From art-school dropout to $12k/month world traveler

I have no right to brag.

None of this went according to plan.

But I think it makes a decent story, and I hope there’s something useful in it for you.

Art school was a mistake

When I was 21 years old, I dropped out of art school. I had 1 year left to graduate.

It was an emotional decision, not a rational one. I remember looking at my courses¹ for the semester and thinking, “Why am I even doing this?”

I knew why. I picked art because I was already good at it, and I didn’t want to work too hard.

And here I was, 3 years in, frustrated over my pointless classes. You reap what you sow.

I thought about the $140 textbooks I’d have to buy and never read. About spending a year going through the motions to get “good enough” grades.

All for what? It wouldn’t help me get a job. Artists don’t get hired for their grades. They get hired for being exceptional. The best artists practice obsessively, every day, to master their craft.

But I wasn’t like that. I like art, but I didn’t love it. It took me 3 years to realize that I would never be a professional artist. I was wasting my time.

Now what? I could start over, get a real degree, get a safe job, all that.

But I was sick of classes. Tired of busy work. I coudn’t see myself starting over. It felt like defeat. Not, I wanted to take charge of my life. To spend my time and energy on the what I wanted, not what some curriculum said. And I wanted to travel the world, while I was still young and free, before life’s burdens made it impossible.

There was only one option. I’d drop out, and become a freelance graphic designer.

How to make nothing and influence no-one

The same day I dropped out, I found my first freelance gig on Craigslist. $30/hour, and it was an exciting new startup. Things were looking good!

The first project was small, but I obessed over it. I wanted it to be perfect. 6 hours later, I proudly sent my client the designs.

They responded, “It looks good, but come on, this was not 6 hours of work. Don’t try and bullshit me.”

He paid me for 3 hours, then cut contact.

I had to find more clients. It was hard.

Big business had design teams. They didn’t want to hire some random kid.

Small businesses didn’t see the ROI in design. They’d pay $50 for a logo, but I couldn’t live off that.

I tried for months, but I couldn’t get enough clients.

A job is good too

Accepting defeat, I got a job. It was a little 8 person startup. They paid me $15/hour to make infographics for their blog.

It wasn’t what I’d wanted, but it turned out to be what I needed.

It gave me a sense of purpose and worth. I had my own desk with my own computer. Because it was such a small team, I felt like my work actually mattered. And the pay was more than enough to support myself. I felt confident for the first time since I’d dropped out.

Maybe everything would be ok after all.

The bribe that changed everything

A few months in, my boss came knocking. He had been trying to hire a web designer, but couldn’t find anyone. He asked me if I’d be interested in moving into that role. I’d have to start studying it in my free time.

No thanks. Not interested.

I was an artist, not a coder. I had peeked over my roommate’s shoulder while he did computer science homework. One look at that horrible wall of text was enough for me. No way, I could never do that.

A few weeks later, boss came back.

“We really need help with this. Can you pause the design work for the next 2 weeks and just go through this beginner video course? We’ll pay you like normal.”

I was being bribed to sit in my chair for 2 weeks and watch videos all day. Even I wasn’t stubborn enough to turn that down.

• Day 1, HTML basics, I was surprised that I actually could understand it
• Day 2, CSS basics, oh, this is kinda like graphic design…
• Day 3, started learning JavaScript, wow, this is…

Wait a second…

I think I like this.

Switch lanes

The more I learned, the more I liked it. By the end of my 2 weeks training, I was sold. This was going to be my new career.

Goodbye starving artist, hello well-paid programmer.

6 months later, the office had gone crazy. Lies, drama, bad vibes abound. I got out.

I job hunted for months. It was soul crushing. My resume sucked. No one responded. I got a lucky break after I submitted a ridiculously high-effort application for an open position at a respectable agency. Starting salary, $56k/year.

I lived frugally² on 25% of my paycheck. I wasn’t sure what to do with the rest, so I just saved it.

Meanwhile, the job quickly became a part of my identity. My parents were proud. My siblings were envious. It was evidence that I hadn’t screwed up my whole life by dropping out. I could get a respectable job, even without a degree.

Besides the money, I felt like I was part of something again. You know how companies say “we’re a family”? It really felt like that. My coworkers became my best friends. I showed up to work every morning with a big smile on my face.

Until they laid me off.

Aight Imma Head Out

It came out of nowhere.

