The science of friendship

A group of friends sitting and laughing around a coffee table

A good friend sent me a podcast yesterday. It was a panel of academics sharing research on the relationships of friends.

I thought I’d go for a short walk and listen to 10-15 minutes of it. But it was so insightful and entertaining, I spent an entire hour just walking laps around my apartment complex in the cold and rain.

It’s called, “Time for a Friendship Reset?” by Aspen Ideas to Go. For anyone who wants to listen to it, it’s available on Apple Podcasts and Spotify.

They discuss how limited the research on friendships is. In doing so, they share relatable and digestible experiences we’ve all gone through in our friendships.

Here are a few of my biggest takeaways:

  • Men tend to bond with each other through activities and often avoid maintaining friendships with openness, vulnerability, and communication.
  • There’s a powerful script when trying to save an eroding friendship: Here’s why I loved our friendship in the past—you made me feel this way. Then it seemed like this happened and now I feel this way. I’m sorry I didn’t have to courage to say anything until now. How have things happened from your perspective? What can we both change moving forward?
  • It’s totally natural to feel jealous of our friends. The same is true of those who take up time with our closest friends.
  • Friendships are often more powerful than family relationships. While you can’t choose your family, friends are close bonds that are entirely based on two people choosing to spend their time, love, and attention with one another. There’s no contract like there is with a spouse or a blood relative. That’s also why it hurts so bad when someone chooses to let the friendship die.

If you check it out, reply to this email and let me know what you got out of it!

10 tricks to living a shittier life

An ostrich with its mouth wide open

Since attempting suicide in 2017, I’ve been obsessed with living a better life. I’ve even made a career out of helping people improve theirs.

But for those of you who have it too good, are too fulfilled, and are looking to downgrade…here are 10 easy tricks to help you start living a shittier life today.

1. Talk shit about people when they’re not around.

By saying things about others you would never say to their face, it makes you more resentful and cowardly. Also, when you gossip and badmouth around friends, they’ll subconsciously wonder if you do the same to them when they’re not around.

People get drained by toxicity. This is a great way to decrease people’s energy when they’re with you.

2. Laugh at exercise.

67% of Americans are overweight. That’s totally fine. The number should be higher.

Exercise has a plethora of benefits: increased confidence and energy levels, mental clarity, heightened motivation and willpower, increased general attractiveness, lower risk of disease later in life, and more strength overall.

So it should be avoided at all costs. Try viewing it as this uncomfortable, sweaty activity only meant for athletes. Be confused as to why anyone would put themselves through physical strain. Making fun of it will make you feel better for not doing it. Tell people you love your body by doing nothing to protect or improve it.

This is a great way to feel worse physically and mentally throughout your day.

3. When in conversation, focus on being right.

99% of people know something you don’t. But they must never know that.

Act as though you are enlightened and have all the answers. This will make conversations with you boring and non-collaborative. Be the teacher, never the student. Don’t ask questions. Constantly preach your knowledge to others, especially when they don’t ask for it.

When someone disagrees with you, the goal should not be to understand where they’re coming from and find common ground. The goal is to explain why they’re wrong and you’re right. Shame them into believing this if you have to. That will guarantee they never will and it will disconnect you both entirely.

This is a great way to keep people from feeling safe to explore their thoughts around you.

4. Drink more coffee, soda, and booze than you do water.

75% of Americans are chronically dehydrated. Again, those are rookie numbers.

Consuming a lot of caffeine and sugar can increase anxiety and stress levels. Downing alcohol frequently weakens the immune system and lowers sleep quality. This is all a perfect cocktail (pun intended) for a shittier life.

Drinking water protects organs and tissues, carries nutrients to cells, and flushes bacteria from your bladder. Sounds awful.

Skip a cold glass of water and reach for coffee first thing in the morning. This is a great way to start the day in a manic state.

5. Avoid doing the things you think would be cool to do.

We all have things we’ve been talking or thinking about but have taken zero action on. Learning Spanish. Dance classes. Starting a business, blog, or podcast. Painting. Piano. Pickleball.

The more we avoid actually doing any of these things, the more regret we’ll feel when we’re older. The pain of longing is guaranteed to feel shitty.

There will always be 1001 reasons why it’s inconvenient to start something. Let those excuses keep you from having more fun, improving your skills, and being more fulfilled.

This is a great way to wake up at 60 and question why you didn’t actually pursue your dreams.

6. Start and end your day by looking at your phone.

If you’re looking to add compulsion and anxiety to your life, this is one of the simplest ways.

Rather than giving your mind space to wake up or wind down, feed it with notifications, news, and chaos. Reading, stretching, or meditating would make the rest of your day more peaceful and present.

Fuck that. Keep your brain spinning every waking hour.

This is a great way to never feel done and to be addicted to a screen.

