From the Barracks to Bali: How Going Solo Made Me Feel More Connected Than Ever
First Digital Dollar Project | Timo Mason
Welcome to the First Digital Dollar Project
Every week, a solopreneur shares the honest story of how they earned their first dollar online. They also join me on Substack Live to dive deeper into their journey.
Each story follows one path from idea to struggle to income. You will see the doubts they faced, the pivots they made, and the exact steps that led to that first sale.
Whether you are still searching for your breakthrough or already building momentum, these stories show you what is possible when you take action.
This post is a guest contribution from Timo Mason🤠 , a fellow solopreneur sharing the story of that first sale.
More on the project:
When I finished high school in Germany, I had 0 clue what I wanted to do with my life.
Only thing I knew was that sitting around in a cubicle the whole day was not gonna happen.
I was the type of kid who marched from one side of the classroom to the other just to get my 10K steps in.
And I heard about this national defense institution where you actually make good money, strolling around.
So the idea of the “get-paid-to-walk” concept of the military seemed... practical. :)
Also, one big issue I had in high school was the cynical mindset of some fellow students.
It wasn’t unusual to see a student with a thick stack of blank paper, refusing to share even a single sheet with a classmate who had nothing to write on.
And I REALLY despise this type of behavior.
So the promise of camaraderie everyone talks about…
The brotherhood, the “dying for one another”, really spoke to me.
So little Timo signed up.
For two years, the military would be my world.
Waking up at 5 am every day, strict rules, and constant uniformity.
I thought I was signing up for purpose and belonging, instead, I found the exact opposite…
Lonely in a Room of Twelve
There’s a strange kind of loneliness that comes from being surrounded by people you don’t connect with.
I remember one mission particularly.
We were twelve guys packed into one room.
Sleeping, eating, and existing together in the same air for 10 weeks (no free weekends.)
It should have felt like a brotherhood.
But while everyone scrolled TikTok, drank, and joked about nothing changing in their lives, I was sitting there on my laptop, building something no one understood.
Most of the guys were in the military because it was “easy money.”
A stable job, no performance goals you have to hit, just do what you get told and you’re good.
This straightforward dullness was seen in every aspect of their lives.
You could feel the emptiness in the conversations, that quiet resignation that this was just how life went.
I didn’t belong there.
So while they were numbing themselves with TikTok and beer, I was quietly creating something new.
A small online project that might, just might, lead me out of the system entirely…
The $25 Moment
Back then, I was still in the barracks, twelve beds, one room, and Wi-Fi from the 70’s.
And while everyone else was killing time, I was building my first Notion template.
I called it Twitter HQ.
It’s a content management system I built to organize and scale my ideas on X.
It didn’t have crazy automations or a Oscar-worthy design, but I was proud of my product.
One night, while I was half asleep after a 5 a.m. wake-up and another day of drills, I got a notification.
“You made a sale!”
Someone had actually bought it.
Twenty-five dollars.
It sounds small, but to me, it was the loudest message the internet had ever sent:
“You can do this.”
Someone out there, not in Germany, not in my barracks, had connected with something I made.
They saw value in it.
And that one sale, as small as it was, felt like a bridge being built to a new world.
That sale wasn’t just $25.
It was proof that I made the right choice, not giving in to the habits of my environment.
Replacing TikTok with Notion & Gumroad, and German beer with some solid instant coffee.
I didn’t realize it at the time, but that $25 wasn’t the reward.
It was the signal that told me it was time to leave everything I knew behind me…
Freedom Ticket
A month before my contract ended, I bought a one-way ticket to Bali.
We were stationed in the beautiful city of Strasbourg, technically France, but you’d never know it from how the guys lived.
Every weekend, they’d drive across the border back into Germany just to hang out in a familiar city.
They had zero interest in exploring French culture, meeting locals, or even trying to learn French.
I despised this mindset of closing down towards new experiences, and just staying with the familiar.
So I went full in “french-mode”
Or at least however far you can go without speaking a word of their language
I even have photographic proof of me holding baguettes, trying my best to embrace “French culture.” :)
Everything about their lives was German.
Their mindset, their habits, their sense of “home.”
Leaving the country, let alone the continent, was unthinkable to them.
So when I said, “Yeah, I’m taking a one-way ticket to Bali next month,” they didn’t even know how to process it.
They were kind about it, wished me luck, shook my hand, but I could see it in their eyes.
For them, Bali was just a vacation spot on Instagram.
For me, it was a declaration of independence.
When the plane lifted off, I thought I was chasing freedom.
But I didn’t realize that the start of my full-time solopreneur journey would max out a completely different emotion.
Connection.
Landing in a Different World
By the time I actually arrived in Bali, I was already half-finished as a human being.
36 hours of travel behind me, sixteen of those spent on the stone floor of the Athens airport, using my backpack as a pillow.
I’d taken the cheapest ticket I could find; I’m still German in that way. ;)
When I finally stepped out into the humid air, everything felt different.
Warm, alive, unpredictable.
There was no uniform or daily routine planned to the minute.
It was chaos, but it was beautiful chaos.
Within days, I started meeting other creators, freelancers, and entrepreneurs.
People who were building their own paths, just like me.
For the first time, I didn’t have to explain why I was doing what I was doing.
Everyone just got it.
There were conversations that lasted until sunrise.
Brainstorming sessions that felt like group therapy.
And shared moments that made me realize I wasn’t alone at all.
The same solitude I feared had turned into connection deeper than anything I’d found in the military.
What I Wish I Knew Before Going Solo
Here’s the thing nobody tells you about becoming a solopreneur:
The freedom part is easy.
