How I Funded My Escape and Survived Years on the Road.
The day I decided to leave my 9–5, the first thought wasn’t where will I go? or what will I do? —
It was How will I afford this? That’s the question that keeps most people stuck.
The truth is, funding an escape isn’t always glamorous. It’s not some secret lottery ticket or a single big break. It’s a mix of sacrifice, small daily choices, and building systems that get you freedom.
This post is the unpolished version of what it really takes: the saving, the side hustles, the fear, the tools, and the reality of surviving once you’re on the road.
Back then, my routine was predictable: wake up, commute, work, repeat. It wasn’t terrible, but it wasn’t living either. The turning point came when I realized my time — the one currency I could never get back — was leaking away into things I didn’t truly value. You can see exactly why and how I used to feel in my post Why I Left the 9-to-5 to Start A Lifetime Quest (And What I Found Instead).
Packed Offices by Dylan Nolte through Unsplash
But coming back again! The point is, if you’re in a 9–5, you know the trap: you barely have time to breathe, and that lack of time keeps you chained in place. The irony? The only way out is to carve out some of that time for yourself. That was my first real “top of mind”.
Scenes from “The Truman Show,” directed by Peter Weir, 1998. Screenplay by Andrew Niccol
So after I decided to escape somehow from what I felt was not for me, I basically tried to get the most money I could at the moment, while at the same time, reduce all the costs I could.
I started making small sacrifices.
I stopped chasing “little luxuries” that gave me momentary comfort but delayed my bigger goal.
Each “No” to a night out, to a takeaway coffee, to a new pair of sneakers, to convenience, was a quiet “Yes” to freedom.
With that extra I saved in a couple of months, I started flipping things (buying stuff on the internet and reselling them within my country)
It was a way of creating my first side hustle, which basically consisted of 2 segments, sport clothing and beauty salon supplies, pretty much did that for years, even after quitting my 9-to-5. It gradually helped me move from in-person work to remote work, and eventually stuck with it until I bought a one-way ticket.
The spark, the sacrifice and the saving phase
I would like to say to you “be balanced”, but being honest my truth was the opposite, especially after I got the spark of what I wanted to do, I went deep into making it happen, started sacrificing social times, no hang-out that could represent a mixed waste of either health, money or time, woke up 2 hours earlier, dedicated to the side hustle and working out, I got ruthless with money.
Not in a miserable way, but in a purposeful way. Every expense went under the microscope:
Was this moving me closer to escape, or keeping me in place?
I tracked everything.
I cut “leaks” I didn’t even realize I had, subscriptions, impulse buys, eating out just because I was too tired to cook. Instead, I funneled that money into what I called my “freedom fund.”
It wasn’t glamorous, and yes, it was lonely at times. Friends would go out; I’d stay in.
But I held onto this: every penny I didn’t spend was a step closer to my first ticket out.
Parque Nacional Bastimentos, Isla Bastimentos, Bocas del Toro – Panama – by Jesse James Johnson
Building Systems Before Leaving
Saving was only half the battle.
The other half was building systems that would keep me afloat once I left.
(Yes, the first 50% will put you out, but this second 50%, your system is what will keep you on the road, actually going… pretty important right?)
That meant:
Imagining how I would be making money?, how much money do I need at first?
How much money do I need to sustain myself in different places?
How can I also save money on the road?
Una National Park, Kulen Vakuf – Bosnia & Herzegovina – by Jesse James Johnson
After starting to save money and planning the escape.
For me, the decision was to take what I studied and polish every primary and secondary skill,
trying to build a good remote job work profile.
In that way, my plan was:
- Earn and save money, in the meantime, preparing to switch to:
- Remote jobs & freelance gigs in my fields (UX Design & Marketing), teaching online, writing, shooting videos, taking pictures, or creating content, at the end basically anything I could do with a laptop, without the need to be somewhere physically.
- Creating honest budgets I could stick to.
- Do volunteering work to save money on the road. (Yes, you can save a lot of money on accommodation, food, sometimes even getting paid on Volunteering platforms + You can get to know amazing people and often beautiful places! You can check how life is doing workaways, the true experience after more than 10, or directly get your subscription here, it will give us months for free to you and me. :)
- Plan and research potential destinations ahead upcoming the next 3-6 months.
based on the flexible situation of remote working + budget & volunteering conditions.
And then repeat, sometimes flowing according to needs, sometimes trying to get to see a season somewhere specific, visiting a particular city or getting to do something very specific, fulfilling small quests and lifetime dreams, not in order but flowing within, sometimes following opportunities, sometimes following heart… It wasn’t about having it all figured out —
It was about knowing I had enough structure to react and not panic in case things got tough.