7. Give in to most of your cravings.

We all indulge. But try to avoid moderation. Make indulgence a lifestyle. Give in to temptations several times a week.

Junk food. Porn. Entertainment. Booze.

Doing this over and over again will supplant this story that you’re addicted to your cravings. When really it’s just a habit you currently have that can be broken or replaced. But don’t let your mind know that.

Treat yourself to whatever meal you want. Skip exercises or difficult things. You’ve earned it. Your body doesn’t care that you’ve earned it but hey…you’ve earned it.

This is a great way to be less fit and powerless against your compulsions.

8. When talking to others, talk more about yourself than about them.

Being interested in others is the best way to make them interested in you. They’ll feel seen and heard. People will enjoy your company more. They’ll feel connected to you.

Steer clear of that. Avoid asking curious questions. Definitely don’t ask follow-up questions to prove you’ve been listening. Try to stick to your stories and your opinions. Keep it one-sided.

This is a great way to weaken rapport and have worse conversations.

9. Take responsibility for the emotions of other people.

There are 7.98 billion people on the planet. If you do or say anything that could offend, frighten, or rub someone the wrong way…you should be arrested.

You’ll never agree with anyone 100% of the time. So it’s best to walk on eggshells and muzzle yourself to avoid any confrontation or misalignment. Don’t be yourself. Definitely don’t ask for what you want. If there’s even a slight chance of someone else being uncomfortable, stay silent.

It’d be easy enough to apologize or have a conversation if you ever do hurt anyone. But it’s best to avoid it entirely.

This is a great way to remain a shell of yourself.

10. Stay soft.

View discomfort as the worst-case scenario. Challenging moments will strengthen you. They’ll sharpen your communication and problem-solving skills. Avoid that.

You should be triggered easily. We all care about things. But you should get unhinged whenever you see or hear something you don’t like or agree with.

Shun people who have differing opinions from you. Judge them. Question their morality and humanity. Try to shame others into believing what you believe. It’ll never work. But you’ll feel superior and enlightened.

This is a great way to stay mentally weak and to keep your head in the sand.

Hope that helps! Let me know if these 10 tips help you decrease your quality of life.

One question: the best feedback you’ve ever gotten

Two men giving feedback to one another at a conference table

Receiving feedback from our friends, family, and colleagues is one of the quickest ways we can improve ourselves.

It can also be extremely painful.

Our egos can get hurt. Not everyone’s opinions are valid. We see what people really think about us.

But building thicker skin and understanding we’re far from perfect are some of the most valuable things we can do. I ask for suggestions for this blog. I do regular improvement sessions with my closest friends. It can be uncomfortable but it always leads to something better.

If none of that interests you but you want to make improvements in your relationships, health, or work…ask this question to the people closest to you.

What’s something you’re afraid to tell me because you think it would hurt my feelings?

The answers you hear may sting in the short term. But you’ll start being more mindful, improving skills, and seeing reality for what it is.

Try it out. Let me know how it goes.

I tried to skip a vacation but my friend wouldn’t let me

A gorgeous lake and a partly cloudy sky

For the first time since starting my business in 2020, I’m busy.

It’s something I never want to be. Many Americans use the word “busy” as a fake complaint. They’ll groan about it while flaunting it like a badge of honor. How am I? Good! Busy. Super busy.

But to me, busy just means a person isn’t in control of their time. The number of tasks outweighs the available hours for those tasks. It implies a feeling of rushing from one thing to another.

So when people tell me something like, “You must be so busy,” I correct them.

“No,” I reply. “Just productive.”

This lands well with some people. With others, I sound like a douche.

Anyway, this month has been different. I have genuinely been busy and it’s been a shock to my nervous system. It’s the fullest my plate has been all year.

Coaching. Restructuring my community’s website. Chess tutoring. Jiujitsu class. My new podcast. Writing my book and these blogs.

You can have anything you want, but you can’t have everything you want. And this month, I’ve felt the quality of my attention and production slip. My bandwidth is being allocated to too many different things.

To add fire to flame, this is the most vacation I’ve taken in a single month.

I know that’s a terrible thing to complain about. But deadlines can make it difficult to be 100% present when you’re trying to get away. There’s guilt involved. The story that replays says, “I could and should be getting work done right now.”

Two weeks ago, I spent the weekend at my family’s lake house. Yesterday, I got back from a four-day stay in West Virginia with my mom and sister. This weekend is a trip to Deep Creek Lake with close friends.

It was the last night in West Virginia. Flooded with anxiety about getting everything done, I texted the group and pulled out of Deep Creek.

I woke up to a few responses saying they totally understood and they hoped to see me soon. That felt nice.

Then my buddy called me.

“What’s up man,” I asked.

“Yo dude,” he started. “Saw you weren’t coming to the lake this weekend. What’s going on?”

