas of growth I’ve experienced this year has been pursuing things that terrify me. I fucking went for it.

I started a business with no Plan B. I flew to another country to pursue a relationship. I put myself out there in ways I couldn’t comprehend two years ago.

In other words, I’ve leveled up tremendously. The only way to level up is to do scary things until they aren’t scary anymore. Then there’s a new level of scary things. And so on.

This is the next level for me. Leaving my home and going to a scary, unfamiliar place.

Again, I’m ready. And I’m not.

So let’s do it.

Sweating my way to Canada (pt. 3)

My friends Dennika (left) and Anya (right)—Tofino, Vancouver Island.

If you haven’t read parts one and two of my journey to Vancouver Island, go do that first. It’ll help me sleep at night.

Today, I’ll wrap up the story and share the insights I gained from my 16-hour travel day.

Flight 2.5: Montreal to Toronto

After missing my first flight ever, I plopped down at the gate and waited for my new flight to Toronto. I had an hour and 15 minutes until it boarded, which felt like heroin.

It feels strange to write this now, but at that time I felt truly depressed. I felt it all in my face and chest. This was my deepest, darkest fear and it had actualized.

But over the course of that hour, I quickly calmed my nerves by meditating over two facts:

1) There was literally nothing else I could’ve done to avoid missing my flight.

I got unlucky. The delay. The jammed luggage door. The random COVID test.

Perhaps Usain Bolt would’ve caught up to the gate in time. But for me, there was no glaring instance of stupidity that kept me off that plane.

Shit just happens. Sometimes everything goes our way. Something it feels like the cards are stacked against us. Usually it’s something in between those two.

This stoic concept of what I can control vs. what I can’t arrived quickly to me. It’s a habit I’ve built over the years. But the second fact which took over my entire body was this.

2) My life is pretty damn good.

Let me explain.

I was sitting in that chair legitimately feeling the highest levels of anguish and heartache I’ve felt in years. After about 40 minutes of reflection, I thought, Holy shit dude. If THIS is what causes these emotions for you…that’s proof your life is amazing.

For most, what unravels these formidable feelings are things like…

• losing a loved one
• feeling lost in life
• having clinical depression

For me, it was adding five hours to my day and having to get on one extra plane as I headed to an unbelievably gorgeous island with unbelievably gorgeous people.

Some people really have it rough, eh?

A wave of light and gratitude swept over me. My sadness was gone. My frustration was gone. I got on my flight, joked around with the flight attendants, and headed to Toronto.

Flight 3: Toronto to Vancouver

We landed.

I got an A&W burger and a rootbeer float.

I called my friend and told her about my trail of tears.

We laughed.

The plane boarded and we took off for a five-hour flight to Vancouver.

Flight 4: Vancouver to Vancouver Island

There was another delay and for the second time that day, I was sure I would miss my next flight.

Please no…I’m so close.

I could see the island. The last flight would be 11 minutes long.

When we finally docked, most of us jogged off the plane. Just outside the gate, there was a man yelling, “To Vancouver Island?” My ears perked up.

“Yes sir,” I exclaimed.

“Right down there to C53,” he said confidently.

I put my hand on his cheek and said, “Thank you, my Guardian Angel.”

Well, I wanted to do that but I didn’t want to miss my flight. I followed his directions and speed-walked to C53.

I made it to the gate to find a young couple showing their boarding passes also out of breath. It was the last gate open in the entire airport. The plane was waiting for us because they knew several passengers were coming from my Toronto flight.

I walked directly up the steps to the tiny plane, sat in my seat, and texted my friend:

“It’s done. I’m on the last plane. Justin Trudeau can’t kill me. He forgot I bleed red white and blue.”

The flight took exactly 11 minutes. It was the most turbulence I’ve ever experienced on a plane. And I couldn’t have cared less.

We landed, I thanked the flight attendants profusely for waiting for us, and I walked out.

“Dillan,” I heard.

My friend was waiting outside the terminal for me. I dropped my luggage and melted into her arms.

This was my first time meeting her in real life. She was smaller than I pictured and smelled just as good as I had imagined.

I made it. My vacation could begin.

