Unlocking life achievements

I’ve never been a “bucket list” person. I see the appeal of capturing life goals in lists, but I’ve not been someone who has done that to date. On the other hand, I think I’ve always been good about identifying things that I’d like to achieve – particularly in the workplace. Examples of those included gaining certain titles (first Director, later Vice President), leading teams of a certain size, and working internationally. Probably the most relevant life goal in terms of this blog, was my aim to achieve early retirement by age 50 – a date I’d originally set at 55, and then later reduced to 52 and then by 50 years of age.

On my daily morning walk, I found myself thinking about my last blog post, concerning my recent trend of taking long walks/hikes of up to 20 miles. Not being someone who views themselves in the slightest as athletic, these kinds of achievements were not something I foresaw myself targeting in years past. But here I am, feeling really driven to hit these targets and being highly motivated to do so, but without a clear view as to why. These seemed a topic worth exploring, and this article is an initial attempt to start on that process.

In recent events

As of my last article, I’d achieved my first 20-mile walk or “urban hike” if you will. In that case, I walked from my home to a grocery store the next town over, and returned back again in a single day. A week after that, lessons learned in hand, I set out to do it again. This time I had fancy new walking shoes (I’ve always hated spending money on footwear but believe me, I get it now), better socks, and a new route. That day, I ticked off yet another 20-mile walk, this time to a taqueria in a nearby town where I met my wife, Lorri for lunch, then walked home. My second 20-miler was easier, you won’t be surprised to learn. But reflecting on my goal I found I wasn’t done yet either.

I mentioned my interest in backpacking in the earlier post, and this being one of the motivators for me to take on these walking challenges. Discussing this further with Lorri, we decided my next outing should be some kind of multi-day solo adventure. After spending some time with Google Maps – where I plan all my routes (thank you, Street View!), I settled on something to meet this aim. I planned a two-day hike, targeting 17.5 miles on day one and 14.1 miles on day two, for 31.6 miles total. My my start and end points were each a >30 min drive from home, so this route would require a drop-off and pickup (my wife is very gracious), as well as an overnight stay at a motel – one conveniently located near a favorite brewery 🙂

Mission accomplished: but why?

To make a long story short, I achieved my latest goal! -and with two fewer blisters than the three I ended with last time! I think I know how to prevent the one I did get (I’ve done a lot of reading on the topic). So a challenge to address next time, it seems. But otherwise, this was honestly way easier than I’d thought it would be, despite it being the longest two-day hike of my life, and the first of those I’d done since I was at least half my current 48 years. I was also carrying more weight than usual given the overnight stay – about 13 lbs total between water, gear, and clothes. Sure, I was tired, my calves ached, and my feet hurt after the first day. But I was pleasantly surprised how well day two went once I got limbered up and accustomed to walking. The morning Advil assuredly didn’t hurt either, if I’m being honest.

Left image: Stats for day 1. Right image: Same for day 2
(Yes, I’m too lazy to fix the different white balance points!)

But the question I was reflecting on this morning was why this was important to me. To be frank – and I hope it’s not a letdown, I’m not certain I have the answer yet. Yes, part of it does involve an interest in backpacking. I needed to prove to myself that fundamentally, I’m capable of these durations + conditions to even consider longer trips. But that aside, what else is at issue here? Some of it may just be enjoying the idea of setting a challenge and achieving it. That’s a pretty nice rush, right? Doing so via athletic pursuits is rather foreign territory to me, to be truthful with you. I’ve always been pretty quick to give far less than my all to such pursuits so doing otherwise is definitely charting new ground for me.

Merely the latest in a list of items of interest?

I’ve written a lot here about the idea of time freedom. I’ve truly enjoyed this aspect of my current phase of life as much as I’d hoped I would. For me, it’s the best part of this FIRE path so far. But I didn’t go into this period with a long checklist of things I wanted to achieve. True, I did have some things in mind that I wanted to explore, while still others were added as I went. Thinking back over the past nearly two years, that list includes (but is not limited to – see this article for a laundry list!) things like:

That last one is pretty new so I haven’t written about it prior. I’m currently nearing completion of my WSET Level 2 certification in wine, and may proceed to the tougher Level 3 course. As I’ve mentioned before, I have a really fun part-time “job” working one day a week as a Wine Educator in a local area tasting room. I don’t need this certification to do that job competently, though it will make me better at it. Mainly, I just enjoy the content and growing my skills in wine tasting, evaluation, and general education. Perhaps this educational path will lead to something else, but I have no established plan to do so.

And maybe that last point is just it: I enjoy being able to set goals and achieve them at this point in my life, irrespective of whether I “need” to do them or whether I’m certain it will lead to something else of value. Perhaps this is just the “random walking” through interest areas that my YouTube partner in crime and I have discussed on the show before? I suspect this is the most likely explanation, but am not really sure either. I like it as a starting point in any case. If you have any other thoughts, I’d love to hear from you in the comments!

Lots of questions with few answers

What I don’t have for you, my patient readers, is a tidy way to wrap up this post. I’m not entirely sure why I continue to pursue these goals related to walking long distances. But I’m not losing sleep over that mystery. It’s been fun, educational, and I really enjoy the challenges (and achievement!) associated with it. So what’s next? I’m planning on doing a single-day marathon-length walk soon. It’s pretty exciting gearing up to do these walks, I must say. And maybe that’s also part of it – the pre-work and anticipation about whether I can achieve the next milestone is pretty great!

