A weekend of nothing

“Take a picture of us taking a picture of us.”

Readers of this blog know last week was an impactful one for me.

An intense level of burnout led me to change my entire workflow moving forward. That began this weekend.

Minus any trips, vacations, or special events…this Saturday and Sunday mark the first weekend in a year I didn’t work at all. No sessions, no planning, no creating.

I hiked with my buddy. We played chess. My friends took me rock climbing. Two besties are in town from Rwanda and Philadelphia (two equally foreign and exotic lands). We all got brunch in DC Sunday morning.

It was lovely, to say the least. There was no optimization, no brainstorming, no building. Just stories, laughter, and quality time with close peeps.

I love worky-type stuff. But space away from anything (and anyone) is essential. I forget that sometimes.

To “regular” people who enjoy their weekends, this may sound odd. But these past two days have quite literally felt like a vacation to me. I have to learn how to do nothing once or twice a week. Like anything, I’m assuming it’ll come with practice.

Days one and two are checked off. I’ve already begun the process of maneuvering my time slots with my weekend clients.

It turns out most people are accommodating when we simply ask for what we want.

I could get used to this.

New principles

A man in a suit sitting and working at his desk

Last week, I watched this video on non-negotiable principles.

The dude in the video—Alex Hormozi—is super bro-y but he provides a ton of gold. The video made me consider my business’s principles.

I’ve had them written down on my whiteboard since the start of the new year. I realized five was too many. I couldn’t even name them off the top of my head if someone asked. That means they were just sentences that sounded nice.

So I trimmed them down to three.

1) Curiosity before solutions.
2) Help people so much, they don’t need me.
3) Take nothing personally.

It’s not like customers and clients are going to start flooding through my door now that I have three principles. But even seeing this refined list on my whiteboard makes me feel clear and established as to what I stand for.

If I hire people in the future, I now have a set of must-haves. My favorite line from the video is:

“Most people shouldn’t work for your company.”

Because most people won’t embody all three of these principles. That’s okay. It’s about finding the ones who do.

We don’t need to run a business to have two or three core principles, though. What are yours?

I’d love to hear them.

Logo poll

Hi friends!

I need your help. I ran a design contest for the new logo of my LLC.

Can you please take 10 seconds, look at the final eight designs, and tell me which one is your favorite.

Here‘s the link.

The future of this blog

My backyard.

I don’t believe in having idols.

Taking inspiration from people we admire is great. But seeing someone as God-like or more than human seems creepy to me.

That said, one of the people I look up to most is Derek Sivers.

His book Anything You Want is the reason I wanted to start my own business. He’s given several TED Talks. And last month, I interviewed him for my book on creating.

I’d like to share an answer of his and how it inspired my newest creative endeavor.


“Why is absolute control over what you create so important to you? Self-publishing (and printing) your books, coding your website in HTML, building things with your hands, etc.”


“I hate bloat. It feels like pollution.

Quick-publish tools are filled with bloat because they have to cover every scenario.

Install WordPress and publish the word “Hello!”, and you’ve installed 884 PHP files, 602 Javascript files, 19 database tables, and hundreds of thousands of lines of code that are filled with bugs and security holes.

Or just type “<html><h1>Hello!</h1></html>” and save it as index.html, uploaded to a simple Linux server, and voilà. You now have a website with only one file and one line of code.  No security holes.  No problem to maintain it.

I hate dependencies. I have no subscriptions. Well-meaning companies say, “Oh don’t you worry about that, we’ll take care of it for you for only $10/month!” I think long-term so $10/month is $6000. And now you’re dependent on this company. If they raise their rates or go out of business, you’re screwed because you made yourself dependent on them.

So for each of these situations, I’d rather avoid the bloat, save the $6000, be un-dependent on any company, and just figure out how to do it myself.

That said, for the book publishing, I just wanted the highest possible quality, and I wanted to keep the rights so that I could do whatever I want with the books in the future. I could license them, translate them, rename them, give them away for free, or whatever I want. When you sign your rights away to a publishing company, the copyright is no longer yours to do what you want with.”