Sweating my way to Canada (pt. 2)

The Strait of Georgia.

Yesterday, I wrote about the beginning of my travels to Vancouver Island. Read that first if you haven’t already.

Also, people have been asking me where Vancouver Island is.

It’s here.

We left off at me getting on my first flight to Montreal. I walked onto the plane dripping with sweat and shame.

Flight 2: Montreal to Vancouver

Montreal is just north of New York state. The flight there from DC only takes an hour and a half.

We flew there on the smallest plane I’ve ever been on, besides when I went skydiving. I was half-expecting the pilot to say, “Good morning passengers! Thank you for attending my very first flight. I’ve never done this before and I’m excited to try. Luckily, no one will notice if this Fiat of an airplane goes missing. Message your loved ones and then put your phones on airplane mode. Seatbelts on please.”

Despite that, we made it over the Canadian border with few casualties. I even had the fortune of having an empty seat next to me—the poor man’s first class.

I had a short layover before my flight to Vancouver, which I thought was lovely. But as time ticked on my anxiety came pouring back in. I forgot about customs. I forgot about delays. I soon welcomed a three-hour layover.

We landed in Montreal and to my horror, the plane just sat there.

Ten minutes. Twenty minutes. Thirty minutes…

The captain came on and spoke for about 60 seconds, first in English and then in French. I’m not exaggerating at all when I say I didn’t catch a single word of what was said.

Neither did the other passengers. I looked around and saw confused and frustrated faces. A coup was boiling. I faced the woman in the row across and we exchanged glances. Our energy was: If I attempt to overthrow this plane do you have my back? I absolutely did.

It was at this time I was certain I would miss my next flight. Then again, my anxiety was certain of that when I got out of bed at 5 in the morning.

We finally got off the tarmac and docked. They said the bag I had to check in DC would be coming up the mini-elevator just outside. I walked off the plane and stood in the cluster of 15 others waiting for their bags.

The tension was palpable. I wasn’t the only one who had a quick connecting flight to catch. It was kind of a bonding experience. I would’ve loved to start an army with those folks.

An agent came up to the metal elevator and tried to pull the door open. Nothing.

I wanted to offer to help since I’m so incredibly strong and healthy and handsome. But I was in the back of the crowd.

I heard three more yanks of the door handle and felt the tension grow even stronger. This dude couldn’t open the gate.

He walked away and passengers began trying to open it themselves. After a minute, he returned with one of the flight attendants. She pushed some buttons but nothing was happening. I considered leaving my bag and spending a week on the island without clothes. I’m a minimalist anyway.

After 15 minutes, they finally managed to open the elevator and basically chucked our luggage at us. We were all grateful for this. I said, “Thanks guys,” and for the first time in my life…I began sprinting in an airport.

I’ve wondered for years how unprepared a person has to be to jolt through a terminal. I’ll never judge another person ever again.

I made it through the mile-long labyrinth following the “Connections” signs. They might as well have said, “Lol fuck you Dillan welcome to Canada.”

Thank you. Thank you, Montreal.

I sped through customs which I’m sure looked sketchy as hell. The first two machines wouldn’t read my passport so I had the kind woman help me out. I said, “Sorry, I’m going to miss my flight.”

She looked at me with a face that said: Oh, you’re the one who has a flight to catch. We’ve never had one of those.

I made it through, constantly checking my watch. My flight had boarded already and was taking off in ten minutes.

I passed each airport boss like a video game and was walking down a long corridor toward what would end up being my final foe.

She was checking passports and having all the other frantic passengers move to the right. When she pointed me toward the left I was confused.

“You’ve been randomly selected to take a COVID test, sir.”

I’ve been heartbroken before in my life. I’ve been betrayed. But this…

I have no idea what my face looked like but for the first time in my life, I turned into that entitled customer.

“Miss, I totally understand, and I’m so sorry, but is there any way I can not take this? I’m going to miss my flight. Like, if I take this test I will miss my flight.”

She told me rules are rules and offered to help me sign into the portal to take my test. I pushed the iPad’s buttons passive-aggressively as if doing so would foster sympathy. Yes I DO fucking live in Annapolis. No I DON’T know the Canadian area code of where I’m staying. Fuck you Canada!