Buying the plane ticket, quitting the job, posting the “I’m going full-time” announcement.
That’s the fun stuff.
The hard part is living with yourself when the money isn’t there yet.
So let me save you some pain and share what I learned the expensive way.
The 2 Obstacles That Almost Broke Me
1. The Scarcity Trap (Even When You Have Money)
I saved money in the military.
Enough to survive in Bali for months without making a single sale.
But having money didn’t stop me from living like I was broke.
I’d skip meals to save a few dollars.
Sleep in the cheapest rooms I could find.
Avoid anything that felt like “wasting money“ because deep down, I didn’t trust that this online thing would actually work.
My bank account said I was fine.
My brain said I was one bad month away from failure.
So I lived in this weird purgatory where I had freedom but refused to enjoy it.
Every expense felt like I was betting against my future self.
Even buying decent food, it all felt like I was hemorrhaging money for a dream that might not pan out.
What got me through: The shift from Notion templates to Custom GPTs.
Twitter HQ had proven people wanted systems for Twitter growth.
But I realized I could deliver the same value faster with AI.
So I built the Viral Tweet Typer GPT.
Same niche, same audience, but instead of a notion template where they have to come up with content themselves, it was an AI tool that did the heavy lifting for them.
The best part was I had proof it worked.
I’d written tweets that got over 5 million views using these exact methods.
So when I launched it, people didn’t hesitate.
They saw the results I was getting and wanted the same system.
That product hit different.
Not because it made me rich overnight, but because it proved people would actually pay for what I built and that I could evolve beyond just selling Notion templates.
That psychological shift from “I’m surviving on savings” to “I’m making money from my work” changed everything.
Suddenly, spending money didn’t feel reckless anymore.
2. The Backup Plan I Didn’t Want to Use
I always knew I had an escape hatch.
If everything went to hell, if I burned through all my savings, I could call my parents and ask for a return ticket to Germany.
But that option felt like a psychological landmine.
Using it would mean admitting I failed.
That the whole “solopreneur in Bali” thing was just a phase, a stupid idea from a kid who didn’t know how the real world worked.
So I never touched it.
But knowing it was there messed with my head.
Because part of me wondered: Am I actually committed to this, or am I just playing pretend with a safety net underneath?
What got me through: I stopped thinking about the backup plan as “failure insurance” and started seeing it as smart risk management.
Having a safety net doesn’t make you weak.
It makes you strategic.
The Lesson That Changed Everything
The Dumbest Mistake Is Trying to Figure It Out Alone
For months, I tried to “figure it out” by myself.
Build products, test ideas, fail, repeat.
And sure, I learned a lot.
But I wasted so much time reinventing solutions that someone else had already cracked.
The breakthrough came when I started actually talking to people who were one step ahead.
Not hiring coaches (though that works too), but just asking for feedback, learning from their mistakes, borrowing their frameworks.
The takeaway: Stop trying to be self-made.
Build a network where people will call out your bullshit, show you what you’re missing, and push you to think differently.
What I’d Tell Someone Starting Today
If you’re reading this from a cubicle, a university lecture hall, or a barracks like I was, here’s what you do:
✓ Don’t wait until you’re “ready” - you never will be.
I wasn’t ready when I bought that ticket to Bali.
I didn’t have a massive audience, a proven business model, or even confidence that it would work.
But I did it anyway.
And that’s the only reason I’m here now.
If I’d waited until I felt “ready,” I’d still be in Germany, scrolling Twitter, dreaming about the life I was too scared to start.
✓ Build your network before you need it.
The biggest mistake I made was trying to do everything alone.
Don’t be me.
Start connecting with creators now.
Reply to their posrs, join their communities, offer value before asking for anything.
Because when you finally go full-time, those relationships will be the difference between quitting and scaling.
✓ You’re already proud of yourself (you just don’t know it yet).
If I could go back and tell myself one thing before buying that Bali ticket, it’d be this:
“I’m proud of you for doing this.”
Not for succeeding or hitting some revenue milestone.
Just for trying.
Because most people never do.
They dream, they plan, they talk about it.
But they never actually buy the ticket.
If you’re even considering going solo, that already puts you ahead of 99% of people.
So stop waiting for permission or the “right time.”
Just start.
More Together Than Ever
Today, I’m not in Bali anymore.
Right now, I’m in Thailand.
Next month, who knows.
But that’s the point.
I’m not running from anything anymore.
I’m running toward something I’m building on my own terms, with my own rules.
The military taught me discipline.
Bali taught me survival.
But going solo taught me something neither of those places could:
You don’t need permission to build the life you want.
Not from your parents, not from your friends, not from some system that tells you how you’re “supposed” to live.
You just need the guts to start, and the patience to keep going when it gets hard.
Becoming a solopreneur was the first time I truly felt free to build what I wanted and to prove to myself that the life I imagined wasn’t just a fantasy but something I could actually create.
If you’re ready to start building your own path, I break down exactly how I’m doing it in my newsletter.
AI-powered writing, personal branding, and all that good monetization stuff. :)
See ya soon
— Timo Mason 🤠
The Vision of First Digital Dollar Project
By the end of 6 months, we’ll have created more than content.
We’ll have built proof that there are infinite ways to start.
That your background doesn’t determine your future.
That the first dollar is possible for anyone willing to ship, learn, and iterate.
Your story matters.
Your first dollar was a turning point.
Let’s celebrate it together.
Contributors: First Digital Dollar Project
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Find out how 20 solopreneurs with different products, different offers, different strategies, different paths earn their first digital dollars.
the barracks with 12 guys but still feeling lonely wow, ty for the motivation, I'm always trying to keep my spirits up and uplift others at the same time.