Build your career while traveling the world

And a farewell to all my friends and family

Greetings from Canggu, Bali.

Yes, I cut my hair. No, I didn’t mean to cut it this short. It’ll grow back.

In 2020 I read Phil Knight’s memoir, Shoe Dog—the story of Nike. In the book, Phil talks about the opportunity he saw to bring high-quality Japanese shoes to the US market. But… he wanted to travel the world first. So, he put his business goals aside to enrich himself.

The perspectives he gained while traveling helped him build Nike into the behemoth it is today.

Shoe Dog inspired me greatly when I first read it. In the years since flipping through the final pages, I’ve spent over half the year traveling.

Unlike Phil, I didn’t have a clear idea of what kind of business I’d build after traveling. I just knew seeing more of the world would expand my horizons. And it certainly has.

In fact, I’ve been able to travel the world while increasing my salary 300%. My career didn’t suffer after making this decision. It flourished.

Lifestyle design comes first

I didn’t just end up here. I’ve wanted to travel since my early twenties. I just didn’t know how I should approach it without sacrificing my career and a juicy tech salary. I also have people that rely on me to support them. How could I financially support my mom and siblings while traveling without compromise?

After Covid, the marketplace decided that knowledge work could be done from anywhere. Bingo. This was not a new idea, it just became more widely accepted after lockdowns. In any case, the stars aligned and I knew what I needed to do.

My criteria for my next role was simple:

• This role only needs me to own a laptop and have internet access

• There is at most 1 meeting I need to attend per week for this role

• My performance is measured on my outputs (impact), and not my inputs (time)

At my current company, we’re all aligned on work-life integration. We’re also encouraged to travel and work anywhere. It’s a good fit. I feel acknowledged and validated in my needs, and that makes me want to do my part to help us grow.

By the way… If you want to realistically travel the world and make six-figures, go learn Product Design, Software Engineering, or Digital Marketing. Anything else is a waste of time (too many useless meetings to meaningfully travel).

There are risks in staying complacent

Every time I fly somewhere new I am consciously leaving my comfort zone. I have to adapt to my new environment and create a new routine—many times in a country that is not English-speaking. I got a taste for this feeling in my mid-twenties when I decided to be homeless in the Bay Area for 7 months 🤪

This constant pressure has helped me grow exponentially as a person.

But the lesson doesn’t stick. My early-to-mid twenties feel like a blur. What I did every day was mostly the same. For years I stagnated. I realized that the most dangerous thing that can happen to anyone is operating at an unconscious level.

But by challenging myself every time I go somewhere new, I have clear chapters in my life now on things I’ve experienced, where I’ve learned something new, and when I’ve had a specific mindset shift.

Novelty really is the spice of life, fixing what would otherwise be a bland existence.

Your environment heavily influences you

Every time I go back to the US I feel terrible—physically and emotionally. The food makes me bloated, there’s the threat of gun violence every time I go out, getting ill could mean bankruptcy—the list goes on.

It’s the best country in the world to get rich, by far, but you don’t need to live there to take advantage of its benefits anymore. In fact, the ideal situation now is to earn in dollars and spend them abroad.

And lord knows, I need a change of pace. Vegas literally makes me sick now. I think I’m spending 6-8 months abroad just to push back the depression I feel when I look out the airplane window and see nothing but brown landscapes and the same copy-pasted homes.

So, like I did all those years ago deciding to drive to the Bay Area with no plan, I’m doing something similar in late July/ August (but with a bit more planning).

I’m getting a one-way ticket to Barcelona… and not coming back to the US until I finish the one goal I didn’t achieve in my twenties: build a million-dollar business.

I’ve toyed around with building businesses in my twenties. Nothing has really stuck, but I also wasn’t focusing on the right types of businesses. I was going after get rich quick schemes, trends, and not solving a deep problem. Most importantly… I didn’t stick to anything.

Am I quitting my job while I entertain this plan? Absolutely not. Like I said, you can travel the world while building your career. I enjoy the people I work with, and I have the freedom to do whatever I want, wherever I want.

But I’m hungry. I’ve almost reached the top of what I can earn as an individual contributor. Some months I’ll spend $20,000 and feel like I’m still not spending money on the things I want to.

The next step in my career is management, which means meetings all day, which means not traveling comfortably. Been there and done that as a Product Manager.

For me, it’s not enough to have a successful career. I feel like I’d have wasted my potential if I don’t build something and look back on my life when I’m older. I want to flex my ego further outward.

Burning the boats

I’m effectively excommunicating myself from the US until I build something that generates $100,000/mo. Just for the hell of it and because it sounds fun.

What about family or friends? I will miss them, but won’t this be a great story if it works? Even if it doesn’t?

Yes, yes, I know this sounds a bit excessive. Perhaps you’re right. But only imbalanced people generate enough momentum to make meaningful changes in their lives. And I am a fan of making life-altering decisions to push my personal growth forward exponentially.

If you enjoy my antics and want some light entertainment as you sip your morning coffee, make sure you stay subscribed. There is more to come.

- Jonathan