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

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!

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! ?