My first thought was, Shit, I use WordPress for my blog. Am I a loser?

While I might in fact be, I got an idea. In the next year, I’m going to transfer this blog over to a website that I code entirely by myself.

I’ve tried my hand at learning to code before. I got the fundamentals of HTML and CSS down. But I’ve always stopped short because I never really had anything to work on. There are only so many sample cat websites I can make until I get bored.

WordPress is easy and convenient. I don’t mind that. But creating my own site from scratch just sounds fun. I can already feel my future headaches as I try to learn Python or Javascript.

This won’t happen this month. It’ll be a slow and steady process. And I’m excited.

As I do with my book, I’ll keep you updated with every step along the way. Stay tuned.

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?

Thanks, ya’ll

I got several messages about yesterday’s blog.

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

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

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

I ran away

The sun shining through the woods

Last week, I joked about running away from everything and spending time off the grid. This weekend, I did just that…sort of.

I’m pretty sure I had a mental breakdown from Tuesday to Sunday.

I’ve never experienced anything like it. I’m still sorting things out so I’ll try to make sense of much of it today. In this blog, I’ll go through:

  1. What happened
  2. What I learned
  3. What changes I’ll make moving forward

Let’s dive in.

1) What the hell happened to me?

I woke up exhausted on Tuesday. But not a typical exhausted.

I’ve gotten bad sleep before. This was different. This wasn’t sluggishness or fog. I was awake. It was strange.

I felt no excitement or joy…None.

Whoa. I ran an experiment. I wrote out all of my favorite things and imagined myself doing them at the highest level. Spending time with friends and family laughing hysterically. Growing a business I love. Living in my new NYC apartment. Playing in chess tournaments…I felt nothing.

I wasn’t looking forward to any of it. In fact, I resented and was angered by anything I had to do last week. Client sessions, admin work, plans with a friend. I didn’t want to do any of it.

This was a shock to my system. I’m always excited. I love projects. I love talking to people and spending time with those I love.

But the only thing I truly wanted to do was run away to a cabin in the woods and not talk to a soul. Unfortunately, that wouldn’t fly.

I had a week of calls. Much to do, like any week. My next vacation is Brooklyn at the end of the month. My first thought was, Just make it until then. Not a chance.

The problem-solver that I am, I worked hard to find the source of all this.

I went through every interaction, every experience, everything I did and said in the past two weeks. Is this a trauma thing? Am I nervous about something? Did I do something I feel guilty about?

No. No. And no.

Then what the fuck is wrong??

Mindfulness told me that nothing was wrong. There was nothing to fix. But that’s much easier to say when I’m not in the thick of it.

I used my Ph.D. in Bro Science to dissect things. It felt as though my brain wasn’t producing dopamine. It was hard to laugh. I had zero motivation to do anything. I dreaded waking up and attacking the day.

Anyone who knows me knows I’m always laughing, I’m always motivated, and I love waking up and getting moving.

I cried a few times.

Here’s why:

  • I felt awful
  • I had no idea why I felt so awful
  • I both wanted to be consoled by my friends and not talk to anyone
  • I felt guilty for showing up to calls as (barely) half a person
  • With my limited knowledge of mental health, I thought about how many people experience way worse than what I did

Not fun.

This continued each day. I went to bed hoping I’d wake up refreshed and back to normal. Then I’d get up disappointed and reluctantly head into my office.

On Thursday, I had a session with my coach. When I laid out everything I was going through, we dove in. Without recounting the entire session, here were my major takeaways:

  1. I need more support.
  2. I work every day and didn’t even realize it.
  3. I’ve built an accidental brand of someone who’s unstoppable and has it all figured out (lol).
  4. In the 10 days of February, I had given myself to (held space, helped, served) 53 people for 36 hours.
  5. I’m working on too many things.

Holy shit. I was totally burnt out.

With this blog, with becoming a leader in my coaching community, with building more and more relationships in life and business…

People have been asking for my time and attention more than ever before. My output—the amount of value I’ve been trying to give—has been blowing up like a balloon. That balloon popped last week.

