Stay on the Path to FIRE or Dive Into Entrepreneurship?

A few years ago when I started seriously planning my route to FIRE, I was fairly confident that I’d be content working the 8-12 years in my current industry until I had saved enough and earned the freedom to call it quits. Over the past few years, and more rapidly over the past 6 months, I’ve been considering the prospects of instead pursing a lifestyle of unjobbing and small-scale entrepreneurship a lot more seriously.

If you’re unfamiliar with the ideas of unjobbing or a lifestyle business, I recommend Jake Desyllas’ awesome book: Job Free (affiliate link) where Jake walks the reader through all of the options for achieving a job free life (as an aside, I also really enjoy Jake’s podcast: The Voluntary Life). My most dominating thought over the past few months has been that trekking to a 40-hour-per-week job every day is suddenly much less fulfilling and more oppressive than it used to be, and I really crave more freedom and flexibility in my life. Since I am only ~20% of the way to my FIRE goal, leaving my job would require that I still earn income, but I would hope to be able to do it more on my own terms, doing things I enjoy.

I’ve saved enough in my retirement accounts that they will grow substantially if left alone for the next 15-20 years, and I believe it would be fairly easy to find fulfilling and balanced sources of income that cover my expenses until then. Depending on how driven I am and how successful any ventures I get into are, I could possibly even continue to save.

If I’m being fair, I believe some of this feeling is fueled by a bit of boredom and burnout in my current job, and I might just need to try out new employment. But… when I look for other career opportunities, I am less thrilled about the idea of reporting to work for someone else than I ever have been.

I am generally risk averse when it comes to decisions like this, and I often stick with what I know will work, but a voice in the back of my mind has been getting louder and louder as it tells me to challenge myself. That voice wants me to take a leap of faith and prove to myself whether I will actually enjoy a more open and entrepreneurial lifestyle. From my current position it looks very appealing, but it might not be as rosy once my hustle is the sole factor in whether I get paid or not.

Another influential factor is the fact that I read and hear positive stories from other people on a daily basis. This is a heavy dose of self-inflicted confirmation bias, but I often listen to entrepreneurially focused podcasts that encourage a life driven by lifestyle businesses and flexible work, and I read lots of stories of other like-minded folks taking non-traditional career risks and being rewarded.

The long-term planner in me also sees this alternate path as more advantageous if we find ourselves starting a family in a few years. Right now seems like a great time to take a risk and try out some new things, before I actually have any responsibility to support a family. If things go well, I earn enough money on my own terms and I’m more available as a parent than I’d likely be when working a traditional job, and if things go badly I at least gave it a shot and can go back to the working world. I’d even like to seriously consider the possibility that if the time comes, I could transition to being a stay-at-home-dad, while still taking advantage of the occasional side income opportunity.

My current half-baked and very vague plan is to save cash until I have enough to cover 1 year of expenses, and then re-evaluate whether I actually have the guts to quit and try out something new. In the mean time, I hope to really challenge all of my fears, but also evaluate the risks. I also hope to really push myself to do as much side hustling as I can, so that I can possibly have a number of promising side hustles to expand on immediately, if I do quit.

So the big question is, am I just being impatient? Will I sabotage the progress I’ve already made toward a fully-funded FIRE life by trying to shortcut my way to a more free life now? What haven’t I thought of that should be part of my decision?

[featured image: Wonderlane]

Posted in Musings
  • This is a tough question and I battle with it a lot. But then I think about the survivorship bias. People who fail aren’t the ones posting about it online. Also my current career handcuffs me the longer I stay as once I start to get the idea to leave for greener pastures, a nice raise and bonus come along. It’s a tough decision but I’m going to work for the man a little longer.