I shared about my workload and my fear of not being fun. He listened respectfully, told me he understood, then challenged me.

“I totally know how stressful deadlines can be, man,” he offered. “But I think now’s a great time to lean on your people. We got your back. And I think there are steps we can take to make this happen.”

He came up with a few ideas. They involved carving out specific times for me to tinker on my laptop while they took care of other things. He told me I could work in their van while they got the boat ready and could come pick me up.

“Fine dude,” I chuckled. “You win.”

I decided to go. But it had way less to do with his proposed solutions and more to do with the fact that he called me in the first place to get me to come. It felt like a slap in the face.

It said, Hey dummy, don’t skip out on memories with your friends. The workload will eventually end, but you won’t be able to get those memories back if you miss out on them.

His language was much lighter and kinder than that, but it had the same effect.

I’m lucky to have friends who push me to live a better life. It’s not something everyone has access to.

20 years from now, we’ll tell stories about drinking beer on a boat. Because no one ever tells a story that starts, “Dude! This one weekend, I stayed home and got a bunch of work done…”

Put first things first.

Being ghosted by my best friend—What I learned

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

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

But I’m still in the dark.

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

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

1) A friendship is just another relationship.

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

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

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

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

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

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

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

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

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

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

We don’t.

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

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

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

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

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

Speaking of communication…

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

May 2022, after a Savage Race.

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

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

It can be done in many ways.

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

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

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

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

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

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

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

Here are the questions my friends and I dive into:

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

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

In summary:

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

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

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

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

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

About New York…

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

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

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

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

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

Wait, but why?

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

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

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

Well, yes and no.

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

Logical reason:

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

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

My God.

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

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

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

But not comfortably.

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

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

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

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

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

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

Emotional reason:

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

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

Just a couple’a cool dudes.

I liked him immediately.

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

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

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

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

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

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

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

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

Ain’t that the truth.

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

TLDR:

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

How to send a cold email to someone you respect

An iPhone with email apps on the home screen

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

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

The answer is intricate and complex…

I emailed them.

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

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

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

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

Cold Email Must-Haves

1) A personal and human intro.

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

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

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

2) Why you’re writing to them.

Cut to the chase.

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

3) A clear and simple call to action.

What specifically are you asking for?

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

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

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

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

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

4) Give them an out.

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

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

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

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

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

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

Key Principles of a Cold Email

1) Keep it short.

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

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

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

2) Care.

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

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

3) Be persistent but not annoying.

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

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

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

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

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

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

“Hey Steph!

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

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

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

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

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

Dillan ✌️😇”

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

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

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

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

Solving vs. Managing

A solved Rubik's Cube

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

I have no clue.

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

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

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

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

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

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

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

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

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

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

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

I thought I wanted to move to New York

What I’ve been doing

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

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

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

It was a lot.

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

And I’d like to reflect on both.

What I learned about New York City

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

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

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

Cons:

1) No established community

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

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

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

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

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

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

More on that later.

2) The cost

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

What the fuck.

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

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

3) The trash

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

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

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

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

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

4) The homeless

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

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

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

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

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

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

Pros:

1) The adventure

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

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

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

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

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

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

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

2) The food

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

And the fucking pizza. The hype is real.

3) No car

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

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

4) The discomfort

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

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

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

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

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

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

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

What I learned about myself

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

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

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

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

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

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

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

The next steps are:

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

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

Alone in the city

My makeshift travel work desk.

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

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

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

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

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

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

Vital Climbing Gym. It’s hard to beat.

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

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

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

And that makes sense.

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

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

Then I went to a chess meetup.

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

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

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

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

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

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

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

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

We started playing.

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

My new home.

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

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

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

I’ll share those stories tomorrow.

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.

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.

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.

Stupid games

Dice and pieces on top of the board of a game

Naval Ravikant said, “Play stupid games, win stupid prizes.”

This sounded a bit harsh and over-dramatic when I first heard it. It took me a while to actually get it.

We often play “stupid” games:

  • trying to be the smartest person in the room
  • looking really cool on social media
  • making as much money as humanly possible
  • being on our phone for hours each day

I have coaching clients who have played tons of these games. I’ve played tons of these games.

The question is: What does it look like to win the game you’re playing?

If you climb your way to being the absolute coolest person on Instagram (whatever that means), what would you be able to do with that? What would that mean for your life? What would that fulfill?

If you feed your phone addiction and make sure you never miss a notification, or respond to every email as quickly as possible, what would winning that game look like?

In my experience, the prizes of these games often include being kind of happy for a short time…then going right back to whatever our normal state is. After that, it’s feeling disappointed that this thing didn’t bring us enlightenment.

An even darker example is texting and driving, one of the stupidest games out there. 400 fatal crashes happen each year from driving while using our phones.

