The Art of Living: My Personal Experiences with Making Plans Versus Embracing Serendipity

 

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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The Importance of Curiosity

 

 “The important thing is not to stop questioning. Curiosity has its own reason for existing.”
― Albert Einstein

Curiosity just might be the most powerful force in the universe. It's the motivation that's never exhausted. Curiosity is the engine of learning. Curiosity is the driver of innovation and positive change. Great things, amazing things, are routinely accomplished through curiosity. Spark a person's curiosity and you give them the ammunition to conquer the world.

Or something like that.

The science of motivation tells us curiosity is one of the most powerful intrinsic motivators there is. Humans inherently love learning. Our brains are the most complex structure in the known universe for a reason. Curiosity and that love of learning is what drives me to develop this project, and it's no coincidence it's a foundation of our Tribe and our School.

I've long been interested in curiosity. As a public school teacher, I've long understood the sheer value of sparking curiosity in my students. It makes the entire school experience for students infinitely better if they want to be there because they're curious. Grades improve, retention and the ability to apply ideas and concepts gets way better, behavior problems disappear, students become empowered and have the ability to solve real problems, etc.

Unfortunately, it's exceptionally difficult to spark curiosity in a public school setting, at least among every kid. Class sizes are simply too big, we waste too much time preparing for and taking standardized tests, and we have too many required classes and strict curricula. We certainly try; every administrator, teacher, and support staff knows the inherent value of fostering curiosity. The systems, just too big, too impersonal, and too structured. Curiosity requires freedom and maneuverability. Curiosity requires flexibility and the removal of barriers. Our schools can't provide this because we expend all our resources trying to meet totally unrealistic expectations. 

Our School will utilize curiosity as a basic foundation of everything we do, from deciding which classes to offer to deciding who will teach them to exactly what students will learn. In future posts, I'll expand on this idea. But curiosity is also hard-wired into everything we do. Including our Tribe.

“Listen with curiosity. Speak with honesty. Act with integrity. The greatest problem with communication is we don’t listen to understand. We listen to reply. When we listen with curiosity, we don’t listen with the intent to reply. We listen for what’s behind the words.”
― Roy T. Bennett

Our Tribe (and our gym) is filled with genuinely curious people, which includes curiosity about each other. If you eavesdrop on any conversation at our gym, they're never like "so how's the weather" conversations. They're conversations about who were are, what we do, what motivates us to train, or other deeply-inquisitive questioning. It's clearly obvious we have a gym filled with people who listen to understand. 

It's no surprise our gym is filled with people who experience grand adventures; their curiosity towards each other applies to a curiosity about life. And that curiosity about life is what pushes us to experience new, exciting things. It's what allows us to overcome fear and experience real adventure.

It's rare in today's world, and it's one of the things I think makes us a little different. It's why I think we can make a real dent in the universe.

~Jason

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Life Lessons, Revisited.

 

Way back in 2012, I wrote a blog post about the life lessons I had learned in the previous six or so years on a rather all-encompassing quest for self-improvement. Since that time, I've mostly striven to implement these nine lessons as often as possible. It's proven to be a pretty decent roadmap.

The List

1. Help others. If everyone spent time actively seeking out ways to help each other, the world would be a lot better place. Each of us has the power to change that if only we recognized just how much we have to offer to those around us. Whether it’s something big or small, strive to help others. Make a difference.
 

2. Figure out what you enjoy. Do it more. Understand what brings you joy. In almost every case, humans crave excitement, not happiness. Once you understand that concept, living a fulfilling life becomes a lot Hell of a lot easier. Set up your lifestyle to experience excitement more often.

3. Figure out what you don’t like. Do it less. What don’t we like? Most assume this involves avoiding pain whether it be physical, emotional, spiritual… whatever. While it’s not always pleasant, it’s not pain that brings unhappiness. Boredom brings us unhappiness. Understand what you find boring, then set up your lifestyle to experience less boredom.

