Reflections on 30 Years of Trial & Error

The month of May tends to bring a heavy mix of anticipation and scramble into my world as things seem to be on the cusp of the “glory days”; and by that I mean summertime. It is so sweet yet oh so fleeting here in our little mountain paradise.

So to capitalize, it’s as if there’s this obligation to get out and enjoy every bit of it—whatever and whenever possible—knowing damn well that soon the leaves will be falling and the snow will be flying. Which are both beautiful in their own regard, but it is still a little saddening at first to see those glory days come to a close.

When autumn comes, I start to plan. It’s this cycle where I reflect on what went well and what didn’t over the past year. Then from Mid-November thru December I map out ways to improve. These plans aren’t just what will be done tomorrow, but more so in the long range to be carried out over the course of the next year.

Then in January, I do my best to start implementing them into action and it never fails that I have this projection of achieving some kind of orderliness come May in hopes that the ship will be tightened down to endure the whirlwind of summer. Yet, year after year, it seems like there’s always a few loose ends still floating around. I’m beginning to wonder if it will ever be different. Or is it indicative of the cyclical nature and phases of life always changing? Rather than battling to keep this relentless grasp on it all, perhaps the trick is to anticipate change, understanding things may not unfold the way I’ve planned them out in my head and find satisfaction in simply knowing I made the effort to do my best.

In similar fashion, growing up I remember having this evolving idea of how orderly things-to-be would occur and that ultimately I’d reach some kind of life ‘mastery’.
As life progressed, that concept remained with a reoccurring theme that always seemed to be “right now is OK, BUT; once I have this, or once I know that, then I’ll really be able to ______.” As if there’s this point where it won’t be so much doing—doing the “figuring out” and building, but rather, things will become more a matter of being—being a pro, or being at the top, etc. As if everything would be figured out, where I could then just oversee and manage it all.

All I can do is smile and laugh at the fact how that’s not quite the way it’s all unfolded. What’s really happened is my Friday nights have evolved from staying up past my bed time to play video games, to multiple rounds of beer pong, to burying my head in a book or two.

I recently enjoyed a great read of “Ego is the Enemy” where author Ryan Holiday shares a perspective that life is an endless loop of three phases: aspiration, success, and failure. I found that to be so very true. Sometimes we make a lap around that loop within a matter of days or weeks. Sometimes years. And sometimes it seems like we’re in all three phases at once, pertaining to different aspects of our lives.

It is interesting to look back and see the era’s my life has progressed in thus far. Growing up into the early teens was this era of discovery, like with most people I assume. Mischief, trouble, lots of “firsts” and lots of lighthearted fun.
Like the days out building forts and catching crawdads. First loves and school dances. Or that time in middle school I got busted for smoking.

I had snuck out with some friends on a Friday night. The claim was that we were going to smoke weed, but who knows what it actually was; probably some old dried up tobacco or oregano. I remember we used one of those pieces of paper that come in a tin of Altoids to roll it up with. Didn’t really work out so well but we thought it was cool nonetheless.

The following Monday at school we all got called into the principal’s office. My hands were sweating I was so nervous. One of the girls who tagged along on our little Friday night excursion was concerned about our attempt at smoking, so she told the school about it.

I remember my stomach just dropping sitting in that office, concerned about them talking to my parents. It was later in the day when we got called in, so as soon as school got out I raced home to tell my parents about it before the principle called. I just felt like they needed to hear it from me first. That may have been the one and only time I got grounded, but I remember feeling so relieved about telling them. Like I had done the right thing and “manned up” to the situation. That was a good lesson in being up front and integrity.

I was fortunate enough to have very supportive parents. That and the fact I was their only kid probably helped too. Once I took a liking to skiing and snowboarding, my folks would make a point to get me up to Loveland Ski area almost every weekend before I could drive, which I will be forever grateful for. But the one and only time I took this bus up there was the day I shattered my arm and dislocated my elbow.

There was this fallen tree that hung over this cat track, maybe 10 feet off the ground. I wanted to be like all the pros I was watching in the films, so of course, I would slide the log over the cat track, jump off and land on the hillside below. I did this a few times before eventually catching my edge on that log, sending me head first onto the cat track. I put my arm out to break the fall and next thing I remember is that tingling feeling you get when hitting your funny bone.

I was alone and can’t remember exactly how I got back on my feet, but when I did my left arm was just sort of hanging there, so I cradled it with the other one and got moving. Must have been the adrenaline, but there was no pain on that run down to the base area. In fact I distinctly remember making some turns trying to savor what I knew was my last run of that season. I made it right to the ski patrol shack where they had to cut the sleeve off my shirt.
The pointy part of my elbow was facing up and it looked like there was one of those mini nerf footballs in my arm. Then I got my own personal ride all the way back to Denver on an ambulance instead of that smelly bus. It was only January too. In fact, that is how I started out the year 2000.

