Years and years ago, I read one of my second-tier favorite books, "Rework". It's a business book, but also contains a Hell of a lot of great life advice. Once such piece of advice has to do with making plans. Specifically, the silliness of making plans. The authors make the point that all planning is, really, just guessing. Jason Fried, one of the authors, makes the point in their blog Signal v. Noise. Since I first read this years ago, the idea has had a profound impact on how I approach life.
Those who know me well know I LOVE strategic planning. I can spend every hour of every day researching and analyzing all kinds of variables to synthesize a plan for the future. Solving complex, seemingly-unsolvable problems with weird, synthesized, unorthodox solutions gives me the kind of deep, primal satisfaction I can't put into words.
But there's an inherent problem with this "hobby." I'm continually planning for a future that may or may not come to fruition. More often than not, it's the latter. Life sometimes throws you curve balls. And sliders. And changeups. And forkballs that start off right over the plate, then drop off the table. Hell, sometimes life buzzes your head with a 98 mph heater. </pitching analogy>
Anyway, even the best-laid plans can get blown up by unforeseen circumstances. Because planning really IS guessing. When those circumstances are bad, it's not too difficult to adjust course a bit to navigate whatever hardships arise. That's the the crux of being resilient. That's the crux of developing plans that can adapt.
But what if those unforeseen circumstances are good?
The Life Story, Summarized
Prior to 2003, I had a life plan. I had meandered through high school, went to college, got a job as a teacher, and had been planning to repeat the same year again and again, complete with the white picket fence life, until I retired. Then I planned on a retirement filled with woodworking or some other mundane hobby until death. It was the plan society (and everyone in my life at the time) expected me to follow. And I had obediently complied.
But then unforeseen circumstances hit, both really, really bad and really really good. Not too long after Columbia disaster, I was faced with a choice that would turn out to have, in retrospect, a profound impact on my future. I had to choose. Stick to my life plan, or, for the first time in my life, take a real chance and embrace serendipity.
I made the choice that terrified me.
That entire life plan I had been following to the tee was absolutely shredded and, for the first time in my entire life, I realized I didn't have to live my life according to the detailed plan society gives us. We can make our own plans.
Since that time, I've always had a plan for the future. A roadmap, if you will. Something to point me in a direction. But it's little more than that - a plan to head in a particular direction. That approach led to all kinds of unexpected adventures. I ran 100 mile races, wrote books, learned how to do Internet marketing, became a fame-ish barefoot runner, traveled the country in an RV for two years, took up Brazilian jiu jitsu and kickboxing, wrote extensively on sex, gender, and relationships, did a pro MMA fight, started an online men's group, became a real estate agent, make a bunch of lifelong friends, and did a few things I'm not putting in print. :-)
Which brings us to the recent past.
When Shelly and I decided to leave San Diego, we knew where we wanted to live (Colorado's Western Slope), and we had a vague idea of what we wanted to accomplish (eventually buy a house, eventually open a jiu jitsu gym, enjoy the quiet solitude of a rural community, and maybe eventually start dabbling in homesteading.) That was our direction. But we were incredibly open to embracing whatever came along. We knew our openness to new experiences coupled with our tendency to do shit that terrifies us would likely present some interesting opportunities.
Life hasn't disappointed.
When we first arrived, the rental market was terrible, which forced us to buy a house immediately. That turned out to be an incredible investment. Then, due to scheduling, we changed the gyms and befriended the owner who had to leave town due to family circumstances. So we bought the gym. Shelly, a college business major and high school teacher, somehow ended up as a badass animal control officer. At our gym, we've met multiple interesting, amazing friends who have enriched our lives in ways I never could have imagined. Then COVID came along and basically destroyed our business financially, but also brought a few people into our lives who, thanks to their sheer awesomeness, have taken our lives in a direction I would have never foreseen and, relevant to this blog, have inspired this very Tribe/ School project.
I've spent most of the last seventeen years occasionally reflecting on my life and the countless amazing adventures I've experienced. Sometimes that includes imagining the alternate reality where, back in 2003, I hadn't embraced serendipity. What if I hadn't made the choice that terrified me? What would my life look like right now, today? The thought of that rattles me to my core.
We're All Going to Die
The Columbia disaster. That was THE event in 2003 that changed everything for me. As far back as I can remember, I've always been enamored with space. When I was in third grade, I checked out a book on the planets of our solar system every week for the entire year. In seventh grade, myself and two other students placed second in the nation in a contest NASA ran to design a moon colony. First place would have won us a trip to Space Camp. Even into adulthood, I watched shuttle launches. And re-entries. Including Columbia's last trip.
I was taking a mental health day from my teaching job in Michigan. I had been feeling pretty burned out. I hadn't gotten out of bed by mid-morning, and was watching TV and absent-minded flipping through channels. I came across one of the cable news channels covering Columbia's re-entry. About ten minutes into watching the live coverage, Columbia broke apart over Texas. I can't quite describe how I felt - it was some combination of disbelief, grief, and... numbness. I don't know how long I laid there blankly staring at the TV. I have no idea what the anchors were talking about. All I remember is a thought, which started as a tiny spark deep in my mind, slowly grew into an epiphany I had never really considered before.
I was going to die.
I have no idea why the Columbia disaster triggered that first confrontation with my own mortality. But in those moments, my life forever changed. I assessed my life up to that point and came to the disturbing conclusion that I had never actually lived life. EVERYTHING I had done, every decision I had made, were done because someone else directed me. I had chosen the safe route at every turn in my life. And I got extremely emotional. Even writing about it triggers those emotions as if it happened yesterday.
The real kicker, though? I started assessing the things I seriously regretted NOT doing. Every time I took the safe route, there was an alternative route that promised some sort of adventure. And it was a looooong list. And, in light of my newfound sense of my own mortality, I started imaging myself on my death bed. And that growing mountain of regret I had been curating.
That was the scariest thing I had ever imagined.
A Life Worth Living
That fear of regret on my deathbed has turned out to be an incredibly reliable test for each and every life decision I make. When confronted with a choice between safe and comfortable and scary and adventurous, I ***always*** choose the route that terrifies me. YOLO! And it almost always results in something amazing. Even if it turns out poorly, it still gives me the opportunity to really grow as a person. Regardless of the outcome, it leaves me free of that god-awful crippling regret that defined the first 27-ish years of my life.
In the seventeen years since, I've truly lived a life worth living. If I were to die tomorrow, I would have no regrets.
But I sure as Hell don't want to die tomorrow. In those seventeen years, with Shelly as my co-conspirator, I have truly learned how to LOVE life. And that always involves choosing the terrifying choice. As I sit here right now, today, we find ourselves on the precipice of all kinds of grand escapades, including this project and other terrifying-but-potentially amazing adventures.
Magic happens when we open ourselves up to new experiences and have the courage to do that which terrifies us.
So yeah... I have a plan for the future. But that plan really is just a guess. It's a direction. But as the distant and very recent past has proven, embracing serendipity is how you live a life free of regret. We're all going to die. When we're on our death bed and we're assessing the lives we've lived, remembering our adventures will be a hell of a lot better than wallowing in regret over the adventures we turned down because we were too scared.
Now go out and make the scary choices. Embrace adventure. Live a life worth living.
~Jason
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You the man Robillard!! get ahold of me
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