Challenges in a Post-FIRE Life

Since reaching semi-retirement in 2018 and actual financial independence in 2019, life has been a whirlwind!

In the past two years, Whitney and I have traveled to over 30 countries, spending about 9 of the last 24 months in total traveling internationally. We are actually supposed to be traveling through South and Central America for 5 months right now visiting another 15 countries, but COVID had other plans… We’ve also visited over 30 of the US states in the past two years. We’ve spoken at a national physical therapy conference as well as some state conferences and schools. We started a new website (Travel Therapy Mentor) and began making weekly live videos to help and educate others currently following or planning to follow a similar path, talking about travel therapy and occasionally mixing in finances. We even bought our first house last month!! Who knew you could do so much in 2 years’ time?

To people following along with my journey, this probably seems like a great beginning to my post-FIRE life. Actually reading back through that list, to me it sounds pretty awesome as well! In reality though, despite the way things seem, I’ve had a lot of struggles in the past two years adjusting to this new life. This is a topic that is difficult for me to write about, because when I think about it logically, it seems ridiculous to write about challenges when I’ve been so incredibly fortunate to get to the position that I’m in now.

At the risk of seeming tone-deaf with so many others struggling to a much larger degree in their lives, I think it’s pertinent to discuss challenges I’ve had in my post-FIRE life for others seeking some form of early retirement. I had some inkling soon after semi-retirement in 2018 that FIRE wasn’t going to be the panacea that I’d envisioned when I wrote about it being just the beginning, not the end, but now the picture is much more clear to me.

Here are some of the main things that I’ve struggled with and am currently still working through. First I’ll cover the issues and then how I’m doing my best to resolve them.

Loss of Purpose

Prior to 2018, my life had been spent working toward goals nonstop and at full speed.

  • As a teen, I worked 30+ hours per week most weeks during my last two years of high school.
  • I worked full time during my first three years of college to save money and keep debt minimal.
  • After undergrad, I completed a very difficult Doctor of Physical Therapy graduate program, while simultaneously achieving all time strength and body composition goals in the gym, while doing extensive research on health and fitness.
  • Upon graduating from grad school, I worked as much as I possibly could while spending free time deep diving into side hustles and learning about personal finance and investing, in order to save 85%+ of my income each year.

In almost every phase of my life, I’ve imposed additional demands on myself in an effort to sacrifice in the short term to improve my long term prospects.

Once finishing my all out sprint toward FIRE in 2018, I was suddenly faced with being 29 years old and having no clear long term goals anymore. During the entire journey approaching that point, I thought once I achieved what I was aiming for, I’d be relieved and happy —that all the sacrifice would be worth it and I could then do whatever I wanted.

What I actually found was a short period of elation, quickly followed by uncertainty, fear, and at times even depression. I had doubts about everything I’d done and began to think there must be something wrong with me. After all, isn’t financial independence what everyone spends their lives striving for? Shouldn’t I be happy now?

Lack of Structure

I’ve never been someone who is good at going to bed and getting up early. In fact, it was not uncommon for me to revert to staying up all night and sleeping most of the day during breaks from school for as long as I can remember, even into my graduate program. (And I found a partner in Whitney who’s my equal on staying up late and sleeping all day. Whether that’s a good or a bad thing, the jury is still out, HA!)

Fortunately, I’ve had imposed structure and schedule with school and work for my entire life to keep my on track. I always thought of this as a negative thing before, but now with some reflection, I realize that structure and a schedule is vital for me to feel productive and content.

During breaks from school when my sleep schedule would be completely destroyed, it didn’t bother me because I knew it was just temporary “vacation” from real life demands that were going to quickly return. Upon reaching FIRE and having the ability to maintain a night owl sleep schedule indefinitely, it quickly became clear that this was a recipe for disaster for me long term. Upon waking up after staying up most of the night and sleeping most of the day, I found myself with no desire to work on anything productive and a strong feeling of depression. This is far from what I was expecting. I thought that freeing myself from an imposed schedule would be a surefire ticket to being happier. That’s certainly not the case for me.

Paradox of Choice

If you’re unfamiliar with the concept of the paradox of choice, it’s worth learning more about. Essentially, this is the counter-intuitive notion that human nature is such that, the more choices you have, the less happy you are with any particular decision you make. Since FIRE involves the ultimate number of options, I’ve found that this can really be a bitch. I think this is best illustrated with a couple of examples.

While Whitney and I were spending an amazing month in Chiang Mai, Thailand exploring the city and having a great time, I often found myself on social media feeling jealous of friends that I saw hiking amazing trails on the west coast of the US and visiting cities in Europe.

Meanwhile, the next year while we were exploring most of Western Europe soaking in the sights and amazing food, I found myself feeling jealous of friends that I saw hiking mountains in Chiang Mai and snorkeling in southern Thailand.