But what is ‘winning’ texting and driving? Not having to wait 10 minutes to see what our friend texted us?

In 2020, my mom was completely stopped at a red light waiting for it to change. A young man hit and totaled her car at 50 mph. He was texting.

I always think, I wonder what he was doing on his phone and I wonder if it was worth it? He played a stupid game and won a stupid prize.

So which games bring us awesome prizes?

For me—and I would argue for most of us—it’s all the cliche stuff:

  • being a great friend/son/daughter/etc
  • getting physically/mentally fit
  • improving skills
  • being kind and curious

So, what games are you playing?

If you were to win that game, what would that look like? Would it be worth it?

Friend red flags

Three friends standing atop a mountain cliff

One of my besties came over yesterday and we discussed building new friendships.

As we get older and as our relationships evolve or fade, we learn a ton about the kind of people we want in our lives. The people we surround ourselves with are a reflection of our own values and desires.

She’ll be moving to DC this fall. So I asked her what her red flags would be while building a community there.

When she asked me what I wouldn’t accept in a friendship, a few things came to mind:

1) Negativity.

We’re all human. We’re all allowed to feel unpleasant emotions. But it’s hard for me to tolerate someone consistently complaining about things out of their control—especially if they’re taking zero action to make it better.

Any sort of victim mentality is a no for me dog. I like surrounding myself with people who take ownership of the life they’re creating.

2) Meanness.

Similar to #1, I guess.

I can’t stand passive aggression or bullying. Not so much when it’s directed at me, but when someone is mean to other people.

It sounds almost childish, but it makes my blood boil. When someone’s condescending, belittling, or downright nasty…

3) Dry conversations.

This is now starting to sound like I’m building a job application for the role of “Dillan’s friend.” I’m just trying to point out the traits that would make it difficult for me to build a deep connection with someone.

Whether it’s a friend, colleague, or romantic partner…if we can’t sit sober for three hours and have fruitful conversation, it just won’t work for me.

Sharing experiences, insights, and ideas. Telling stories. Asking curious questions. If this stuff isn’t present, what the hell are we talking about?

Anyway, I’ll be accepting applications online.

What are your red flags when it comes to making new friends?

Ty

Yesterday, I posted a blog about some burnout I’m feeling.

I got nine different texts from people asking if I was okay or offering to reschedule plans this week.

Every few months, I check the analytics of this blog. But I often forget that people actually read it.

I just wanted to say thank you.

Thank you for spending a minute with me each morning. Thank you for your support.

It’s an honor! 💙

Good friends vs. great friends

“Good friends consume together. Great friends create together.”

I heard this from comedian Hasan Minhaj in an interview last month. It hit me right in the soul.

With my friends, I have:

  • acted on stage
  • made podcasts and YouTube videos
  • written articles
  • partnered in business ventures

There’s an extra level of fulfillment that comes from this stuff. More so than watching a show or consuming another form of content together.

We get to collaborate. We get to bring something to life that otherwise wouldn’t have existed without our teamwork. We get to learn more about the other people we build with.

Today, my bestie—Connor Russo of LifeLikeLabs—and I are recording the first episode of our new podcast.

The idea came after I shared the quote from above. The goal isn’t to get a certain number of downloads or listeners. It’s to create something fun (and hopefully valuable) together.

On top of that, we hired my other bestie—Scott Clampet, aka Hudat—to make the music, edit, and produce the show. The entire thing will run on the power of friendship (gross).

We’ve committed to doing five episodes. The plan is to record them and then release them all at once. If we hate the process, we’ll stop. If it’s fun and people seem to enjoy it, we’ll continue.

Regardless, I’m super excited. Stay tuned!

The dating market

I’ve been sitting at my desk for ten minutes thinking about what to write for today’s blog.

To be honest, I have COVID brain. It’s a bit hard to focus.

So instead, here’s a video interview I’ve watched three times now. It’s on a subject that has been fascinating me lately—relationships between men and women, attraction, and the dating world.

Some of it may even seem controversial. But as a single man, it captivated me.

Enjoy.

The 6 people in every relationship

Is it possible to be our genuine selves around other people?

That may sound a little woo woo but it’s the question I mulled over yesterday. I connected with a coaching friend and she told me about a lesson from the book Mastery of Love by Don Miguel Ruiz.

In it, he talks about the performance we put on in each of our relationships. Let me explain.

When we’re with another person—friend, partner, family member, colleague, stranger…there’s three versions of us:

  1. Our true, authentic selves.
  2. The version of us we’d like the other person to see—knowingly or unknowingly.
  3. The person they actually see with their own lens.

That happens for both parties. Six people total. This blew my mind.

I’ve always been fascinated by how we can be completely ourselves but in different ways. As in, I’m “myself” when I’m with my mom, my best friend, my clients, etc. But they all get slightly altered versions of me.

