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- I Sold Everything to Travel The World
Welcome to the first Friday edition of…
THE JAILBREAK!
(along with 650+ readers 🗝️)
[read time: 5 mins]
Since I was a kid I’ve dreamed of creating a life of freedom.
A life that would allow me to:
(If you want to watch the video instead… 👇️ )
But I believed I was going to have to spend my life:
Inside a cubicle
Doing work I didn’t care about
Waiting until retirement to see the world
Those moments terrified me but they started my journey of creating a life that was the exact opposite.
How I Got Here…
Around 9 months ago my girlfriend and I sold 90% of our belongings, booked a short-term lease across the country (on an apartment we had never even seen), packed our lives (and our cat 🐈️ ) into one car, and never looked back.
Quick skate break at Black Dragon Canyon on the way to CA
Now I switch locations every few months to explore new cities, to surf and snowboard, or just because I want to.
I’m writing this from beautiful Reno, NV where I plan to spend my winter absolutely destroying Northstar and Heavenly Ski Resort. 🏂️ (Then I’m off to Seattle!)
Here’s how you can do the same:
Step 1: SELL YOUR SH*T 📦️
To live like this you need to start valuing experiences over possessions.
Most people buy and keep things they don’t need.
Most people don’t travel the world.
Coincidence? Nope.
If you want to achieve true location freedom, minimalism needs to become a part of your life because it’s what makes rapid travel possible.
Freedom is the goal. Freedom from unnecessary baggage — and I mean that both literally and figuratively. Minimalism helps with both.
What Stays and What Goes?
This was a question I really struggled with when we were making the jump into this lifestyle and moving 12 hours across the country from Colorado to California.
So I devised a challenge…
We can only take what fits into this Volkswagen Tiguan…
Everything that doesn’t fit in the car has to go through this pipeline:
The Funnel of DEATH:
Sold (If item can help fund moving expenses)
Donated (If item isn’t valuable but someone could use it)
Thrown Away (If item isn’t valuable and nobody can use it)
Left Behind (Items you don’t have room for—AVOID THIS)
The Pain of Minimalism
The first time you try and part ways with some of your material possessions, especially ones you’ve had for a long time — it can really sting.
Circa 2017 Jack shredding some Panic! At The Disco
I sold one of my guitars because traveling with multiple just wasn’t practical but it took me a few weeks to even feel okay with the IDEA of selling it.
Looking back, I haven’t regretted it once.
It helped me pay for the moving expenses that enabled some of the most amazing experiences of my life. (And the person I sold it to could seriously shred so it’s definitely still getting some love!)
Life is full of trade-offs but I’ve never regretted trading in material possessions for meaningful experiences.
Step 2: GET MONEY 💰️
Minimalism is super important but it’s not going to pay your bills.
These are the paths you can take to secure a location-independent income stream that will allow you to work from anywhere in the world.
Path #1: Remote Work 💻️
Fully-remote roles are easier to come by than at any point in history and this is actually the route I took to supporting my location-independent lifestyle.
I learned how to code specifically to land a remote job that allowed me to travel. I spent years learning Python, SQL, and Data Engineering because I knew the tech industry was incredibly friendly to nomads like myself.
Path #2: Freelancing 📊
I like to think of freelance as a stepping stone from a 9–5 to entrepreneurship and it’s a great way to supplement your income, and develop new skills, all while having the freedom to work from anywhere.
I made a list of the Top 20 Platforms for Finding Remote Jobs and Freelancing Gigs if you want to find one yourself!
Path #3: Online Business 💼
Working for someone isn’t for everyone. Lucky for you, the digital age has made it easier than ever to start your own business that will allow you to separate your income from your location.
A few examples:
Digital Products
Newsletters
Membership Sites
E-commerce
SaaS
Content Creation
Step 3: LEAP OF FAITH 🤿
People are less shocked to hear that I sold all my things to travel around the world than they are to hear that I moved into a new apartment without seeing it in person…
Yes, it’s a little risky, but with the advent of 3D apartment tours, video walkthroughs, and just plain old pictures — it’s simpler and safer than you’d think to move across the country without seeing your new home first.
To find a new apartment (we don’t mess with Airbnb) I usually start by scouring the entire area that I want to move on Google Maps.
How far away is the closest grocery store?
Do I need a car to live here? (or vice versa)
Is this a safe place to live?
What’s the closest beach or ski resort?
Can I get my morning pumpkin spice latte???
After that, head over to NomadList.com and see the stats for the place your considering moving too. (Toilet cleanliness score now included! 💩)
There are a million questions that you could answer just by doing a detailed look at the location you’re hoping to move to. So that’s always step 1.
Then it’s time to bounce from Apartments.com to ApartmentFinder.com to Zillow.com and back again! Get a list of all the apartments that match your criteria and price range — BUT DON’T STOP THERE!
For each apartment you like, email the leasing office with your price range, the dates you’d like to live there, and ask if they have any rent specials or hidden fees. (I have consistently gotten $1000 off my rent package from just asking about these things!)
🎥 Video of the Week:
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or…
🤔 Focus Foundry:
(Weekly Tips on Beating Distraction in the Digital Age)
🎨 METHOD:
The Pomodoro Technique boosts productivity with structured work and break intervals. Work for 25 minutes, then take a 5-minute break. Here’s my favorite Pomodoro timer.
⚒️ TOOL:
The Freedom App blocks distracting websites and apps across all your devices. Schedule focus sessions to automatically eliminate digital interruptions and stay on track.
🧠 MINDSET:
Embrace 'Digital Minimalism’ and limit your digital engagements to the ones that are truly important, minimizing the clutter of excessive digital.
Thanks for reading another issue of THE JAILBREAK!
See you next Tuesday,
- Jack Ross ✌️
Jack Ross (Data Engineer, Writer, Nomad)