5 things I’d tell my 18-year-old self

Dillan Taylor at Kings Dominion in 2012
Kings Dominion, fall 2012.

My 10-year high school reunion is tonight. I’m thrilled.

I can’t believe it’s already been a decade. I remember wearing the tye die tank top in the photo above, walking through the neighborhood near our freshman dorm, and smoking a joint with my roommate.

“Dude,” I coughed. “When my sister is a freshman in college, we’ll be 30.”

“Whoa,” he retorted.

At the time, that idea seemed so far away that it would never actually come true. But now it’s less than two years away.

Before I take tequila shots with a bunch of people who didn’t know my name in high school, I’d like to reflect on who I was when I graduated. In the moment, I’m sure I felt like I had finally grown up. In reality, I was just an insecure teenager with a driver’s license.

If I had an hour with that 18-year-old doofus, what would we talk about? Would he be impressed by me? Would he judge my mustache? What would I say to him?

Probably these things…

1) You’re supposed to feel confused, self-conscious, and clueless.

No one has their shit figured out, especially at 18. We’re all just dumpster fires hiding behind beautiful Instagram photos and Facebook posts.

It felt like you were the only insecure kid in high school. But you’ll soon realize that everyone else was just really good at hiding it. I didn’t start feeling truly confident in life until I was 23. And that was after failing college and trying to kill myself.

As a life coach, I work with people of all age brackets. I know 50-year-olds who are still figuring out what they want to be when they grow up. You’ve got plenty of time.

You’ll never “arrive.” There is no solution or formula to life that makes the rest of it smooth sailing.

So just keep putting yourself out there and trying new things. Your values and interests will change as you do. But you have to take action and go out and explore.

2) Don’t go to college until you can specifically state what you want to work on and why school is the best choice for that.

You were a trash student, dude. A 2.2 GPA in high school.

Why do you think putting tens of thousands of fake future dollars on the line would make things easier for you? On top of that, you’d have no supervision and access to all the booze, drugs, and women you could imagine. Does that sound like it would produce high levels of commitment and productivity?

Swallow your pride and stay home for now. Get a job at a restaurant, start saving money, and build creative skills. It will suck to see your friends go off to four-year universities. But you’ll be grateful in four years when you’re not paying $1000 a month for a piece of paper you’re not using.

3) You’re not really valuable right now, but you absolutely will be.

I don’t mean you’re useless as a human being. But at this time, in both the dating market and the general economy, you don’t have much to offer.

It sucks to hear, but if you start slowly building your skills, you’ll be super attractive years from now. That goes for women, businesses, and collaborators.

Right now, girls tend to be attracted to fun. You’ll see that when you go out drinking.

But as you go deeper into your 20s, they tend to be attracted to confidence, drive, and security.

So, if you start working out, developing skills you can sell, and treating yourself and others with respect…you’ll be unstoppable.

4) Be as kind as you can as quickly as you can.

The phrase “Nice guys finish last” is bullshit.

What it actually means is don’t sacrifice your values to make others happy. But do care about the happiness of others.

The more you make people feel welcomed, heard, and cared for…the more they will want to be around you and take care of you too. The most important thing in life (aside from your physical health) will be the relationships you build over the years.

Stop talking shit about people. Stop complaining about things you can’t control. Always seek the lesson and value in every situation.

That is the ultimate kindness: seeing life as something happening for you and not to you.

5) Don’t listen to me.

I can talk for hours about all the things I wish I did more of and less of.

I could tell you to take great care of your body, become financially literate, ask out more women, start playing chess or doing jiujitsu, build a writing habit, and never make a Twitter or Instagram…

But you’ll figure all of these things out from sheer necessity.

The best way to learn how to do something is to learn how not to do it. I can give you all these insights because I’ve done so many things poorly.

And to deprive you of mistakes and regrets you’ll experience would be to limit your ability to grow and learn.

Go out and do stupid stuff. Create cringe memories. Overdraft your checking account.

The people who know the most are typically the ones who have been through the most. Put yourself through the wringer and you’ll have no choice but to be the best version of yourself.

Now go, my son. Smoke a bowl and play guitar for four hours.

You’ll find your way eventually.

All my friends are getting married

^^Not the bride and groom.

In the past year, of my close friends: five got married, four got engaged, and two had a child.

As I inch closer to 30 years old, this all feels more and more normal. But it brings up a plethora of emotions as a guy who’s spent most of his life single.

This weekend, I saw one of my best friends marry the woman he’s been with for nearly a decade. The wedding was at a stunning art museum, I got to spend time with my favorite people on the planet, and I got seven hours of sleep in three days.

They’ve been one of those couples who have acted like husband and wife for years: living together, running a business together, and having more chemistry and compatibility than just about any other duo I’ve ever known. I’m not sure which brought more tears to my eyes: hearing them exchange vows or watching them mosh to Panic! At the Disco on the dancefloor.

My friends mean the world to me. My relationships with them are arguably my deepest held value. If I had it my way, every single one of them would do wildly fulfilling work, live long and healthy lives, and be with a partner who supports and cherishes them. So far, so good.

But naturally, there’s a murkier and more selfish side to all this.

I’m proud of the life I’ve created. I have my dream career, take excellent care of my health, and have a disgusting amount of meaningful connections.