Lacking better ideas on how to close, I thought I’d share a few of the photos I took with my phone on my most recent journey. These are a great reminder to me that I live in a beautiful part of the world and these walks are a wonderful way to experience the area. I hope you enjoy them. Thanks as always for sharing your time with me! Mahalo 🙏

You are much stronger than you know

A few weeks ago I posted a new short form video to Two Sides of FI, the YouTube channel I produce with my show partner, Eric. These videos are often highlight clips taken from our full-length videos which we share between episodes. This one was a little different. In that video I talked about the idea of spontaneity, something I thought a lot about during a 13-mile walk* I took the day prior. I’m not going to rehash the content of that video, as I think that’s covered well there. I hope you agree. Rather, I’d like to write about the walk itself.

What I didn’t state in the video is that walk was the second-longest I’d done in my life. In fact, the longest was a 14-mile hike in Utah that my wife, Lorri and I did nearly twenty years ago in 2003, when I was in the best shape of my adult life. We basically lived inside the boundaries of Acadia National Park at that time, didn’t yet have a child, and hiked often. So even though 14 miles is a long hike no matter what, it wasn’t too much of a struggle as I recall. This picture seems to support that, as we don’t seem what I would characterize as miserable.

Me and my wife smiling next to the sign at the end of the trail after completing our hike
2003 (Utah): Happy at the end of our fourteen-mile hike

Time for a new challenge

Fast forward to now: I’m closing in on 50 years old faster than I’d prefer, am certainly heavier vs. 2003 though thankfully otherwise in excellent health, and while I still walk and hike at least five days a week, most of my excursions are around three miles long with occasional hikes of 4-6 miles. I’m still good to go on trails marked as Moderate intensity, but a longer Strenuous graded hike on a hot day will definitely kick my ass. But I can get it done. But it’s certainly been a very long time since I hiked more than 7-8 miles in one go.

So honestly, for me it was kind of a big deal that last month with almost no advance thought, I decided to walk out my door and not stop for more than 13 miles until I arrived two towns down the road at my targeted lunchtime stop. The reason I gave Lorri for undertaking this endeavor was my interest in doing some backpacking, and needing to see what my endurance was like these days. But if I’m being honest, the main reason I undertook that challenge was simply to see if I could do it. It turned out that I could!

I was really happy with that achievement, which was the equivalent of walking a half-marathon. But I knew I was capable of more. I hadn’t fallen apart after more than 13 miles of walking and honestly didn’t feel too bad the next day either. So yesterday I decided I had more tests I wanted to take on. My family was going to be busy with other things, so the timing was great. After considering a few route options, I set out to walk to a grocery store in the next town. Taking a longer route on back roads through vineyards and ranches, it would be about ten miles to get there. Depending on how I felt at that point, I’d either take a more direct route home for 17.5 miles total, or what I really wanted to do: reverse my earlier route for a total of 20 miles.

Raising the bar + going for it

Completing either option would have been a huge achievement for me, and the longest hike/walk I’d ever done at either 25% or 43% longer compared with the Utah hike I described above. The first ten miles went fine and then I grabbed a quick lunch. After sitting for 20 minutes to rest and eat, I set out again. After a little deliberation, I decided I just had to go for 20 miles. What was the risk? Even if I couldn’t make it back I could always call for a ride. I felt pretty confident that I could make it though. If I’m being honest, I kinda knew it, and would regret choosing the shorter walk home had I done it.

That confidence aside, I was pleasantly surprised how well it went. Yes, my split times got a lot worse in the back half of the walk. My usual ~19-20 min walking pace slowed quite a bit to yield the average shown above. It was a hot day, and my hips, feet, and legs were definitely tired. Listening to music helped, particularly some more aggressive industrial + metal for when I started dragging. So I soldiered on, drinking water from my trusty CamelBak all the while, and got through it. I took a pit stop before the last two miles and grabbed a cold drink at a store, as the now-tepid water I was carrying wasn’t gonna get me to my goal. Once I got back to my neighborhood I did an extra lap around the block to ensure I hit my target: 20 miles. I had done it!

My daughter was really surprised (and sounded a bit concerned) when I told her how long I’d walked. Teens aren’t great at measuring the passage of time so I’m not sure she realized I had been gone for eight hours and walking for nearly all of that. My response to her amazement was pretty simple: “You are stronger than you realize.” I’ve always believed that’s true, though I’ve not often considered athletic achievements when saying that to myself. I was, after all, one of the kids always picked last for teams in gym class. Always. So choosing something so sporty to test myself with was kind of a big deal.

I think it’s important to remind ourselves of just how much we are capable, and that’s the core lesson I took from this experience. Perhaps we don’t always need such tests to do that, but they can be a pretty helpful tool to prove it to our ever-doubting brains. I do know that until recently, I wouldn’t have conceived of taking this on, nor made the time to do it if the idea had crossed my mind. “Giving up” a whole day for a walk like this is certainly a good example of the power that time freedom really offers, and why I consider this the greatest benefit of my early “retirement”.

What tests have you intentionally or by circumstance undertaken, proving to yourself just how strong you are? I suspect anyone reading this has great examples of the same. You are all stronger than you may know. I wish you all the best.


*when all my time moving is spent on paved or unpaved roads or on the shoulders of the same, I term these excursions as “walks” – no matter how rural they might be. This is in contrast to hikes, which for me indicates that I’m traveling on trails, navigating irregular terrain, etc. In the end they can both have lots of elevation change and range from Easy to Strenuous grade, and are definitely both exercise, but I choose to differentiate the way I use the terms. 🤷‍♂️

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