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

The value of taking inventory: a 20-month checkpoint

First, sorry to have been away so long! I see that it’s been two months since my last post – my longest writing gap so far. To be honest, I just haven’t had topics about which I wanted to write, such that I was willing to take time away from other things on my plate. That changed today while on a walk with my wife, Lorri.

If you’ve worked in retail, manufacturing, or in a whole host of other trades, you understand the value of taking inventory. One of the key lessons I’ve learned since leaving the workplace more than 1.5 years ago is that this applies to our personal lives as well. What do I mean? I’ve found there is tremendous value in taking time to reflect, allocating the mental space needed to think about what you’ve been up to, your accomplishments, lessons learned, etc. I didn’t do a very good job of that -and often enough during my career, but this blog has been a big part of me changing that.

Some time after I wrote an article reflecting on my first year in early “retirement”, I decided I wasn’t going to write another milestone post until my two year mark. Sitting here penning this piece, I realize that I’ve changed my mind. Today marks 628 days since my last day at my last job in biotech, just over 20 months or 1.75 years ago. Most days, that phase of my life seems really far away, but on occasion it feels rather near. The former makes good sense to me as I feel like, despite the challenges that came with COVID-19, I’ve done a lot since embarking on this next chapter in my life. And so I thought it would be a fun exercise to take inventory of those things here.


So what have I been up to? I don’t know if I can top the pace of my first six weeks post-FIRE, but I feel like I’ve done a lot. While not an exhaustive list, in no particular order, I have…

  • Started Two Sides of FI, a YouTube channel and podcast, with my good friend of 35 years, Eric. As I write this, we’ve released 29 full-length episodes as well as many highlight videos and Shorts, which have been viewed nearly 700 thousand times, and we have nearly 13,000 subscribers to the channel. Wow! I’m so proud of this project and remain humbled that people value the content we produce. This has been the most fulfilling aspect of my FIRE journey so far, without exception.
  • Learned* video and audio production and editing. The asterisk denotes that this learning is very much ongoing. But I feel like I now know just enough to be dangerous re: Final Cut Pro, Garage Band, and the processes needed to put out video and audio content.
  • Completed three iOS app development courses and wrote a few apps. I spent a good chunk of the first 4+ months after moving to this effort, and really enjoyed it. I completely threw myself into this and had planned to do so even before leaving my job. I’ve not done much with this lately but who knows? I may pick it up again.
  • Qualified as a FAA-certified Part 107 commercial drone pilot. Last year I bought a drone and wasn’t entirely sure of where that would take me. But since the videos were going to be used on YouTube and I had some interest in other commercial uses, getting the license was the right path. Will it ever go beyond simple hobby use? Who knows?
  • Volunteered at my local COVID-19 vaccine clinic. One of my post-FIRE aims was always to do more service. Due to COVID and other more selfish reasons, I haven’t done really well on this aim – yet. But I did enjoy taking a weekly shift at the town clinic during the big vaccination push in those early months after shots were available.
  • Worked part-time at a local winery tasting room. I never saw this coming but my love of wine, enjoyment of education, and need for socialization made a once-weekly tasting room job a great fit. I’m still doing this nearly a year later with a really great group of people, and I truly enjoy it – as well as the industry discounts! 🍷
  • Given two talks and career counseling to students. I had the honor to be invited to speak to two groups of undergraduate + graduate students about careers in biotechnology and my own path. Since then I’ve had a number of career counseling calls with students. I get a ton out of these and wonder if it may turn into something I want to do more with.
  • Took the longest vacation of my life – 5 weeks! Like many, we didn’t get to see family and friends for over a year due to COVID-19. It was wonderful to get such a long time to travel with my wife and daughter, seeing so many people we missed. This kind of trip, along with some shorter road trips, simply couldn’t have happened were I still working full-time.
  • Found a great online community in the FIRE Discord server. I’ve been a fan of online chat since the earliest days of the internet. But I didn’t realize the value I’d find in socializing with a group of like-minded FIRE folks such as this great group has provided me. Talking about FIRE can be tricky so forums like this are a wonderful thing to have.
  • Taken several online classes. Outside of the iOS coursework, I’ve taken classes in topics including financial markets, personal finance, and most recently world history (admittedly we’ve been a little delinquent on this last one lately). I love learning and look forward to taking some classes at our local community college or university in the future!
  • Started a homebrewing club with Lorri. Making connections with people and socializing is important. The combination of moving to a new town, not having a “day job”, and COVID made both things tough. It’s been great to combine our love of beer and brewing with the opportunity to meet people. We’re a few months in now and it’s going really great.
  • Done a ton of cooking and learned new cuisines. 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 to make mole negro. Eventually I moved on to Indian cuisine, which was a really fun change-up. I’m still cooking nearly all the family’s meals at this point and it’s something I truly enjoy.
  • Taken hundreds of walks and hikes. I’ve taken a walk nearly every day since I stopped working, and most weeks I also take a longer hike with Lorri. This has been great for so many reasons: when solo, I listen to books or podcasts, or simply take time to reflect. When my wife and I walk/hike together, it’s great phone-free time to just catch up, talk about future plans, and enjoy quiet time together. I can’t imagine not having this in my life now!
  • Read many more books than I had in years. While I’ve always been a reader, admittedly the pace of completing books slowed a lot for me as my career advanced. I’ve now completely turned that around and between audiobooks, ebooks, and the paper kind, I get through tons more these days. It’s also wonderful having a library just a short walk from home!


