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.

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.

The journey down south (pt. 1)

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

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

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

Day 1

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

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

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

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

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

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

Then something happened.

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

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

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

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

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

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

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

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

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

The app disagreed. So I called.

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

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

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

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

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

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

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

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

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

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

(Here’s part 2.)

To Florida and back

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

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

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

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

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

Then the retreat just south of there.

I feel a sense of bliss. Here’s why.

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

But we all need breaks.

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

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

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

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

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

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

See you in two weeks. ✌️

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

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

I think that’s bullshit.

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

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

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

So what’s wrong with this?

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

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

And that’s my point.

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

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

“Where the hell did four months go?”

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

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

  1. Newness
  2. Gratitude

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

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

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

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

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

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

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

It only takes a sentence.

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

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

Anyway, my two questions for you are:

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

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

What we don’t see

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

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

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

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

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

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

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

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

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

A bookshelf stacked with books of all kinds

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

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

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

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

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

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

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

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

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

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

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

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

Quitting vs. giving up

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

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

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

The difference between quitting and giving up.

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

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

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

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

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

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

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

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

The gift of suffering

We were not suffering in this photo.

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

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

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

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

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

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

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

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

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

✌️

Grow a mustache—Why you should be more polarizing

A man with a mustache and sunglasses looking into the distance

(Yes, ladies. Even you.)

The idea

I want to alienate more people. Let me explain.

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

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

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

Then everything changed when the fire nation attacked.

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

The stache

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

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

The thing I noticed immediately? Mustaches are polarizing.

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

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

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

Then I thought about other areas I could apply this.

The meaning

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

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

Lower quantity. Higher quality.

So what does this mean for us?

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

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

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

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

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

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

Grow a mustache.

You can do it (actually)

A group of athletes running a marathon

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Keep running.

2am nightmare

Every month or two, something shitty happens.

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

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

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

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

I canceled my last call just to take a nap.

Anyone else experience this?

I’m scared to talk to women

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

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

But that’s 95% of dudes.

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

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

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

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

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

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

How did we start talking to these ladies? Bowling.

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

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

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

Writing is still hard

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

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

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

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

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

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

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

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

I call it a “problem” for two reasons:

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

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

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

Anyway, here have been my biggest lessons so far:

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

Stay tuned. ✌️

What I learned from Will Smith’s slap

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

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

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

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

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

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

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

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

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

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

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

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

Was I disgusted by what he did?

Of course.

Will I go see the next movie he stars in?

Of course.

Sick thoughts

I’m sick. It’s not COVID.

This usually happens twice a year when the temperature changes. Cold symptoms. Cough. Congestion. Sore throat. It’s not fun but I tend to survive.

One thing that the pandemic has taught me is how often I used to go out into the world while sick. I’d go to work, hang out with friends, or go to the gym.

My Ph.D. in Bro Science tells me that coughing in the same room as others is a great way to spread whatever it is. I feel a refreshed sense of courtesy.

On Friday, when things felt super mild, I called my friends before going over to their place for dinner. I explained exactly how I felt and they told me to come on over.

But for the rest of the weekend, I canceled all plans. I’m coughing up a storm. My head feels like it’s full of mucus. The only plus is that my voice is twice as deep from the sore throat.

This is starting to sound like, “Look at how virtuous and ethical I am for canceling events while I’m ill.” But I seriously used to push through stuff like this in the past. It’s crazy to me now.

Once when I was quite sick, I showed up for my shift at the restaurant I used to work. The GM took one look at me and asked, “Are you sick, dude?” I said yeah and he promptly told me to go the fuck home.

Who would’ve known it would take a global pandemic for me to see that being around others while sick isn’t a great idea?

Not me.

On confidence

Confidence is not a necessity. It’s a reward.

I’ve had nearly a thousand coaching conversations with people. I’ve heard it every week for over a year.

“I just need more confidence.”

In other words: “I must first have this internal emotional change. Then and only then will I be physically able to do what I want to do.”

It’s totally understandable. But it’s nonsense.

If confidence is the belief in oneself, how can we have such faith when we’re unskilled and inexperienced in a thing? Unless we’re full of ourselves, we’ll naturally be nervous and unclear. That’s okay.

Being scared has nothing to do with us being able to do something. We do scary stuff all the time. If we don’t, it’s not because of inability; it’s because we choose not to.

Running a business. Talking to people we’re attracted to. Improving a skill.

We often think: “I need to learn X so I can do Y.”