I put myself in quotes because I’m beginning to wonder what that word even means. Does it mean comfortable? Does it mean I feel aligned with my words and actions?

It feels like our “true selves” are constantly changing based on our environments and social settings.

Even in my conversation yesterday. She’s a newer coach in our community and we connected over all the lessons she’s been learning as she’s been taking more action.

At no point did I feel like I was putting on a show. But right when she shared this six-people concept, I realized I was on the call trying to be more helpful than usual. It hit me that I logged onto the Zoom thinking, “Be as valuable as you possibly can.”

Trippy.

My takeaway from this?

It can be insightful to ask: Do I want this person to perceive me in a certain way? Would that feel like I’m putting on a show?

More feedback

I’m in Philadelphia visiting two of my best friends.

Connor, Laura, Dill.

(This picture was taken last year.)

They hosted me yet again for a lovely weekend of fruitful conversation, laughs, and suburban Philly walks.

One of the things my buddy and I did was a feedback exchange.

These can be tough. He even told me he was uncomfortable before he started diving into the things he wrote for me.

But I’ve done several of these now, and they have only led to…

• both parties growing/improving
• deeper connection
• intense gratitude

We had to answer these questions:

1) When have I hurt you?

2) What do you think would be most beneficial for me to improve?

3) What’s something you’d like me to know?

4) When have you been impressed by me?

5) What do you think I do better than most people?

On Monday, I’ll write about how it went and what I got out of it.

I wrote letters to all the people I love—Then I read them to them

A pencil, a piece of paper, and an envelope lying on a marble table

Back in October, I visited a few coaching friends in Vancouver Island, meeting them in person for the first time.

While at one friend’s house, we were discussing the things we felt incredibly grateful for. The same thought popped into my head that always does when I ponder what I appreciate most: my tribe of friends, family, and colleagues.

But this time, I had an insight.

Rather than vaguely trying to express this more to the people in my world, I decided I would be as intentional as possible.

I would craft hand-written letters to those who matter most. I would thank them and explain as best I could why they mean so much to me. Then, I would read the letter to them.

I’m not even close to totally completing this task (which I think is a good sign). But I have done several and would like to share what I’ve learned.

1) Expressing gratitude is euphoric.

Let’s get the selfish stuff out first.

Anyone who’s ever done a metta (loving-kindness) meditation knows the immediate rush of joy that comes from truly wishing someone well. We imagine someone we love and we picture them being free from harm and fear. We envision them being totally fulfilled. We see them laughing with the people they love.

This felt more impactful because I was sitting five feet from each person I read a letter to.

I could see their smiles and tears. I got to hug them afterward. I got to hear them stumble to find words that match the moment.

The idea of the exercise is to leave nothing up to the imagination. “Here are the specific reasons why I love you.”

Once that message gets across, the powerful connections I had with each person felt twice as strong.

2) This exercise is the easiest thing to do that brings life-changing results. Low input; very high output.

That sounds kind of businessy. Let me explain.

Each letter takes about 20 minutes to write. I type it out in a Google Doc first. This only takes about five to ten minutes because it’s effortless to write words that are sincere.

Then it takes another ten minutes for me to put pen to paper and transcribe the Doc.

The next time I would see the person, I would: tell them what I did, grab the paper as they panicked, and start reading it aloud.

In less than 40 seconds, our relationship would become wildly stronger.

I even gave this as a Christmas gift to my aunt and uncle. I have no idea if that’s just a cop-out from getting a “real” gift. But they both absolutely loved it so I think I’m off the hook.

3) There are a lot of things we keep to ourselves.

Here’s what I mean.

I’m lucky to have candid and loving relationships with my friends, family, and colleagues. But no matter how open and communicative we are with one another, there will always be thoughts and emotions we feel that the other person isn’t 100% aware of.

That’s also why I suggest doing a feedback exercise with those close to us. It paints a clearer picture of the lens our friends use to look at us.

We can let our actions tell the story. That’s a lovely thing.

But we can also remove the middle-man and get right at the heart of things. I’ll end with an example.

I wrote one of these letters to my dad.

In it, I told him what he did that meant the world to me. Last year, when I decided to not go back to school, quit my full-time job, and start my own business, I thought he’d be furious.

I was out front of my mom’s house, pacing on the sidewalk, when he told me on the phone I had his full-fledged support.

When I relayed this to him in my letter, he had no idea about the impact of that moment.

All this to say: We can always express our love and admiration for people more than we normally do. There’s always more to know.

I highly encourage anyone reading this to write just one letter to someone they appreciate. Tell them why they’re loved. Tell them what they mean. Tell them how much they’re needed.

Then see how they light up.