I got to the doctor and asked her to shove those q-tips up my nose as quickly as she could. I thanked her and bolted out of the facility.

I can’t remember the last time I sprinted as fast as I could in a non-exercise or sports context. My footsteps and breathing were so loud people were getting out of my way 30 feet ahead. I dropped my boarding passes. I dropped my neck pillow twice.

I was a mess.

My gate was at the very edge of the terminal. Gate 8. I saw the sign for it. I was cramping up. Just keep running. You’re right there.

My flight departed at 2:15. It was 2:15 on the dot.

As I ran up to the gate, I heard, “To Vancouver?”

“Yes,” I exhaled…

“You’re too late,” she replied.

There it was. My deepest fear realized. All that stress and work and sweat. I had failed the mission.

She said, “Did you want to get to Vancouver Island tonight?” It took every ounce of my being to not respond, “Yeah, that’s actually why I booked my flight for today.”

But all that came out was a deflated and defeated “…Yes please.”

I hunched over the desk. I felt lost. I had lost. She got me a new flight to Toronto, then to Vancouver, and then to the island. It added five hours to my day.

“Thanks, Carol,” I whimpered as I read her nametag. “You’re welcome,” she responded, business as usual. “Sorry you missed your flight.”

“Me too,” I said.

As I began walking to my new gate, I looked out the window and saw the plane I was supposed to be on edge away to take off.

I moped my way to a seat, updated my friend who was picking me up on the island, and played a game of online chess.

Stay tuned for part three, where I’ll stop complaining and dive into the lessons and insights I’ve gained from this day.

Sweating my way to Canada (pt. 1)

The summit of Mt. Benson in Nanaimo, Vancouver Island
The summit of Mt. Benson—Nanaimo, Vancouver Island.

I just had a week of vacation in Vancouver Island. The purpose of the trip was to visit friends and embrace the most gorgeous spectacles of nature I’ve ever seen.

It was tough to get totally excited for all this though because big travel makes me intensely anxious.

My deepest fears are that I’ll miss a flight, have to pay hundreds of dollars, and realize that I’m simply too stupid to be left to my own devices.

But I followed Canada’s tedious criteria for entering their country, prepped days before, and hoped for the best. I had three flights taking me to Vancouver Island. Here’s how they went.

Flight 1: Washington, DC to Montreal

I got up at 5:30am and my roommate kindly drove me to the airport three hours before my flight.

The Air Canada agent was noticeably kind and great at her job. We started joking and laughing with each other. Then the balloon popped.

She was scanning my documents and sadly said, “Oh no…Mr. Taylor…”

My heart sunk. Was I being arrested? Did I forget about a felony I repressed from college?

I was half-expecting her to say: “Mr. Taylor, I’m so sorry but it says here you’re simply too stupid to be left to your own devices. We’re going to have to provide you a chaperone until you land on the island.” That actually would’ve relieved my stress.

Instead, she told me my COVID-19 test wasn’t going to be accepted in Canada. Those Communists! I remembered the testers from two days prior who said my rapid test was fine for travel. My brain went all Karen and I wanted to write a strongly-worded email.

Pretending to keep my cool, I asked, “What are my options?”

She told me there was a rapid-PCR testing site two terminals away. She also told me the test cost $275.

I speed-walked with my head down, ready to pay a quarter of my rent for a stupid test I already got. When I got to the other terminal, a clerk told me the test site opened in about 40 minutes.

This is why we come to the airport early, I thought.

I sat out front, waited for them to open, and compulsively played online chess to pass the time.

When they did, I paid a million dollars or however much it cost, got my test, and they told me I would get my results in about 40 minutes. I wanted to ask, “Can you ‘science’ it extra hard to speed up the process?” Instead, I reopened my app and continued playing.

They called my name 45 minutes later. The sheet said: “Dillan R Taylor: Negative.” I thought, Yeah, that sounds about right.

By the time I speed-walked back to the lovely Air Canada agent, I was coated in sweat. The airport was freezing and I disrobed down to my v-neck.

She gave me my boarding passes and I headed to security. The dude took my ID and the first pass, looked at me confused, and said, “This isn’t you, dude.” I thought of the ‘You’re not that guy, pal’ video.

