There’s a memory from our recent trip through the desert Southwest and Baja that I keep coming back to. We were in Kofa Wildlife refuge at a spot we’ve been to twice now. I had woken up early to hike up the hill behind our camp to look for Bighorn Sheep. I walked out onto a point that overlooked a pool that had gathered in a large depression in the red slickrock. I sat there, binoculars in hand, scanning the canyon and the hillsides, the first bits of sun hitting the red rock and beginning to warm my face. I didn’t get any glimpses of sheep, but what I did get was a powerful, pervasive, yet subtle feeling that I was exactly where I was supposed to be, doing exactly what I was supposed to be doing. It was a profound sense of rightness. It was deep down, at an animal level, outside of intellect or reasoning. Tears came to my eyes when I told Jocelyn about the experience later that morning. Two days later I said goodbye to the job I’d had for the past decade.

The Leap

The decision to make the leap and leave my career as a software engineer was years in the making. At the time I left, I had been working in the software industry for almost 20 years. For most of that time, I loved the craft and I built something of an identity around it. I got a particular sense of satisfaction from seeing an application come to life, the craftsmanship of creating elegant code that solves tough problems. I worked at the same company for over a decade, long enough to grow with it, to care about it and the people that I worked with. In many ways, it was the the perfect job. Fully remote, allowing me to travel and work from the road, well paid, lots of vacation time, a boss who I respected and who respected me, and products I believed in for the most part. Eventually though, for reasons I still haven’t quite been able to discern, I just lost the passion and interest in it.

A few things happened that probably contributed to the loss. The company was bought by a private equity firm and after a few rounds of layoffs and executive turnover, the culture changed dramatically. The place that had felt like mine started to feel like someone else’s. The introduction of AI and an incessant push from the new executive team to use it for everything also took away much of what I loved about the craft. I don’t think AI is inherently bad, it’s just not how I prefer to work. Prompting an AI to write code instead of writing elegant and efficient code myself takes away much of the joy of craftsmanship that I found in the work. I was also feeling pulled in a different direction, away from screens and the digital world and toward wilderness, water, trees, and human connection not mediated through a Zoom link. Underneath it all there was also the awareness that I am no longer young and time isn’t an unlimited resource. With middle age, I was starting to feel the weight of my own mortality, that my time here is limited, and so is my good health. The window to do some of the things I want to do in life may be closing. I started to wonder, “If not now, then when?” Eventually I found that I was having a hard time focusing, and for the first time in my career, I noticed that I was beginning to dread Mondays. All of this combined to make it clear that for both my own sake and the sake of the company it was time for me to make a change.

So, I jumped. It wasn’t an impulsive decision, but more like finally going through a door that had been slowly opening for a couple of years. I had some ideas of what I wanted to do instead, but no detailed plan. I was trusting that keeping myself open to possibility would show me a path forward. Trusting that the finances would work, and that Jocelyn and I would navigate the uncertainty together.

The Long Game

As I said, the final leap wasn’t an impulsive decision. It was actually more than ten years in the making.

Sometime around 2012 or 2013, I came across Mr. Money Mustache and the FIRE (Financial Independence Retire Early) movement. He was a former engineer who retired in his 30s through frugality, diligent saving, and investing. His irreverent style and anti-consumerist bent really appealed to me. His classic post, “The Shockingly Simple Math Behind Early Retirement” opened my eyes to the possibility that with diligent saving, simple investing, and frugal habits anyone could take control of their most precious commodity, their time. I was hooked by the idea, not because of some retirement fantasy of playing video games all day, but because of the freedom that it promised.

