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?

I did NOT win a trophy

The chess tables at the Waldorf Chess Club

I played in my second chess tournament this weekend. It didn’t go well.

My first competition was in December. That one went much better.

In typical fashion, I showed up an hour early. I was the first one there. I met the head of the Waldorf Chess Club and we chatted about chess and sandwiches.

The other players piled in and we got sectioned into quads: groups of four. We would play each person in our quad once for a total of three rounds. I took math in college so I put this together quickly.

To spoil the whole thing, I lost all three of my games.

Here’s how each of them went:

  1. Neck and neck until he ruined my pawn structure (weakened my position). Beat me in the endgame because of my bad position.
  2. I tried to be crazy flashy and sacrificed two pieces for a fancy checkmate. I miscalculated and was then just down two pieces.
  3. A super even game that went down to the last few minutes. He was up a pawn and used that to beat me in a King and pawn endgame.

Here’s what I took from all this.

Losing sucks…

But it is valuable. For many reasons.

After a strong performance in my first tournament, I thought I was hot shit. I needed to be humbled to snap back to reality. Mom’s spaghetti.

As I learned in Brazilian Jiujitsu, being humbled, getting your ass kicked…It makes us kinder and more patient people. It gets us out of our heads. It destroys our egos. Our wellbeing stems not from our success, but our willingness to grow.

Only when our armor is damaged can we begin to make repairs to it. Otherwise we just walk around thinking we’re invincible.

I barely remember the winning moves I made during my first tournament. But the losing moves in this last one are engrained in my psyche. I can envision them right now as I’m typing this.

It’s an unfortunate truth, but losing is the best (only) way to get better at chess. That’s probably true in any endeavor: business, relationships, instruments.

When I meet with my chess coach next, we’ll have plenty to analyze.

Round 3 of Dillan Taylor's second chess tournament

The people I played this weekend were much stronger than those I played in December. It was a reminder that I must consistently go against better players.

The first competition pumped me up to improve at chess. It was a Winning is fun! I want to do more of it kind of motivation. This one energized me even more. But this time it’s a Losing is awful! I want to do less of it sort of thing.

The losing will never stop. It’s part of leveling up. It’s out of my control.

The only thing I can control is what these losses mean for me.

Back to the drawing (chess) board.

Second chess tournament

I’m about to leave for the Waldorf Chess Club’s Quads #45 Classical tournament.

If you’re wondering what some of those words mean…me too. But it sounds quite impressive.

In December, I played in my first competition and did well. This one will be much more challenging.

The pre-standings for Dillan Taylor's second chess tournament

You’ll notice I’m in the lower tier of players. That’s just my provisional rating, but it’s still hard not to let it affect emotions and expectations.

Today we play three games (rounds). They will be the longest games I’ve ever played—70 minutes for each player, 10-second delay. That means each game could take two to three hours.

The first round starts at 10am, the second at 1:30pm, and the last at 4:30pm. Long day.

I feel I got spoiled in December by not losing a game, which means I’m undefeated in my chess career. I’m not planning to lose today, but I’m emotionally prepared for it.

Playing better players is the only way to improve. So I’m excited to make some blunders and analyze my games with my coach.

Wish me luck.

On Monday, I’ll tell you how I did.

How to become better than me at writing

Dillan Taylor sitting at his desk and getting ready to write
The face I make before I start typing.

I’m not a phenomenal writer.

But I’m 20 times better than when I first started this blog. That was almost three years ago.

I’ve read a few books on copywriting—how to keep my words concise and easy to digest. I can give people simple suggestions to improve their writing…

  • Write short sentences.
  • Don’t use $100 words when $1 words can get the point across.
  • Read this piece and watch this video. They both take 60 seconds.

But I’m not even close to an expert. And that’s the point.

We don’t need to have more information (or even more skill) than others. Most of the time, the people who are “successful” are just the ones willing to put themselves out there.

Did I just call myself successful? Well, I certainly feel like I’ve had success. But I felt that way when just three people were reading my stuff.

I’ve had blogs with over a thousand unique readers. Some of those posts include my thoughts on death, my trip to Canada, and my move to NYC. I’ve had people I don’t know email me talking about their favorite pieces.

I don’t say this to brag. I say this because I never set out to be a “great writer.” I just wrote one of these almost every day for three years. It took a year and a half for people to really start giving a shit.