4. Seek challenges. Humans thrive on challenges. They may come in the form of the physical, mental, social, or emotional. They may involve work, lifestyle, exercise… whatever. Figure out what makes you uncomfortable, then do it with reckless abandon.

5. Learn from everyone. True wisdom is the realization that we’re a lot stupider than we like to think. Every single person we encounter has lessons to teach us if only we accept our role as a student. You have two ears and one mouth; use them in that proportion.

6. Surround yourself with genuine friends. Find friends that you can trust, will help you when you’re down, have the power to challenge your way of thinking, and can ignite your inner fire. The ability to make you laugh and play is important, too.

7. Embrace minimalism. We surround ourselves with way too much stuff under the guise of security. We falsely believe our problems will disappear if we reach some imaginary line of material comfort. Instead of pissing away your days attempting to fill your life with more shit, embrace minimalism. Use your creative energies to develop unorthodox solutions to the minimalism. It makes life a lot more interesting. If you need to spend your cash, spend it on adventure.

8. Realize we can’t predict the future; act accordingly. Too many people spend too much time plotting the course for tomorrow without really embracing today. Don’t miss the opportunity to make today special. In almost every case, you can make today special by helping someone and doing something exciting. Remember, you may die tomorrow.

9. Embrace change. Some will tell you not to fear change. That’s bullshit; change is scary as Hell. Instead, embrace that fear. The exhilaration from the fear of change is what makes it so exciting, and we crave excitement.

~Jason

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You Get to Set the Rules.

 

Years ago, I wrote a blog post on BRU about Chris Guillebeau. His book "The Art of Nonconformity" was one of the earliest influential books that, ultimately, got me to this project. While Guillebeau talked about a lot of great ideas in that book (many of which are covered in this short PDF), the one that suck the most was the kind of advice that's almost so simple, it never occurs to you:

You don't have to live your life the way people expect you to. 

When I first read that, it was a mind-blowing revelation. I took stock of every aspect of my life, and realized pretty much every decision I had ever made was because someone expected me to make that decision. Needless to say, the last decade has been one long string of pretty damn amazing adventures based on experimental lifestyle design. When you realize there really aren't any rules, you get to make your own. 

That's kinda the point of this current project. Mix equal parts of the lifestyle myself and my family want to live with a genuine desire to solve some tricky social problems and... POOF! We get this project. But this post isn't about this project.

It's about making your own rules. 

You see, society wants us to fit in. Put your head down. Do what you're told. Don't rock the boat. Because society likes predictability. Conformity. Follow the rules. 

And if you don't? Society gives you stern, disapproving looks. Wags a finger. Society may even [gasp!] talk behind your back.  And that's about it.

Turns out society is a bit of a passive-aggressive bitch. 

Which is great you you and me. Because it means there's really nothing stopping us from making our own rules. The rules we want to play by. The rules that work for us.

Yet so very few people actually take that plunge and live the life they want to live. Instead they follow the status quo. And they're miserable.

Why?

I think it's fear. Fear of the unknown. Fear of rejection. Fear of failure. Fear of success.

Part of the problem is we imagine this journey to an unconventional life is going to be a lonely journey. Just ourselves and our goofy ideas.

But that's not how it works. Not at all. 

In "Tribes" Seth Godin said "The secret to leadership is simple. Do what you believe in. Paint a picture of the future. People will follow."

When you overcome the fear to try something new, when you venture past "safe" and into "exciting", there will be people, the right people, who follow. And that's your Tribe.

The Two Distinct Reactions

When I describe this project to people, I get two very distinct reactions. This one:

 

 

And this one:
 

There's absolutely no in between.

And that's okay. 

One of the most valuable lessons I learned back in the barefoot running days is that the moment you start making your own rules, most people don't get it. But some do. And you have to trust those few who get it will be your key to changing the status quo. They will be the key to making your own rules.

So stop letting society set the rules that define your life. Become a heretic. Make your own rules. Live the life you want to live. Life is too short to miss out on all the fun.

What do you have to lose?

~Jason

 

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