As I’ve reminded myself countless times in the past: It doesn’t matter how good we are at time management—there are only 24 hours in a day. We can’t trick Father Time.

I was giving 100 things 1% of me. As opposed to giving one thing 100% of me.

That session gave me a ton of clarity on what was going on. But it didn’t make me feel any better.

The next day on Friday, I was in a session with someone and I realized I hadn’t been listening to them for about 60 seconds. My eyes started watering.

I felt terrible. It was unprofessional of me to try to power through this. I finally understood the merit of taking a mental health day.

So I took a mental health weekend.

I reached out to the seven people I had sessions/plans with, told them I needed to escape for a few days, and then asked to borrow my friends’ dog, Hank.

I got an Airbnb an hour away. Seven of seven people responded with nothing but well-wishes and heart emojis. ❤️

I packed some clothes and a book, picked Hank up, and we headed off the grid.


2) What the hell did I learn?

When we got to the place, I dropped my bag and phone off. Hank and I left immediately to explore the local hiking trails.

When we got to the first one, I let Hank off the leash and he galloped around the trees with glee. Hiking with a well-trained dog should be an American pastime.

He found a stick and handed it to me. I thanked him for the gift and we walked aimlessly.

A few things hit me in those first few minutes in the woods:

  1. I don’t do this enough.
  2. Intention is a beautiful thing, but so is doing something without a goal or purpose.
  3. Life is 40 times more enjoyable outside without a phone.

The sun was going down so we went back to the Airbnb. I fed him and ordered dinner for myself.

The evening was spent reading, playing with Hank, and thinking.

When we woke up, I gave him breakfast and we went straight back out to the trails. It was snowing. He looked even more graceful sprinting through piles of white.

Back at the place, I made a cup of coffee and started reading a novel. A few minutes in, I realized I was enjoying it more than I had in the past. 90 pages in and it felt like I was soaking it in for the first time.

What was different?

Then the insight struck me. This was the first time in months I had picked up a book simply because I wanted to read it. It wasn’t for my routine. It wasn’t my 30 minutes of morning reading. I was just reading a good book on a snowy morning with some coffee and a dog lying at my feet.

“I need more mornings where I don’t care what time it is,” I said out loud.

“Quiet, I’m trying to sleep,” muttered Hank.

I stopped reading when I wanted to stop, not because it was time to stop. I could get used to this whole “not scheduling every hour” thing.

We played more tug-of-war, cleaned the place up, and checked out. Before returning home, we hit a nature park and wandered around for an hour or two. Every ten minutes that passed was like a percentage increase in my life battery.

I discovered that this stuff…time in nature, electronic-free walks, mornings without a clock…these were no longer self-care luxuries. At the level I’m at now, they’re necessities.

With that said…

3) What the hell am I going to do with all this?

I brought Hank back home and chilled with my two friends for an hour. I told them about my mental state. They listened with care.

When they asked how the Airbnb was, I said, “Necessary, not enough, and expensive.”

While it was helpful, it didn’t remove the physical sensation in my eyes and throat. But it did show me what I needed to change.

First, I need to stop working on Sundays.

I’ve been willing to do sessions on weekends because several of my clients have 9 to 5s and I don’t do evening calls. But that means when I’m not taking a trip, my week looks like this:

Mon—write book, organize week
Tue—sessions, chess lesson
Wed—sessions, group calls
Thu—sessions, newsletter
Fri—sessions, creative work
Sat—sessions, maybe fun
Sun—sessions, chill before week starts

No days off. Literally. That’s stupid.

My brain has no time to shut off or unplug. I’m always on.

Last night, I turned my phone on airplane mode and watched six episodes of Avatar: The Last Airbender (I have no idea who played in the Super Bowl).

Even that felt like a rarity. How often do we watch something on TV while on our phones? How many God damn screens do we need at one time?

So, here are my to-dos:

  1. Get back to everyone I’ve been blowing off.
  2. Reschedule my sessions/calls.
  3. Tell my clients I can’t work Sundays anymore.
  4. Spend more time without my phone and not looking at the clock.

I’ve already halted two projects I was working on. Taking those off my shoulders gave me an immediate wave of relief.