We can get really good at things if we have two things…

Consistency and the willingness to be messy.

I can’t even read my earlier writing. Most of it makes me cringe. But if I worried too much about that early on, I wouldn’t have written anything and I wouldn’t have improved.

It’s not sexy advice. But to get good at anything, we just have to do it a lot and be okay with doing it poorly.

We don’t need to read “one more” book. We don’t need another course. We just need more practice.

Keep that up…and maybe you’ll build yourself a mediocre blog like me.

Writing is hard

A teal typewriter on a desk with empty sheets of paper next to it

I’ve been working on my book for five months now. Most of that time has consisted of two things.

Interviews and procrastination.

Early on, I was worried I wouldn’t have enough content to write more than a pamphlet. Once I began actually writing and transcribing my recorded conversations, I realized I actually had to cut some folks out. That was a relief.

There were some interviews that, while I’m incredibly grateful for them, just didn’t hit as hard as others. “Trimming the fat” sounds cold. But writing this book felt like less of a chore once I decided to only include chapters that lit me up. I narrowed it down to seven people—including duos.

My last interview was a dream come true. I had a long conversation with James and Anthony Deveney—the hosts of one of my favorite shows, Raiders of the Lost Podcast.

They started their movie podcast in June of 2020, in the middle of quarantine. Since then, they’ve gained half a million followers and have grown arguably the best film podcast to date.

Their story was captivating and inspiring. They were also two of the nicest dudes I’ve ever met.

They took me through their journey of pursuing their dream: being full-time content creators. It’s one thing to see people doing something cool. It’s another thing entirely to hear about what they had to do to get there.

James just quit his full-time job a few months ago once the podcast was able to totally support both of their lives. I’m thrilled to tell their tale.

As for my process of writing, so far it’s looked like this:

  1. Record interview.
  2. Come prepared with strong questions to ask.
  3. Play the interview back with a Google Doc up.
  4. Transcribe the major bits of conversation while playing and pausing the interview.
  5. Use willpower to not immediately edit my writing (i.e. write shitty).
  6. When a story or concept of my own comes to mind, make a note of it in the doc so I can come back and write about it later.
  7. Use the Pomodoro technique for productive time management: 25 minutes on, 5-minute break.
  8. Finish this first run-through before hiring my editor.

Right away, I’ve recognized the necessity of an organized system. If I were winging it every time I sat down at my keyboard, it would be chaos. With this structure, it’s actually pretty easy to write this damn thing.

The only thing getting in my way is initially sitting down to start. It’s the Resistance which gives me all these reasonable-sounding excuses for why I don’t have to start typing just yet.

Luckily, I eventually brush that voice aside and begrudgingly begin writing. Without fail, I enter a flow state in five to ten minutes.

What’s my biggest challenge now?

First, it’s making the time to actually write. I need three to four hours of deep work in order to make meaningful dents in this. Unfortunately (or fortunately), I run a full-time business that’s doing well. That means I have a lot of client calls. Sessions require a ton of mental energy, so I refuse to write for four hours in the morning and then do calls in the afternoon. My brain would be fried.

Second, the debate is creeping in on whether I get a publisher or I just publish it myself. But I’m trying not to focus too much on things that are farther away.

Regarding the first challenge, it’s highly likely that I push back the release date. The plan was my birthday, March 2. The new plan is probably my mom’s birthday, May 5.

Since I don’t have half a million followers like James and Anthony, I doubt anyone will make a fuss about this.

Am I working as hard as I possibly can on this?


Am I having a ton of fun?

Yes. 😇

I’ve meditated every day for four years—And I still suck at it

A man sitting cross-legged while meditating

Meditation is an odd thing.

When I started getting my life together in summer 2017, I downloaded HeadSpace. Andy’s soothing voice introduced me to the simple concepts of mindfulness.

Following the breath. Focusing on each physical sensation. Noticing thoughts and images that appear and vanish.

Within a month of consistently doing three, five, or ten-minute meditations, I felt a shift in my emotional state. It wasn’t that I was less emotional per se, but the default response to my emotions became slowed down and lightened.

Someone does something shitty ➡️ I’m pissed off!

Turned into…

Someone does something shitty ➡️ Sensations of heat and tingling in my neck and face ➡️ Thoughts of me telling this person off ➡️ Noticing that all of that is just in my head ➡️ Deciding not to react in a shitty way.