That morning I walked in smiling, that evening I walked out carrying my stuff in a box.

But I was still smiling.

While packing my things, I had seen a silver lining.

I had no job, no responsibilities, nothing to keep me tied to any particular place. And I had a bunch of money saved up.

By laying me off, they had made the choice so easy, they basically made it for me.

I guess I’ll travel the world. ¯\_(ツ)_/¯

I traveled for 4 years, keeping my expenses low, favoring cheaper countries, staying in cheap hostels, or couchsurfing for free. I traveled with a single backpack, taking $40 flights with no luggage fees.

I freelanced as I went, but I wasn’t working that hard. Many months I didn’t work at all, and just lived off my savings.³

Back to work

Eventually I wanted a job again. Freelancing was solitary. I wanted to work with others for a change.

But my ego felt threatened.

For years people had been telling me “all this traveling is great, but when will you go back and get your degree? When will you get a job again? Maybe that place you worked before will take you back.”

I hated the idea. It would be like admitting defeat. No, if I was going to get a job, it had to be triumphant! Something bigger, better.

And for my salary, I wanted to double it. That’s right! Double it! 😤 How you like that?!

(Are.. are we sure? 112k? With a 4 year gap on the resume? 😨)

Yes! Shut up! DOUBLE IT! 😤

The Gretzky Moment

I started applying. A lot.

And got rejected. A lot.

It was demoralizing. What if my years of carefree adventure really had made me unemployable?

After 3 months of rejections, I was in Discord whining about my latest failed interview to a guy I’d just met called LB

LB: My sense is that you should reach out to TT and see if they’re hiring

Me: Thanks for the tip! But it looks like they want someone very senior, 10 years of experience. I have 5 😕

LB: Again, I’d ping them. You miss every shot you don’t take.

I didn’t realize at the time that LB’s little push would change my life.

Getting my dream job

After talking to TT, I wanted that job bad. I didn’t even realize I was capable of wanting a job that badly.

I spent the weekend building a demo that I hoped would knock their socks off.

When I sent it to TT my mind was racing.

• “What if they’re too busy and don’t see it.”
• “What if they already hired someone while I was busy making this thing?”
• “What if it doesn’t work properly on their computers?”
• “What if I just wasted all that time for nothing?”
• “How stupid am I, doing a stunt like this instead of just sending my resume like a normal person?”

TT responded. The CEO had seen my demo. His reaction: “Please instahire”

A few days later, I signed the contract. They offered me 12k/month. 144k/year. It was even more than double my last salary. I couldn’t believe what I’d done.

Easy come, easy go

Everything was amazing at the start. I was strapped to a rocket that could only go up. We were an all-star team, growing fast, changing the world. My family was blown away by my new salary. I felt like a rockstar.

But soon, the rocket sputtered and fell back to earth. Layoffs and cutbacks. I was out before the end of the year.

While the job was short-lived, it left a lasting impression that I didn’t expect.

It made me realize how I’ve underestimated myself. Before that job, I wouldn’t have thought I belonged on a team like that.

These guys were like legends, with accomplishments and decades of experience that made me look like an amateur in comparison.

And yet, I earned my spot alongside them. I did great work, and I was valued and celebrated as part of that team.

I try to recall that memory whenever I doubt myself. There’s the proof. I really did it. I was good enough for them. I was good enough for my parents and family. My friends. And most importantly, I was good enough for me.

So what?

There’s a lot of things to take away from my story.

If you’re cynical, you’ll note the huge role that luck played, and how my successes were temporary.

Well cynics, you’re totally right!⁴ Just don’t forget: luck is always a factor, and everything is temporary.

If you’re more optimistic, you’ll notice that a lot of my good luck was actually the opposite of what I wanted.

• Dropping out. I didn’t want that. I really thought I’d become a professional artist, until I realized too late that I wasn’t cut out for it.

• My design job. I didn’t want that. I wanted to be a freelancer, the job was a last resort when I failed to find clients.

• Learning to program. I fought against it! My boss had to bribe me to try it! I was stupidly stubborn, I had no idea how much of a favor he was doing for me.

• Traveling the world. I had dreamed of it ever since I dropped out, but there was no way I’d quit that comfortable job at the agency. Laying me off, they made the hard choice for me.

If luck can work so strongly in your favor even when you’re resisting it, imagine what could happen if you cooperate?

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