Moving forward, I’m going to be doing less. Less but better. Less but with more time, love, and attention. I’ll do more by doing less. Yes. Less.


I’m immensely grateful to have people in my life I can be vulnerable with.

Even this blog. I’m lucky to have an outlet where I can share stuff like this.

I also think about my mom.

I work for myself and have no one to worry about other than me. What if I was a single parent with a full-time job? I couldn’t just cancel everything and escape. Again, I’m lucky to be able to do what I do.

Please, if you’ve been through anything similar, share it with me. I’d love to learn more about the scope and scale of mental health.

Thanks for making it this far. I’m back and feeling pumped to do much, much less! 😘

Getting away

Hank the dog

Today, I’m borrowing my friends’ dog and staying in an Airbnb in the woods.

I canceled all my calls and obligations. Here’s what I sent seven people.

“Hey…! I’m so sorry. I know this is last minute but I’m experiencing some crazy burnout and need to get away. I’m rescheduling everything this weekend and running away to a cabin in the woods. Hope this lands well!”

I can already see I got back four responses from people with nothing but support and well-wishes.

This has never happened to me before. I don’t know the source of this anxiety and overwhelm. It came out of nowhere.

This is new territory for me so I’m learning how to manage it. I dare say there are several learning and growth opportunities here.

I’ll let you all know what those are when I return from playing with this dog off the grid. No phone. No wifi.

Just me, Hank, and a book.

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?


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! 💙

Off the grid

I’m a workaholic. I learned that this winter.

When I stopped doing outreach for my business in December, I got depressed for two weeks. It turned out a huge piece of my identity was wrapped up in my ability to create clients and income.

These past few months have been me learning how to slow down. Some weeks are easier than others. These are good problems to have.

But today, I’m feeling burnt out and I have no idea why.

Every now and then, I have the insatiable urge to spend three weeks in a cabin in the woods. Off the grid. No phone. No one can reach me. Just me, my notebook, my laptop (without wifi), and a few books.

I’m resenting any and all obligations. It’s kind of scary.

So what do I do when this happens? What can I do?

1) Understand that this too shall pass.

2) Check my health trifecta:

  • Am I getting good, consistent sleep?
  • What have I been eating?
  • Have I been exercising regularly?

3) Declutter.

Remove things from my schedule and physical space.

Sometimes I tell people straight up, “Hey! I’m terribly sorry, I know this sounds strange. But I’m going through some burnout right now and I’m making the executive decision to clear my schedule. Would you be willing to reschedule for two weeks from now? Thank you!”

Plus, getting rid of half my stuff in any room cheers me up immediately.

4) Tell someone about it.

Powerful emotions should never be kept to one’s self. I’m lucky to have friends with whom I can share my demons. It’s a sin to not take advantage of that resource.

I plan to do all these things this week.

If the blog goes silent, I’m probably writing posts off the grid in the mountains of Montana.

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.

I got drunk this weekend—and I don’t hate myself

Saturday night, my two good friends hosted a dinner party in DC. Me plus four of their other friends.

We drank wine (and scotch), ate delicious food, and played a plethora of board games. Laughter was had and new connections were made.

After the second glass of wine, I asked them if I could crash on their couch.

The next morning, I woke up with their cat laying on top of me. The sun was piercing through the balcony window. My head was pounding.

But I was happy.

I hadn’t had any alcohol in over a month. Readers of this blog know I take month-long pauses from drinking. Sobriety fascinates me. It wouldn’t shock me if, at some point in my life, I give up drinking entirely.

But lately, I’ve been eyeing my relationship with alcohol under a microscope. I don’t want to rely on it to have fun or be social. But I want to feel free to drink with friends if I so choose.

That’s what happened this weekend. It felt like I just had some drinks and played games with my buddies. Nothing embarrassing happened. I didn’t do or say anything misaligned.

When the three of us (four, counting their baby) woke up, we chatted, reviewed the night, and enjoyed coffee together.

I learned the two necessities for me to enjoy a night of drinking: responsibility and not having any work to do the next day.

