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

New town, no job…no friends?

There is so much to look forward to when you move: setting up a new home, a chance to purge the junk you’ve accumulated, exploring your new town – just to name a few. All of those things and more are very much the same when you’re no longer working. In fact, you’ve got more hours available each day to enjoy them! And you can make those numerous Lowe’s / Home Depot trips at times far less busy than you could if you still worked. But there’s something important that you don’t often see discussed on FIRE blogs or videos: the challenges of making connections and building friendships in a new town without a workplace as a central meeting point.

A brief review of recent history

I left my job nearly fifteen months ago and my family moved a few weeks later. Our new home is about three hours away from where we used to live. That means our friend group of more than eight years is within range for weekend visits, but of course those require planning. In addition, all of my close friends are still working full time – or even quite a bit more. That means weekdays are totally out and weekends are their main time to “get everything else done”. So our availability is totally different, which makes perfect sense. Admittedly I have a hard time remembering this sometimes when awaiting replies to my many text messages (sorry!).

A few weeks ago there was an otherwise inconsequential event in my life that started me thinking more about this topic. As we discussed on a recent episode of Two Sides of FI, I had made weekend plans with friends near our former home. For perfectly sensible reasons, my friends needed to postpone. I was really disappointed, and even more so than I’d let on to anyone involved. The change of plans made me feel like I didn’t matter as much to my friends as they did to me – which was of course a very silly and wholly irrational reaction. But the emotions I felt were very real, I assure you.

Why was this little thing so impactful? I had really looked forward to those plans, it seems. But why? Sure, it would have been fun to see friends. But we didn’t have anything monumental planned for that weekend, after all. And we’d likely all get together in just a few weeks (we did, and it was great). The answer is pretty simple: I haven’t made many friends since we moved, and I’m almost solely relying on my out-of-area friendships for that connection. There are a variety of reasons I haven’t yet made many friends in my new town, COVID being just one of them. But there’s a simpler reason well within my control, and one I just hadn’t yet realized.

Making friends for the world to see

Your place of work is not the only opportunity to make friends, of course. Many people build friendships through civic groups, clubs, or places of worship. But at least for me, my closest relationships have always come from the workplace, so it’s what I know best. There is no easier place for me to find like-minded people, and the collision factor of working in an office provides many opportunities to learn about people. From there originate the kernels of what later yields close friendships. It’s a very different beast to start from zero in a new area where you are no longer working – at least for me, anyhow.

My ever-astute wife, Lorri, pointed out something rather eye-opening to me while filming 2SFI: I hadn’t really been doing very much to make connections and build new friendships since moving. Honestly I hadn’t really thought that my inaction was such a big part of it but of course she was 100% right. People clearly weren’t lining up on our doorstep to introduce themselves and hang out with me – I have no illusions that I’m so interesting or fun to be around such that they’d want to do that. So naturally I had to be much more motivated about the whole thing. Obvious, right? Truly, it hadn’t been to me until that moment.

Current status + steps taken so far

I’m not lacking for social interaction in our new town. In fact, one of the very reasons I took the job one day a week at the winery tasting room is for that engagement with others. That goal has been achieved, and I’m really enjoying it. But it’s not likely I’ll make effective friendships from a largely tourist customer base. However, just working in wine has given me a springboard to meet others in the industry who clearly share common interests with me, and that’s been great. Lorri works part time at a brewery. As you’ve gathered, I like beer, and frequent those establishments as well. So any of these things could well yield friendships. Recently, I’ve started to more actively seek out opportunities to meet industry folks. I think I’m off to a good start and have met some great people but clearly need to keep it up.

As I wrote above, clubs are also a great place to connect with people through common interests. Both Lorri and I are 20+ year homebrewers and love engaging in activities around beer. There is no local club dedicated to homebrewing in our town, so we are starting one! After polling for interest in a few online forums, our first meeting is a week away. I’m excited for the possibilities here. In addition to hopefully making a few good friends, this is also an opportunity for me to teach, something I really enjoy. So even if I’m wrong about it being a great way to make friends, I know I’ll find benefit from starting up this organization.

