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

Mothers won’t agree, but nine months sure flies by!

a clock with wings - time flies

Retirement is full of changes, and after nine months that isn’t any different. Nine months or around 40 weeks is regarded as the average length of a full term pregnancy for humans. From my own family’s experience, I wouldn’t say that those months sail by unnoticed. Expecting moms experience a seemingly never-ending series of changes, many of which are unpleasant or uncomfortable. A new addition to the family is of course a happy outcome and that makes it all well worth it!

This week marks nine months since I left the workplace and my career of 23 years. In most respects, it is hard for me to believe that it has already been that long! I believe that feeling would be even more so were it not for the existence of the COVID-19 pandemic and the lifestyle changes it has manifested for us all. But even in the atmosphere of lockdowns, reduced travel, and limited social interactions, I would say that time has passed quickly. Has there been a “birth” of some project or new venture that will define my next phase of life? Not yet, but as we’ll discuss, that isn’t a problem in the least!

What is the same and what’s changed after nine months?

As I did at the six month milestone, I thought it would be useful to review how things have been going across an array of categories. But I’ll try a new article format in the interest of keeping things fresh!

  • Schedule:
    • I’m still largely using mornings for a mixture of entertainment consumption, chores, and my daily walk. If I have a busy day ahead, I often cook dinner in the morning as well. For those who don’t know me – yes, I’m still up before dawn! That is seemingly just me and has nothing to do with whether I’m working or not.
    • Afternoons remain largely for skill-building and education that may yield my next project or business venture. Importantly, I’ve increased the overall time I’ve spent on this area!
    • I have a couple of Zoom happy hours each week and these remain an important outlet to stay connected to good friends, family, and former colleagues. I feel like I’m talking to the last group less these days, barring a select few people. I’m a bit sad about that given how many colleagues I enjoyed hanging out with. But from my reading I know this is common. Work tied those relationships together and with that gone and with little travel happening, it makes sense.
  • Skill building and making:
    • I’ve pushed much harder to make progress on my iOS development journey in recent months. I’ve now completed or made significant progress on three courses. I’ve also released a simple app on the Apple Store, and developed several others just for the entertainment of myself and some friends.
    • I’m still cooking a lot! I managed to make all seven of the Oaxacan moles (my recipe database is here), which was an extension of a long-standing bucket list item (make mole negro). But I’ve now moved onto Indian cuisine! I’m really enjoying this change and since we have no Indian restaurants in town, it’s rather self-serving. ?
    • I am learning tons about YouTube, video production, and a host of other things from the Two Sides of FI project that my friend Eric and I have begun. It’s still early days for the channel but I remain excited about the different directions it may go. I have much to learn so this needs to take even more of my time and I’m working on that presently!
  • Giving:
    • I had always planned to do more volunteer work in “retirement”, particularly since my financial giving is way down from when I was working. I’ve recently started volunteering once a week at our local COVID vaccination clinic and am really enjoying the gratification I get from it. I felt needed at work and volunteering is filling that gap!
    • I am also taking more phone calls from friends and former colleagues who are interested in early retirement, have financial planning questions, or related topics. At the core this is just being a good friend. I am happy that I now have the time to devote to such things without concern for what work or tasks are being put off, and I enjoy it.
  • Fun:
    • My family is still enjoying learning about our new home in the Central Coast of CA. We’ve continued to explore area hiking, as well as the many wineries and breweries in our town and close by. We are ever thankful for our temperate climate given the need for outdoor activities during COVID restrictions. Location, location, location!
    • Socialization remains as it has been for most of us – very limited. We have one couple we see occasionally and this has been a vital outlet. Moving away from friends and being geographically distant from family has been tough when combined with our present circumstance – and the opposite of what I’d planned after leaving work.
    • While I had been enjoying getting back into the World of Warcraft game, I haven’t played in a few weeks. First, a good friend with whom I enjoyed playing, has been busy with other things. Second, I’ve been enjoying my other pursuits so much that gaming time wasn’t a priority. Don’t worry: I’m far from being done with gaming, of course!
  • Emotional
    • As at the six month time point, my mental state remains… ever changing! Though I’m happy to report that the variability is now much less so. I still have days where my usual excitement about figuring out “what comes next” turns into concern or is otherwise unpleasant. On the whole those days are much rarer now, which is great!
    • I’m also working on taking time to clear my head and allow for uninterrupted thinking. I’ve realized that I have some bad habits to break, and some easy remedies have included taking my walks in silence and not bringing my phone. This is definitely a development area for me but I know it is one that will pay off many-fold!