We were already frugal so none of this was a big stretch, but the idea of FIRE gave me a goal and a purpose for our frugal habits. We bought way less house than we could technically afford according to the bankers and we still live in that same 1500 square foot 3 bedroom, 1 bath (the horror!) house we bought almost 18 years ago and that we paid off 7 years ago. We shared one used car for many years. We commuted by bike and brought a lunch most days when we were still going to an office pre-Covid. We cooked at home the majority of the time. Some years we saved 50% of our income. We have no debt. However, we’ve traveled extensively, pursued our hobbies, and done everything we’ve wanted to do. We have never felt deprived of anything, we’ve just been intentional in how we spend our money making sure it’s on things that we really value.

We’ve been relatively frugal and intentional, but we’ve also been very lucky in some ways as well. We were able to buy our house in 2008 when they were still relatively affordable and we had help with the down payment from a small inheritance. We were able to graduate from college with minimal student debt. I had a high paying tech job. We don’t have children. All of those things helped, and I don’t want to downplay those. However, we still could have easily inflated our lifestyle with a bigger house or fancy cars every time one of us got a raise and not ended up where we are. That is in fact the default path in our society and one that we didn’t want to take. A bit of luck combined with some discipline allowed us to have the flexibility and options we have now. Money can’t buy happiness, but it can buy options. I am now exercising those options that we’ve spent the last decade plus creating.

We are not quite fully financially independent in the sense that neither one of us ever needs to work or earn money again. We are also not fabulously wealthy. We still need to be intentional about our spending just as we always have been. What we do have is a sense of what is enough and the knowledge that real wealth lies in having control over our lives. In the words of Chris Brogan, “The goal isn’t more money. The goal is living life on your own terms.” Jocelyn really likes her job and sees herself continuing to do it for the foreseeable future. This gives us the majority of the income we need to live and so our savings and investments should continue to grow until working also becomes optional for her in a few years. I am immensely grateful for her support and encouragement in making this jump.

The Road

Two days after my last day of work, we were crossing the border into Baja. This trip was a great way to start the transition and ease into this next chapter. On one hand, much of the time was easily filled by the activities of being on the road–deciding where to go and what activities to do, meeting new people, learning about the culture and landscape. On the other hand, there was ample time where we slowed down and stayed in one spot to allow Jocelyn to work. This allowed me to to begin to really appreciate the new freedom. I could spend time preparing food for us, fishing, paddling, writing, and reflecting about my next steps. It allowed me to settle into a simple rhythm in tune with the natural cycles of the day, the ocean, and the desert–away from the screens, distractions, and stresses that had characterized my days for the majority of my adult life. At first it just felt like a long vacation, but as the days and weeks passed, this rhythm became more natural and I began to revel in the freedom and possibility of each day and by extension the rest of my life. What a feeling to have my time be truly my own!

A Complicated Homecoming

Coming home from a long trip always comes with some complex feelings. On one hand, it’s nice to be home, in a familiar place, with endless, glorious hot running water, my own space, familiar routines, the friends and community that have been built over years, and the beauty of the Pacific Northwest in Springtime. On the other hand, it’s hard to downshift to those familiar routines when I’ve become so used to the constant stimulation and novelty that life on the road brings.

Life on the road is in many ways simpler as well. It lays bare the fact that we don’t need that much stuff to live and be happy. We lived well for two months in 40 square feet. We had everything we needed and never really felt lacking for anything. There is a certain freedom in that sort of simplicity. At home, while there is much more comfort, there is also a lot more to maintain. Just keeping entropy at bay takes a significant amount of time and effort. There’s always something to fix, to decide, to deal with. I don’t want to minimize the good. I am glad to be home. However, in the days after returning from a big trip like this, I often find myself longing for the simplicity of the road and wondering why we have all this stuff, this yard to take care of, this house to maintain.

This homecoming was particularly complicated for me because while I was coming back to a familiar home and many familiar routines, there was a big hole where work and career used to be. The job and career that had structured so much of my time, that so much of my life had been built around, that had given me a large part of my identity, was gone. I’m still adjusting to that absence.

Something Bigger

So, on to the big question. What now? I’ve spent most of my adult life focused on myself, my career, financial security, and building a comfortable life. I don’t regret any of that, and it’s what’s given me the foundation to pursue something else. What has become more and more clear, however, is that true happiness and purpose lies outside of myself, in contributing to something bigger.