If drinking to me means being able to do this once every month or two, that sounds lovely.


I got to interview Derek Sivers for my book this week.

He’s one of my favorite authors and TED-Talkers. He showed me that creating a business isn’t this some scary thing.

As expected, his long email of answers was crisp and delightful to read. At first, I was bummed to not get on a video call with him. But I quickly realized that copying and pasting his typed words would save about five hours.

I reached out to a lot of people I look up to with the same invitation. Most don’t respond. Some say No thank you. And that’s totally okay.

Tim Ferriss said, “It’s not about the people who don’t. It’s about those that do, and what you can do for them.”

I’m honored and humbled to have a chapter in DO THE THING! that starts with “Derek Sivers” in bold.

A lesson I’m learning is that we don’t get what we want if we don’t ask for it.

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.

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!

It turns out I’m not perfect

I no-call no-showed a connect call yesterday.

It was with a fellow coach. I accidentally stood her up.

I saw her message saying something like, “Hey! Ready for our call?” My heart sank into my chest. I had completely forgotten to put it in my calendar. Therefore, it didn’t exist.

One of my values is timeliness. When people are late to things with me, I tend to get heated.

But when stuff like this happens, I get humbled and it becomes much easier to practice patience and compassion.

When I get annoyed with something, it begs the question:

Have I ever done this thing that I’m so upset at? Have I been perfect in this regard?


A chessboard sitting on a bed

I’ve been in a chess slump for the past month.

My rating climbed and climbed over 2021. But now I feel I’m stuck around 1650. It feels like I’ve reached a plateau.

This has made me jaded while playing online. I even felt resentful at my last tournament.

The lesson? I’ve learned that my main satisfaction in the game has been my growth in it. It’s time to change that.

But now I’m approaching an advanced skill level. To continue improving, I’m going to have to really start studying and treating it less as a small side hobby.

The other day, one of my favorite chess streamers Eric Rosen said something which hit me hard.

“A lot of players obsess over their win rate or their rating. I think too many players forget about the goal of having fun with the game.”

It’s so cliche. So simple. I was one of these players.

This could easily be applied to any other area in our lives: career, relationships, health. We focus so heavily on improving or pursuing a thing. It can be wildly helpful to pause from time to time and ask ourselves the question.

How can I make this more fun?

Money will solve your problems

A man counting his money

This video changed the way I think about money.

In it, Casey Neistat responds to the question: Can money solve your problems?

In short, he sums up his position with: “For most people who are broke, money will literally solve your problems…It’s hard to worry about how fulfilled you are when you can’t pay your rent or buy food.”

For years, I saw the pursuit of wealth as a greedy and icky game. I was living a contradiction—obsessing over personal finance books and YouTubers, while telling myself that more money wouldn’t make me happier.

It sounds stupidly simple, but this video showed me that it’s okay to want more money. It just depends on why we want it.

Increasing our income in the hopes of status or happiness is surely a dead end. Money doesn’t make us more fulfilled. But with good financial habits, it can allow us to do more things that fulfill us.

Since getting my business to a stable and profitable place, money has allowed me to:

  1. Pay off debt—loans, programs, credit card.
  2. Not stress about paying bills for months.
  3. Buy food without counting every dollar.
  4. Upgrade tech and essentials.
  5. Hire people (my personal favorite).

In the past few months, I’ve hired a new life coach, a chess tutor, a designer for my book, and I plan to hire an editor and producer for the podcast I’m doing with one of my besties (stay tuned).

All that’s to say, more revenue has definitely made me happier. Not the money itself…but what it has allowed me to do.

So let me ask you: Do you want more money? Why? What would you do with it?

As always, I’d love to hear your answers.

Buying nice things

A black pair of over the ear headphones

I don’t really buy nice things. Except when I do.

Aside from some necessary outdoorsy items in Vancouver Island, I haven’t purchased any new clothes since 2019. I shop at Goodwill and the Dollar Store.

Here’s where my money tends to go:

  • Food
  • Books
  • Events—shows, trips
  • Airbnbs
  • Tech (which are usually business expenses)

I’d love a Tesla as much as the next American. But if I had $1m to get a new car, I’d still probably get a used 2016 Honda Civic. Paid in full.

