From Debt to Financial Freedom: 7 Lessons from My Journey to 'Retire' at 39

Happy Sunday!

If you’re reading this, I hope you’re finding some time to relax this weekend. Grab your favorite drink, settle into a comfy chair, and let’s talk about a topic that’s probably crossed your mind more than once: achieving financial freedom. 

But before we get into the newsletter, here are some treats for you…

• If you watched last week’s Pay or Quit Podcast, It’s my turn in our two-part series in which we interviewed each other. If you’d like to know more about me and my journey…Listen here or click the thumbnail below!

• If you’re a big fan of learning on YouTube, like I am, check out my channel @ShawnAustinJohnson 

A few years ago, my life looked very different. I was working full-time as a helicopter pilot while my wife ran our small business on the side, and I would help on my days off. My wife and I were in over $175,000 in debt, living paycheck to paycheck, and juggling just about everything to get ahead. But today, we’re financially free, and here’s the kicker: it wasn’t just from our business. The turning point came from being extremely intentional about the lessons we learned and choices we made, and especially from creating multiple streams of income through 43 cash-flowing properties we acquired along the way.

Here are 7 lessons from our journey that might help you reach your own financial freedom, no matter where you’re starting from.

1. Understand How Money Works: Compounding Can Be Your Best Friend—or Worst Enemy  

We often hear about compounding as the magic behind building wealth, but what we don’t hear as much is how it works in reverse when you’re in debt. Our $175,000 debt wasn’t just a number; it was growing every month, costing us even more in interest.

The key here? Learn how interest works before it works against you.  

Tip: Start by understanding what your interest rates are on any debt and create a plan to pay off high-interest debts first. This simple shift can save you thousands over time and is the first building block to gaining wealth. Once a debt is paid off, real progress happens when you take the amount you were paying and roll it into the next debt, compounding your money exponentially.

2. Live Frugally Now to Build Freedom Later 

During the journey, we didn’t live luxuriously—we lived strategically. We avoided unnecessary expenses and kept our lifestyle in check, channeling as much as possible toward debt and future investments.

Example: We’d skip going out to eat and would eat rice and beans and cheap food more often than not. It saved us hundreds each month.