Chapter 33: What A Life-Altering Decision Looks Like

There are a handful of decisions that shape your entire life.

Most people don’t realize they’re in the middle of one until much later.

But when you zoom out, you start to see the inflection points.

This is a map of mine.

Not because they’re special, but because they might help you reflect on yours.

The ones you’ve made.
And the ones you’re standing on the edge of now.

Let’s start at 18.

18: Choosing San Diego

I picked a college in a place I could see myself living after graduation.

That one decision defined my next decade.

The network I built. The lifestyle I lived. The career I established.

20: Studying abroad

I moved across the world without knowing a single person.

It forced me to get comfortable in the unknown.

I also met Matt, a friend who left a big impression.

Here’s what I took from him:

1. Morning Hundreds: 100 pushups, 100 core, 100 air squats, 100 miscellaneous. Simple. Effective. I still do them to this day.

2. Give First: The law of reciprocity is real. Give more than you take.

3. Learn Sales: After the trip, I got a part-time job with the Padres. I told Matt about it and he recommended I also get a part-time sales job. That advice stuck and pushed me toward my next big decision.

21: Joining a tech company while still in school

From a financial standpoint, best decision I made.

I learned outbound sales. I helped 30+ friends land jobs. I built teams. I got mentored by our CRO. & We grew from 30 → 300+ employees.

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

26: Living alone

After years of living with some of my best friends — through college and post-grad — I knew it was time to grow through solitude.

The post-college chapter was everything you'd imagine. Surfing around work, big nights out, & building a rocketship with friends.

But I needed space.

To think. To evolve. & To reset.

That decision created the foundation for everything that came next.

27: Starting Seaweed Cowboy

One of my favorite chapters.

Born out of a backyard conversation.

A mix of the sales skills I’d built and my obsession with creativity, story, and adventure.

We made short films. Told stories for brands. Made lifelong memories.

And even had a few $20-30k months.

But most importantly, I proved to myself I could build something outside the tech world.

28: Quitting drinking + leaning into endurance

I haven’t talked about this much.

But around 25, I started waking up after long nights hungover, disappointed, looking in the mirror and feeling like I was wasting my potential.

Those feelings drove me to move out and get space from the chaos.

Still, it took almost two years of false starts and falling back into old patterns before I truly committed.

I needed something to explain why I wasn’t drinking anymore.

It started with signing up for a marathon.

Then a Half Ironman.

Then paddling 23 miles across the Catalina Channel.

Then a full Ironman.

Each one built my self-trust.

Each one reminded me what I was capable of.

Quitting drinking gave me clarity.

But endurance gave me confidence.

I felt like I could finally see the future.

29: Moving to Portugal + betting on myself

By this point, I knew what I needed to do.

I talked about rites of passage in chapter 29.

This was mine.

To leave comfort behind. To enter the unknown.

To test myself, evolve, and return transformed.

I made three commitments:

• To apply my endurance mindset to this chapter

• To write, to tell stories, and to master short form video

• & Use that skillset as the foundation to build businesses moving forward

I moved to Portugal with no job, no income, and no plan B.

Leaving behind $15-25k/mo earning potential in my old life.

To bet on a vision and delusional confidence.

Six months in?

I’m closing in on ~30K followers.

I’m helping founders grow their businesses around story & organic content.

The first person I ran through my system?

They’ve added ~100K followers in less than a month.

& have received hundreds of inquiries for weddings & retreats on their property.

(In other words: potentially hundreds of thousands of dollars in revenue)

But none of this would’ve happened if I didn’t take the leap and bet on myself.

Why I’m sharing this

Because there a handful of key decisions that shape your life.

You can change your entire life with one bold decision.

But you often don’t see the impact overnight.

Sometimes it takes weeks, months, or even years.

As Steve Jobs said,

But knowing this makes you more aware of the moments that matter.

For me, all these decisions built on each other.

I’ve spent the last decade:

• Building my mind

• Building my confidence

• & Building my belief system

Studying people a few steps ahead.

Doing hard things.

Rewiring the way I think.

And I’m still just getting started.

If I told you the vision I have for the next 10 years, you’d think I’m insane.

But delusional confidence + willingness to do the work required will take you far.

And honestly… what the fuck else am I gonna do?

I love the pursuit.

I love building.

I love taking ideas and making them real.

I love creating and telling stories that move people.

And I love the impact.

It’s a healthy obsession.

And this is just the beginning.

Wrapping Up

Take a moment and reflect on the core decisions that have shaped your life.

Now, think about what decisions you could make today that will dictate what your life looks like in 5–10 years.

I’ve found zooming out helps.

Think in decades, but act in days.

And if you want to work 1:1 with me in August to design your business’s narrative and organic content strategy — jump on the list here.

Rooting for ya,

—Dodds