In short, I don’t care about “living luxuriously.” I don’t have an Instagram. Humbly bragging about my income on this blog is all the dopamine I need.


There’s a piece of advice from Tim Ferriss that’s stayed with me over the years:

For things you use on a daily basis, bite the bullet and pay for high quality.

I don’t count a car in this category, because a new car payment can simply bleed us of money. But this week, I bought a new mattress and a new pair of headphones.

I figured a week of Covid isolation was the perfect time to invest in these things. My mid-grade mattress was super firm and I was waking up several times a month with neck and back pain. My old wired earbuds were itchy and didn’t keep the noise out.

Were these purchases absolutely 100% necessary? No.

But my God am I happy with them.

I melt into this new mattress. I’m wearing these headphones right now. I can’t even hear my fingers type on the keyboard. They keep the world away and I’ve never felt more focused.

The best thing? Both these items will hopefully last me several years. I don’t have to think about them for a while.

The next plan is to buy a new desk and desk chair when I move to NYC. 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.


The 10 million dollar question

A briefcase with ten million dollars in it
I doubt that’s actually $10m.

I got to ask one of my favorite questions yesterday.

In a session, a client told me he wanted to take more action toward his career. When I asked him what his next steps were, he said he needed to learn more and be better prepared.

I thought, prepared for what? The apocalypse?

“So you’re telling me that you want to get into action, but before you can do that, you need to learn more?” I thought, How much more have you decided you have to learn? On what date will you know enough to start taking action?

But instead, I asked a more direct question:

“If I told you I’d give you and your father each $10,000,000 if you got one customer to pay you for a service in the next week…how would you spend this week?”

His eyes got big and he smiled. “I’d reach out to as many people as I could and offer my services to them. Every day. I wouldn’t care about how many rejections I got because I’d only need one person to work with me.”

“Fuck yeah,” I replied. “So what’s stopping you from doing that now?”

His mouth opened and closed. “You know what, I don’t have a good answer for that.” We laughed.

The power of this question is that it removes the barrier of “I don’t know how.” When so much is on the table, our brains go right toward a version of: I’d do whatever it took.

The action is there. The creativity is there. It’s often just the drive that’s lacking.

When I asked another client that same question last week, she said, “Jesus. Hypothetical money is a powerful motivator.”

So let me ask you:

What’s something you really want in your life right now?

If I told you I’d give you $10 million if you created it this week, how would you spend your time?

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!


Dillan Taylor's COVID test


Tested positive this morning.

This is exactly when I got it last year—late January. It’s a winter tradition I suppose.

But this time I’m fully vaccinated. Now it feels more like an annoying inconvenience than a debilitating disease.

No canceled calls. The show must go on.

You win this round, COVID. But I shall return.

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.”

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.”


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?

Getting a raise vs. having a kid

I got dinner with my old boss last night.

He recently got promoted to VP in his company. He’s also the recent father of two.

When I asked him about the new VP position, he calmly said, “Yeah man. It’s cool.”

When I asked him about his partner and kids, he lit up. He raised his volume. He smiled as he spoke. He talked with his hands. “I love it,” he said. “It’s my favorite job I didn’t know I wanted.”

I pointed out how much more excited he seemed about his role as a dad than his role as a VP. He told me that one influenced the other.

When he detached himself from wanting a promotion and focused his love and attention on his family and wellbeing…he got the promotion.

We so often chase something only to see it evade us. Like magnets repelling from one another.

Fulfillment. Friendship. Opportunites.

These come readily to us when we just stay present, provide as much value as we can to those we care about, and continue to do the things we want to do.

We work on ourselves. We sharpen our axes.

We get what we want when we don’t care about getting what we want.

It’s that time of the year

I wrote a blog yesterday about being financially transparent.

One friend commented: “When we talk about money more casually, we can share insights into career moves, upward mobility, investing, debt, etc!! It’s just so helpful to be transparent with others you want to succeed. ❤️

To continue that train, I want to share what I’ve been doing the past two days: my taxes.

