29 life tips on my 29th birthday

No, I don’t feel older. But I do feel wiser.

Here are some things I’ve learned in these 29 years. Hope you find one of them valuable.

1) Learn the names of employees at restaurants you frequent.

Find great servers, build relationships with them, and ask for them every time. It makes them feel validated to have a regular who prefers them, you can tip them well, and you know you’ll always be taken care of.

Ask them about their life. No one does that. 99% of customers don’t even know their name or they forget it after a night.

I went to the Chipotle near my apartment one to three times per week for two years. There was this quiet dude who was always working. His name is Mike and he was taking on extra shifts to take care of his mother who was sick.

Every time I went in there, I said, “What’s up Mike! How are you man? How’s your mom doing?” He’d give me updates and then pile two enormous piles of steak onto my burrito bowl, free of charge.

All it takes is spending five seconds to treat someone like a human being for them to want to go out of their way for you.

2) Ask 3 questions before stating your opinion.

When someone says something you disagree with, hold off on your counterarguments and rebuttals. It’s more important to ensure you know exactly where they’re coming from and why they believe what they believe.

Steelman their argument. Articulate their opinion so that they’re pleased with your summary.

This has three useful effects:

  1. It makes them less combative and defensive.
  2. You avoid arguing with things they don’t believe.
  3. It slows things down and gives you time to decide whether or not you even want to pursue a disagreement.

A simple rule to build this habit is to force yourself to ask three clarifying questions before giving your thoughts. So you believe x because y?

3) In a group of friends, ask: “What impresses you most about every other person?”

When you’re hanging out with two to five people, this is a fun and wholesome game to play. Everyone takes a turn going from person to person and saying what they most admire about them.

No matter how close you are to these people, you’re bound to hear and say things you’ve never heard or said before.

Everyone feels more connected and heartwarming conversation ensues.

4) When you feel the urge to send an emotional text, wait 24 hours.

No one’s ever been told to “stay awake on it.” Get a night’s sleep and see if you want to send that same text tomorrow. You probably won’t.

I’ve saved myself from sending countless passive-aggressive or annoyed one-liners and paragraphs. These kinds of messages never lead to fruitful solutions. They never make the recipient go, “Oh you’re frustrated? I’m so sorry. Here’s why I was wrong and I’ll never do it again.”

All context is lost over text. If it’s that important and the feelings are still there the next day, call the person.

Don’t hit “send” when you’re in a state. That state will pass, but the message can’t be unsent.

5) Have your phone out of sight when watching movies or TV.

Two screens are too many. Just sit and enjoy the story.

Especially if you’re watching with someone else. It’s meant to be a shared experience.

Too much dopamine-searching weakens attention span and makes us less present. Do what you’re doing. If you’re watching a film, watch the damn film.

6) Know what success actually is.

What we think it is: Someone who is really good at something, doing things we could never figure out.

What it actually is: Someone who worked on something for years and years until we all see their polished results.

Just keep at your thing and eventually you’ll be amazing at it.

7) Buy expensive noise-canceling headphones.

Use them for work, to listen to music or podcasts while you cook, or just to quiet the world around you.

It’s one of the best purchases you can make. I suggest Bose.

8) If a book is bringing you zero value or entertainment, just put it down.

I used to have this rule that I had to finish every book I started. Slogging through boring pages was torture. All that rule did was take weeks (sometimes months) away from me reading something I might’ve actually enjoyed.

If it felt like a chore or a battle to get through the last three chapters, stop reading it. There are too many phenomenal books out there for you to be wasting your time on one that sucks to you.

You might hate a book but love it five years from now. But do your present self a favor and spend time diving into writing that fills you up.

9) Status is fun, but it’s a mirage.

Money. Clout. Reputation.

These things aren’t meaningless. I love making great money. I love building relationships with people who have wealth and power.

But these things will never complete us.

How many times do we have to hear rich and famous celebrities tell us being rich and famous does nothing for our happiness and fulfillment? Status can be fun but it will never be the final piece of the puzzle.

If your basic needs are met, if you’re healthy, and if you have loving relationships…and you’re still waiting on more status or success to be fulfilled, you will remain empty.

There’s nothing wrong with wanting to make more money or wanting a more interesting life. But real fulfillment comes from spending quality time with great friends and family, learning hard and rewarding skills, and being a grateful and healthy human being.

10) If you hate cooking, pick an easy and healthy meal to make every day.

It doesn’t have to be every day. Most days will do.

I love cooking…for other people. But when I’m home alone, I feel zero motivation to experiment or spend more than 20 minutes preparing a meal for myself. I just don’t care.

So, rather than wishing for more invisible willpower, I just choose a simple and nutritious meal I could make basically every day.

For a while, it was scrambled eggs with black beans and salsa. Protein. Carbs. Tasty.

Sometimes I’d use peri sauce instead of salsa. Sometimes I’d cook sausage instead of beans. Make it flexible and repeatable. This removes the headache of figuring out what to eat for at least one meal per day.

11) Frequently ask, “If I knew I’d die 10 years from now, how would I be living my life differently?”

Then do those things.

12) Set up regular hangouts centered around activities.

An easy way to consistently spend quality time with people and get out of the house.

Love knitting, board games, or walking? Find a friend or a group of people who enjoy it too. Then pick a day to regularly meet with them and do that thing.

Some examples from my life:

Thursday morning swims with a bestie.
Tuesday night chess club.
Sunday rock climbing with the bros.
Biweekly phone calls with my friend living in Rwanda.

We expect our relationships to take care of themselves. Proactively scheduling things is a lovely and efficient way to ensure we actually tend to them.

13) Run errands without your phone.

When was the last time you left the house without your phone?

Next time you have stuff to do out and about, leave the black rectangle at home. You won’t be on-call. You’ll have no choice but to be present and engaged with your surroundings. You’re more likely to spark conversation with strangers.

Feel the peace that comes from spending an hour or two completely unreachable and offline. Nothing to compulsively check. Nothing to experience other than the world around you.

14) Write letters, not cards, as gifts.

Giving a $5 card with a sentence on it is such a common tradition and it has always seemed odd to me.

People do it for “the thought.” But there are so many other, more personal and meaningful ways, to express that sentiment. Namely, taking 5-10 minutes to write a letter.