Hilarious, I thought. But he handed me my pass and it was someone else’s name. Fuck!

I jogged back to the check-in and got in the back of a much longer line than before. I finally understood why people on viral videos acted so entitled while traveling. That shit was stressful and it felt like the world was against me. If only the folks in line knew what I was going through.

I made it back to the sweet woman who was ruining my life and she apologized and gave me the correct boarding pass.

I told the TSA agent I was in fact that guy, pal. He didn’t laugh at my joke and I took my shoes off to prep for security. At this point, a body cavity search didn’t feel implausible. Have your way with me, Reagan International.

Check-in: done. Security: done. Bathroom: done.

I made it to my gate with 12 minutes left until boarding.

At least the worst was over…he typed foreshadowing part two of this story.

I’m back

This morning, for the first time in 27 years…I pulled my back out.

I’m sitting at my desk and typing these words slowly as to not spike any agonizing pain.

It’s my first day back from my week-long vacation.

So many blogs to catch up on. So many stories and lessons to share.

But not today. Today, I work and rest in stillness.

I got several messages last week from folks asking where the damn daily blogs were.


Just know, I was having quite the time. But I’m back now.

No pun intended.

Oh man

Today, I flew on four planes to get to Vancouver Island.

Too tired to write about it now.

See next blog.

Doing shrooms in NYC

In March, I joined an online coaching program and met Tomas, a guy who would soon become a close friend.

This weekend, seven months later…I met him in real life.

He’s been sober for six years, so before the trip, I was boasting to my friends that I would save money this weekend by not buying any booze and by going to bed early each night. That didn’t happen.

It turned out that even though Tomas doesn’t drink or do drugs, he’s an incredible host and wingman who loves to have a good time. I felt like I was in college again, a man-sized child lost in the largest city in the country.


• stayed out until 4am each night
• played chess hustlers in Washington Square Park
• befriended strangers when we were out and about
• set up coaching sessions with those strangers
• ate mushroom chocolate and woke up tripping with no idea where in Brooklyn I was
• got late-night tacos both evenings
• left my credit card at the last bar we went to
• saw Seth Meyers walking with his son five feet from me in the park
• got offered blow by the CFO of VICE
• decided I would move to the city about ten times and changed my mind each time

Can I do this every weekend? Absolutely not.

But it’s times like these I never want to give up. I’ll gladly sacrifice my comfort for a day or two for memories and moments like I just had.

This weekend was…fun.

Dillan Taylor playing a chess hustler in Washington Square Park

20 years ago

I’m visiting my buddy in New York City next weekend.

20 years ago today, that city was attacked by terrorists.

There are plenty of past and current events with more death and destruction—some led by us—but being invaded leaves a different kind of unease.

It feels worse to have a stranger sneak in and steal money from us than it does our little brother taking cash from our wallets.

I have friends who lost family members on 9/11.

I’m not a sentimental person, but I’ll spend the day reflecting.

Initial thoughts

My coaching friend ran a workshop yesterday and had us do a lovely exercise.

We ran through the different aspects of the root chakra: physical, home, and financial health.

In each category, we broke them down into subcategories and had to write our immediate emotional thoughts. Here were mine.


• Sleep: sacrificed, suboptimal
• Water: great, peeing a lot
• Diet: mostly good, unorganized
• Exercise: consistent, necessary
• Stretching: infrequent, in the doghouse
• Hygiene: clean, fresh


• Vibe: minimal, intentional
• Relaxation: bed, office
• Safety: solid, dogs


• Income: vital, growing
• Savings: not enough, a little each month
• Debt: mountain, heavy
• Toxic money: none really
• Income goal: $100K+, relief, safety, freedom

The coolest part about this exercise is how many of my responses surprised me. Try it and see what thoughts pop up.

Not today

Some days I sit down and spend an hour writing what I hope is an articulate and thought-provoking blog.

But not today.

Today I just felt like writing this.


I’m going to a wedding today. My first one since pandemic began.

A friend from college. Approaching 30 is weird.

The only thing I’m nervous about is my tendency to go to bed around 9:30pm. Maybe not tonight.