I’m having a blast. Here’s why.

Not listed: The $14m I spent on DoorDash.

This is my first time doing taxes as a business owner. So I hired an accountant. He gave me a to-do list.

Auditing and investigating my 2021 has been wildly insightful and fun. I texted that to my friend and he responded, “Only you would enjoy doing taxes…”

What I love is that it’s a story that’s told through my spending and earning. Going through my account statements and going, Oh yeah, I can’t believe I used to pay for that service!

The income chart makes me laugh. I can remember earning my first $500 in April and feeling like I made it. I remember not sleeping and shaking at my desk in June from anxiety. And I remember the euphoria and peace in September when I finally started making more than my monthly expenses.

I can’t believe how much I spent on bills, coaching, and food. We always know it’s a lot but it’s wild to see it all added up.

I’m pleased with my story. And I’m excited to see how 2022’s unfolds.

Should we be able to talk about money?

A man counting money in the form of cash in his hands

Money can be a sticky thing.

There’s this age-old taboo that says we shouldn’t talk about money or ask people about theirs. I think we should step away from that.

But first, why does money make us so uncomfortable?

The number one reason is that it’s an enormous source of comparison. I’ve fallen victim many times to what I call “travel glamor shame.”

That’s when we see our friends—or enemies—in some beautiful foreign country and then we immediately hate ourselves.

How much money a person makes can be hard to dismiss. I say I treat every single human being with the same humor and respect as the next. But the difference between someone making $25,000/year and $250,000/year doesn’t go unnoticed.

And that’s the thing. I don’t think it should go unnoticed. I just think we shouldn’t care.

We can have both. We can talk about the discrepancy of a person’s income without treating them any differently.

I’ve been talking about money frequently with other coaches in my community. How to value our services. How to make more of it. Why it’s not this evil thing.

2021 was the year of building my business. By September, I had gotten it to be highly profitable and sustainable. But the months before that were riddled with uncertainty, doubt, and anxiety.

All that to say: I’ve learned so many lessons about making money that I want to share. But I usually feel bad talking about them because I don’t want to come off as arrogant or like I’m gloating.

What’s funny is, whenever I do share about my finances with other coaches, they tend to find it inspiring. “It makes it seem more real and possible,” one coach told me.

That’s the point.

When I talk about my money, the vibe isn’t, “Look at how cool I am.” It’s, “Hey, I’m an idiot. And if I can do this, you can too if you want!”

I know people who make six figures who either love talking about money or despise it. I know people who make less than $30k who either love talking about money or despise it.

This blog was a tad rambly but I’ll end with this statement.

If we treat money like Voldemort, like this unspeakable thing, I think it just causes more stress and pressure around it.

The importance of bosses

Dillan Taylor's boss at the Cheesecake Factory, Mark Milecki

When I had a job, I always thought it must be pretty challenging to be someone’s boss.

I expected them to…

  1. Be a confident and competent leader.
  2. Express kindness and care toward their employees.
  3. Maintain an organized system.

That’s a lot to do all at once.

I’ve worked in restaurants, at a home remodeling company, and on a farm. I’ve had phenomenal bosses. I’ve had terrible ones.

A good leader can be the difference between dreading going to work and looking forward to it. A strong captain can make us feel safe. They can even become a mentor to us. I still keep in touch with the best bosses I’ve worked with.

The #1 reason people quit their jobs is because of poor leadership. Here’s a graph that paints the picture.

From The Hustle.

Luckily, I’ve never really experienced any of this. I’ve just had some bosses who had no ability to build connections with employees. It just felt like they were kind of…there. They didn’t light anyone up and it felt like they were easily replaceable.

I’ve learned how to lead from the great bosses I’ve had. While I’ve never hired anyone, I use their lessons on a weekly basis with my team and community. I still remember how they made me feel.

The way things are going, I’ll never have another boss in my lifetime. But I’m quite pleased with my track record.

I’ll end this with a statistic.

Of the highest performing and most fulfilled people in the workforce, 91% of them answered “Yes” to this question:

Do you feel like your boss cares about you as a person?