Outline plainly what this person means to you, what you love and appreciate about them, and how they’ve helped you and made your life better. Then read it to them.

It doesn’t matter if this is on printer paper or on a notecard. It’ll mean so much more to them than a funny card with your signature on it. They’ll remember how it made them feel for years.

15) No one is thinking about you as much as you are.

From your perspective, you’re the main character in the movie. But for everyone else, you’re a supporting character at best and a background extra to most.

Stop obsessing over everything you do and say. Not a single person is thinking about you even 1/10th as much as you are. They’re just worried about being the main characters in their movies.

Go to the gym. Share your opinions. Apologize and improve when you make mistakes and get feedback.

Because no one cares as much as you do.

16) Take month-long breaks from booze and sugar.

Pick a month. I typically do January and October.

You’ll get excellent sleep, eat better, and have more energy and willpower.

Can’t do this? You might have a problem.

It’s crucial to prove to yourself you don’t need something like alcohol to have fun, be fun, or live an interesting life.

17) Keep a list of your friends’ goals.

What they’re working on. What they want most. Their latest wins.

Check in on them and see how these things are going. It takes minimal time on your end and they’ll feel seen and supported.

18) When you’re feeling stuck, answer these 3 questions:

  1. What do you want most right now?
  2. What’s in the way of that?
  3. What’s step 1?

19) No one has ever been rejected into a coma or black hole.

The fear of being rejected is 100x worse than actually being rejected.

Ask that person out. Give that sales pitch. Ask for help.

The absolute worst thing that can happen is they say no. Now you’ve gone from not having that thing to not having that thing. You’ve lost nothing.

20) They’re not texting you back because…

They don’t want to.

People who are excited to converse and engage with us will prove it by continuing to converse and engage with us.

Short texts. No response. Never calling back.

These don’t necessarily mean this person hates you. You’re just not a priority to them right now. That’s okay. It doesn’t make them bad people. It just means you shouldn’t keep exhausting yourself to keep the conversation alive.

The number of times in high school and college I kept texting a girl who clearly wasn’t interested in me…I thought, Maybe if I just send the right text, if I just send the perfect joke…she’ll want to get with me.

Never happened. People who want to talk to you will talk to you. If they put in zero effort, stop being needy and move on.

21) The 10/80/10 rule.

10% of people will dislike you no matter what.

10% of people will love you no matter what.

The other 80% will decide based on how skilled you are, how fun you are, and how delightful you are to talk to.

22) Be an ESPN sportscaster.

Bring up the accomplishments and highlights of your friends and partners. Hype them up. Show them off. Congratulate them in front of other people and on your own.

“Look at this! Let’s see that again! Isn’t that incredible?”

They may seem embarrassed but underneath that, they’ll feel super supported and respected.

23) Never set a secret expectation for someone.

If you want something from someone, tell them. No matter how overt or passive-aggressive you are, they can’t read your mind.

Quiet expectations are a one-way road to resentment, disappointment, and unspoken tension.

Be clear and direct about what you want.

24) Be on time.

It’s the easiest way to show respect for others and yourself. It also relieves the constant burden of feeling rushed and frantic.

Being the person who’s always late to things is a childish reputation to have.

25) Download ‘News Feed Eradicator.’

Hate scrolling on Facebook but don’t want to delete it?

Download this browser extension. It hides your Facebook news feed. No more being hypnotized by the algorithm.

26) Keep a list of your biggest insights.

Realizations, discoveries, mindset shifts. What have you changed your mind about lately?

It’s like finding old photos of who you were and what you were working on in the past.

27) Tell your friends “I love you.”

Especially guys. You’ll wish you said it more when you die.

28) Under 50 and don’t like what you look like shirtless? Prioritize exercise and diet.

It’ll only get harder. Now’s the time.

Hire a trainer. Get someone to help you figure out what to eat.

Give yourself more energy, confidence, and brain power by taking care of your body. If you were responsible for taking care of someone else’s body, would you fill it with sugar, simple carbs, and processed foods? Would you make sure that that body was never active?

Be kind to your future self and take care of your present self.

29) The quickest way to earn someone’s respect is to be able to take a joke.

There’s a difference between bullying and poking fun.

If someone is messing around with you, laugh. Join in on the joke.

This shows people you don’t take yourself so seriously and that you’re secure with yourself. I struggled to take jokes when I was younger because I was wildly insecure. Every jab felt like a missile.

Now, I make fun of myself more than anyone else. Life’s short. Be less serious and more silly. You’re no God.

Final thoughts:

Hope you enjoyed some of these. Hope you disagreed with some of them. Email me and let me know what you think.

See you next year for my 30th!

Moving out and moving on

First morning in my Annapolis apartment—October 31, 2020.

This is the last time I’ll sit in this chair, at this desk, typing on this keyboard.

In a few hours, my friend will be here to help me pack everything I own into a U-Haul and then a tiny storage unit. I’ll squat at his house for the next week and a half. Then I’ll get on a plane and fly to Buenos Aires.

Packing up the office.

I got sad and nostalgic for a few seconds yesterday when I was taking everything down. But it quickly turned to excitement for the next chapter.

A new question has come to mind when it comes to change: “Did I think I would die with this thing?”

When my roomy told me she was moving out, I couldn’t stay glum for long because I knew I wasn’t going to die with her as my roommate. Just two 57-year-olds drinking Bud Light seltzers and playing Uno.

I sold my dresser and bookshelf yesterday—furniture I had as a child. Did I think I was going to die with those things? No.

That means between now and the day I die, I got rid of them at some point. This is that point.

I built my career in this office. I learned how to make money, create content, and play chess in this office. Now it’s time for me to get to whatever the next level is in another office.

It’s funny. Humans are so good at turning empty boxes into homes. But I was really just borrowing this room. By next week, it’ll be filled with someone else’s life and they’ll have no idea who I was or what I did at this desk.

Anyway, it’s time to move on. My priorities for the next month are simple:

  1. transition smoothly to Argentina
  2. finish the first draft of Do The Thing!
  3. post consistently on the podcast

Onward and upward!

My 2023 Q1 goals

Happy New Year!

Like most people, I feel a surge of motivation and ambition when the dates change. And like most people, that intensity tends to fade come February.

So this year, I thought I’d try something new: quarterly goals.

