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  • Writer's pictureDillan Taylor

9 bite-sized lessons from 2023

This year, I moved to South America, learned Spanish, got a girlfriend, and launched a new company.

Here are my favorite lessons I learned in 2023.


I. There are people dumber than you, worse off than you, and less ambitious than you...doing exactly what you want to be doing. They just put themselves out there more.

My buddy told me that when I was nervous about moving to Argentina.

This year I met tons of traveling entrepreneurs working from their laptops. Most of them were lovely, super sharp, and way more skilled than me.

But some of them were morons.

I talk to lots of people working 9-5s who want to jump ship and build their own thing. They view it as this daunting and risky leap of faith.

But there are dummies who are doing it. They're making great money and they're loving life. That doesn't mean it's easy and it doesn't mean anyone would thrive being a creator or entrepreneur.

It just means if a college dropout of average intelligence like me can do probably can too.

II. You've already accomplished goals you said would make you happy.

(From Uncle Alex Hormozi.)

Here was my dream (ie: the checklist that once completed would make my life easy every day forever):

  • run my own business

  • make $10k in a month

  • be free to travel and live abroad

  • be in great shape

  • have thriving relationships

I have all that stuff. It's amazing and I'm so grateful it makes me cry sometimes...

But I still feel tired, insecure, and unsure. I still often crave more.

We're wired for dissatisfaction and anxiety. We need missions and projects to work to play.

So I think it's just about finding the game you really want to play. Where you're dying to get out onto the field every day. It'll be challenging. You'll want to give up sometimes. But you'll only get better as the years go by and have more and more fun along the way.

It's not: "Once I get this result, I will be happy."

It's: "So long as I am playing this game, I am happy."

III. The #1 privilege in life isn't race or's being amazing at what you do.

If your product or service solves people's problems, they will buy it.

If you're fun to be around and make people's lives more fun and fruitful, you will have friends.

If you love, support, and communicate well with your partner, your relationship will last.

Great things happen to those who show up on time and keep their promises. They get invited to things. They get customers. Doors open for them.

IV. You don't have to figure out why. Just move on to what you're going to do about it.

I've coached lots of people who start the session saying they want to figure out why they do a certain thing.

It sounds beautiful and powerful. Let's understand the root of this thing so we can remove it or change it, right?

But I've learned that diving deep into the why is often just procrastinating the real work of doing. Here's how the convo usually goes...

Client: "I want to figure out why I feel so insecure as a business owner."

Dillan: "Great! Once you figure out exactly why you're insecure, like it's 100% clear...what would you do next?"

Client: "Well...I'd reach out to more potential customers, finish the website, and stop comparing myself to people on LinkedIn."

Dillan: "Awesome, let's start there."

V. Are you doing good or sounding good?

It's easy to criticize. It's hard to come up with alternatives or solutions.

The biggest turnoff for me in any human being is cynacism: complaining, critiquing, and whining without doing anything about it or offering anything of value.

Being pessimistic doesn't make you cool or witty. It's boring and super low-risk.

Because if the pessimist is wrong, they don't have to suffer any consequences. It's the person who risks betting something will work out...who suffers the pain of being wrong.

To be clear, we need people to criticize bad behavior and inefficient systems. It's how we advance humanity and build better stuff.

But in this modern age of internet heroes, it feels like looking good is more important than doing good. Folks have gotten adept at dunking, shouting down, and saying all the just and "correct" things.

But what does that actually do? You made a snide comment toward someone you deem to be racist. So who have you helped and how have you helped them? Or have you only helped yourself appear more righteous? I have no clue, but it's an important question to ask yourself.

Most people actually fighting the good fight aren't posting in the comment sections or saying words at a dinner table. They're reporting from the front lines in Israel or starting organizations. I know folks who talk about injustice. Then I know people working at companies who give health care to low-income communities.

Doing good is 100x better than sounding good.

VI. If you have no clue how to start a business, just put a service together and give it to 100 people for free.

Make an offer so good, people feel silly saying no to it.

To start Grindstone, I invited 10 creators to get 1-on-1 coaching and a community of calls, interviews with successful creators, and customized help with their content.

For free. Shockingly, these were the easiest sales calls of my life.

We then treated these creators like they were paying us $10,000 per month. The goal is not to get them to pay; it's to blow them away.

Some of them started paying. Some referred their creator friends. All of them left amazing reviews for the website.

Make something awesome and give it away for free. Good things will follow.

VII. Never answer "How are you?" with "busy."

It's the most boring answer possible. It's just bragging disguised as complaining.

When people tell me they're busy it lets me know they're not in control of their time or priorities.

So I prefer the word "active." I want to live an active life, not a busy one where I'm rushing from thing to thing.

If you have 10 priorities, then you have zero priorities.

VIII. Take advice from people you want to be like.

Inversely, don't take suggestions from someone you don't want to be like in that realm.

I talk about relationships with people in relationships I want to emulate. I talk business with entrepreneurs I want to emulate. I talk fitness with people who have bodies I want to emulate.

When I lived in the mountains of Envigado, Colombia, I met a fellow traveler in the apartment next to mine.

He was 56, single, overweight, and hadn't been in a relationship in 20 years. Not bashing the guy, just stating the facts.

And he was kindly asking me about my girlfriend. How'd we meet? What's she like?

But then he asked the dreaded question....

"What's her zodiac sign?"

Oh no. I told him I had no clue. Then he suggested I read into astrology because it was a proven science.

He smelled my skepticism.

"It can really tell you a lot about how compatible you are with someone," he continued. "How do you judge that sort of stuff?"

"Uhh," I began. "Usually from how it feels to be in a room with the person for long periods of time, how aligned our life values are, and how well we solve difficult problems together."

He nodded his head absently.

Astrology aside...I was not about to take relationship advice from this guy who had no credibility in the world thriving partnerships. It's like taking investing advice from your buddy who lives paycheck to paycheck and is overdrafting his checking account.

But maybe that's just the Pisces in me.

IX. It's easy to be in the top 1% of something.

This is a photo from my yearly recap. In several categories, I ranked in the top 1% of online chess players.

But I'm no professional. I'm just an above average player who enjoys chess and plays most days. For the last three years, I've watched chess creators, played in tournaments, and gotten slightly better each month.

Most people give up before getting to an above-average level. Actually, most don't even play the game. Whether it's chess, saxophone, or speaking Russian.

The bar has never been lower. If you just show up, do the thing, and don't stop...three years from now you'll look like a master to everybody else.

Effort + Time = Being really good.

How do you learn a new language? Do three lessons with a tutor each week speaking only that language. Then wait three years.

How do you grow an audience with a blog? Write articles each week and get feedback on them. Then wait three years.

How do you get fit? Do 30-minute, strenuous exercise three times per week. Then wait three years.

You don't need the secret recipe. You don't need trendy productivity or diet hacks. You just need to do consistent work and then not stop.


I want to thank each and every one of you for reading my self-righteous babblings. This blog grew from 350 to almost 1000 readers this year.

Let's keep the train moving.

As always, follow me on Twitter for shorter updates and ideas.


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