Fortune (and Compelling Autobiographies) Favors the Bold

Pre-birthday reflections on a life lived in bold.

18 year old me scaling a mountain pass outside Queenstown, New Zealand in 1994.

In late 1994, I decided to ride my bike around the world. The decision was made under the influence of magic mushrooms and was neither practical, nor thought through. I had never traveled out of the US except for a couple trips to Canada and Mexico. I was barely 18 and had only been out of my parental home for a few months and had spent little time on my own. While most people abandon such grand ideas made under the influence for practical considerations like these, I’m not most people, apparently. A short time after my psychedelic trip, I was making tangible plans for my pedal-powered geographical trip.

I decided to start my trip in Australia, but a co-worker suggested I visit New Zealand first since its size was more manageable and filled with more attractions than Australia. In December, I boarded a plane to Auckland to start the adventure of a lifetime. Just me, a horribly overloaded bike, a Lonely Planet New Zealand guidebook, and a 100 tabs of acid.

New Zealand turned out to be the beginning and end of my world bike tour. I put zero effort into planning, hoping Lonely Planet and the acid would do it for me, but those hopes were dashed as soon as my plane landed. I had no route, no direction, and few coping mechanisms for the loneliness and despair I would experience. This was long before smartphones or the internet could provide me direction or ability to message people back home (international calls were ~$3/minute). And there was no marijuana, my main coping mechanism at home. Much of my six week long trip was spent in a fog of loneliness and depression, replacing weed for booze, and doing way too much acid. The one notable exception to my misery was the two weeks I spent biking with Paul, a man I met on the road.

How Happy Rolls

I recall telling my New Zealand tale to a world famous endurance athlete a few years ago. He was thoroughly impressed that I did something so ballsy at such a young age. Funny enough, I never viewed the trip that way. I was too focused on how miserable I was and how it wasn’t the trip I meant to do. The disparity between self-assessment and external-assessment has been a lifelong bugaboo. I’ve lived an extraordinary life, but often failed to recognize that because I’m too busy criticizing myself for not doing the things I did the way I envisioned.

But luckily my harsh self-assessments seldom stopped me taking big, bold actions. If anything, they prompted bigger, bolder actions because I labeled my previous efforts as lacking for various reasons. The New Zealand trip would be the first of many adventures in my adult life, the contents of which are in desperate need of being articulated in a book.

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I’m turning 50 years old in a few days. As happens around most of my birthdays, and particularly so with this milestone age, I’ve been pondering where I’ve been, where I’m at, and where I’m going. There is so much that’s not the way I want it in my life and, related, in the world. Alongside this disappointment is a bounty of profoundly meaningful experiences, relationships, and good fortune. I consider myself to be one of the most blessed people I’ve ever met. And I’ve met a lot of people.

Reflection of a writer as an older man.

Though I’m subject to the vagaries of entropy and getting older, I do not feel or look old. As I’ve written about here before, a key to my youthful attitude and appearance is my dogged refusal to settle down, and my lack of tethering to a static lifestyle, especially to high paid careers and expensive tastes. This lack of tethering has enabled me to make bold choices over and over and over again. Some of those choices worked out great, others fell flat, and others resulted in getting my ass handed to me. Each of these outcomes provided an essential lesson I had to learn, and I’m not sure I’d have done anything differently, even with the choices that went south.

I won’t delve into the particulars today, but my life’s boldest moves happened in 2019, the consequences of which make the disappointment of my truncated world bike tour look beyond trivial. My boldness earned the scorn of many, and I lost virtually every worldly thing except my health and wits—fortunately, my two most valuable assets. I was chastened by my losses, and the last six years have been uncharacteristically devoid of bold action. For my 51st trip around the sun, it’s my intention to cut out the timorous act, to live boldly, to take big chances, to be willing to lose and win big. I look forward to sharing that journey with you as it unfolds.