What if there was a new year…every three months? Is it possible to keep things fresh and exciting more frequently? How can I balance repeatable systems with novelty? I don’t know if this is the answer but it’s an experiment I’d like to try.

It’s funny. Since starting my coaching practice I’ve made it a point to not be like any regular company. I got into entrepreneurship because I didn’t want a boss or entity telling me what to do or how to do it. I’ve rebelled against the traditional ways of doing things in business.

But as I become more experienced in my career, I’m realizing I’ve been throwing the baby out with the bathwater.

Not that I assault babies (for I do not do that anymore). But maybe if there are practices that companies do, it’s not because they’re all mindless drones who can’t think for themselves. Maybe common procedures are common because they work.

Anyway, let’s find out. I’ve broken down my quarterly goals into four categories: coaching, content, life/health, and people.

Between January 1st and March 31st, here are my major goals in 2023…

Coaching:

  • reach out to at least five people every Monday to connect
  • stay curious and ask follow-up questions
  • get to 40 Google Reviews
  • propose $20k/year

Content:

  • new morning writing schedule—Do The Thing! on MoWeFr, this blog on TuTh
  • finish the first draft of my book
  • get to 20 YouTuber’s Guide to the Galaxy episodes
  • get to 45 total YouTube videos uploaded

Life/Health:

  • stretch every morning
  • teeth cleaned (dentist) and ears cleaned (ENT)
  • check testosterone levels
  • move to Buenos Aires
  • enroll in Spanish conversation course

People:

  • work on best man speech with my comedian friend
  • ask out 25 women (in person, face-to-face)
  • create a CRM for my friends with their goals, projects, and wins

And finally, an affirmation…

“On April 1st, 2023, I will be in Argentina, drinking wine with new friends, with 500 YouTube subscribers.”

Have Q1 goals of your own? Email them to me.

Let’s do this!

I’m moving (not to NYC)

A sign in the middle of the desert pointing to different South American cities

My roommate just announced she’ll be moving out in March. This sparked three emotions.

  1. I’m super excited and proud of her for leveling up her life—starting a bigger and better job and moving in with her boyfriend.
  2. I’m sad to end the best living situation I’ve ever experienced.
  3. I can’t ignore the anxiety that comes from figuring out where to pack up and go next.

As you might’ve guessed from the title, I’ll address #3 in this post.

My immediate thoughts were on staying in this apartment, finding a replacement roommate, or getting a one-bedroom nearby. But hidden underneath was the reminder that I was supposed to move to New York City this fall.

Not only do I feel like I’ve given all my readers blue balls by not actually going. I also just have an itch for adventure that hasn’t been scratched. The last time I went somewhere totally new and had to rebuild myself, my community, and my skills, was when I studied in Germany at 20 years old.

Oktoberfest, 2014.

That was eight years ago. Now, I’m (hopefully) much wiser, more competent, and more secure. If the immature boy that was Dill can live in another country, make life-long friends, and learn a foreign language…what’s stopping me now?

The obvious answer is nothing. Well, nothing but fear and excuses.

Cut to the chase

After the teaser email a few days ago, I got bombarded with texts asking where the hell I was off to. I must say making people wait for it brought me sadistic pleasure.

I’m moving to Buenos Aires, Argentina. 🇦🇷

Just for a few months. One of my besties has really helped me along with all of this.

“Do I go here for a year,” I asked. “Or do I stay put for another 12 months until I figure something else out?”

“Dill,” she replied. “You’re thinking in terms of one-year leases. Why don’t you lower the bar and just go somewhere for one to three months?”

Genius.

She lived in Rwanda for years and met her husband there. Needless to say, this is someone I’m glad to have in my corner when it comes to living in another country.

When I confirmed my interest she started blasting me with articles and how-tos. I read every single one. Best South American cities for foreigners. Cheap Spanish classes online. How to secure health insurance and visas abroad.

What seemed like a nice little fantasy quickly became a set of clear-cut action steps. I renewed my passport and bought my plane ticket.

Why Buenos Aires?

I’ve been wanting to travel to Argentina’s capital city for years. It’s gorgeous, clean, and safe (especially relative to other South American cities).

But on top of that, it’s reliably rated as the #1 spot in the continent for digital nomads: people who can work anywhere in the world so long as they have a laptop and internet connection. As an online coach, a podcaster, and a writer…this is perfect for me.

For anyone interested, here’s a breakdown of the city from NomadList.

As with any place, there are tradeoffs. Let’s go through the cons first.

Cons:

1) It’s a 10-12-hour travel day away from my friends and family.

You might be asking, “But Dillan, didn’t you say a few months ago your #1 value was close proximity to the people you love?”

Nothing gets by you, dear reader.

Yes, quality time with my peoples is something I cherish. That’s what the two-month excursion is for. 60 days will fly by I’m guessing.

Two friends have already shared ideas of coming down to visit. My birthday is right before my departure and my community’s annual coaching retreat is just after my return. There will be no shortage of friend time in these coming months.

Plus, Buenos Aires has a thriving and organized entrepreneurial community. Meetups, events, coworking spaces…It will be hard for me not to befriend like-minded individuals who also speak English.

I plan on taking a weekly Spanish conversation course. But with only two months, I’ll be leaning into my English-speaking compadres.

2) Uh, I think that’s it.

Some sites claim the internet is slow in South America. But others have said it’s no problem. So we’ll see.

A market street in Argentina

Pros:

Okay, the fun part.

1) As stated above, BA is a clean, safe, and beautiful city. It has beaches, high-quality nightlife and restaurants, and quaint and quiet suburbs.

Aside from the dirt-cheap public transportation, the city is incredibly walkable. I plan on living in the neighborhood of Palermo Soho, which at most would be a 10-minute walk to my gym and coworking space.

BA is said to feel more European than South American. It’s super organized and stylish. I’m certainly one of those things.

2) Same timezone.

Simple as that. I wouldn’t need to change anything about my schedule. Sessions, calls, sleep cycle…None of it shall be touched.

3) It’s ridiculously cheap.

The average cost of living (including rent, utilities, food, and fun)…is around $1000/month.

What.

I pay more than that in rent alone.

A nice bottle of wine in BA is $3. A nice dinner? $9. The luxury one-bedroom apartment I’m looking at booking is $700 per month. It’s nicer than my current two-bedroom and costs $400 less.

