Don’t know where to start? Learn from my 3 unconventional first steps toward ultimate freedom

TL;DR — Ultimate freedom comes down to small steps and big leaps over time. What you do today forms what you will accomplish tomorrow. I’ve taken my first steps. Learn from my mistakes and lessons.

If you met me two years ago, I was content. Living in the Midwest USA. Working a 9-5.

If you meet me now, I’m a whole new person. In a good way!

  • I’ve 3x’d my income
  • I’ve grown my business to $300k
  • I’ve bought international real estate
  • I’ve traveled and lived in 7 countries
  • I’ve fallen in love with a girl who doesn’t speak my native language

These are all first steps to a truly free life. One that allows me to do what I want when I want where I want.

But it wasn’t all easy. And I’m not there yet.

So take it from me – these 3 tips to take your first steps toward a life that feels like a dream.

1. Write your own obituary

Sounds morbid. I know. But I can’t tell you how important this step was in figuring out what I wanted to do with my life.

Dream of your funeral.

  • How old were you?
  • Who is attending?
  • What stories do they tell?
  • What do they say about you?

Now write your obituary.

What did you accomplish? Peer into your future life.

James's obituary

This exercise is so powerful is because it forces you to realize …

  1. that you’re going to die,
  2. that you’re probably not living the life you’d always dreamed of,
  3. and most importantly, that you have the opportunity to control the rest of your life.

How amazing is that?

Now, read your obituary and see what things you have to change in order to live the life you want to live.

Work backwards from your deathbed to 10 years from now. What does your life look like and how close are you to achieving your dreams laid out in the obituary?

Now 5 years.

1 year. What does your life need to look like 12 months from now in order to hit your goals?

Like I said, this was lifechanging for me. My obituary was the reason I felt so confident quitting my job with zero plans, starting my own company, leaving my home country, and buying real estate in a South America.

All in under 2 years.

Change is possible. You just have to determine what change you want.

2. Start building before you HAVE to

Don’t do what I did and quit your job with zero plans. Sure, it was a calculated risk. But I wouldn’t recommend you put yourself through the stress I suffered.

Before you take any drastic steps, start building the life you imagine on the other side of that step.

For example, if you’re thinking about quitting your job and starting your own company, start working on that now.

Get a few customers. Work out the kinks on your offer. Make some money. 6 months go by, THEN quit.

Another example: Enjoy your 9-5 job but miserable paying 50% (or more!) tax in Europe? I don’t blame you 😂

Even if you’re not from Europe, the world is trending more this way (read: socialist). You never know when your country may institute a wealth tax, exit tax or just plain unfair tax policy.

Prepare for this. Go remote. Get out of the EU. And set up a residence in territorial tax country (foreign-earned income is taxed 0%):

  1. 🇲🇴 Macau
  2. 🇵🇦 Panama
  3. 🇲🇾 Malaysia
  4. 🇬🇮 Gibraltar
  5. 🇵🇾 Paraguay
  6. 🇸🇬 Singapore
  7. 🇳🇮 Nicaragua
  8. 🇨🇷 Costa Rica
  9. 🇭🇰 Hong Kong
  10. 🇸🇲 San Marino

(List courtesy of Nomad Capitalist.)

Although half of these countries sound absolutely lovely to live in, you don’t even have to live there permanently.

(Note: I sometimes wish I weren’t from the United States, so I had this opportunity to reduce taxes. But sadly, we Americans have citizenship-based taxation.)

So that life you laid out in your obituary? You won’t build it over night. It’ll require work. It’ll require concentration and discipline. It’ll require some sacrifice.

But in the end, it’s all worth it.

3. Optimize for quality of life

Going back to your obituary, can you imagine yourself living where you are right now for the rest of your life?

Listen, I was content in the Midwest.

  • My business network was growing.
  • I had a great social life, a nice core group of friends.
  • I loved the general friendliness and hospitality of American people.

But was it my dream to grow up, marry, have kids, retire and die in Indiana? Absolutely not.

After quitting my job and starting my own thing, I finally had the freedom to be location independent. I could go literally anywhere.

So I up and left.

In the last two years, I’ve lived in 7 countries and explored South and Central America.

I maintain a lot of those relationships I had. I have a much larger network now than I did then. My business hasn’t suffered, nay it’s grown because of my travels.

Yeah, I’ve reduced my taxes and learned a new language and fallen in love with a Colombian girl.

But best of all? My life is better.

  • More sun
  • Better diet and food
  • Better fitness routine
  • More focus on my business
  • Expanded business network

I could go on and on. But the point is this – Optimize for your quality of life.

So that’s my advice:

  1. Write your own obituary and work backwards to live the life you’ve always dreamed
  2. Start building before you have to
  3. Optimize for quality of life – not anything else

Avoid my mistakes while you’re at it 😅

Let me know what you think of this essay. Does it come at a good time in your life? I hope so.

DM or email me.

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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.