I’m sure I neglected to add many things to this list. And it’s probably way too long so I do wonder who will even read it. But even so, it’s been really rewarding to sit, think, and write this piece. A few thoughts come to mind: While I now have way more “free time” than ever in my adult life, I’ve never been bored (I get asked this a lot). Rather, like many early “retirees”, I don’t know if I’ve ever been busier. The difference is that now with rare exception, the day is full of the things I/we want to do, and not things at someone else’s direction. But this list does at least help me appreciate why I always feel like I’ve got plenty that I want to do!

Looking at the list, it’s a mix of things I’d planned to do since before I stopped working, along with quite a few I just stumbled into – the YouTube channel is a great example of that. There was absolutely no plan to do that and yet it’s become my biggest time expenditure post-FIRE, as well as the most rewarding part of each week. And this is the benefit of this chapter of my life. I now have the freedom to wander around, trying things, and seeing what sticks. And like with iOS coding, I can simply set things down after trying them – temporarily or perhaps permanently. Who cares?

As I’ve written many times here before, I know just how fortunate I am to be where I find myself. I remain thankful for all of you who read these pieces, sharing your own experiences with me as you follow my journey. I wish you all the best in whatever you aim to achieve.
Mahalo. 🙏

Excelsior!

I’m originally from New York State and as such, I know the state motto: “Excelsior”. The translation of this from Latin is generally stated as “Ever upward”. I can hardly think of a better sentiment to share at the end of 2021, another challenging year for everyone. I’ve been quiet of late on this blog and I wanted to ensure I didn’t let the end of the year pass without writing at least a short post.

First, I’m doing well, and I hope you are too. As I write this, it’s now been just over 1.5 years since I left my career behind. I remain incredibly grateful and excited about all the opportunity ahead of me and for all the “possible futures” (a term I am borrowing from my Two Sides of FI show partner) that may come. Despite the challenges we all know, my family and I have made many nice memories throughout the year. Barring a few colds that have run their courses, we’ve remained healthy, and we are very thankful for this. Thanks are due to all who worked tirelessly to produce COVID vaccines, diagnostic tests, and who have endeavored in so many ways to keep us all safe and healthy.

I’ve decided not to write another milestone post until at least my two year mark. But to briefly summarize a few happenings from the last six months:

  • Our YouTube audience has grown a lot and we’ve now published 23 full-length episodes
  • We took a five-week long trip to visit family and friends we’d not seen in well over a year
  • Lorri and I started a (beer) homebrewing club in our town, and it’s coming along nicely!
  • I found a great online community in the FIRE Discord server
  • I have started to explore a new podcast + book idea (stay tuned!)

I’ve been a bit less regular about this blog of late and as I’ve mentioned before, it’s hard for me to predict what will come for it. I’m often inspired to write about what I’m thinking, and I’m happy to do so as I have good ideas. But given the energy the YouTube channel is taking – and I’m loving every minute of it! – it’s not too surprising that I don’t want to write as often or on my former weekly cadence. I remain appreciative that anyone wants to read my thoughts and I’m grateful for all the feedback I’ve received over the past 1.5 years.

Above all, I wish you the very happiest of holiday seasons, and for a healthy, productive, and rewarding year to come. I do hope that your own paths remain “ever upward” in their trajectories, and that 2022 (and beyond) brings you fulfillment of your own goals and dreams. Excelsior!

image credit: Photo by Jamie Street on Unsplash