The big reason I didn’t move to NYC was the disgusting cost of living. But now I feel like I’m being financially irresponsible for not moving to Argentina.

Conclusion

There are hundreds of reasons I could rattle off as to why I’m excited to sell all my belongings and fly to South America. The feelings of accomplishment, the new relationships, the skills I’ll develop.

But underneath it all, I’m just pumped to inject some novelty into my life.

I’ve grown into an entirely different human being these past five years. From attempting suicide, to starting to build my life, to working at a restaurant, to starting a blog, podcasts, and YouTube channels, to working in sales, to quitting that sales job to start my own business, to playing chess and doing jiujitsu, to making my business profitable and sustainable, to writing a book.

It’s been a wild ride. I’ve tried a plethora of new things and have been lucky that much of it has stuck.

But I’m still craving something to drastically take me out of my comfort zone. I thought it was New York. It wasn’t (not yet, at least).

So for now, I’ll be enjoying these holidays and the last few months with the best roommate I’ll ever have. I’ll sell or donate all my furniture, books, and clothes. I’ll continue to live frugally to save and invest my money.

And of course, I’ll keep writing about all of it.

Stay tuned. ✌️

Add accountability to your life

A coach looking at his clipboard and holding his team accountable

Grindset: a funny term for one’s ability to work their ass off every day without anyone telling them to do so.

Some people are able to build on their own, get lost in deep work, and grind away using only their passion and discipline. I am not one of these people.

Let me explain.

When I interviewed Courtland Allen, founder of Indie Hackers, he mentioned the accountability problem.

“It’s crazy how most people don’t do the things they know they should,” he said. “Exercise, spend time with friends, eat well, create things…We know this stuff makes our lives way better but we don’t do them. But we’ll easily show up on time to a nine-to-five job we don’t really like every single day. That’s crazy to me.”

Why is that so much easier? Because we have people holding us accountable to do so.

If we show up late to a job, we experience some sort of damage. It’s embarrassing. We could get written up. Our bosses and coworkers are watching.

But when it comes to writing a blog, recording a podcast, or building a solo business…it’s just you. There’s no one over your shoulder telling you what to do and when to do it. If you take a day off to watch TV, no one will reprimand you.

Earlier this week, I wrote about how my creative projects burnt me out. Aside from reorganizing and reigniting myself, I did something else to help with the problem mentioned above.

I got an accountability partner. Actually, I got two.

They’re both fellow life coaches and dear friends. With one, we log our working hours using Toggl and send the other person our weekly summary every Monday. With the other, I got a bit creative.

I made a shared document between the two of us with a weekly list of my creative goals:

  • 2-3 YouTube clips
  • 2 TikToks
  • 2 blogs
  • 1 podcast episode every other Thursday
  • a reflection of how it went

As I work on these goals, he can see which ones I get done. If they’re not all completed by the following Monday, he gets to grill me. A la accountability.

I can already feel the power of having to report to someone. I love the freedom of not having a boss but accountability keeps me at this desk until the job is done.

If you’re having trouble exercising, for example. If you hired a personal trainer and bet $3000 you’d never be late to a session, it would become super easy all of a sudden.

We often don’t do things because we don’t feel incentivized to do things. We say things like, “I can never remember people’s names,” or, “I can’t wake up early.” But if I told you I’d give you $1m to remember the next 20 names you meet and wake up at 5 am every day for the next month…you’d have no problem.

So what do you want to do more of or less of? Who can you ask to help hold you accountable?

Reply to this email and let me know.

Don’t let the result be the goal

A bullseye dartboard with a dart near the middle

My favorite thing about interviewing creators is hearing the same philosophies or mindsets for different crafts.

I’ve sat down with YouTubers, founders, comedians, doctors, athletes, musicians, authors, and more. Here’s something they’ve all said.

“You have to enjoy what you’re doing. It’s okay to set goals and to want to make money. But if status, wealth, and success are your only driving factors, you won’t make it.”

Benjy Himmelfarb, a DC standup, said a comic’s first two years are just about getting comfortable on stage. As I’ve been interviewing YouTubers for my podcast, they’ve said the exact same thing.

When we start a new venture—a business, a new job, creating content—the beginning is mostly about figuring out how to get good and how to find our voice and styles. Nine times out of ten, the people who are doing the best are just the ones who’ve been doing the thing consistently and committedly.

Occasionally we see young phenoms who start crushing it immediately. But those are rare. We just think they’re everywhere because they get a ton of exposure.

Eric Rosen is one of the biggest names in the chess world and has 575k subscribers on YouTube. It took him a year of consistently streaming and posting to start to experience success.

Courtland Allen sold Indie Hackers—a community for online business owners—to Stripe for millions of dollars. But this was after 10 years of him starting companies that failed, coding every day, and being uncomfortable in Silicon Valley.

Courtney Maginnis has spent over a decade doing comedy in New York City. She’s worked with College Humor and Comedy Central and still works a nine to five to support herself.

Point is, building true skill and leverage takes time.

If the result is the goal, we’re just suffering while looking at the clock. As cliche as it sounds, we have to enjoy the process.

Right now, my YouTube channel isn’t that great. The first few interviews I used were for my book so they’re just grainy Zoom calls. I don’t know how to make good thumbnails. I have to refine my interviewing and editing skills.

But I’m loving the conversations I’m having and working on the show is the most fun I’ve had of any of my creations. So if I stick with it, I have no doubt it’ll be great. But what metrics are keeping me going?

The idea of 100k subscribers sounds amazing. But that will probably take years. That can’t be my compass.

So my one and only goal right now is to make it to 100 episodes. Once I get there, we’ll see how I’m feeling.

To end, I’m not suggesting we don’t set financial goals or look at metrics. I just don’t think doing something unfulfilling in the hopes for success is sustainable.

We don’t necessarily have to do what we love. But we should at least like what we do.

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

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

Here’s the timeline.

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

Clybourne Park, 2016.

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

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

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

So I’d start the thing.

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

It was always exhilarating. For a week or two.

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

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

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

Our Blink 182 cover band setting up, 2011.

So why does this happen?

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

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

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

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

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

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

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

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

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

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

The first podcast I ever recorded, 2018.

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

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

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

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.