It doesn’t take much

Avocado toast with: bacon, eggs, tomato, and sprouts & a mixed berry cream cheese pastry I forgot the name of. Without exaggeration, the best dessert I’ve ever had in my life.

A few weeks ago, one of my friends told me she was stopping by in the morning.

My insecure self began wondering if I did or said anything I needed to apologize for. Then I wondered if she just wanted me to hide her boyfriend’s Christmas gift.

She showed up with paper bags. “This is to celebrate all you’ve done.”

The night before, I got dinner with her and her partner and told them about a huge business opportunity that had just come my way.

“I’ll always buy you pastries to celebrate your wins,” she said. I hugged her.

Normally, gifts aren’t my love language (they’re quality time and words of affirmation). But food is a different story.

Aside from being wildly appreciative to have a tribe of friends who support me and want the best for me, my insight was this:

It really doesn’t take much to express that.

That food was delicious, but she could’ve also just said, “I’m really proud of you and happy to see you working toward what you want.” It would’ve meant just as much.

It sparked a question for me to ask consistently.

What’s the simplest thing I can do to make this person I love feel heard, cared for, or supported?

The answer is never anything complex or demanding.

Icebreaker deck

This is not a paid promotion.

As a gift for yourself or someone else, I highly recommend BestSelf’s Icebreaker—Deeper Talk deck.

This deck of cards is loaded with powerful questions which spark phenomenal conversations. When friends are over I’ll often take these out and take turns picking random cards and asking these questions in a circle.

Time flies every single time.

It’s like having a game night but you also get to have deep and intimate conversations with the people you’re with.

10/10.

Friend systems

I had my biweekly phone call with one of my best friends yesterday. She lives in Rwanda.

Last week I realized we had been keeping the chain going for a year and a half. And we have no plan on stopping.

What an easy system for staying in touch. We just picked a time that works for us, set a calendar event for every two weeks, make adjustments when we need, and just show up.

On the call, I thanked her for her consistency in this.

She chuckled and said, “You made the calendar invite. All I do is answer the phone.”

But that’s exactly it. That’s all we need. It’s a system that runs itself.

It’s a small amount of effort which has led to countless hours of connection and deep conversation. She knows everything about me. My…

Wins. Fears. Opportunities. Projects. Relationships. Heartbreaks. Accomplishments.

She’s heard me at my highest and lowest points this past year. I’ve never met her husband but I feel like I’ve known him for years. Just from an hour and a half chat every two weeks.

The point of this blog is not to tell others to do exactly what we do. It’s to highlight how easy it is to do something truly vital in life: stay in contact with your God damn friends.

One day we won’t be able to.

Whenever that day comes, I’m looking forward to saying, “I’m glad we did that,” as opposed to, “I wish we did that.”

A weird key to success

A man wearing a snorkel and flippers in the middle of a crosswalk

It’s strange to claim that I’m successful. But I certainly feel like I am.

As we’ve heard many times before, the word “success” means something different to everybody. It’ll mean something different to me even three months from now.

But for now, I can pay my monthly expenses comfortably, I have an amazing tribe of people in my life, and I use my time exactly how I want. Success.

I’ve read tons of self-improvement books and watched just about every motivational video on YouTube. There are loads of tips and strategies successful people teach us.

Having a routine, practicing mindfulness, failing often.

But I’d like to reword that last one.

Whether we’re developing our careers, our passions, or our relationships, I’ve discovered this truth:

In order to be successful we must be willing to look like a fool.

A healthy business comes from the willingness to put ourselves out there. I’ve messaged people asking to connect and they’ve ghosted me with a wide birth—probably thinking I’m selling something or working for a pyramid scheme. (Four people this year have straight up asked me, “Is this an MLM?”)

No, this is Patrick.

Early in my coaching career, I was terrified to reach out to others. My fear was that everyone would see me as a salesman when I just wanted to talk or reconnect.

Would I invite them to a session? Yes, maybe. But if they declined I didn’t care at all. I just love talking to people.

These fears were beaten out of me as I continued to reach out to people every single week. Now when someone doesn’t respond or ghosts me, I couldn’t care less. Who’s next?

As far as my passion for chess…

I started playing consistently during lockdown last year. One of my best friends said we should play.

It was something we could do online together. And we’re both competitive so I had the drive to improve. My sole purpose for several months was just to beat him. He was better than I was and each time he beat me it stung.

But I kept coming back for more. I started studying and practicing each day. Here’s my rating over the past 12 months.

Dillan Taylor's chess rating

Notice the dips and plateaus. Those periods were not fun. They were discouraging.

But like the stock market, if we zoom out and look at the big picture, the long term, we can see that I’ve only gotten better as I’ve stuck with it.

Chess, like many things, goes like this:

Step 1: “I’m getting pretty good! I feel like I could beat anyone….”
Step 2: “I’m not sure I even know the rules. I suck. Maybe I should switch to checkers.”