I’ve found that no matter how awesome my current adventure is, there’s a feeling of regret that I didn’t do something else that I had the option to do. This probably seems ridiculous to you, and if I read this three years ago I would have thought it was ridiculous as well. But, it has really been a thief of joy and contentment for me these past two years. The more options I have for things to do and places to go, the more I regret whatever decision I make.

Limited Motivation

Prior to reaching FIRE, I wrote pretty regularly on this blog despite being busy with work, side hustles, and travels. I’d grown to really enjoy the process of getting my thoughts and ideas down in written form and interacting with readers. I thought that once I didn’t have finances or work to occupy my time and mind, I’d write even more often.

In reality, I’ve found myself very unmotivated to write or really do anything productive many days. This might not seem like a problem to you, but I’ve realized that a feeling of progress and productivity is vital for me to be feel content. A life of nonstop leisure is no life at all for me. As the saying goes, I don’t enjoy the sunshine without the rain. Without some form of “work” occasionally, I find little joy in leisure activities and down time. On the other hand, if I get things done first, then the down time is a treat and enjoyable. I think this is another result of human nature and evolution.

Declining Health and Fitness

At the end of grad school and the beginning of my working years, health and fitness including bodybuilding and powerlifting were a primary part of my identity. It’s almost all I thought about throughout the day. I’d dream about squats and deadlifts and envision myself breaking personal records. Unfortunately, at some point, this focus was almost completely replaced by personal finance. Gradually I started working out less and eating worse, until I got fed up and made some big changes at the beginning of 2018 which included losing almost 50 pounds and getting back into lifting. I even made a decent amount of money while losing that weight with Healthywage. I thought that was going to be the end of my days of being lazy and eating poorly. I was wrong.

Spending 5 months in Asia in 2018 along with 4 months in Europe in 2019 made eating well and lifting often very difficult. During our travels, we eat out for most of our meals and want to try a variety of local foods, which are almost never low calorie dishes… Theoretically the periods in between international trips should be the perfect time to get rid of some of the weight gained while traveling, but in reality this has been more difficult than I imagined. The lack of structure and loss of motivation mentioned above leaked into my health and fitness. Counter-intuitively, making it to the gym and eating healthfully was actually much easier when I was busy with school and work. I think this has a lot to do with having more time to think about food now, and talk myself out of going to the gym.

Solutions… Or at Least Lessons Learned

At this point if you’re thinking, “wah, wah what a complainer,” I don’t blame you. After all, these are trivial issues to have in the grand scheme of things, and I fully realize that. The interesting thing about all of it to me is the large chasm between how I thought my post-FIRE life would feel and what my level of happiness would be, versus what it actually is. I tried to be realistic with myself along the journey. I came up with a long list of things I wanted to do and work on after FIRE so that I would be “retiring” to something instead of solely away from something, but boredom hasn’t been the issue that I thought it might be. Instead of boredom, it’s motivation, purpose, and lack of goals that I’ve had to contend with these past two years. After countless hours of reflection and self evaluation, I’ve made some discoveries that have really helped and that I anticipate making a long lasting difference for me.

Almost all of my post-FIRE struggles revolve around a lack of goals after achieving everything that I had set out to achieve. Previously, I had no idea just how vital goals and making progress toward them were for my mental health and happiness. I used to wonder why so many billionaires continue to work extraordinarily hard when they could indulge in a life of leisure, but now I understand.

The truth is, happiness is not found in realizing a goal or milestone, but in the process of working toward it. Long lasting contentment doesn’t exist, leisure isn’t satisfying without work put in to complement it, and happiness is not a destination but instead a continuous journey toward self improvement and progress. The sooner we come to terms with these ideas the better off we’ll be.

Here are some action steps I’ve taken to improve my situation and some things that I am continuing to work toward:

  1. Setting a self imposed schedule starting with being consistent on earlier sleep and wake times.
  2. Setting new long term goals to work toward with regards to health, fitness, knowledge, and impact on the world.
  3. Maintaining projects with “work,” mostly involving writing articles for this blog and Travel Therapy Mentor, as well as potentially even putting more time into writing a book I started a couple years ago.
  4. Concentrating on eating mostly nutritious meals, but not depriving myself of occasional treats and unhealthy foods I enjoy.
  5. Helping and doing things for others as often as possible. I find much happiness in doing nice things for others, and that has become much more evident in the past couple of years.
  6. LIFTING WEIGHTS CONSISTENTLY. This seems to be a linchpin of sorts in my life. Nothing has ever done more good for my mental health, self image, and overall happiness than lifting weights consistently. I’ve found that I can consistently go from a terrible space mentally to satisfied and content after an hour of heavy deadlifts or other compound lift. I can walk in the gym feeling depressed and walk out feeling like superman.

I hope that some of these realizations and lessons learned will help you in your own journey toward FI or in your own post-FI life. At the very least, it should be entertaining to make fun of me complaining about things even while being in such a fortunate position. Let me know your thoughts in the comments!


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