I wanted to hate NYC—I don’t

The street of Williamsburg, Brooklyn

Sunday was the first night of my two-week trial run living in Brooklyn. It was heavenly.

I get anxious every time I see the Manhattan skyline. Coming into New York City always feels like I’m entering a foreign warzone. My survival instincts kick in and I feel awake and on guard.

Last month, I talked with a friend who’s planning to move out of state and away from where she grew up—just like me. She’s continued to push the date back, so I lovingly called her out.

“It sounds like you’re creating reasons to not do it,” I said. Luckily for me, this landed well.

This is an unfortunate human tendency: constantly building conditions that must be met before doing the scary things we know will make us grow. We think: once I…

  • have more money
  • feel more confident
  • get a new job

Then I’ll be ready. But conditions will never be perfect. Any meaningful life decision will come with 1000 logical-sounding reasons for not doing it.

And yet, this is what my brain has been going through. As much as I rebel against this, it turns out I’m human too. I’ve been contemplating all the reasons I shouldn’t move to New York. (This video didn’t help.)

  1. I’d be leaving my well-established community—my mom, sister, and several best friends
  2. It’s ridiculously expensive
  3. Eventhough I’m a social extrovert, it’s scary to have to make new friends

Aside from creating as much income as I sustainably can in the coming months, the remedy for these fears seems obvious. I have to put myself out there.

It sounds simple (it is), but that tends to be the solution to most things.

I have a phobia of heights, so I put myself out there and tried top roping (rock climbing) with my friends. Last year, I had to build a coaching business from scratch, so I put myself out there and reached out to as many people as I could and offered to coach them. New York intimidates me, so I’m putting myself out there and am going to meetups and events by myself.

Tonight, I’m going to a chess gathering at a brewery. It’s called Chess & a Beer, two of my favorite things. For the last two nights, I’ve gone to dinner by myself. I also joined the local climbing gym.

The rooftop of Vital, the climbing gym in Williamsburg Brooklyn

Anyway, it’s hard not to jump back and forth between all the pros and cons of living here.

I walked through the local park and experienced more in 10 minutes than I do in one night in Annapolis. I heard at least six different languages spoken, saw a men’s league soccer game, got a free margarita from a cute bartender, ate excellent Mexican food, toured a gorgeous rooftop gym, and walked alongside the East River overlooking the lit up city of Manhattan.

This was all within a 20-minute walk of one another.

It’s been one full day. It feels like it’s been an entire week.

The journey continues.

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.

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)

Ideas vs. execution

Dillan Taylor's business ideas

I have a running list of business ideas in my Notes app. I’ve done nothing with 99% of them.

People can be super protective of their ideas.

But ideas are cheap. They mean nothing. They’re just words on a screen.

I don’t even know what some of these ideas mean. “1 hour blog or copy editor”??

Anyone can write a sentence in their phone. Execution is an entirely different thing.

Coming up with ideas is safe. It’s fun to fantasize about these things coming to life.

What’s scary is trying to make them happen.

I loved the idea of building a coaching business. I didn’t love putting myself out there and trying to get people on a call with me (at first).

When people are coming up with business or content ideas, my advice is always the same:

Just help one person. If you can get one person to give you their time, money, or attention, then you can get two.

And so on.

But people spend all their time in the blueprint and strategy stage. That’s a brilliant way to get nothing done, but to feel as though a lot is getting accomplished.

Getting rid of all my stuff

I want to be fully prepared for my move to NYC.

Part of that process means taking as few items as possible with me.

My bed. Some clothes. My electronics.

For everything else, I’m starting over. New desk. New furniture. New desk chair. Maybe a book or two. Everything else on my Kindle.

As I minimize my possessions, I can already feel my mental energy charging. Life just feels easier when we don’t own that much stuff.

I made a list of things I’d like to buy when I get to Brooklyn. I’m excited.

Quantity over quality

Here’s an excerpt from Atomic Habits by James Clear:

On the first day of class, Jerry Uelsmann, a professor at the University of Florida, divided his film photography students into two groups.

Everyone on the left side of the classroom, he explained, would be in the “quantity” group. They would be graded solely on the amount of work they produced. On the final day of class, he would tally the number of photos submitted by each student. One hundred photos would rate an A, ninety photos a B, eighty photos a C, and so on.

Meanwhile, everyone on the right side of the room would be in the “quality” group. They would be graded only on the excellence of their work. They would only need to produce one photo during the semester, but to get an A, it had to be a nearly perfect image.

At the end of the term, he was surprised to find that all the best photos were produced by the quantity group. During the semester, these students were busy taking photos, experimenting with composition and lighting, testing out various methods in the darkroom, and learning from their mistakes. In the process of creating hundreds of photos, they honed their skills. Meanwhile, the quality group sat around speculating about perfection. In the end, they had little to show for their efforts other than unverified theories and one mediocre photo.

TL;DR: Experience and action-taking beat pondering and planning any day.

Done is better than perfect

Yesterday, my friend and I recorded the first episode of our podcast.

It was…good. Not great. But definitely good enough.

In January, we recorded a few conversations with my phone as practice. Those were fun, light, and valuable. But that was in person.

I noticed the difference immediately yesterday. Over Zoom, the timing is way more awkward when it comes to interrupting someone. The comedy didn’t flow as well.

Plus our mics seemed to have different volumes. That all combined to make an overly-professional first half. Then we clearly got comfortable halfway through and began vibing off one another.

The goal was accomplished: to have fun with my friend.

And at the end of the day, the most important thing was done: We actually did it. It exists.

We could’ve spent weeks prepping and planning the perfect episode. But that sounds like an amazing way to not do the thing we actually want to do.

Perfect is the enemy of done. Connor’s partner gave us immediate feedback. So episode 2 is now guaranteed to be better. We have a place to work from.

When we finish five episodes, we’ll release them all at once.

Hope you guys don’t hate them.

COVID goals

A young boy sitting alone on a bench under a tree

Since I tested positive yesterday (again), I had to cancel my fun stuffs for the week.

Several dinners. My third chess tournament. My sister’s basketball game.

I dare say I’ll survive, but it is irritating.

The good news? My schedule cleared up for me to slow down and do some reflecting and resting.

One of those items includes diving into my goals for the year.