The guiding principle I’ve decided on is simple: service. It feels good to be able to give freely of my time and talents to help the people and causes that are important to me.

There’s a concept from the activist and scholar Joanna Macy that really resonates with me called The Great Turning. The idea is that we are at a civilizational turning point. A move away from an industrial growth society built on extraction from the earth and each other and toward a society of reciprocity and care that supports and sustains life. She calls it the most important work of our time. I believe it is and I want to be a part of it. I also believe it happens through small acts of care in our communities, not necessarily from flashy, big actions. It’s building and caring for our relationships, protecting and preserving life where we can.

This work also doesn’t have to take itself too seriously all the time. To that end, I want adventure, travel, music, dancing, good food enjoyed with people I love. Enjoying life with the people we love is it’s own sort of resistance to a culture that wants us to work ourselves to the bone in isolation so that we can buy stuff we don’t need.

So what does that look like in practical terms for me? Well, so far it looks like volunteering to do forest defense and habitat restoration work with Bark, and habitat restoration with Oregon Natural Desert Association. I’ve also volunteered with Adventure Scientists to place acoustic monitoring devices in the forest as part of a biodiversity survey. I’ve helped out at my friend’s farm and I will be spending a large part of the summer helping my parents in Montana. I’ve volunteered with Rhythm Seed farm right down the street from my house to help in their mission of building local food sovereignty and security. I’m also planning on extensive travel including heading back down to Baja at the end of the year. There will be plenty of outdoor adventure from backpacking to skiing to hunting. I’ve gone skiing a couple of times despite the dismal amount of snow here in the Northwest and being able to go midweek, after a storm, when the snow is the best, has been amazing. There has been and will be music, festivals, and dancing. I’ve planted our own garden here at home and I’ve taken on the food shopping and cooking duties in our household. I’ve been enjoying improving my cooking skills and making fresh, healthy meals from scratch. I’ve been making yogurt and kombucha. I repaired our 20 year old refrigerator, keeping it going for a few more years I hope ,and saving us at least $1,000 if we would have had to replace it. In all of this, I am also trying to remain conscious of the fact that I don’t need to fill every moment with something. I don’t need to be busy for the sake of being busy or to look productive. I need to leave room for reflection and for serendipity to perhaps lead me in a direction I wasn’t anticipating.

Honest Assessment: 3 Months In

I want to be honest about the ups and the downs I’ve experienced in the last three months. I think that’s more important than just presenting an idealized version fit for social media about how amazing life is.

First though, yes, it is amazing in many ways. Waking up every day and having the day be truly my own, to make of it whatever I want, that is an incredible feeling. I am sleeping better than I have in years. I am spending much more time outside and away from screens doing things in the real world with real people. I am exercising and eating well. I feel great mentally and physically. Each day feels like a gift.

Yet, there is still discomfort. The uncertainty that arises from these liminal spaces. That feeling of owning my time and being totally responsible for how I spend it, while liberating, can also feel overwhelming. The freedom can sometimes feel a little too close to aimless drifting. I wonder if I’m squandering this incredible gift. If I’m making the most of it. The majority of my time and much of my identity has been structured by my job and career for decades. I was a software engineer. Now what am I? What do I tell people at dinner parties when the subject inevitably comes up? I’m still figuring that out and I suspect I will be for a long while. Some days that feels exciting, and other days it feels paralyzing.

Thinking back to that hillside in Kofa, I’m realizing that what I had been waiting for was permission to live differently. The permission arrived that morning in that particular place and at that particular time. I’m working to settle into the uncertainty and to trust that the path will reveal itself in due time as long as I’m paying attention and moving forward. If you’re thinking about making a similar leap, I can tell you it’s survivable and that it’s worth it. If you’re looking for your own permission, maybe this is it.