The second process slowly became a habit.

By adding a simple and short mediation practice to my mornings, the rest of my days were drastically improved. I was kinder, more patient, and more appreciative.

Since I’ve been doing this almost every day for four years, one would expect me to be floating in the lotus position on the cusp of enlightenment.

But instead, I’m just a dude.

Half of my meditations consist of me forgetting I’m meditating. I’ll plan my day, get chaotically lost in thought, or worry about one of a thousand things coming up. Clearing my mind feels impossible.

Because it is impossible.

I now use the Waking Up app for my guided meditations. In it, Sam Harris provides a useful model:

“If someone had a gun to your head and told you not to think about anything for 15 seconds, or they would shoot you…you’d be dead in two seconds. If need be, you could probably keep your hand in fire for that long. But we can’t help but think.”

I hear people bash meditation all the time. “I’m not good at it…My mind is too jumbled…It doesn’t work for me…”

Welcome to the club.

Aside from severe mental health issues, every single person has something to gain by trying some kind of meditation practice. Even if it’s just three minutes of noticing what’s going on around them.

It’s not about doing more; it’s about doing less. Less reacting, more noticing.

My mentor often reminds me of a piece of advice he was given years ago:

“Don’t fit meditation into your life, fit your life into your meditation.”

For me, when I don’t have a ton of time in the morning, meditation is the first thing I skip in my routine. I regret it every time.

Conversely, when I don’t feel like doing it (which is most days) but do it anyway, I’m grateful 100% of the time.

Join me as I float to nirvana.

It’s never enough

Pizza crusts on a plate

Yesterday, my best buddy and I won $1,000…each.

It was a raffle for subscribing to The Hustle, an extraordinary newsletter on the worlds of tech and business. I’m a sucker for those things…

“For each person you refer, you both could win a billion free socks!” Or something like that. My friends often roll their eyes. But look who’s laughing now.

The $1K comes in the form of an Airbnb gift card. This is phenomenal because it feels like I’ve won free experiences, as opposed to the less-sexy prize of $1K in my savings account.

I’d be grateful either way. And this blog is about that ‘g’ word.


Lol jk. It’s about being grateful.

Something happened five minutes after I saw we won. Something I’m embarrassed to share.

I started thinking about all the trips I have planned in 2022 and about how nice it would be to have my lodging paid for. Brooklyn in February, road trip to Florida in April, NYC again in May, European road trip in July…

Then I thought, Ah man…There’s no way $1K is going to cover all of that. If only it were $5K…

I actually thought that. It took five minutes for me to feel like a free $1K wasn’t enough! Am I insane??

I immediately laughed at myself. “Yeah Dill, some people really have it awful. What ever are you going to do?” Silliness.

Unless I’m a sociopath, the point of sharing that is to highlight the human tendency to always want more. That’s why conditional happiness (or the hedonic treadmill) is a dead end.

Conditional happiness: “I will be happy/fulfilled/satisfied once I have or do this thing.”

Then we get whatever that thing is and we are happy…for five minutes. Then we go right back to our default state.

One of my clients got his dream job, his dream car, and is financially set for life. He told me that none of that brings him sustainable fulfillment. Robin Williams was loved by the world, made millions of dollars, and pursued his dreams successfully. And he hung himself. I got free God damn money and got upset it wasn’t more.

It’s up to us to build a default state of gratitude and appreciation.

I’ve decided to forgive The Hustle for only sending me $1K. Please send your condolences directly to my email.

Philly feedback

Connor Russo and Dillan Taylor

Here are my biggest takeaways from the feedback exercise I did with one of my best friends this weekend.

1) I struggle with portion control.

My buddy said something that hit me hard.

“I like hanging out with sober Dill way more than drunk Dill.”

He brought up the fact that I used to drive home drunker than was comfortable. That part was easy to swallow because I remember the day I vowed to never do that again—December 28, 2019.

But as for being drunk Dill, he called me out on something I’ve battled with since I was 18: the number of drinks I have when I drink.

On average, I only drink about twice a month. But when I do, I drink like I’m 20 years old. I haven’t reprogrammed my brain. When I have a beer, I want a second. When I have a second beer, I want a third. And so on.

TAKEAWAY: I will buy smaller quantities of alcohol when drinking with others. Six-packs, single bottles of wine, etc. If it’s not in the pantry then I can’t drink it.