When in reality, it’s: “I need to do Y and then I’ll learn X.”

Do first. Then feel confident as a reward for doing.

Don’t wait for it to fall into your lap.

RSS

I’ll be making an RSS feed for this blog soon.

That way, readers won’t have to check it every day. The posts will get sent directly to anyone who subscribes.

Stay tuned.

Quitting coffee (for a second time)

A cup of coffee on a table surrounded by a pile of coffee beans

Last year, I tried quitting coffee cold turkey. It sucked.

It led to two of the most miserable days of my life. I had to cancel my calls the second day because my head hurt so bad. It felt like the life had been sucked out of me.

I figured, I only drink a small cup each morning. Nothing crazy. Apparently, that’s all it takes to spark a caffeine addiction.

To be fair, I’d rather have a caffeine addiction than need something like booze or cocaine to get me going in the morning. But it pisses me off that I “need” any substance to function.

People laugh about it like it’s a good thing.

“Don’t talk to me before I’ve had my coffee.”
“I need my coffee.”
“I’m not a human without my coffee.”

We’re basically okay with being a slave to a chemical. What if we were to say, “Don’t talk to me at night until I’ve had my evening beer.”

I’m not shaming any addicts or people with prescriptions. It’s just strange to me that we have a culture where the norm is to physically require a powerful chemical—which caffeine is.

If this sounds harsh, keep in mind: I’m talking to myself here.

So today I started the weaning process. I used 50% less ground coffee and less water. This morning’s cup was weaker and smaller. I’ll continue chipping away at this until I run out of filters. Then I’ll switch to black tea.

The end goal: Only drink water and a few supplements in the morning. Coffee will only be a treat on vacation.

I’ll keep you all updated. If this blog suddenly stops, I probably went into caffeine withdrawal.

Startups suck

The whiteboard of a startup business with planning and sticky notes

That sounds harsh. Here’s what I mean.

When I visited my friends in Philly this January, I walked one of them to the train station. We were chatting in the freezing cold about the next steps for my business.

I mentioned I wanted to help startups. I had always been fascinated by them from afar but have had no interest in creating one myself.

What she said struck me.

“I mean, you do run a startup,” she said. “You manage a profitable business. You provide a service that other people pay for all on your own.”

Whoa, I thought. “I suppose that’s true,” I replied.

She reminded me that we seem to have unhealthy images of what startups actually are. Millions of dollars of venture capital. Software as a service. Founders who work 10-hour days and neglect their health.

I don’t want to do any of that. And I don’t have to.

I’m rereading Rework by Jason Fried. It’s a business book on how to optimize for fulfillment, not profit or growth.

In it, he argues that when starting a business, we don’t need business plans, we don’t need to grow if we don’t want, and we don’t need a big team. All we need is to sell a product or service to people willing to pay for it. Then, we need to make sure our revenue is higher than our expenses.

That’s it.

Jason also suggests not using the word “startup.” Just say business.

Before starting my coaching practice, I saw the “world of business” as this intimidating, unwelcoming entity. But there really isn’t a “business world.”

There’s just the world. It’s made up of human beings. They make decisions. They buy stuff. I had this idea in my head that startups were these mystical and magical creatures. They’re not.

In starting a business, all we need are three things:

  1. A product/service
  2. People willing to buy it
  3. A way to take their payments

If we can’t define these three things first, there’s no business. There’s just an idea.

That conversation with my friend a few months ago was short and simple. And it uplifted my spirits moving forward. As I continue to meet startup founders and learn about what they do, I’m not thinking, OMG I’m talking to a startup founder right now. I’m thinking, Wow, this person is really interesting. I’d love to learn more about what they’re going through.

As always, things are much simpler than we think.

Anyone can talk

A man talking through a cup phone

For years, I said that family was one of the most important things to me. But that was a lie.

How do I know?

Because my actions tell the whole story. I never went out of my way to help my mom. I rarely spent quality time with my sister, aunts, or uncles. I visited my other half of the family when it was convenient.

Billionaire industrialist and vigilante Bruce Wayne once said, “It’s not who I am underneath, but what I do that defines me.”

The cliche states that actions speak louder than words. Basically, anyone can talk. Talking is easy. It feels good. Sometimes, people are so good at talking, they trick themselves into thinking they’ve already done something.

That’s why ideas, plans, and roadmaps bore me. It’s all just words.

That’s not to say we shouldn’t prep for the future. I’m just far more interested in what a person is doing than what they say they’d like to do.