Maybe tonight I party it up in the dirty Jersey.

Pray for me.


Last night, I talked to one of my best friends on the phone for two hours.

I remember doing that when I was seven years old.

I hope I’ll continue to do it until I’m 87.

The person you should be like

A blooming flower in a field

Until I was about 25, I thought relentlessly, Who should I be like?

I looked to successful friends, role models, even characters in movies or plays.

When I was in high school, I would listen to the music my friends liked even though I didn’t really enjoy it.

Last year, in trying to make YouTube videos on self-improvement, I tried my best to copy my favorite filmmakers who made the same content.

After starting my own business, I read countless business and self-help books to figure out who I should emulate to become prosperous.

In my work, my relationships, and my creative endeavors…I’ve spent an ungodly amount of time asking that same throbbing question…

Who should I be like?

As we get older, one of the frustrating (and uplifting) things we realize is that cliches are cliches for a reason: They remain true.

We can turn to one of the top five cliches to answer this uncomfortable question:

Be like you.

In a world of seven billion humans, there is only one person on the planet who has the exact same combination of interests, strengths, and perceptions as you have. And it’s…me.

Just kidding. It’s you.

Of course, it’s necessary to be influenced by others. Soak in ideas and motivation from the people you respect. There’s always something to learn from everyone.

But only you can take what you learn and make it totally your own.

I’ve written about 1000 blog posts on this site you’re reading. There’s not a single word I haven’t taken from something else.

My mom and teachers taught me how to read and write.

All my ideas have come from experiencing the outside world—conversations with friends, stories, and lessons I’ve learned and pondered over.

But they’ve made it onto this screen because they’ve traveled through the filter that is my brain and then out of my fingertips and onto the keyboard.

Thus making them mine.

The same is true for everything you do and say.

What do you value and cherish? What excites you? What do you love?

Do that. Do it all the time. Get really fucking good at whatever you hold dear to your heart.

Because that’s you.

When you do that, you don’t have to be like anyone else. You can be the coolest person on earth.


From strangers to family

Carlos Catania Brazilian Jiu Jitsu

Last night was my first day back to the jiujitsu gym in four months.

I took time off because I had a bunch of family events for the holidays and trips and flights I didn’t want to miss out on. I didn’t want to increase my chances of getting COVID.

Spoiler alert: I got it anyway.

There are a number of life lessons I could write about (and have written about) from my short time doing jiujitsu. But today, I want to talk about something you can apply to any type of practice or community.

Being a n00b

Last winter, I remember hopping into class for the first time. It was fucking terrifying.

The thing was, I wasn’t really scared to get my ass beat—though that would happen each and every night. I was aware that that was simply part of the process going in.

No, what intimidated me was jumping into something with a group of people who already knew each other for years.

My thoughts: They are a family. I am an outsider.

I felt the same way when I started acting in the theatre program in college. They are a family. I am an outsider.

It’s tough when everyone:

• tells stories you were never a part of
• knows everyone’s names and facts about them
• is constantly talking and laughing with everyone else besides you

How to change things

To be clear, by no means was I ever excluded or belittled at my gym. There’s just a noticeable difference between feeling truly close with the people you practice with and not.

The lesson here: That closeness doesn’t happen overnight.

It’s analogous to building trust with someone. It’s an organic and slow process.

Slowly but surely, I would talk more, tell more jokes, and get enough time in with my gym peoples to tell stories of my own.

One day, I was talking to a classmate before class, and I said something like, “People should feel lucky to come in and join your guys’ gym.”

She raised an eyebrow and unironically retorted, “You mean, join our gym.”

Holy fuck. I’m in.


I got lucky to become closer with an amazing group of people. Not every group of coworkers, athletes, or neighbors will come together in such a way and that’s okay.

The point here is: When you enter a new community, the feeling of being the outsider can be daunting and often discouraging.

You may think, They already have their group. They don’t need me.

But if you keep showing up, keep listening, keep caring, and the group is a good bunch…then after a bit of patience and consistency, you’ll find you have another family.

My old thoughts: They are a family. I am an outsider.

My thoughts now: We are a family. Outsiders welcome.