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.

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.

(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.

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.

(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.

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.)

(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.

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.)

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.

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.

“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.

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.)

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.

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.

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.

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.

Thursday

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.

Friday

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.

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.

Saturday

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.

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.

Tomorrow…

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.

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.

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 Chess.com 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.

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.

Apologies.

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

No pun intended.

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

Too tired to write about it now.

See next blog.

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.

I…

• 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.

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.

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.

Physical

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

Home

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

Financial

• 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.

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.