2) I can be more welcoming to opposing opinions.

I love and appreciate the fact that we’re all so different, but sometimes when someone sees certain things differently than I do, I get confused.

Adam Grant introduced me to a useful term: logic bully.

For years, I thought breaking things down rationally was the only way to solve problems and get at truths. Unfortunately for me, that’s not how everyone operates.

My buddy pointed out that I could be more light-hearted in my disagreements. Even if I’m confident in my opinion, it could be more harmonious if I didn’t treat it as an objective fact.

Depending on the topic, this one will definitely take a lot of work.

TAKEAWAY: When I disagree with someone, I will slow down. I’ll try to steelman their points, separate the person from the idea, and ask questions as if I’m agreeing with them for the sake of the argument.

3) People love positive reinforcement.

It’s healthy to be able to do what my friend and I did—articulating areas of improvement and airing grievances. But he pointed out that hearing praise and appreciation from me just feels incredible.

The challenge is (especially for men I think) this can often sound cheesy.

Telling people what we love and respect about them and highlighting what they do really well…it takes practice.

I tell my friends I love them on the phone. I hug them. Sometimes it doesn’t feel natural. Sometimes they have no clue what to say. That’s okay.

I’d rather feel a bit corny than have my friends question how I really feel about them.

TAKEAWAY: Continue to consistently tell the people in my life what they mean to me and what I think they do well.

I encourage you to do your own feedback exercise with your friends!

More feedback

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

Connor, Laura, Dill.

(This picture was taken last year.)

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

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

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

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

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

We had to answer these questions:

1) When have I hurt you?

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

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

4) When have you been impressed by me?

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

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

The Hustle

One of my 2022 goals is to expand my knowledge when it comes to the world of tech, startups, climate, and business.

This newsletter may be my favorite content I’ve ever subscribed to.

It’s free, it’s concise, and it’s wildly entertaining and informative.

I refuse to be a 40-year old who doesn’t know anything about the latest technology. If I did nothing but read The Hustle each week between now and then, I’ll be in great shape.

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.

Football is scary

An American football on the grass of a field

Yesterday, my mom took me and my uncle to a Washington Football game.

The only sports I care for are MMA and soccer, but I always say yes to a live sporting event for three reasons:

  1. I’ll enjoy any event if I’m with people I care about.
  2. It’s always fascinating to see people who are at the highest level perform (in this case, NFL players).
  3. The people-watching is golden.

Today, I want to talk about that third one.

Growing up, football was my favorite sport (sorry, Bow Wow). Then around high school or college, I noticed something that turned me away from it.

People truly treat it like a religion.

Don’t get me wrong, I love how a sport can bring people together and evoke powerful emotion in millions of people. I enjoy listening to folks passionate about a sport discuss the business and inner workings of what makes the game tick. I enjoy the roars of crowds at games like the one I went to yesterday. Depending on the UFC bout, you can find me standing and screaming at the TV.

But what leaves a sour taste in my mouth is hatred—disgust for other players or fans (i.e. human beings) because of the jersey they’re wearing.

I’m not saying every single football fan is filled with rage, but it’s not uncommon.

When I was in high school, I would go see my team play against our rivals. I despised them. I wanted them to lose every game. I was convinced I didn’t like them as people without ever speaking to a single player.


For no other reason than the arbitrary fact that I attended my school. If circumstance led me to attend the rival school, I would’ve felt the same about my school. If I grew up in another state, I wouldn’t have even known either of these high schools existed.

Thus the religious context comes into play. When I see babies or toddlers with Steelers jerseys on, I doubt those kids chose to be Steelers fans. Likewise, if we’re born into a Muslim or Hindu family, we’re unlikely to be raised as Christians.

At the game yesterday, I saw fans flipping other fans off, telling them to “stop fucking talking,” and ironically clapping in their direction when their team did something good. There was an essence of mob mentality, meaning I saw people do things they would never do if they were in a living room with just one opposing fan.

There was no genocide, but in what other contexts do we act this aggressively toward other people?

I’m probably being overly dramatic. I just think it’s odd to see people feel so identified with a group of people they’ve never met. And it’s not even that group of people; it’s the shirts they’re wearing.

This blog likely triggered a few football fans. Apologies.

But maybe that proves my point?

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!

