Financial Freedom Isn’t What You Think It Is

What it’s like to “get there”—and where we get it wrong.

Image by Kyle Kesterson

In 2021, I, like many others, experienced a bout of good fortune when some of my investments suddenly skyrocketed. For much of that year, I found myself in a financial position in which I felt that I would never have to work again (“felt” being the keyword here, as I was not in the same position come 2022, when certain markets dropped upwards of 90%.) Ultimately, I was wrong—I did ‘have’ to work again if I wanted to maintain my current lifestyle. But for about a year, I was living a life of total financial freedom.

For that short period of time, I had “made it.” This is what the American Dream is all about, right? Getting to a place of zero financial limitations. The millennial version of that dream is the FIRE movement (“financial independence, retire early”), which preaches a path to escaping the hustle so you can kick your feet up at age 35 or 40 and live entirely off your investments. Since FIRE took off a few years back, Finfluencers across the Internet have shared countless videos and blog posts with tips on getting aggressive with saving and investment for the ultimate purpose of never having to work again.  

Prior to achieving this milestone myself, I had a deep desire to be able to finally relax around money. For so long, I couldn’t wait to “get there” so I could truly unwind and chill, perhaps for the first time in my life. I romanticized this ideal of total freedom: I don't have to do anything. I’m finally free. It’s going to be amazing.

I had worked my entire adult life to get to this point, and then suddenly, almost overnight, I was “there.” And much to my surprise, for the first month, it didn't feel nearly as great as I thought it would. In fact, I felt pretty nervous; even scared. What if I blew all my money? What if I made some big mistake and it all disappeared? I had trouble sleeping. I was ruminating a lot. I was tense and on edge. This definitely wasn’t the relaxation and ease I was expecting.

Then the clouds parted and I was able to settle into my new existence for a good three or four weeks. I felt genuinely relaxed. I was confident, happy, and feeling secure, and I started to imagine all the incredible things I could do with my newfound freedom. Life was good for that month.

Then I decided to stop working on a project I was building at the time, partially due to the windfall and partially due to some feelings of frustration and misalignment. I now had a pile of cash, so why bother dealing with the challenges of pushing the project through to completion? I decided to bow out. 

Before long, those nice, relaxed feelings were replaced by more difficult ones. The hollow feeling of lacking purpose in my life started to creep in. Then there was the loneliness of wanting to do things with other people during the weekdays, but they were all busy working. I also started to feel a bit useless because I wasn't contributing or being of service. Rather than feeling free, I felt empty. Pretty soon I was miserable in this new existence of financial freedom.

Whenever things are feeling off in my life, I do some introspection to uncover why I’m feeling the way I feel and what it is that I really want. With a little digging, it quickly became clear that what I actually wanted was to be of service. I wanted to have a purpose and to contribute to the lives of others in a way that was meaningful. I wanted to be connected to my community and engaged in important conversations. That was what mattered most to me. I realized that no matter how much money I had in my bank account, one of my main priorities in life was to be engaged with others in truly meaningful ways—ways that filled my cup and brought positive change to people, companies, and communities. 

I’ve seen the FIRE movement and the tech-world dream of selling your company for a small fortune confuse a lot of people about the true meaning of financial freedom. The end destination is not necessarily sitting on a beach or being on permanent vacation. That lifestyle gets old very quickly. Most people I know who have made it to that particular destination on their path have ultimately gone back to work doing the things they love or at least get some enjoyment from. 

My brief stint of “living the dream” taught me that our notions of financial freedom can easily become a trap, offering us an alluring opportunity to avoid the inevitable challenges and hard work involved in doing things that matter in the world—things that ultimately bring meaning and purpose to our lives. 

For me, real freedom is being able to work in a way that meets three basic criteria: doing what you love, what you’re good at, and what others want and/or need. The place where these three things collide is the sweet spot of a life well-lived. And despite what it may seem, you don’t need a ton of money to do that. What you need is the willingness to invest the time and energy in figuring out what you want to do, and the tenacity to find a way to do it, even if that means starting small and building gradually over time. In fact, when it comes to this equation, it may be more beneficial to have less money because it forces you to engage in some kind of (hopefully purpose-filled) work. For whatever reason, when I had the money, I opted out of being on purpose and it really sucked. It was an opportunity to isolate myself, to withdraw from community and connection. Something that I ideally will never do again. 

For the last two years, the market has been way down. My wife and I have a mortgage and (hopefully) kids on the horizon. I’ve been working now for a couple of years as an executive coach, a vocation that satisfies the equation above for me. Given the lifestyle I want to live, I’m definitely not financially free at this moment, and it feels good. I’m grateful to spend my time doing something I’m great at that fires me up and provides a valuable service to others. I feel a sense of purpose. I’m connected to others in a very meaningful way. I feel the energy coursing through my spirit. I genuinely enjoy the way I spend my days. Going forward, no matter my wealth, fulfilling this equation will be my MO. There’s no amount of money that would tempt me to walk away from this, because it would also take my meaning, sense of purpose, and well-being with it.

The way we define freedom is deeply personal to each and every one of us. It’s worth reflecting on what financial freedom really looks like for you: Is freedom never having to work again? Is it being your own boss and being able to take as much time off as you’d like? Is it the equation above—being able to do what you love, what you’re good at, and what others want and need? Is it the ability to provide for your family without stress? Whatever the answer is for you, start to shift your time, energy, and money in the direction to create a life of true freedom and purpose. 

Along the way, give yourself some time to kick your feet up on the beach, too. I bet you’ll find that after a few days or weeks, you’re ready to get back to working on what you love.