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  • Writer's pictureDillan Taylor

The biggest lesson I just relearnt

Plaza San Martin, Buenos Aires.

My biggest hurdle growing up was my obsession with what others thought about me. I had to be funny, entertaining, and seen as a cool dude.

It didn’t matter if I actually was these things. So long as the character I was playing was performing well.

I tried to mask my insecurities in middle school and high school by being a class clown and by making fun of others for laughs. Come senior year, I started taking ADHD medication (which I didn’t need) and became twice as self-conscious. Only now, I was too timid to even talk to my friends.

Thank God TikTok wasn’t around back then.

I know none of this is all that unique. Who isn’t an uncertain and anxious mental mess as a teenager? But it seemed like everyone around me had everything figured out at the time. People knew how to be smooth. Guys knew how to get girls. My friends seemed to know things about business and politics I couldn’t comprehend.

But as we’ve all gotten older, I’ve been able to connect and reflect with the men and women I grew up with. Each and every one of them has said the same thing:

“I was super insecure in high school.”

Act 1: Learning something simple

Things got better when I went off to college. I stopped taking Adderall, stopped smoking weed, and started partying and making new friends.

I was becoming more confident. I was beginning to grow into myself. But not for the sustainable reasons I hoped for.

It was mostly the booze.

I still had no idea who I was, what I valued, and what skills I brought to the table. Maybe I could carry on a conversation, but I was still a wildly insecure person.

And once everything came crashing down in 2017, I failed out of college and moved back home. That was the darkest time of my life. But it’s also when I started becoming the man you all read from today.

My self-improvement journey began. I listened to Jordan Peterson’s lectures, started going to the gym, and built a meditation practice. Personal Development 101.

As I became more mindful and more healthy, I quickly embodied one of the age-old pieces of advice:

Stop caring about what people think about you.

It was freeing. I stopped looking at myself through the eyes of other people. I just worked on myself, did my job, and corrected myself when I made mistakes.

There’s a quote I love: “I am not what I think I am. I am not what you think I am. I am what I think you think I am.”

In other words, we have no idea how others actually view us. We just create stories in our heads that are our best guesses. So there’s no point in working tirelessly to figure it out. Should I try to put the puzzle together of what my coworker thinks of me or should I just show up, get my work done, and be as respectful as I can?

I started saying no to things. Derek Sivers calls it “Hell Yes or No.” When faced with a decision, if it’s not a “hell yes,” it’s a “no.”

It felt like I solved life.

Act 2: Discovering nuance

I quit my full-time job in 2020 to start my own freelancing business. I would eventually find life coaching and pursue that as my career.

In the coaching space, we often talk about the concept of people-pleasing: sacrificing your own wants or values for those of other people. It’s often a pernicious habit that drains us and keeps us from doing the things we actually care about.

But then I heard a coach say something that has stuck with me ever since. It was in the middle of a workshop I was running on people pleasing.

“I think people-pleasing gets a bad rep,” she said. “Obviously we shouldn’t be killing ourselves for other people all the time. But I think being a good friend or partner means doing things you don’t want to do from time to time. If you tell your friends you don’t want to go to dinner with them four weeks in a row…don’t be upset when they stop inviting you to dinner.”

This was the first challenge to my “only do what I want” principle.

I love my friends. I cherish my family. Am I jumping with joy at the prospect of every hang, every phone call, every event?

Of course not.

But I’d rather be a person who shows up for the people he loves than put every single decision through a matrix. I want to be able to say I’m sorry. I can set boundaries and make sacrifices.

So this concept of not caring about what others think about me…it was incomplete.

We have to care about what others think about us. It keeps us from acting like assholes, smelling like garbage, and letting our lives rot away. It’s what allows us to make friends and keep them. It’s what gets us hired. Life is significantly better when other people like being around us.

So I went from, “I don’t care about what other people think about me,” to, “I care about what the right people think about me.”

My friends and family. You guys, my audience. My podcast listeners. The folks who care about me and want me to continue to grow. I listen to these people. I use their feedback.

Act 3: Relearning

I’ve been in Buenos Aires for a month now. In one month, I fly back to the United States.

I’m dreading it.

The amount of growth and fun I’ve had here, the people I’ve met, the work I’ve gotten done…It’s been a pivotal moment in my life.

Among the many insights I’ve gathered in my short time here, one sticks out. I think about it when I’m in a taxi flying through the city streets, drinking coffee at an outdoor cafe, and sitting here in this coworking space.

Right now, I’m seated next to around 20 other digital nomads. They come from Europe, North America, and countries that neighbor Argentina. I know many of their names. I’ve partied with a few of them.

Most of them know I have a blog, a podcast, and a coaching business. They know about my travel plans, the wedding I’m in this summer, and my current career goals.

And none of them are thinking about any of that right now.

Not a single person in this room is wondering how I can get more YouTube subscribers, how I can charge more for my coaching, or where I’ll choose to live when the summer is over.

I’m the only person thinking about any of that. They’re all on their laptops reading Slack messages, coding features, or yawning through Zoom calls.

No one cares about how good my Spanish is. No one cares about how jacked I look. No one cares about how big my podcast is growing.

And if they ever do, it’s for a fleeting couple of seconds.

“Oh wow, you have a podcast? That’s awesome!”…Then they go right back to their own desires and insecurities.

Alex Hormozi has a quote I come back to once or twice a week:

We will always be the main character in our movies. So we sometimes make the mistake of thinking other people view us as lead or even supporting actors. But outside significant others and very close relatives, we’re usually just side characters at most and background extras at the least.

Does it make sense to obsess over the opinion of someone who views you as an extra in their movie?

It’s almost arrogant to believe we hold so much power. We act as though the comfort and emotions of others are in our hands. If I go into a cafe and speak horrible Spanish and it’s awkward for the barista…so what?

Did I ruin her day? Will she need therapy because of my horrendous vocabulary?

If so, she has much bigger problems to sort out.


In summary:

  1. Stop caring what people think about you.

  2. But make sure you still act in a way that the people you love and respect enjoy being around you.

  3. So long as you are a kind and respectful person, keep putting yourself out there and doing what you want. No one is thinking about you nearly as much as your anxiety is telling you they are.


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