Chapter 56: The Paradox Of Your 20's

I turn 30 today.

Which is really fucking weird to say.

It feels like just yesterday I was graduating college and hightailing it on a plane to Thailand with some of my best friends.

Flash forward to the final week of my 20s, and I can’t stop thinking about the paradox of this decade.

Your 20s ask a lot of you.

Pick a career. Make money. Build friendships. Make memories. Stay in shape. Travel. Find a partner. Save. Figure out who you are. And do it all at once.

You’re handed a massive checklist, but little guidance on how to juggle it all.

When I was 23, I thought I had it all figured out.

In hindsight, I didn’t know shit.

But I did make a handful of deliberate choices that benefitted my future self, even when those choices reduced comfort, fun, or certainty in the moment.

So in today’s letter, I want to share the five decisions I made in my 20s that put me in a position I’m proud of heading into my 30s.

Decision 1: Prioritizing sales experience (21)

During my senior year of college, I got a job at a tech company.

My schedule looked like this:

Wake up at 6:30

Lift at 7

Work from 8–1

Class from 2–5

Practice from 7–9

Between classes, work, and my final season of lacrosse, I had limited free time.

But I learned how to sell, helped friends land jobs, built teams, and got mentored by our CRO as the company grew from 30 to 300+ people.

By 25, I was a director at one of the fastest-growing startups in San Diego.

I didn’t know it at the time, but this was the best decision I made in my early 20s.

Decision 2: Embracing solitude (26)

After college, I lived (and worked) with some of my best friends.

It was exactly what you’d imagine. Daily shenanigans, big nights out, and making great money while working at one of the fastest-growing startups in San Diego together.

For a while, it felt like a dream.

But after three and a half years, I knew I needed to make space for what came next.

So I moved out to live on my own, about twenty-five minutes away from 99% of my best friends.

I still remember my first dinner sitting on the beach near my new place in Cardiff, realizing this decision would likely alter the course of my life.

With fewer distractions, I began using my time more intentionally.

I started reading, writing, and reflecting more.

I stopped going out simply because it was the weekend.

Mostly, it just gave me quiet. And I didn’t realize how badly I needed that.

Decision 3: Stacking proof (27)

By this point, I had honed a money-making skill and created space to think more clearly.

What I hadn’t done yet was prove to myself that I could build something outside the world I already knew.

Seaweed Cowboy started with a conversation in a friend’s backyard.

It was the collision of the sales skills I’d built and my natural pull toward creativity, story, and adventure.

It became one of my favorite chapters of my 20s.

We made short films, told stories for brands, and created lifelong memories.

I’ll never forget standing on stage at our first sold-out premiere, realizing that moment stemmed from a simple idea shared in a backyard twelve months earlier.

It became a six-figure business in the first year.

But this decision wasn’t about the money.

It was proof to myself that I could take an idea and help make it real. (s/o to the Seaweed Cowboy boys — none of this would’ve happened without the squad)

After that, I stopped wondering whether I was capable of building something.

Decision 4: Quitting drinking and embracing endurance (28)

On January 1st, 2024, I woke up hungover.

I stood in front of the mirror, frustrated, and finally admitted something I had been avoiding for a long time.

If I wanted any chance of living up to my potential, I had to quit drinking.

By that point, I’d had too many Sunday “I can’t keep doing this” conversations, only to fall back into old patterns.

I realized willpower alone wasn’t working…

What I needed was structure (and a reason I could explain to others.)

So at 8:37am on January 1st, still drunk from New Year’s Eve, I signed up for a Half Ironman.

The next day, I dove headfirst into training and channeled my energy into something productive.

Ninety-nine days later, I completed my first 70.3 Ironman.

Three months after that, I paddled 23 miles across the Catalina Channel.

Four months after that, I completed my first full Ironman.

By that point, I had zero interest in drinking.

I was firing on all cylinders and in the best shape of my life.

Quitting drinking gave me the clarity I had been craving.

But endurance gave me something deeper.

It allowed me to look in the mirror and be proud of the man looking back.

It gave me a deep conviction in myself.

Somewhere along the way, I stopped second-guessing myself.

Decision 5: The leap into the unknown (29)

In the months leading up to turning 29, I knew what I needed to do.

After eight years in tech, producing short films, and becoming an Ironman, I needed to go all in on myself.

I sold 80% of my things and moved out of San Diego with no job, no income, and no plan B.

I left behind $15–25k per month in earning potential to bet on a vision I couldn’t fully articulate yet.

That same month, I came across a sign in a restaurant. It read:

“I don’t know where I’m headed from here, but I promise it won’t be boring.”

I’ll never forget that moment, because it captured exactly how I felt.

Even though I was committing to moving across the world, what I was really committing to were three things.

• Applying my endurance mindset to reinventing myself.

• Building media leverage through writing and short-form video.

• Using that leverage to build businesses aligned with the life I wanted to lead.

But the most important part wasn’t the outcome.

It was taking the leap, and learning to roll with the highs and lows that came with it.

The pattern is clear

I didn’t see any of this as a pattern while I was living it.

Honestly, I wasn’t thinking that far ahead.

But looking back now, I can see how each decision quietly built on the last.

I didn’t “find myself” in my 20s.

But I am entering my 30s as someone who is comfortable with uncertainty, willing to take calculated risks, and committed to playing the long game even when the path is unclear.

That mindset, combined with the skills and leverage I built along the way, has me more excited than ever about what comes next.

Wrapping up

I don’t pretend to have it all figured out at my ripe old age of 30.

But I have spent a lot of time thinking about my life, my choices, and how I want to live.

If there’s one thing I can leave you with, it’s this:

Pursue a future version of yourself you admire.

How do they think? How do they spend their time? What skills do they have? What habits do they practice? How do they make decisions? What do they value?

The clearer you are on that version of yourself, the sooner you can start moving like them.

And while this letter reflects on my 20s, the same idea applies whether you’re in your 20s, 30s, or 40s.

These choices shape your mind, your body, and how you show up in the world.

Don’t get wrong, there is no one “right” path.

The decisions I made are mine, and mine alone.

All you have are the cards in front of you.

And how you play your hand from here will dictate your future.

No pressure or anything :)

—Dodds

P.S the doors for the next cohort of story30 open this week. If you want to work with me to build a short form content strategy that grows your audience and business, you can jump on the waitlist here.