And the cycle repeats. At every level.

The point is, when I’m not feeling on top of the world, I play with less confidence. But I play nonetheless. I may get destroyed and that always hurts…but if I just keep at it, the graph will continue to go up.

And finally, relationships.

A turning point in the health of my friendships came when I decided to be completely candid with my thoughts and feelings. In other words, I became good at having difficult conversations.

Speaking my mind. Setting boundaries. Being vulnerable.

I’m lucky to have a phenomenal group of friends, and it has been through my willingness to be open that these relationships have grown even stronger.

TL; DR

It can be quite scary, but if we are willing to risk foolishness, we’ll get good at just about anything.

Fuck Off Day

A woman waving goodbye to her toddler son as he runs out with his backpack

Last night, I went over to my best friend’s house for dinner.

He and his partner were telling me about the move to intentionally add alone time into their relationship. Now every Tuesday around 4pm, they take turns leaving to go do something and give the other person the house to themselves. Tongue in cheek, they’ve been calling it “Fuck Off Day.”

It’s funny because a person could hear this and think, Oh, you’re trying to spend more time separated...sounds unhealthy.

When in fact, it’s one of the healthiest things I’ve ever heard a couple do.

They have an incredible relationship. And this practice is intended to maintain that strength.

I’m not an expert in love…but this truth can be applied to everything else in our lives:

Space from people, environments, and activities (especially ones we love) is essential.

Let’s go through some examples in order.

People:

We all need alone time. We need to know what it’s like to simply sit with our thoughts and emotions.

I used to think I was just a wildly extroverted guy. Then I realized I was just surrounding myself with people so I never had to confront my anxieties. When we’re alone, there’s nowhere to hide.

Aside from that, time away from those we care about creates room for us to miss them.

It’s in someone’s absence that we truly notice what they bring to our lives. Until they return. We can’t fully appreciate something until it’s taken away from us.

Since I moved out of my mom’s house, we’ve grown ten times closer. She’s not my roommate anymore. She’s my amazing mother.

When I visit friends from other cities, I cherish every hour of conversation I have with them. I know that when the weekend is over, we’ll go back to our lives hundreds of miles apart.

In breakups, we can logically know that it’s for the best…yet we still feel the agonizing pangs of loss not having this person to laugh or be romantic with.

All this to say: We need space from people to solidify how much we love and appreciate them.

Environments:

Why do we take vacations?

For the Gram, yes. But also to just fucking get away.

Away from our routines, our neighborhoods, our kitchens.

There’s something liberating about being in a totally new place. We’re often not even sure what the place is going to look like or what it has to offer. We just know we’d like a change of scenery.

I take one trip every month. Sometimes to another state. Sometimes out of the country. Why?

Because I work on weekends. Several of my clients work nine-to-fives and I don’t do calls on weeknights. That means I often work seven days a week. And that means I can only take so much before I have to get the fuck out of here.

I love this office but after a certain amount of time, any room can feel like a prison cell.

So I go somewhere. I visit a buddy. I see my family. I go hiking. Sometimes I just take the weekend off and host a friend here at my apartment.

It’s actually nice to not do my morning routine for a few days. But then, after taking that space, I quickly crave my old environment. I miss my desk, my roommate, my bed.

Then when I return home, I feel refreshed. I get back into my habits and rituals feeling reignited.

All because I took some time away from them.

Activities:

I love chess.

But there’s a reason I don’t play it for eight hours a day. It’s the same reason I don’t do anything for that long.

I’d get sick of it.

I had a session yesterday with a super ambitious salesman. He loves his job and is always eager to do well and help his team.

But the job is so time-consuming that he feels he doesn’t have any time for himself. So we created some boundaries for him to set and build that time (i.e. space).

I asked him: “What would you be able to do with the free time you create?”

He responded immediately: “I’d do my job better.

He wants space from his job so he can be more present and capable when he’s in it. That’s how I feel about chess, coaching, and everything else. That’s why we need rest days from the gym—to allow our muscles to rebuild themselves and recover.

TL; DR:

Intentional time away from the people and things we love strengthens our relationships with them.

The sexiest thing in the world

A hanging pot of pink flowers

I’ve been in relationships for a number of different reasons.

• I was attracted to her
• I cherished the flow of conversation
• She made me laugh

But there’s one thing I’ve found to be the most powerful catalyst in a sustainable relationship…

Curiosity.

A genuine fascination with how another person thinks, feels, and experiences the world.

I’m not just talking about romantic partnerships here. Friends. Family. Colleagues…One of the most basic human desires is the desire to be heard and seen. We want to feel important and interesting.

If we don’t, there’s no fire. There’s no passion. There’s no connection.