(Keep in mind, I’m criticizing myself here.)

Here’s a pretty personal example.

One of my close friends has basically been radio silent for the past year. He doesn’t answer my calls or texts. I worry about his health and wellbeing. I get no answers.

He sent me a super long text on my birthday a few weeks ago. He apologized profusely. He told me how much he loved and respected me. Reading it made me cry at my dining room table.

When I responded to try to set up a call…nothing. I haven’t heard from him since.

Anyone can talk. It’s through our consistent actions that we prove who we really are (thanks, Batman).

If we want to be kind and loving friends, we have to show our friends we support them and are curious about them. If we want to care about our health, we have to exercise regularly and eat mostly well. If we want to be productive, we have to sit down and do the work every week.

So what can we do with all this?

Try this exercise: Take five minutes and write out all the things you value most. Then, take another five minutes and write about the actions you take on a regular basis for those things.

Notice where things are lacking. What can you do more or less of? What needs to change?

As always, let me know how it goes. 😎

Next level

A man playing a virtual realty video game

I’m shifting my business. It’s scary.

2021 was the year of building my one-on-one coaching practice from scratch. Mission accomplished. It had grown to the point where I had to stop pursuing new clients in December.

So I spent this winter focused on my current clients, writing my book, and learning how to slow down. The last time I created new income was at the beginning of January. I’ve been living off a decent cushion for myself, but I can’t move to Brooklyn in October if I don’t build something new beforehand.

In my community, we say: “What got you to this level is what will keep you from getting to the next level.”

What got me to the level I’m at was my client-creation process:

  1. Reaching out to people individually, connecting with them, and building a relationship.
  2. Inviting everyone I talked with to a coaching session. Coaching as many of them as I possibly could and seeing if it was a good fit.
  3. Making it easy for them to work with me (financially and schedule-wise).

I loved it. I still do. My one-on-one clients are some of my favorite people on the planet.

But there are only so many hours in a day, week, and month. Rather, I only have so much energy. I’m not some super-entrepreneur who can put in 10-hour days. Even if I could, I don’t want to.

First of all, people don’t actually work 10-hour days. We can’t even work for eight hours. Sure, we can be in the office for that long. But we only have about three to four hours of genuine focused attention at our disposal.

Secondly, with what I do, I get drained pretty fast.

My job consists of listening deeply to a person, being wildly curious about them, and challenging them. Doing this with multiple people for multiple hours would make anyone tired.

That said, I can’t keep doing the 3-step system I mentioned above. It got me here, and it’ll keep me from getting to where I want to go.

So what will get me to the next level?

Something scaleable. A service where I’m not trading my time for money. Here’s what I’m thinking:

  • A group program for entrepreneurs.
  • Only high-paying referrals for one-on-one clients.
  • A content marketing strategy.

In the first sentence of this blog, I said I was scared. That’s not quite true. I’m unclear. And that can often be mistaken for fear.

At this stage, I’m interviewing startup founders to hear about their stories and challenges. It’s already giving me a clearer picture of what I can help folks with. But I don’t quite know what service I want to provide yet.

Luckily for me, I learned a valuable lesson last year: We don’t have to know how to do something in order to do it.

On top of that, we don’t have to be fearless in order to do what we want.

I don’t exactly know what I’m doing yet. But I know I’ll do it.

And when I do, I’ll tell you all about it.

(PS—Connect with me on Twitter for more regular updates and insights! @DillTho)

Hungover without the alcohol

A woman holding a glass of wine

Two nights ago, my sleep tracker told me I got two and a half hours of sleep. I woke up in pain.

I trudged through my first two sessions yesterday. Then for my third, he asked if we could reschedule. I was elated.

I said sure and I regretfully texted my personal trainer to reschedule our afternoon workout. Then I did something I never do.

I took a nap.

Three hours later, I woke up feeling human again. The day ended with a few fun and energy-filled calls.

But I wanted to briefly mention some Bro Science…

My hypothesis: Much if not most of the pain we feel during a hangover is sleep deprivation.

Firstly, when we drink, our sleep quality goes out the window. It doesn’t relax our minds; it sedates us. But alcohol aside…

I go months without drinking. Those periods don’t just lead to me feeling amazing. I have to eat well, exercise, and sleep 7-9 hours each night. There have been sober mornings of awful sleep and it genuinely feels like I’m hungover.

That’s what yesterday felt like.

So aside from the nausea, the headache, and the dehydration…how much of the physical pain of hangovers is simply because our brains didn’t get any sleep?

