Choosing FIRE: considering the top regrets of the dying

I came across this image in a Reddit post earlier today, after which I found this article in The Guardian. My initial response was to share the picture on social media and then with my friends on the FIRE Discord server. Why the latter? Because I was sure it would resonate with them. Contrary to one popular dismissal of the financial independence/retire early path, most don’t elect FIRE because “they hate working”. Rather, achieving FI enables a means to live life the way one chooses, including the option to stop working if and when they want. In other words, to reduce or eliminate the requirement to spend the majority of one’s waking hours working instead of doing other things of interest.

I fear that I can’t add much wisdom to the profoundly important words written above. If nothing else, I thought it would be a good opportunity for me to reflect on how my FIRE journey is very much related to several points contained within. Above all, I hope in sharing this that it might cause you to consider whether you are making the best choices you can to honor your inner needs and desires, avoiding later regrets. To repurpose something I usually say in another context, the best time to start doing so is yesterday, and the second best time is today.

I wish I’d had the courage to live a life true to myself, not the life others expected of me

I’ve never felt pressure from family to achieve X, nor was I told that only path Y was the “right one” for me. I know this isn’t the case for everyone, and I’m truly thankful that I’ve not experienced this. As such, I’ve felt comfortable living the life I wanted to live as an adult. But I have certainly had my choices challenged by former colleagues or friends at times, particularly when it came to job changes. Most often they had good intentions and believed they were supplying me good career advice. But I was on a different path and the difficulty was that I didn’t feel comfortable explaining that until the very end of my career. Quite honestly, I wasn’t very courageous about describing my path and the rationale for it, and that created challenges.

I didn’t always know about FIRE but I did know early in my career that I wanted to retire early. I also didn’t know how I’d achieve that early on. I didn’t magically come to my career “leveling up” strategy. Rather, it evolved through several early moves in my career and seeing the benefit of the same. I realized that by building breadth in skills, and not fearing moves into new companies and stretching beyond my comfort zone, that I could accelerate my path. Importantly, my wife always supported me in this despite the challenges it meant for our family. We believed in the end goal we were seeking. While my path was not the traditional one, I’m not sure that it was courageous. But I can say that I’ve tried to honor what I knew in my heart I wanted to do. And here I am!

I wish I hadn’t worked so hard.

I really like this point and yet I’m of two minds on it. First, the obvious one: By achieving FI at age 46, I eliminated the requirement to work until traditional retirement age. I therefore created the option to stop working so hard, and I took advantage of that just over a year later when I left the workplace. So conceivably, I have been largely successful in avoiding having this regret. Right? Mostly.

In my case, electing this path meant a series of tradeoffs were made along the way. Part of my journey included several roles at start up companies, meaning very long hours spent at work and therefore away from home. It also meant frequent jobs changes and associated moves away from family and friends. In the second half of my career, the roles I had involved extensive travel, which meant more time away from my wife and daughter. All of these had impact on my family and meant that I wasn’t always there for specific events, or at times in my daughter’s early years, just to name a few. Were those the “right” decisions? My wife and I accepted them with eyes open and as a team. But they had a cost.

To be clear, I’m not complaining. Yes, I worked hard. But many people work just as long or longer hours, do harder/manual labor, do it for many more years than I did, and are compensated far less for their efforts. On net, I believe the choices I made were the best for my family and so I do not regret them. But it’s worth reflecting on what it took to get here and be doubly appreciative for what I have now. I am very thankful that I no longer need to work so hard.

I wish I’d had the courage to express my feelings.

Me being me, this one warrants a whole post unto itself. But I’ll be brief in the moment. Suffice it to say, I don’t usually shy away from my feelings. One of my favorite things about my FIRE journey is that I now feel the freedom to share more openly about it. Don’t be mistaken – I still hold back at times, as my Two Sides of FI show partner is correct in reminding me. But through this blog and our YouTube channel, I’ve become more comfortable with openly sharing my feelings (to an increasingly larger audience!). That’s been really good for me and I hope that it helps others as well. At times, I admit that all my corporate training still wins out, and I choose my words more carefully than I should, muting the emotions underlying the point I’m making. But i’m improving and I feel strongly that having the freedom that FIRE has provided is helping – in all things, not just in content creation. And I’m really happy about that.

I wish I had stayed in touch with my friends.

Generally speaking, I think I’ve done a good job with avoiding this regret. I’m a pretty nostalgic person and enjoying keeping in touch with friends made through the years. That said, leaving the workplace and my prior and subsequent moves have created physical distance between me and my friends. True, I now have the time to travel more frequently to see them. Since leaving the workplace, I have taken several opportunities to visit out of state friends, which wouldn’t have happened were I still working. And this has been hugely positive for me. Not having a work calendar and a vacation days allotment is so freeing.

On the other hand, as we’ve discussed on the YouTube channel, FIRE does have a way of creating distractions if not challenges to friendships. Not everyone sees the validity in this path and may have difficulty talking about it. Honestly, it’s hard when you don’t feel comfortable discussing something so important to you with close friends because of how they react to it. I’ve certainly not worked through this yet but it is something I think about a lot. I do need to write more about this, if nothing else. I’ve got more to process here, and it’s important. This is one area in which FIRE path folks need to be prepared. I want to remain close to my friends irrespective of my path, assuming they’re willing.

I wish that I had let myself be happier.

We can’t control everything in life. Misfortunes and hardships may come at any time. That said, it is often spoken that we choose how we react to these things. I will freely admit I did not always choose happiness. While working, I often let many things get to me, compete for my time, and challenge my wellbeing. Like many, the ever-present cellphone became a real difficulty for me. The text messages and emails from customers and colleagues were never ending, and I found these impossible to ignore. This certainly affected my mood at times as my family will attest. Naturally I could have done more to deal with this, and I’m surely not saying FIRE is the only solution! But electing to follow this path has been an important part of me deliberately choosing happiness over stress.

The important point to make here is that I am very happy and I am increasingly choosing to be so via this path. I know how fortunate I am to have achieved what I have, and I remind myself of that often. I am truly grateful that my wife and I get to choose our path forward from here. Are our options limitless? No. We don’t have a Fort Knox-like stash of gold to fund an insanely lavish lifestyle. But we do have the freedom to live well without the requirement to work – and that’s huge! We are in good health, are relatively young, and have many options available to us. It is now on us to create the life we wish to live from here on out, for the remaining years we are vertical on this planet. It is overwhelming in some respects but we absolutely look forward to the challenge of determining what to do to maintain and grow our happiness in our life together!


Will I have regrets as my life nears its end? I have no idea. Like most people, there are things that I wish had happened differently; that I had made better choices or avoided hurting others by my actions or via neglect. I am far from perfect and I can’t change that. I do know one thing: I think it highly unlikely that I’ll regret my decision to follow a FIRE path. I wish you life devoid of regrets and full of happiness. Mahalo. ?

image credit: Photo by Brett Jordan on Unsplash