So I wanted to provide this template for my readers to do the same for their goals. It goes as follows:

  1. What’s the goal?
  2. Why do you want to accomplish it?
  3. What are the specific, measurable, and timely criteria?
  4. What habits do you need to put in place?
  5. How surprised would you be if you didn’t accomplish it?
  6. What are the top three reasons you could not accomplish it?
  7. Who do you have to help you?
  8. How can you make things easier for you to succeed?
  9. What actions must you take next?

In the Notion template I included, I started off with my goal to publish my book this year.

Give it a try yourself!

You don’t have to 10x

Not a coaching client.

I check in with my coaching clients regularly.

I’ll ask things like:

  • Where do you feel like you’re at?
  • What have you gotten out of these sessions so far?
  • What do you think the you of three months ago would think about you now?

The most common answer I hear always makes me smile…

“I really can’t believe how much I’ve grown.”

This is not an ad for coaching. It’s a reminder of what’s possible.

By simply having conversations about what we want, what we think is in the way, and what we’re going to do about it…We have no choice but to get better.

In other words, the folks I’ve seen grow the most and the quickest are just the ones who consistently show up. They rarely do anything extravagant or nebulous.

James Clear paints this picture well. He explains the power of getting 1% better each day for a year.

From his blog post: Continuous Improvement.

At no point in this hypothetical year was there a week of 10x-ing. (Is that a verb?) It’s just small, simple improvements at a steady pace.

1% better each day for a year makes a person 38 times better than they were before.

A lot of people feel like tiny upticks aren’t impactful enough. So they get no increase at all.

As one of my clients once said:

“.1 is greater than zero.”

An annual reflection

Here’s a reflection I made for the new year…

3 answers for each.

In 2021:

1. What are you most proud of?
2. What were the biggest challenges?
3. What are you most grateful for?
4. What did you learn?
5. How did you change?
6. What did you do too much/too little of?

In 2022:

1. What do you want to accomplish?
2. What do you want to learn?
3. What do you want to change?
4. Who do you want to be?

What’s your garden look like?

A garden of potted plants

I did a fun exercise with a client yesterday.

I had him write out a typical, average day in his life—morning routine, workflow, diet/exercise habits, fun, partner/friend time, evening winddown…

Then he had to answer a question: If you lived this exact day every day, would it allow you to accomplish your goals in six months? A year? Three years?

In other words: If you change nothing about the way you live your life, will you get to where you want to go?

He gave me an image for it. He told me it’s like his life is a garden. “I know what plants I want to thrive in my garden. Are the seeds I’m planting and leaves I’m watering today going to grow those plants?”

“Not even close,” he said.

“Awesome,” I replied. “What would need to change? Where are the discrepancies?”

We talked about him putting himself out there more socially, delegating more responsibilities at work, and spending more time on side projects and hobbies.

He committed to going to an event: a meetup or a swing dance club, to hiring out more roles, and to dedicating an hour a week to something non-work-related.

A simple plan was made. But it all came from the question…

If you change nothing about the way you live your life, will you get to where you want to go?

Another Dry January

I’ve done four Sober Octobers in a row now.

Last year, I added a “Dry January.” This year, I’m adding a third month of sobriety—probably June. (“Jeez Louise I’m not drinking June?”)

I look forward to these months. Feeling clean, healthy, and rested.

Three friends and clients have joined me this month.

No alcohol until February. Care to join us?

Email me if you’re down.

My 2021 goals

Well…here they are.

My aspirations for the year: Make $10K in a month, pay for chess tutoring, run a triathlon, get a stripe on my jiujitsu belt, read 70 books, do scary things, and be a powerful coach.

I managed to do them all.

Normally, I don’t set goals. But Ali Abdaal changed my mind on that.

Notice how there are gaps between my goals on the whiteboard. That’s because I erased some as the year went on.

It’s fun to set out to accomplish certain things, but we must also be able to pivot and make adjustments.

One goal was to “Get 1000 YouTube subscribers.”

Two months in, I couldn’t care less about my YouTube channel.

It was fun to reach toward tangible things like making a certain amount of money in a month. But it was even more fulfilling to strive for the more intangible goals.

Those were more about being than doing.

Being a great coach. Being courageous.

A year from today, I’ll let you know how my 2022 goals went.

Happy New Year!

It takes a lifetime

I used to shame myself for not sticking to a habit.

I saw it as “slipping up” or “breaking.”

Then I had James Clear clear (get it?) this up for me:

People say a bunch of different things about the timeline of habits.

They say things like, “It takes 21 days to build a habit,” or, “It takes an average of 66 days.”

But none of that is true.

The question behind that question is: “How long do I have to work until the action becomes automatic?”

And here’s the unfortunate truth: It takes a lifetime to build a habit.

We’re constantly breaking good habits and dabbling in bad ones. The work never stops.

It’s not about never breaking. It’s about how quickly we can get back to work and keep moving in the direction we want.

Another trip to Brooklyn

A man standing on the Brooklyn Bridge looking over Manhattan

I’m moving to NYC in October 2022.

That decision came from a fairly nutty weekend spent there in September. I visited my coaching buddy and met him for the first time in real life.

We got very little sleep in those three days.

In a few hours, I’m heading up north for another round.

Here’s my plan before I move house:

1) Every two months or so, I’ll go up and stay with my friend for a weekend.

I want as much exposure as I can before moving my life there. It’s a three-and-a-half-hour trek, which is roughly two solid phone calls with friends.

The point here is to eat the food, meet some peeps, and desensitize myself from the fast-paced culture. Shockingly, things move a lot slower in the suburbs of Maryland than they do in New York City.

Finally, the main goal is to spend time around neighborhoods I might want to move to. So far, I’m thinking Williamsburg—which I hear is the yuppy and trendy area of Brooklyn. I’ve never tried elitism, but I’m down for anything.

This move is very much a business investment. I want to be surrounded by young folks who are pursuing fun and interesting lives and who have money to pay for someone like me to help them do just that.

I told that to my two friends in Brooklyn and they both said, “Yeah, you want Williamsburg. You’ll have to yup it up.”

2) In the spring, I’ll get an AirBnB for a week or two in the neighborhood I’m thinking.

I’ll take a few days off, but this won’t be a vacation. It’ll be a beta test.