New rule; fewer blogs

Last month was an eye-opening experience for my mental health. After hitting a wall, I made some changes.

No more working on Sundays. No calls past 3pm. Friend and family time are to be prioritized.

I just made a new rule:

No blog-writing when I’m on vacation.

Simple, I know. But I’d often take my laptop with me when going out of town. That, or I’d write a bunch before leaving and schedule them out.

Either way, it would lead to low quality and throw-away writing.

This is already an “almost-daily” blog. Now even more so.

The freed-up headspace when I was on vacation was refreshing. Normally I feel panic and guilt as I question when I can find time to write a few sentences. It really takes me away from the moment.

Not no mo.

Done, or perfect?

My friend and I are recording a podcast episode today. Our first one didn’t go so well.

It wasn’t absolutely cringe, as the kids say. But it was tough to listen back to.

We gave too much backstory. We didn’t interrupt each other enough. It felt like we were taking turns giving TED Talks.

But we wanted to start a podcast simply because we enjoy our conversations and hope others would too. Something happens when you hit “record,” though. When you see that blinking red light, the butterflies settle in. It’s easy to feel like everything spoken must be funny or groundbreaking.

I’m so glad we had a mediocre first recording. We can’t grow or improve until we run a test and gather data.

We could’ve prepped and planned for months, trying to create the perfect conversation. But what we did was so much more efficient.

We said fuck it, let’s just do it and see what happens.

Done is better than perfect. Because perfect usually means doing nothing.

A simple technique for better conversations (that you can start using today)

Naturally, people enjoy talking to someone who asks questions and expresses curiosity. We all want to feel heard and feel important.

Whether it’s conscious or unconscious, people notice pretty quickly when a person only talks about themselves. The first thing I detect in someone is how often they ask (genuinely curious) questions. If they never do, I almost always find them less interesting.

But there’s a limit.

If we only ask questions in a conversation, it can feel like an interrogation real fast. That tends to make people uncomfortable or feel guilty that they talked about themselves the whole time.

So what if the person we’re talking to isn’t a skilled conversationalist? If they’re not giving us much to work with…

We can use the “2 for 1” rule.

Two questions. One personal story or idea. Repeat.

This ensures a back and forth. It lets the other person know, Hey, I’m a human being too. I’ve been through stuff. I can relate.

Try it out with your coworkers or with strangers. Let me know how it goes.

Success?

Is success a number or a feeling?

Is it a dollar amount in our bank account…or not being stressed about bills?

Is it how many followers, subscribers, or connections we have…or the level of connection we feel with the people we’re in the same room with.

Is it our weight…or the refreshing and limber sensations of a healthy and active body?

The 10 qualities of a Professional

According to Steven Pressfield, there are amateurs and there are professionals. Here’s what sets the pros apart:

1) We show up every day.

Vacations are nice and rest is necessary. But inside those boundaries, we’re on the clock.

2) We show up no matter what.

Again, time away from working is rejuvenating. But if we only do the work when our bodies feel like it, we’re doing ourselves (and those we serve) a disservice.

3) We stay on the job all day.

Our to-do list should be reasonable and doable. And our day ends when it is complete, not when Resistance begins to settle in.

4) We are committed over the long haul.

Perhaps we’ll be doing something different a year from now. But we’ll still be working consistently with purpose, providing value, and growing our skills.

5) The stakes for us are high and real.

We don’t create because it’s a hobby. We create to pay our rent, buy groceries, and afford trips with our friends.

6) We accept payment for our labor.

We are here to serve people and solve problems, yes. But we must be compensated for doing so. Otherwise, we’re not working; we’re running charities.

7) We do not over-identify with our jobs.

We write. We collaborate. We design. We’re not writers, collaborators, or designers. Our work is not our life; it fuels our life.

8) We master the technique of our jobs.

We improve each week because we know we’ll never know all there is to know. We become black belts in what we do.

9) We have a sense of humor about our jobs.

While the stakes are high, we don’t take ourselves seriously. We shrug off failures as part of the game. If we’re getting pummeled it’s because we’re on the field and not in the stands…and we’re grateful for that.

10) We receive praise or blame in the real world.

Some people love what we’re doing. Some people despise it. Both are okay. We appreciate the kind words and learn from or disregard the nasty ones.

I certainly don’t embody all ten of these each and every day. But all I can do is take care of myself and remind myself of the simple truth…

That the hardest thing to do in the world is to sit down in this chair and do the work.