Life on the Road
(The Real Cost, The Real Quest)
It is a matter of time, so you know you are embarked on a quest…
Which is beautifully different from a journey:
| Journey | Quest |
|---|---|
| Defined destination | Unknown outcome |
| Predictable path | Full of detours |
| Measured success | Measured growth |
| Comfort zone | Expansion zone |
In a quest, we often start with questions, not answers. We face challenges we didn’t anticipate. We meet people who change us. And most beautifully, we end up becoming someone we never expected.
Tools
You can’t see the future, but you can try to be prepared for different situations.
The following list is a compilation of tools, platforms, and apps that can help you on your quest:
- Learning any skill
- Volunteering
- Looking for Remote Jobs
- Health Insurance
- Checking Visas & Legal Requirements
- Passport Index
- Visa Index
- Your embassy & Destination official entity
- Looking for Flights
- Looking for Routes & Transportation
- Cellphone Data Services
- Planning
- Handy apps & platforms!
I explain more about every single above mentioned in here. Where I also included some bonus ;)
These are a few of the apps, tools, and platforms that helped me before and on the road,
however remember:
1. Reviews are amazing! But more often, the best recommendations come from people.
2. Tools are just tools. They won’t make the leap for you. They remove friction and give you the confidence to try. The most powerful platform you’ll ever use is your own mindset and discipline.
Once you start thinking like whatever the traveler you are, or want to be — stretching resources, adapting, being resourceful, saying yes to opportunities — the whole world starts opening up.
So my point is,
3. You don’t need to wait until you’ve downloaded every app or found the “perfect system.” Pick one, start small, and learn as you go. The tools will help.
But the road itself will teach you far more than any platform ever could.
Us at Asenovgrad hike, Bulgaria – by Jesse James Johnson
Falling in love… step by step with Slow Traveling
I learned quickly that slow travel was the secret weapon. By staying longer in places, I cut transport costs and could negotiate cheaper rent. I picked up work exchanges, volunteered at hostels, and got creative with meals — street food over restaurants, local buses over taxis. It’s a blended feeling of being on the road, but at the same time getting to possess your favorite places in another city, in another town.
Of course, it wasn’t always smooth. There were nights I stretched the last bit of cash, times I questioned if I had made a huge mistake. But there were also the small wins: realizing I could live on half of what I once thought necessary, or waking up in a new city knowing I had bought this freedom with my own discipline.
What surprised me most wasn’t just the lower cost of living we are able to create for ourselves —
But how my definition of “enough” completely changed. Back home, we often thought security meant a steady paycheck and all the bills on autopay. On the road, I learned security could also mean fitting everything I owned into a backpack, knowing I could make $10 stretch across three days,
and trusting that memories, new friends, life experiences and resourcefulness were more valuable
than a padded bank account.
Top Left, Galapagos Island, Ecuador – Top Right, Inishboffin Island, Ireland – Bottom Left, Saboga Island, Panama – Bottom Right, Huacachina, Peru
by Jesse James Johnson
Personal Note:
I’ve never kept any of this a secret, and I’ve always been open about sharing it —
mostly because if these stories motivate even one person to chase their dreams,
Then all the vulnerability is worth it twice over.
I genuinely believe that if someone truly wants to take this leap, it’s possible.
That belief feels even stronger when I think about people from Panama, Latin America & Caribbean, the Balkans & Eastern Europe, Africa, Asia, Polynesia, or basically any so-called “developing country.” In places like ours, traveling isn’t part of the culture in the way it is in many wealthier nations. It feels almost “out of reach,” not because we don’t dream, but because the system is designed to make it harder to try different things. The 9-to-5 often demands longer hours, commutes are brutal, and workers are far less protected by law. Saving money is harder, and opportunities can seem scarce if not non-existent.
And yes, the deeper you go into some regions, you might find conditions are far worse.
And it is exactly in those most affected places where you could also find the disparity of a passport power, the limitations or advantages that come from luck of being born in one part of the Earth.
And yet, this is also why the growth that comes from traveling is so powerful. The perspective you gain, the independence you build, the ability to see beyond what your immediate environment taught you — these are priceless. For us, stepping out into the world isn’t just about exploration; it’s almost an act of resistance. It’s proof that even when the odds are stacked, the quest for freedom, growth, and connection is still possible.
Una River near Bosanska Otoka with friends Eso, Chris, Abdullah, Maddie and Lorena – Bosnia & Herzegovina – by Jesse James Johnson
Thanks for joining, Thanks for reading! See you soon
– And go for it!
Peace
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This is A Lifetime Quest — and maybe it’s yours too.