So what’s next?

As I wrote above, there is no “birth announcement” about what comes next – YET. At times I find myself feeling like that means I’m somehow behind the curve. But it is at these times that I remind myself of my plan – I now have the freedom to take the time (or not) required to figure out what comes next. Skills building and pure educational time is a central and essential aspect of that! Importantly, there is no pressure to keep to any specific schedule. The hallmark of achieving financial independence is a lack of any requirement to “do something” that will generate income. I’m seeking the “next thing” because I want to, and am excited to create / do / experience something new!

I remain absolutely convinced that one of my many wandering paths will yield the fruit that will manifest as a central element of this next phase in my life. As my good friend Eric reminds me, most often you have to try and “fail” at a variety of things before you land on the one about which you are truly passionate and that will produce what you are seeking. This is so different than what projects in my work life were like, so it’s no surprise that at times I find myself forgetting that is indeed the nature of the beast! But I’m getting better about remembering that. I’ve got a few irons in the fire that could turn out to be that thing – but I’m totally OK if they are not! It’s all learning, growth, and yes – fun.

Once again, I am thankful for all those who are experiencing this journey with me – whether through the blog, the YouTube channel, or just in conversation. Your input and guidance means a lot. Most of all, I am grateful for my family. This is a huge change for all of us still – even nine months later. I am so thankful for the strong support I get even in my most uncertain of moods. I am excited for all that is still to come and know that it will be a great adventure!

image credit: “time flies” by Robert Couse-Baker is licensed under CC BY 2.0

It’s hard to break bad habits developed at work

Kyocera smartphone device

Yesterday I was setting out on my daily walk, during which I generally listen to audiobooks (I’m currently enjoying If It Bleeds, by Stephen King). As I was putting on my headphones I started thinking that I didn’t yet have a blog post topic for this week. I generally have a few ideas percolating but as yet hadn’t come up with anything I thought was compelling. I decided to take the highly unusual step of leaving my headphones and my ever-present iPhone behind to avoid being distracted. That would help me focus on topic generation, right? I didn’t get 50 feet from my front door before I realized that I already my idea! Once again, I’ve realized that I’m still adapting to leaving the workplace just eight months ago.

The tethering begins! 20 years of my life with smartphones

As has been widely reported, many of us spend a lot of time with our smartphones. As an early technology adopter, I’ve had one as long as they’ve been available. In fact, I had one of the very first: the Kyocera smartphone model 6035, shown in the picture above. It was released in 2001, meaning I’ve had a “pocket tether” for 20 years! It looks like not much more than a Palm Pilot PDA (for those who remember those), but it had text messaging and even a simple web browser! Early on it was definitely just a novelty and not something that “owned me” in any way. Given the cost of cellular data and the very slow speeds of the same, that’s pretty understandable. No one else had one at work, either. So there was no pull coming from that source – yet.

In 2006, two jobs later, I started using a company-supplied Blackberry for work. Things were fine using it that first year. I was still working in R&D and while having access to email at all times was convenient, I felt no compulsion to use it much outside of work. Besides, Blackberry apps weren’t very compelling barring a few simple games. However, once I moved into a new role where I was supporting customer collaborations using not-yet-released products – generally high risk and short timeline, things changed. I began checking my email and text messages much more often. My team was working at odd hours sometimes and I needed to stay in touch with them. My boss wanted to be kept up to speed. My habits shifted to manage these expectations and needs. I started doing a bit of work-related travel again, and the Blackberry made it convenient to keep in touch with my coworkers and customers. This began increasing once I left R&D for a Product Management role. I soon learned that this was only the beginning…

The iPhone and my downward spiral into bad habits

The real step-up didn’t happen until I got my iPhone. In 2010 I joined a startup biotech company leading a nascent customer support organization. We were doing some truly exciting work, but it was also early days for our technology. Not everything went to plan for our customers and my team was out there training them and fixing anything that went awry. I needed to stay in touch with my team, my customers, and the management of the company. As I my remit was global in nature, text messages and emails started coming at all times as well as on the weekend, and I was obliged to deal with them. Time is money and nothing takes a simmering situation to an explosion faster than someone having to wait “too long” for a response. I was one of the key links in the chain that had to stay intact, and my behavior only got worse as our customer base grew. Few things get you moving faster than messages from the CEO of your company, I can assure you!