But as a human being, I’m not free from the natural comparative thoughts.

When I look around and see 80 to 90 percent of my friends with a partner, when I see so many awesome people with other awesome people, the question is inescapable:

Is there something wrong with me?

Am I…

  • too picky?
  • unattractive?
  • not put together enough?

Logically, I’m aware that the answer to each of these questions is no. But logic rarely wins the battle.

One of my biggest fears in life is that there’s something (or multiple things) about me that makes me unlovable. Something with my personality, my looks, or both.

Again, it sounds like paranoia but it’s very much there. That stays between you, me, and the internet.

To be clear, none of these questions, doubts, or anxieties keep me from putting myself out there. I go on dates. I meet women. I even speak words to them.

But the point of this blog is to share my brain with ya’ll—not to gain sympathy but to articulate a hopefully relatable human experience.

I just deleted the dating apps from my phone after trying them for a month. I know people who’ve had success with them, but I found them to be utter garbage. Performing, ghosting, judging…not a fan.

So aside from continuing to build the life I want, the next step is to get better at talking to women out and about. There are two main challenges with this:

  1. I don’t go out much
  2. It’s pretty terrifying

Hence the “get better” part. But as always, I’ll keep you updated.

Seeing all my lovely couple friends this weekend didn’t make me sad. It fueled me. I’m even more energized to create and go after what I want.

And so I will.

Grow a mustache—Why you should be more polarizing

A man with a mustache and sunglasses looking into the distance

(Yes, ladies. Even you.)

The idea

I want to alienate more people. Let me explain.

The goal is not to go out of my way to piss people off. I don’t want to do or say anything controversial just for the sake of being controversial.

But I noticed recently that most (if not all) of my writing has been curated for anyone and everyone. I’ve been painting with a broad brush in the hopes that any kind of person could sit down and enjoy my stories and lessons.

The consequence of that has been me avoiding certain topics I thought would be lost on most of my readers: the ins and outs of my business, hot takes, possibly-arrogant stories…

Then everything changed when the fire nation attacked.

Whoops. I mean, everything changed when I grew a mustache. Here’s what I mean.

The stache

Dillan Taylor and Hank the dog sitting in his bed
There are more pics of Hank in this blog than there are of me.

I shaved my beard and left my mustache about a month ago. Since then, I’ve gone to a wedding, a bachelor party, and have gone out drinking.

The thing I noticed immediately? Mustaches are polarizing.

Some people (women) wanted nothing to do with it. Others went out of their way to say how attractive they thought it was.

Prior to that, no woman had ever mentioned to me in casual conversation how sexy she thought my face was. I realized that was because I was trying to have a face anyone could get down with.

I went from attempting to reach everyone to only spending time and energy with mustachers. They were bought in. They were my people.

Then I thought about other areas I could apply this.

The meaning

When we polarize people, some folks naturally get alienated. Some hate mustaches. Some don’t care about business tactics.

But for the ones who stick around…the connection with them is 10 times stronger. It’s not about trying to get people to buy in; it’s about investing in the ones who are already bought in.

Lower quantity. Higher quality.

So what does this mean for us?

I’m guessing half of my readership cannot actually grow a mustache (ladies…and some dudes [sorry, gents]). But we can think about this as we create things and as we connect with others.

Do you hold any opinions you’d be uncomfortable sharing with the people around you? If not, that’s a problem. It could be a sign that you just go along with what everyone else thinks and that you have few values of your own.

When creating something, are you trying to make it so everyone can enjoy it (like I did)? When we build something for everyone, we build something for no one. Find your people.

In my coaching business, I have high standards for the people I work with. I want committed action-takers who show up on time and do what they say they want to do. That’s not most people.

And that’s the point. Most people shouldn’t work with me.

It’s not about the ones left behind. It’s about finding our people and giving them the world.

Grow a mustache.

I’m scared to talk to women

A guy with flowers behind his back as he picks up a woman for a date

I’ve never been able to go up to an attractive woman and just start flirting with her. I used to think there was something wrong with me—that I was weak or a coward.

But that’s 95% of dudes.

For many years, I thought having “game” was just one thing: being able to court someone and get them interested in spending time with me.

But that’s wrong. I think having game (a term I hate) is more universal.

Here’s how I define it now: building a connection with another person, making them feel interesting, and looking forward to the next conversation.

The cool thing is, we can do this with anyone, not just a potential romantic partner. All it takes is vulnerability, genuine values, and curiosity. Meta skills like storytelling, humor, and adventure are helpful as well.

My point is: I don’t think I’ll ever be the guy who walks up to a group of women at the bar for no other reason than to hit on them. That’s where I’m uncomfortable.

But when there’s a reason for communicating, that’s where I thrive. Example: My buddy and I spent hours talking to and hanging with this group of women in NYC.

How did we start talking to these ladies? Bowling.

They were in the lane next to us. So it only made sense that we joked and laughed with them as we watched each other throw gutter balls. We had a reason to start building that connection.

So, yes. While I find it terrifying to randomly go up and start flirting with a woman, if there’s a reason for it, I’m confident in my ability to get the ball rolling.

I’ve never written about my dating life in this blog. If you don’t hate it, let me know and I’ll keep spilling the tea. ❤️