Where do I go from here?

I think persistence is the name of the game for me at present. As described, I’ve taken a few smaller steps to put myself out there more and actively seek opportunities to connect with people. And I’ve met some nice people who I enjoy hanging out with. But I also know that I’m just getting started. I need to follow up on the leads I have and also seek more. There are a few people with whom I feel there could be a connection. I need figure out if that’s true or if they might just be nice acquaintances. It takes time to build good friendships, after all – and that’s OK. I certainly believe it is effort well spent.

I will certainly continue to get together with my very good friends who live out of the area – several are irreplaceable in terms of their importance to me. And I don’t want that to change! But realistically, I also need to keep seeking opportunities to make friends locally. This town is where we’ve chosen to live and at least for the foreseeable future, will remain. It just makes good sense to find a couple of good friends nearby. Wish me luck!

image source: Photo by Duy Pham on Unsplash

The many learnings from year one of early “retirement”

ONE YEAR since I left my job? Wow. Particularly given the odd pace of “pandemic time”, I find it hard to believe I’m already at this point. But here I am! Looking back at the countdown calendar that formerly hung on my office wall confirms it. On an afternoon exactly one year ago today, I handed in my employee badge and drove out of the company parking lot, almost certainly bringing my 23-year biotech career to an end. A few weeks later my family moved out of the Bay Area to the Central Coast of California. I wrote my first blog post here several weeks later. Now after twelve months and 43 posts, it’s time for another in my series of milestone articles. Will it be my last? Who knows!

After a year I still generally avoid the term “retirement” or I place it in quotes as I’ve done here. At 47 years old, I still think it unlikely that I’m completely done with all things that could be termed “work”. It is true that I leveraged reaching financial independence to step away from the only career I’ve had – and still have no intentions of going back. But it’s also entirely possible that one of the many ideas I’m exploring could turn into gainful revenue generation. Again, who knows? That flexibility is exactly what I was targeting with my FIRE journey. That said, I can’t imagine myself schedule-bound to an office job at someone else’s company. ? It seems more likely with each day that this will continue to be the case.

I have approached this article differently than my earlier milestone posts. Instead of my usual (rambling) long-form, I will briefly summarize some of they key lessons I have learned and observations I’ve made. That seemed a better method to share a broad range of information without a really long article. I’m hopeful that this bite-sized approach will work out well and perhaps will provoke questions that would be fun to expand upon! So without further ado and in no particular order…