In that job and in my final role before leaving the workplace, I traveled a lot – most of which was international. This coincided with the true explosion of social media. That combination meant my iPhone increasingly became a tool to keep in touch with family and friends. I was on planes, in airports, hotels, and taking other transit often. Apps like Facebook, Foursquare, and Instagram became ways to spend idle time as well as to share my experiences with my network. Combine that activity with all the texting and emailing I did for bona fide work purposes, and you have an awful lot of time staring at a small screen. It never seemed “bad” to me, but it was certainly something I spent a lot of hours doing. It makes sense, right? I generally traveled alone and that meant filling the hours and hours of space between work obligations.

Like many people, these behaviors spilled over into my personal life when I wasn’t traveling. My wife, Lorri and I had a number of conversations over the years about “being present” when I was at home, particularly in those years when our daughter was young. I only had weekends and evenings when I wasn’t traveling to spend time with her. She had a great point, of course! I found it next to impossible to put the emails and texts from work aside, but surely she was right. I tried some of the usual remedies like leaving the phone somewhere else during meals, and also attempted not to use it before going to bed – with mixed success, admittedly. My never-ending device time was having a negative impact on my family not to mention myself. Nothing prevents you from going to sleep (or causes you to wake early) like receiving a bad work message at bedtime! Surely these habits stopped when I ceased working eight months ago, right?

Post-workplace realizations

While I no longer have the work-related emails and texts to manage since retiring early – which is great! – I realize that I still spend far more time with my phone than I should. On the plus side, I do use more of that time productively than I used to – audiobooks have been really great for me as one example. However, I realized yesterday how far I still need to go. I’ve developed a bunch of bad habits and I need to change them. I previously turned off most app notifications and that’s been great. Facebook is no longer on my home screen so I can’t see the notifications count badge. That’s not enough. I can and should do more!

Walking without my phone yesterday I realized several important and perhaps obvious things. First, left with only my thoughts, my mind wandered lots of places during that hour walk. I didn’t just think about the blog, but also about some potential business ideas. I also thought about next steps with my new YouTube channel, Two Sides of FI. I also must admit that normally I don’t just use my phone to listen to audiobooks during my walk. I’m often receiving text messages while walking, many of which I answer. What a distraction! Couldn’t I just use Do Not Disturb mode? Of course I could. But I’d still be able to pick up the phone and Google something I saw on my walk, or take a photo and maybe even post it online. Maybe I can’t be “trusted” to have a phone during these times? (I can’t – yet.)

My plan of action

I’m going to stop listening to audiobooks during my walk – at least for now. The core issue is that I am still driven to fill empty space with “stuff”, rather than taking time to just think and experience the world around me. I don’t mean to suggest this is some profound realization I’m making for the world here. Many others have come to the same conclusion! But for me this is an important step in dealing with a long-standing issue. I’m so attached to technology given my nature, and I love having ready access to my phone. But I don’t need it at all times.

With this behavioral change, it will mean I’ll be delayed in responding to some things and I won’t be the first to share others. I know that will be OK and as a result, I’ll have more “technology downtime” in which I can think about more important things. I’d say “or think about about nothing at all”, but that’s not how my brain works. It’s a noisy place but that’s who I am and I’m comfortable with that. I do think my mind could benefit from a lack of competition with audiobooks, text messages, and apps sometimes. I didn’t think about this topic at all during my “9 Secrets to Success in Retirement” article but I’m realizing these changes may be essential to my own success and well being!

How about you? Have you come to similar realizations and done anything in response? I’m open to suggestions! They would surely be of help to me and others, so please share. Thanks!

image credit: https://www.canadianbusiness.com/kyocera-6035/