I’ll have normal workdays. I’ll get a trial gym membership. I’ll go grocery shopping.

For two weeks, it’ll be as though I truly live there.

3) Prep for the move.

This means getting my finances ready to pay $2500 a month for rent and utilities. As well as moving with as few physical items to my name as humanly possible.

I’m basically a minimalist. But when I moved last year, I realized I still owned a shit-ton of stuff. I can’t imagine what non-minimalists (muggles?) go through when they move.

For budgeting, I’ve been using this stupid simple sheet from Female in Finance. A friend turned me on to her and it has helped tremendously.

As for the move, I plan on selling or donating 80% of my stuff so I don’t have to transport it. Books, furniture, my soul.

I’m excited, to say the least. And nervous.

Which is why this is the right choice. If I’m not doing things that scare me, I’m not growing…I’m not leveling up.

This weekend will be much more productive than the last.

So the journey begins.

I’m moving to New York City

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

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

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

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

Here’s why.

1) The opportunity.

In 24 hours in NYC, I…

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

All that to say…there’s plenty to do.

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

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

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

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

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

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

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

2) The adventure.

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

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

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

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

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

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

Until now.

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

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

I’m ready.

3) It scares me.

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

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

I was also anxious.

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

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

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

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

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

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

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

Again, I’m ready. And I’m not.

So let’s do it.

I really don’t want to have a baby this week, but I’d be fine if I did

A baby smiling in the grass next to her teddy bear

Whenever we want to do something cool or useful—travel to a new country, create a business or a piece of content, or have a difficult conversation with someone…

We come up with aggravatingly reasonable justifications to not do that thing.

It’s not in the budget. I don’t know how. The timing isn’t right.

But the timing will never be right.

I look to my mom’s advice on not being ready to have kids. She says…

“I hear so many young people say, ‘Ugh, I absolutely can’t have a kid right now. I can barely take care of myself…’ I said the same thing when I was 29. I was a waitress who partied all the time. But you figure it out. You just do. You have no choice. I had my son and was like…Oh, well, this little boy is my life now. I finished school and started my career. I did all the things I was sure I wasn’t ‘ready’ for.”

My mom obviously doesn’t advocate for shitty parents. She’s commenting on our human ability to adapt and figure things out, especially for the hard stuff.

I don’t want to have a child today or this year. But if I did, I wouldn’t just throw it in the dumpster. I’d do everything I could to make it work! I’d change my budget, adjust my values, and make new decisions for the long term.

Having a baby is a huge example, but we can apply this truth to anything else.

In starting a business or an organization, say, we may feel unqualified to do so. But when we just do it and create clients, customers, and members…we become qualified through practice. Again, we figure it out.

I didn’t know how to run a blog when I started this one two years ago. I had a clunky Squarespace website that was difficult to maneuver around. My writing was meh.

But after posting every day since then, I’ve developed a rhythm and an audience for my ideas. It feels like second nature at this point. Again…I figured it out.

My mom was absolutely not ready to have me at 29. Now I’m about to be 29.

She’s still alive. I’m still alive. So her not being ready was a reasonable fear-based illusion.

What do you not feel ready for?

My 10 Commandments

The front lawn of a courthouse

I’m not the least bit religious, but I do advocate for living a principled and value-driven life.

Here are my 10 Commandments.

Thou shalt…

  1. Pursue a Growth Mindset—seeing everything as a lesson and a chance to improve.
  2. Never be uncomfortable with your shirt off—remaining fit and active.
  3. Treat every human being with the same amount of humor and respect—be they a CEO or a gardner.
  4. Pick your battles, but be confident when expressing your ideas and opinions.
  5. Cherish every minute of quality time you get with close friends and family.
  6. Never order food or watch a show unless with another person.
  7. Never take anything personally—especially rejection.
  8. Go to the gym at least three times per week.
  9. Never text while driving a car—even at a red light.
  10. Spend more time in a day reading or having a conversation than staring at a screen.

Being human, I don’t stick to these perfectly. But having these guidelines has moved me drastically closer to the person I aim to be.

What are your commandments?

Mindfulness isn’t enough

A guy in a hat closing his eyes and practicing mindfulness

I got coached yesterday on some habits I’ve been slipping into which I’m unhappy about.

DoorDashing food, staying up late on my phone, eating junk.

As I talked it all out, I had an insight. It was a simple one (they usually are).

I said: “I’ve been complaining about these bad habits for months. I’ve been reflecting on them and writing about them. What I haven’t done is create a plan for actually doing something about them.”

Being mindful, having an awareness of what’s going on…it’s vital. But it’s not enough.

A person who knows they’re an asshole is still an asshole.

I had a friend once tell me she was aware that she was a shitty friend. I thought, Yeah…but fix that though.

Awareness is the first step, but it doesn’t build the result we’re looking for. So I wrote down the habits I wanted to minimize and then wrote a plan for how I would change my actions to do so.

Examples:

• I can’t DoorDash food unless it’s with another person
• I got an app that turns my internet off at 9:30pm
• If I eat junk then I can’t have it the following day

These are tangible and doable. Battling with my thoughts has been intangible and chaotic.

When mindfulness isn’t enough, create a plan of action.

3 rules for disagreeing with someone

In the past four years, I’ve had debates, discourse, and disagreements about politics, feminism, religion, race, transgenderism, vaccines, and more.

Some were heated and aggressive. Some were fun and fruitful.

I handled myself quite well during some. I sounded like an ass during others.

It doesn’t matter how much we connect or get along with someone else. We’ll never agree with 100% of what they believe. Disagreeing is a natural part of the human experience.

Through my conversational struggles and from the many mistakes I’ve made, I’ve learned three helpful (yet difficult) rules for having more productive disagreements.

Feel free to disagree with them (get it?).

1) Come to terms with this truth: We can never force someone to think, feel, or believe something. They have to get there on their own.

We are not creatures of logic. We make decisions based on emotion and then justify those decisions with logic.

In countless disagreements, I foolishly thought that if I just brought up another point of juicy rationale, I’d crack the other person and they’d see things the way I saw them.

Confirmation bias plagues us all. It will always be easy for us to pick and choose the (supposed) evidence which fits our narrative. We decide what we want to be true and identify with that belief. Then, if someone disagrees with that belief, it feels like they’re disagreeing with who we are as a person.