  • It can be very difficult to resist the temptation to fill all your time with “stuff”. Our careers train us in this way and it takes active effort to get comfortable with anything else. But I think that having truly “free time” is vital to allow the creative process to happen!
  • Like any big changes, leaving your career behind is an emotional roller coaster with many highs and lows. You can’t truly prepare for that, short of just being cognizant that the mental churn will happen and is completely normal. It’s really important to reflect on what you’re feeling. Journaling or blogging can help!
  • Talking openly with your partner & family is really important. Sharing the emotions you’re feeling helps everyone. After all, they are going through this huge change with you! Keeping it in will only create tension that helps nothing. Ask them how things are going now that you’re around so much more and see if anything needs to be adjusted.
  • If your identity is tightly wrapped up in your former job as is common, it will be a substantial change when this is removed. Thinking about your purpose and what defines you and is important now, is really useful. What is your next phase of life going to be about?
  • Don’t fear trying things and setting them down. This is the very heart of having the freedom to choose how to spend your time. If like me you have many interests, it’s perfectly OK to try them out only to decide “that’s enough for now” or “I don’t actually want to do this”.
  • Related to the above – it’s important not to pressure yourself to find “the next thing to do”. At least in my case, this created stress in the first few months. Financial independence means that additional income – while nice, is not required. Your time is better spent exploring, from which may spring that next great idea! But don’t rush into anything hastily.
  • It can be really tricky talking about FIRE and early retirement – particularly with people you’re meeting for the first time. I often refer to my increasingly rare consulting gigs as my “job”. Yes, it’s a cop-out, but it works before I get to know someone well. It’s worth thinking through how you will handle this in advance. You’ll get lots of practice, I promise you.
  • The things you miss about the workplace may surprise you. Giving some thought to this before you depart may help you identify other ways to satisfy those needs – but it won’t be perfect. Again, this is just part of the emotional roller coaster that will surely come.
  • Many workplace friendships are just that, and they won’t all persist after your shared work life is no longer there. COVID + moving certainly didn’t help in my case as visiting people wasn’t an option and Zoom meet-ups are only so effective. But I am convinced that many relationships at work are very much tied to the workplace itself. This is perfectly OK!
  • On a related point, it’s easy to under-appreciate how much socialization occurs at work. What will you do during those weekday “working hours” while your friends are busy? Finding appropriate avenues to engage with others is still really important. Clubs, civic groups, volunteering, and other means to find like-minded people is important – particularly if you relocate in retirement, as I did. Pouring wine at a tasting room one day a week is proving to be fun for me and plenty social!
  • Lots of people make bucket lists of big and small things they intend to do once they retire. I have found since leaving the workplace that I continue to generate ideas of things I might like to do. I keep these out of sight in an “idea funnel” that I revisit from time to time. It’s fun to see how my thoughts change about prioritization; there’s also no pressure to feel like it is a “to do list” that I must achieve. This subtle difference feels really good to me.
  • Building skills and “making” things are really effective ways of continuing to challenge yourself, to keep learning, and also to feel productive. They are also great mechanisms to unearth potential business opportunities or at least new hobbies and avenues of personal entertainment. Knocking procrastinated chores off your to-do list only lasts so long!
  • Just because someone is willing to pay (a lot) for your expertise doesn’t mean it’s the right thing to take on. I’m grateful to have been presented many consulting opportunities over the last year. While tempting, I’ve had to be really careful about not over-committing at the peril of being unable to do all the other things I want to do! Be sure to choose wisely.
  • The freedom gained via FIRE has proven to be well worth it! I love being able to choose how to spend my time. I can’t count how many times I’ve woken up with zero plans and at the end of the day realized what a fun day I had, just taking things as they come. My wife is much more spontaneous than me and I’m finally starting to understand the joy in this.
  • On a similar point, I’m really excited to finally get the chance to test out our interest in longer term travel. This summer we’ll take a five-week trip to visit family and friends. Wow! Like most Americans, we’ve never been away more than two weeks on vacation. It’s a little scary, but almost entirely in a good way!
  • There is no “right way” to do this. From talking to others, whether in FIRE or traditional age, retirement is definitely individual. We each have our goals, our interests, and our individual preferences. I think many of the points herein apply broadly. But you will each need to determine what is important to you and how you will spend this next phase of your life.

I hope you’ve found this post useful. I remain incredibly grateful to be in the position I am, something I reflect upon often. It is my earnest hope that in sharing my experiences I can assist others in their own journeys. Decisions relating to retirement are among the biggest we make in our adult lives. There are many paths to arrive at that goal and so many decisions to be taken along the way. And yet as has been well documented, few people feel well informed on the topic by the time they are deciding when and how to retire – or worse when others have decided that timing for them. I aspire to change that however I can.

Above all, I wish you all the best in your own journeys! If there are any questions that this post has prompted or areas in which you’d like me to dig in further, please comment below or on social media. I’ve learned much from the interactions I’ve had with readers and some of my favorite posts have comes from conversations with you. I just want more of them!

If you’re not yet following my Two Sides of FI YouTube channel (or the audio podcast version: Apple, Spotify, or search your provider of choice!), please consider it! My co-host, Eric, does a really great job of challenging me and asks thought-provoking, and sometimes difficult questions that I’m not always willing to put to myself. And I think you’ll find his perspective as one approaching FI incredibly valuable. Mahalo! ?