Welcome to the Freedom Files

TL;DR — Freedom Files is here. I’ll document my journey to building a life of freedom through time optimization, entrepreneurship and world travel. Learn from my mistakes and lessons.

I was dripping sweat. Shaking uncontrollably. Having just run from gate to gate.

It was November 6, 2021.

I was sitting in the international terminal at the Orlando airport surrounded by what seemed like a Shakira concert full of Colombians. Rethinking my decision to move to Medellín on a one-way ticket just five months after I quit my job and started my own company.

Oh boy… What was I getting myself into? I. Had. No. Idea.

All I knew is I was chasing a feeling. I wanted to feel something.

Two years into corporate life in a gray Midwest city, I felt I was giving up on my dreams.

I wanted to do so many things. To be so many things. To start a business, see the world, experience new things, climb the tallest mountains, meet interesting people.

But in that moment, I wasn’t excited.

I was scared. Nervous. Lost. Directionless.

(Well… Technically, I was heading South. But that’s all I knew.)

In hindsight, I was feeling all those things for the first time in my life. Up to that point…

  • I hadn’t tested myself.
  • I hadn’t gotten to truly know myself.
  • I hadn’t gone so far out of my comfort zone that I couldn’t see beyond myself.

Now, a year and a half later, that’s all changed. I’m the most happy, most successful, most free I’ve ever been.

But that last one – That’s the tricky one.

  • I can choose and feel happiness.
  • I can choose and feel success.
  • But can I choose freedom? Can I feel freedom?

Well… I still don’t have the answers. But that’s what I’ve been exploring over the last two years since I quit my 9-5 on June 7, 2021.

Everyone would say I’m living the freest life possible.

No boss. No bills. A business and life that allows me to travel, meet inspiring nomads and experience really wild things.

But freedom isn’t formulaic. No sir. Freedom isn’t tangible. Freedom isn’t to you what it is to me.

So what is freedom & how do I get some of it?

I don’t know! 🤣 But two years later, I’m a hell of a lot closer to answering those questions than I was.

  • I know freedom isn’t free.
  • I know freedom isn’t a destination.
  • And I know I’m not free in my current circumstances.

I have so much yet to learn from so many free people.

Which leads me to today…

So what is freedom & how do I get some of it?

Welcome to the Freedom Files, where I’ll document my never-ending mission (and others’ too) to a life well-lived – whatever the hell that means.

I’ll walk through all my mistakes, my book notes, my conversations, my lessons learned, my big life decisions – all to help you pick the right paths on your journey too. To live a life freer than you live now.

These are the 3 key areas I’ll explore:

Time freedom —

How can I create more time for myself to spend with my loved ones now and in the future?

what is freedom and how to be free

Money freedom —

How can I create a business and participate in a monetary system that rewards me?

what is freedom and how to be free

Mobility freedom —

How can I explore my own mind and body and the world around it while choosing the right long-term location(s) for myself and my family?

what is freedom and how to be free

I don’t know the answers to these questions. And I won’t pretend I do.

But… I know more than I did two years ago.

Through conversation, content and context, I’ll continue learning and charting my path to freedom.

Join me.

What’s to come?

I’ll continue writing about how I got to this point in my life, what I’m doing to become more free and what I learn from others along the journey.

Who knows what this will morph into? 🤷‍♂️ But I’m curious.

For now Freedom Files is a weekly newsletter. I plan on rolling out videos to accompany the emails and essays as well. But my forte will always be the written word.

Not digging the topic? Opt out if you’d like. You won’t hurt my feelings.

So much to look forward to in 2023. Thanks for being here.

Get essays, event invitations & other resources in your inbox

When you join the Freedom Files (it’s free), I’ll personally send you my list of 17 considerations for moving to a new country or city.

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What should I cover next?

I have a question for you:

If I were to dedicate the next Freedom Files YouTube video to you and one challenge you’re facing right now, what would that issue be?

Typically, I get something like the following:

  • I can’t find a remote job
  • I don’t know the right long-term location for me
  • I don’t know how to start a business
  • I am a digital nomad but haven’t settled in a country
  • I pay way too much in taxes and need a solution
  • I want to invest in countries before they are popular

Let me know by emailing or DMing me. I’ll write about it publicly because many others likely have the same challenge as you do.

Location freedom is near

I started an online business, lived in 10 countries, learned a new language, bought international real estate, and got residency in Latin America – all within 2 years.

It’s possible! I made a checklist to help you live your relocation dream. 

I’ll send it to you ASAP. Just fill out the form below.