The worst part of it all was coming to grips with the reality that it would be almost an entire year until I could snowboard again. But after two surgeries, 3 pins, a Teflon plate and weeks of physical therapy, I was back up there opening day the next season. That was a good lesson in failure and perseverance.

Mid-teens through a good chunk of my 20’s was like an era of passion, spending all my time chasing the pleasures of life. In high school I had a few things I was crazy about; soccer, fishing, music and skiing. I was a midfielder on the Varsity soccer team, played bass in two different bands, had a tight knit group of close friends that meant the world to me, and my girlfriend; she was a total babe. Good times indeed and I rode that ‘wave’ right into the college years.

College life was somewhat of an abrupt change, in a very good way, as it is for most I would imagine. Coming from the foothills of Denver out to Western State, The Gunnison Country presented a whole different perspective on life. However, my stint on Western’s soccer club was very short lived. Things like mountain biking and fishing the Gunnison quickly became priorities over soccer practice. As the college years progressed, I became more and more obsessed with fly fishing and skiing. After all, that was what really brought me out here.

So once I graduated, that’s all I did for a few years—ski and fish (with a little bit of work mixed in there). There was this year, 2010 I think, that really set the bar. Banner season skiing lots of big peaks in the backcountry, followed by some exploring in the Caribbean that spring, to a summer full of fly fishing and guiding around here,
then capping it all off with 2 months trekking and fishing around New Zealand. No doubt, Chasing my passions took me to some incredible places around the world.

Don’t get me wrong, I still very much so hold a burning desire for such pursuits. But passion, to a degree, is more of a blind drive fueled by intense feelings for something, whereas purpose is all about clarity. Purpose takes the I part out of life’s endeavors and is about pursuing something outside yourself as opposed to pleasuring yourself. My late twenties up to now seem to be unfolding into what I would deem an era of purpose. Looking at the things I enjoy or feel moved to do and finding the why behind it all. As Holiday writes in Ego Is The Enemy:

“Whatever we seek to do in life, reality soon intrudes on our youthful idealism. This reality comes in many names and forms: incentives, commitments, recognition, and politics. From earning to pretending . Ego aids in that deception every step of the way. We can very easily find ourselves corrupted by the very occupation we wish to serve.
Purpose helps you answer the question ‘to be or to do?’ quite easily. If what matters is you—your reputation, your inclusion, your personal ease of life—your path is clear: tell people what they want to hear. Seek attention over the quiet but important work.
If your purpose is something larger than you—to accomplish something, to prove something to yourself—then suddenly everything becomes both easier and more difficult. Easier in the sense that you know now what it is you need to do and what is important to you. The other ‘choices’ wash away, as they aren’t really choices at all. They’re distractions. It’s about the doing, not the recognition.
Easier in the sense that you don’t need to compromise. [but]Harder because each opportunity—no matter how gratifying or rewarding—must be evaluated along strict guidelines: Does this help me do what I have set out to do? Does this allow me to do what I need to do? Am I being selfish or selfless?”

This is where I feel I’m at as I reach my 30th lap around the sun this May. Still enjoying myself by all means, but once again in a state of aspiration; building out the long term visions of personal and business endeavors. And with that comes a new awareness of ego and appreciation for humility. There’s confidence, then there’s arrogance. There’s humility then there’s insecurity. The trick is to find the sweet spot; to find the intermediate.

Success—as holiday writes— “well, often we fall in love with an image of what success looks like.” Maybe that’s a job title, size of a paycheck, the amount of recognition or people who know you and what you do. For a long time, I’ve been guilty of searching for some kind of validation from others and the outside world to confirm my success.
But making a conscious effort to change that has been rather liberating. I recently scribbled this to myself on a 5 a.m. coffee buzz;

“stay true to your purpose. Be a good man, be the best you can at what you do—that is “enough”. Recognition, compensation, attention; they’re all “bonuses” of fulfilling your purpose and a high personal standard”.

My observation has been that I’m bound to be judged. I’m bound to be unappreciated by some while valued by others. But instead of being attached to whatever outcome, how about looking within and knowing I gave all I am capable of, and using that as the metric of success?

On the flip side with failure, again, it is a reoccurring phase we all go through. That’s it. Easier said than to accept, but I trust that the more I can embrace it, the better. Just a matter of leveling it out with the ego. Not in a “I’m too good” kind of way. The exact opposite actually. It’s rooted in a fear of failure. Sometimes it hurts to fail, and often times it’s embarrassing. With personal, social and business endeavors, when I strip it down, it has been the fear of failure that has held me back from all the things I’ve wanted to do. All the things I believe in, yet have hesitated to pursue.

My biggest takeaway of turning 30 and what I’ll wrap this up with: No need to worry about always having everything in order or figured out. Come tomorrow, it could all be different. Fulfillment may not always be some kind of accomplishment, but rather a process. Always be open to learning. What I think I know today is bound to change tomorrow. I believe to be great, and to stay great lies in the capability to see myself as a perpetual student of whatever it is I aspire to be, to do, or to know. In the words of Epictetus :

you can’t learn if you think you already know