Financial independence and the freedom to choose…to work?

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More than a year ago, I wrote an article titled “When can I retire?” That piece was largely about achieving financial independence (FI) – that is, when your assets can securely cover your anticipated expenses for the duration of your lifespan without reliance on your current employment income. That said, achieving FI does not mean you have to retire early (RE). It simply means you have the freedom to do so when you are ready. In other words, you have the option to retire. But that freedom gained from FI enables other options as well!

For the last few days I was visiting a college friend. We had a really great time doing all sorts of things, including going wine tasting as pictured here. Hanging out without other people around most of the time (weekday travel is the best, and a real benefit of me no longer keeping a “standard work schedule”) meant we got a lot of time to catch up and chat. Flying home earlier today, I realized his story was a worthwhile jumping off point for an article!

The freedom to pursue a new venture

Until about five years ago, my friend had a very successful career at a fast growing company. He was a business leader at a technology firm that was later acquired by a much larger company. At that point, given his many successes on that career journey, he could have stopped working entirely, just as many choose to do once they achieve financial independence. But he didn’t! In fact, he moved into another career entirely – in a totally different business and segment, at a company he’d helped to found five years prior.

Fast-forwarding to today, my friend is now the CEO of that company, one presently in its ninth year of operation. The business is growing well and he is still working full time. Wait, what? You read that right – and there’s absolutely nothing wrong with his decision! The freedom to spend your time how you wish might including taking the opportunity to be an entrepreneur, to follow your passion, and grow a business. Yes, that may include taking on another job after you leave your primary career. Many people choose this path and find it incredibly rewarding. Sounds great to me!

Is he happy? By all measures I have at my disposal, absolutely. My friend is at a great company, enjoying making products he believes in, working with a strong team of talented people. He and his family are living where they want, and he is no longer traveling the crazy hours + frequency at which he did when he was in his former career. Talking with him, it’s clear that sometimes he misses the positive parts of business travel – as well as aspects of his former career. I can certainly identify with all of that. I loved much about my career! But it’s also clear that he is super happy to be around his family a lot more, helping to raise his kids. I can identify with that too! But wait – wouldn’t he earn more money if he stayed in his former field? 100% yes. And I could say the same thing. But we don’t need to, and we both elected to walk away from our highest earning years to take a different path.

“Yes, there are (at least) two paths you can go by…”

Led Zeppelin certainly wasn’t writing about the then not-yet-named FIRE movement in “Stairway to Heaven”. But that lyric is an apt way to frame the point I want to make: to continue working or not is just one of the high level choices to be made once you achieve FI. The first option can itself take many forms: many continue to work in their existing job for some time, post-FI. It may be because they love the work, or want to keep at it for some period of time. I worked a year longer after hitting my own number. There were several reasons for that, including wanting to finish working on a project of which I was a team member. Other people might elect to stay in their job but reduce their hours or number of days working. Still others may choose to work in a new field entirely, or like my friend, start their own company!

As regular readers will know, I haven’t yet elected to start working in a new career, and I don’t think doing something full time is likely anytime soon – barring perhaps at a business I start myself. Outside of the one day a week I pour wine at a local tasting room, I don’t have “a job” right now. Rather, I have spent most of the first fifteen months since leaving my career exploring different areas of interest to me, learning new skills – like content creation via this blog and the Two Sides of FI YouTube channel, volunteering, and essentially “random walk”ing through a wealth of different things. I’ve also written about and filmed a YouTube episode about all the things I have learned so far after more than a year since I left my career. See those links for more details.

Any of these choices are “correct” so long as they resonate with you and are aligned with your earnest interests. I fully agree with something that my friend told me a few years ago when we discussed my plans to retire early: “People need to feel that they are contributing to something that they are passionate about. Make sure you know what that is.” He’s right! My passions don’t presently include working for someone else, and certainly not in my previous field, but perhaps that will change should the right role with great people comes up! Or if my wife and I elect to start a small business in an area we are passionate about (yes, yes, I know some of you really want me to start a brewery!). Who knows? In the moment, what feels right is exactly what I’m doing: exploring!

What are your plans? If you’re not on the FIRE path but you suddenly won a $10M lottery prize, would you stay in your job or would you do something else? I’d love to hear from you!

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