Yesterday, my friend told me about a heated debate between his two friends regarding the COVID vaccine.

One friend was arguing that the vaccines are probably not safe. He sent a screenshot of a well-sourced article listing the possible negative side effects.

The other friend then went to that same article and screenshotted a paragraph that was conveniently left out: the conclusion which said that the vaccine was ultimately proven to be safe.

I heard this part and thought that would be the shutting of the door to their argument. But the friend merely brushed it off and continued with his disputes.

With the power of the internet, we can find millions of people who agree with every possible opinion known to man. There are people with PhDs who believe the earth is flat. There are intelligent people who think the planet is 6000 years old.

Whether it’s opinions about vaccines or about our favorite athletes…our default is to cling to evidence that supports how we already feel and to shy away from evidence that challenges our beliefs.

Since that’s the case, we cannot ‘logic’ our way through a disagreement.

2) Ask way more questions.

There are several reasons for this.

Firstly, it’s crucial to understand fully what we’re arguing against. The last thing we want to do is misrepresent someone and challenge ideas they don’t actually hold.

We ask questions to paint a crystal clear picture of what they’re actually thinking.

A strawman is a fallacy in which we argue against the worst possible representation of someone’s point.

Example: “Oh, we need to do something about climate change? So you just want us to stop driving cars and stop having kids, huh?”

No…that’s not what they’re saying. That’s a strawman.

By asking curious and clarifying questions (not leading questions meant to achieve a ‘gotcha’ moment), we’re able to steelman. This is the opposite of a strawman, in which we’re able to articulate someone’s opinions perfectly.

A steelman would have us say: “So just to be clear, you believe…” Then they would say: “Yes.”

That has to be our starting point.

The second reason asking questions is so effective is it demonstrates to the other person that we’re not here to attack them. The more curious we are, the more we show we just want to understand them, the more their guard will drop.

This isn’t a trick. We want everyone involved to lower their guard and feel safe to express themselves without reacting in a defensive manner.

Curious questions make it a conversation, not a debate. This is ideal. Debates have winners and losers. But in great conversations, everybody wins.

The final benefit of asking questions is it adds scrutiny to the conversation, exposing the true strength of the person’s argument.

While this should never be the goal of asking questions, it’s possible that the person “defeats” themselves with their own words. It’s a great way to see if this person has given thought and research into this thing they believe or if they just want to believe this thing.

I recently had a disagreement over the COVID vaccines myself. (To be clear, I’m not super passionate about vaccines. It’s just come up a ton in recent months so it’s fresh on my mind.)

My friend who was super wary of the vaccines was sharing his opinions. I did my best to just ask questions. As I did, I felt that their answers were on shaky ground and I found many holes in their arguments.

There were a lot of “I don’t know’s” and “I don’t remember’s.”

Again, I wasn’t trying to slam dunk this person I have a ton of love for. I just wanted to get a clear picture of their beliefs.

Asking questions is hard, especially when we don’t feel curious at all. Curiosity is tough to fake. But it’s the only way to ensure nothing gets lost in translation.

3) Separate the person from the argument.

We’re not arguing with people; we’re arguing with ideas.

I could go on for hours about how much I hated having Donald Trump as our president. But I’m also super close with people who absolutely loved him.

That doesn’t mean I actually hate these people. It just means I don’t connect with their ideas. We don’t need to agree with someone to hug them or to have a beer with them.

So in a disagreement, it’s powerful to avoid saying things like:

• “Where you’re wrong is…”
• “What you don’t see is…”
• “I disagree with you on…”

With phrases like these, it sounds again like we’re disagreeing with them as a person.

It’s better to say things like:

• “My problem with that perspective is…”
• “That argument to me is…”
• “The way I see things is…”

With phrases like these, we make it apparent that we’re just discussing ideas. It’s not a battle over who’s more righteous, more intelligent, or more sophisticated.

Conclusion

We have to pick our battles. I’ve ruined social events because I thought it was the perfect time to argue against Catholicism.

But we should also feel safe and free enough to express ourselves. This can best be done if we change our goals for disagreement.

Instead of wanting to win, we should want to collaborate and learn.

“Seek out people, books or ideas that contradict your current beliefs and one of two things will happen…A) you will discover that you are wrong or B) you will improve your arguments for your own ideas.”

-Mark Manson

Sober October begins

A pumpkin and a fall leaf during October

For the fourth year in a row, I will not be drinking a sip of alcohol during the month of October.

There are a few reasons for this:

  1. It’s refreshing to take a break from putting poison in my body.
  2. It makes it easier to crush it in my other health arenas: diet, exercise, sleep.
  3. Waking up well-rested and without a hangover is one of my passions.
  4. Even though I don’t drink all the time, it’s nice to prove to myself I truly don’t need or crave it.

I’m always excited to start.

And now, each year I’m adding an extra month of no drinking. This year it was January. Next year, it’ll be three months.

Let us begin.

Strengths or weaknesses?

A strong man working out in a Superman tank top
An older picture of me.

I’ve heard people say it’s vital to improve one’s weaknesses. I’ve also heard people argue we must instead build up our strengths.

I disagree with the notion that it must be one or the other. We can do both. Here’s how.

1) The Feedback exercise

This is a sobering and healthy activity to do with the people who know us best—friends, family, and trusted colleagues.

We ask them:

“Hey! I’m doing a research project and was wondering if you could help me out.

What do you think my biggest strengths are? My biggest weaknesses or blind spots?

What can I improve? What can I do more or less of?

What should I prioritize?

Let’s set up a call to go over all this if you’re down!”

This accomplishes several things. It…

• helps one see the lens with which others see them
• points out things a person isn’t aware of—the good and the bad
• provides a solid picture of one’s strengths to exploit and weaknesses to work on

2) Build on strengths

With a list of strengths, we can simply ask:

How can I use these on a more consistent basis?

How can I do what I’m really good at all the time?

3) Fill in the gaps

Here’s a lovely practice from the book Ultralearning:

Keep a running list of each weak spot for what we do. Examples for me include: chess, fitness, coaching, business management.

With my list of weak points (e.g. finding checkmates in chess, extra belly fat, inviting people to sessions) I now know what to practice so I can become more comfortable with them.

TL; DR

We can use our strengths more and work on our weaknesses.