In building a relationship with another human, we can ask two things:

  1. Am I curious about this person?
  2. Do I feel like they are curious about me?

The value of heartache

A woman holding a neon heart against her chest

Life can fucking hurt.

Between people dying, hearts breaking, and a million other things which make us physically ill…we’re guaranteed to feel powerful negative emotions at times.

Yesterday, my coach told me, “There’s no system for grief.”

In other words, sometimes we’re sad and we don’t fully know why and there’s no formula to make it go away right now.

We have to just sit in it. And learn from it.

As readers of this blog know, I try to find the lesson in everything I do. After a painful experience, I allow myself to feel my feelings, and then I’ll ask things like:

What was the value in this?
What have I learned?
How can I use this as an opportunity to grow?

It doesn’t make shitty circumstances and more pleasant. But it is a long-term strategy for drastically improving as a person.

I handle myself with grace and respect when it comes to breakups, tough conversations with friends, and uncomfortable business dealings. I don’t take things personally and I never lose my temper.

How have I gotten so good at these things?

Because I was shit at them in the past.

I’ve tried to shame women into being with me (oh, to be 20). I’ve treated friends like garbage until they did what I wanted (sorry, Phil). And I’ve been stunned and speechless on the phone when a potential client told me “No thanks” (this year lol).

It’s through moments like these—memories that make us cringe—where the real growth happens. If someone doesn’t have any cringy memories, I assume they’re the same person they were in high school.

I treat women with respect because I know from experience how awful it is when I don’t. I’m open and honest with my friends because I’ve seen how sustainable and fulfilling that is over being passive-aggressive. And I’m detached from outcomes in my business because I’ve felt the agony of obsessing over a result and it not going my way.

It sounds David Goggins-y, but we learn from pain. Only if we let ourselves, though. Only if we seek the lessons.

We all want wisdom. But we don’t want the thing that brings us wisdom.

Feel…but learn as you do so.

Why I never lie

A child with painted hands

Until I was about 23 years old, I’m pretty sure I was a compulsive liar.

I lied about: my sex life, my skills, and stories which may or may not have happened to me. The goal was to create a Dillan who was way cooler, more impressive, and more capable than the Dillan I was.

The effect?

Not only was I keeping reality away from my friends and family. I was also muddying my own lens of the world around me. I began believing the lies I was telling.

I also trusted people less. If I wasn’t being honest, how easy was it for others to be dishonest too?

Studies show that people who are carrying a gun suspect way more people to also be carrying a gun. So too with lying.

One of the heaviest burdens a liar carries is having to remember all that they said.

In my junior year of college, I got caught in a lie. I told one person something that contradicted what I told another person. The memory still makes me cringe. I felt like a child who got caught lying about stealing a cookie.

After that moment of disgust, I set out to intentionally break my habit of lying. It was fucking hard and took me about three years.

Even to an honest person, setting out to not tell a single lie is quite the challenge. It’s almost ingrained in our culture to spare the feelings of others and tell white lies to be polite.

I just finished a book—Lying by Sam Harris—which debunks every reasonable-sounding argument for telling a lie.

My two biggest takeaways are:

1) Lying erodes trust in the people we care about (both consciously and unconsciously).

I have a friend who’s one of the kindest and most compassionate people I’ve ever known. But one time, we were hanging out and someone texted her seeing what she was up to.

Not wanting this person to know she was choosing other friends over her, my friend lied. She said she was just chilling for the night to get ready for an early morning.

We laughed it off, but I remember thinking, Has she ever done this to me?

Now I’ve seen that she’s willing to lie to a friend. Whether we like it or not, I’ll never trust her 100% when I invite her to something and she says she can’t go.

2) Fake praise or encouragement is not kind; it’s disrespectful. It wastes a person’s time and morphs their grip on reality.

False encouragement is a kind of theft: It steals time, energy, and motivation that a person could put toward some other purpose.

Sam Harris, Lying

This has to do with short-term vs. long-term thinking.

If we give open and honest feedback (with grace and permission, of course), in the short term we may risk hurting a person’s feelings.

But in the long term, we accomplish a number of things. We…

• become a trusted confidante
• genuinely help this person improve
• cultivate a deeper relationship with this person

Giving and handling feedback well is its own separate conversation. But when I create something, I don’t want people to tell me why it’s awesome. That may feel good for four seconds, but what I really want is to build something valuable.

As uncomfortable as it can be, I can only accomplish that by having people I trust point out my blind spots and mistakes.

An essay is always improved after a round of edits.

On the other hand, if I’ve only been told that my thing is perfect…when I share it with the world and no one likes it, I’m left confused and heartbroken.

We can avoid that by simply being honest.

Conclusion

Where do you tell lies—even white lies?

How difficult would it be to not tell a single lie for the next seven days? I encourage you to try it. It’s more liberating than you may think.