Optionality: An Amazing Superpower

Most people are familiar with the old adage “Fortune favors the bold”. Apparently this phrase goes back more than 2000 years, and is one common translation of a Latin proverb. A great related quip is “Fortune favors the prepared mind”. But I think we can do even better than that one, so here is yet a third gem of similar vintage:

“Luck is what happens when preparation meets opportunity”

-Lucius Annaeus Seneca the Younger (Seneca)

I absolutely love this quote because it says a lot in very few words. In my writing, I’ve acknowledged the role that good fortune plays in the success of many – including myself. We all understand the idea of “good timing”, right? But to succeed, you must be sufficiently prepared to take advantage of the situation when it arises. This element is often under-appreciated in my experience.

Today while hiking I got thinking about the related concept of optionality. This term comes up often on Two Sides of FI, most recently in an episode about market volatility. My show partner Eric and I love optionality. That is, whenever you can take decisions that enable you to have more options down the road, this is invariably a good thing. On my hike, I thought about all the times where I’d done things that enabled optionality and how that worked out for me. Here I’ll share just two of the disparate ideas which came to mind.

Building breadth is a powerful enabler of career optionality

While not explicitly described as enabling optionality, this idea came up several times in my previous Keys to Success series. This wasn’t initially a deliberate strategy on my part – I’m not so clever. But after a few jobs I realized the power that came from broadening my skills + experiences. On reflection, I understood how in each successive company and role, I was learning new technologies, developing new management skills, and understanding new industries. Each of those added new tools to my arsenal which in combination, could be leveraged to advance me in my future roles. They gave me more options!

One example of this was in a pivotal role in my career which I’ve written about before. In this case, I was offered a job which on paper I wasn’t even qualified for: running a customer support organization. I had never worked in nor led such a group before! Sure, I knew the technology area, had a solid scientific background, and had managed teams before. Why would they take such a chance? Were they just desperate?

My new boss confided to me a year later that it was my broad base of experience that got me the job. He’d hired me because with my diverse background, he’d determined I had the skills both for the job at hand and also provided the company options for how to use me for future, not yet identified needs. He was impressed that I’d had such broad experience and success in a variety of different roles. In his mind, that meant he was bringing optionality in the company. Over time this idea played out, as I moved through several different roles in the company. This was a turning point in my career, and I carried this important lesson learned into the roles that followed.

Optionality is essential for financial + mental health

In the Two Sides of FI show linked above, Eric and I talked about the merit of a fixed income allocation in your portfolio. That is, having sufficient assets that aren’t stock-based, such as bonds and cash. The latter are viewed by many (particularly younger) investors as unattractive, boring, or even “bad” ideas – even for those nearing retirement or who have already retired. While incorrect, their thoughts are understandable, since the only market many of them know is the past >10 years of a bull run. Cash (ugh, inflation!) and bonds look pretty boring compared to a booming stock portfolio.

Needless to say, as soon as the market started dropping, those comments fell off quickly. Why? Well, at least partly because those people are too busy freaking out about their net worth plummeting to comment on our videos. I like to think still others are acknowledging what we already know: along with a risk-appropriate asset allocation, having financial optionality is essential. This is particularly important for those who are already drawing down their assets, because they are no longer earning income from a job, and don’t want to run out of money. What do I mean by that?

Having an appropriate cash position means that you can fund your lifestyle without having to sell assets you don’t want to sell. Why wouldn’t you want to sell them? If the market is down, you’d have to sell more shares of stock or a mutual fund to generate the same cash vs. when it’s up. This is inefficient and effectively “locks in a loss” in a down market. Similarly, you’d rather refill those cash reserves by selling bonds, which would be expected to hold value better in a downturn vs. stock.

Having financial optionality is essential, because you don’t need to take actions you don’t want to take. You have choices because you’re prepared for contingencies. But wait – in a good year, won’t my portfolio return be lower than one 100% in stocks? Absolutely! But I don’t care, because I need to have appropriate options in place during a downturn, like now. I’m sleeping fine despite all this churn because I have optionality on my side.


There are a whole host of areas in which I feel optionality is incredibly valuable. I suspect with a little thought, anyone reading this could identify at least several ways in which they’ve benefitted from it. If optionality is not something you’ve deliberately thought about much to date, I’d recommend it. Leverage this superpower for yourself!

image credit: Alexander Schimmeck on Unsplash

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

Financial independence and the freedom to choose…to work?

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!