Core principles

Every individual or business should run on a small set of core principles.

I just updated mine:

1) Curiosity before solutions.
2) Make people feel loved and heard.
3) Serve; don’t please.
4) Do the things I love all the time and get better at them.
5) Take nothing personally.

I read 70 books in 2021—Here’s how

A pile of books on the floor

This blog won’t be much different than the one I wrote last year on how I read 64 books in 2020. Well…the difference is about six books.

In my coaching conversations, I’ve heard many people say they want to work on their reading habit.

Let’s start with that last word.

1) I make a habit out of it. (i.e. I read every day.)

Even if it’s just two pages.

In a session yesterday, my client said, “.1 is more than 0.”

Something is better than nothing. Let’s put that into perspective.

If we read 10 pages a day, every day for a year, that’s 3,650 pages.

That means we could read Infinite Jest, Moby Dick, five 200-page novels, five 100-page stories…and still have 408 pages left.

I like reading for 10-30 minutes as part of my morning routine. Sometimes I’ll read as I wind down before bed.

Not everybody has the luxury of working for themselves like I do. People have jobs and families. But I find it hard to believe a person never has ten minutes to themselves for a bit of reading.

In short, it’s about consistency, not speed. I’m a wildly slow reader. Reading practically every day compensates for that.

2) I don’t read shit I don’t like.

If continuing to read something feels more like a chore or an obligation, I put it down.

I’m not saying other people should do this. I have friends who feel accomplished when they stick with dense and challenging reads all the way through. That’s great.

But personally, that’s not why I read. I want to enjoy myself. I’m not in school anymore and I’m not looking to challenge my brain. I want to be entertained, to be intrigued, and to learn things I can use in the real world.

Time reading something I don’t like is time away from something I could possibly love.

3) I keep book notes.

Dillan Taylor's book notes

In my Notes app, I keep simple, bulleted takeaways from what I read.

I try to put them in my own words to make it easier for me to remember and apply them.

I’m not certain this allows me to read more, but it definitely makes me feel more engaged with what I’m reading. It also allows me to go back a year from now and revisit what I got out of a book.

4) I log what I read on GoodReads.

To anyone who cares about a reading habit, I strongly encourage making a GoodReads account.

There, one can…

• set reading goals
• see what their friends are reading/have read
• get recommended new books
• keep track of everything they’ve read

Be sure to follow me. 😊


The most important two things are to read consistently and to enjoy it.

Reading because it’s “what someone should do” feels dull and pointless.

I got to enter many different worlds this year. Here’s to 70 more in 2022!

The R word

Every now and then I talk about Resistance.

The concept comes from The War of Art by Steven Pressfield—a book I read once a year.

Resistance is the invisible force that keeps us from doing the things we want to do and living the lives we want to live.

It takes many shapes: fear, procrastination, justification, anger, shame…

It says: “You don’t have to do this right now. Do it later. It’ll be easier and more enjoyable if you do this in the future.”

Most of the time, Resistance sounds reasonable. We can’t start until we do this thing, until we have more knowledge, until we have more confidence.

I’m writing a book. Each and every time I sit down to start typing, without fail, I find reasons to wait. I set out to begin writing at 9am, but won’t start until about 9:45.

Readers of this blog know I’m not a big grind-hustle-discipline guy. I don’t think we have to torture ourselves to live a life worth living.

But the simple truth is we don’t get something from nothing.

There are plenty of things worth doing that we won’t feel like doing. Whether it’s something small like reading or working out, or something with higher stakes like starting a company.

We can just start. It’s time.

My internet went out

So I had to write this on my phone.

It’s the little things we don’t appreciate until they’re taken away from us.

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

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

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

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

But this time, I had an insight.

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

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

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

1) Expressing gratitude is euphoric.

Let’s get the selfish stuff out first.

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

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

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

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

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

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

That sounds kind of businessy. Let me explain.

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

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

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

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

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

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

Here’s what I mean.

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

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

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

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

I wrote one of these letters to my dad.

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

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

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

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

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

Then see how they light up.


Merry Christmas, ya’ll!

2 days of rest

I’ll be taking the next two days off.

Enjoy your holiday with those you love!

It doesn’t take much

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

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

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

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

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

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

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

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

It really doesn’t take much to express that.

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

It sparked a question for me to ask consistently.

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

The answer is never anything complex or demanding.