What I learned From a Year(s) of Taking Risks

It was on my first trip to Hawaii, on the island of Maui, that I sat on the slopes of Haleakala Volcano, overlooking the island beneath me and the Pacific Ocean in the distance. As I sat back-to-back to Maui local, Dexter, shooting the shit, I wondered if I shouldn’t be anymore scared—if I shouldn’t be biting my fingernails, shaking my leg, or questioning whether I should be here. Then, after a few minutes, Dexter stood up, reached for my hand, and asked me, “It’s time; are you ready?” A minute later and I was kicking my feet over the ground, sailing over fields of lavender toward the Pacific Ocean, and paragliding for the first time.

Three years and 72 new things later and it would appear that I’m still literally (and figuratively) taking the plunge. Paragliding that day, on my birthday weekend no less, was no. 1 on my life list of doing at least 30 new things over the course of that year, motivated in part by a feeling of complacency and in part by my mother's recent passing. I did 38, and consequently resolved to do at least one new thing for every month following. This past year I did 25, which was particularly marked by attempting a lot of challenges and risks, especially uncalculated risks.

But this isn’t to tell you how many things I’ve done the last three years or downplay anything you are or are not doing. It’s rather context. This series of life lists haven’t been merely a checklist. Rather they’ve been an extension of my life, in some ways setting and maintaining direction for it. But most importantly, I’ve learned a shit ton, and I want to share some of what I’ve learned with you.

By the numbers, several of the things I did have become new hobbies (including paddleboarding and snowboarding), my top-three trips to date all occurred as a result, I threw up three times while flying an aerobatic plane, a couple of the trips have become annual trips (including Spring Training), a couple of the items became new work skills (first and foremost, brewing and bartending), one of the items turned into a relationship, and I was arrested zero times (Truth be told, I didn’t do anything illegal, at least that I know of).

But when I think of the last three years, my eyes start to well up, as I think of just how damn special it has been. And it has nothing to do with any recognition, titles, or awards. It’s simply because who I was three years ago seems but a shell of the person I am now. I feel like I’ve squeezed out a lifetime of experiences and learning into just three years. So this week, as I celebrate my 33rd birthday, I want to share just a little bit about what I’ve learned.

1. Invest in things so much that it hurts if it doesn’t work out. What I mean here, is giving myself enough to something that if it doesn’t produce the desired outcome, that it conjures up strong emotions. I think largely, we live in a society that suppresses this, especially among men. It’s as if being detached is a virtue. And no, I’m not talking about love or a relationship here. It’s something I only recently have observed, which I observed from one of the items on my list, participating in my first cocktail competition. It was something very small, and perhaps trivial, a cocktail competition at a restaurant and bar in California. But I had invested so much time and thought into it, that after finding out that I had lost, I was disappointed that I hadn’t won. But I’d rather give too much and feel deeply, then not give enough and feel nothing at all. Even for love. As the song “Gamble Everything for Love,” by Ben Lee, says, "You can gamble everything for love if you're free."

2. Lead your life and the dreams will take care of themselves. I can’t take credit for this mantra, which I’ve taken to heart from Randy Pausch’s book, The Last Lecture. I use to think that dreams were just that, dreams. And then I started verbalizing my dreams and putting them out to the universe, and then they started coming true, or at least true enough for my satisfaction. This started happening when I began living and leading the kind of life I thought I should be when I started challenging myself more and taking more risks. I don’t think that’s any coincidence.

It's not about how to achieve your dreams, it's about how to lead your life, ... If you lead your life the right way, the karma will take care of itself, the dreams will come to you. -Randy Pausch

3. Disconnecting actually fosters deeper connections. This is an important one for me. At the same time I started taking more risks, I began taking at least one trip (near or afar) every three months in which I completely unplug from technology. I still often do it, though sometimes it’s just for a day (and often something or somewhere I’ve never been), when my friends will receive a text from me, telling them where I’m going and when I’m returning. I truly believe that the best version of myself is when I return from those trips. I can work all I want all day and week, but if I have nothing to give others and the world at the end of it, then what good is it?

4. Give fewer damns (and fucks). So this comes in part from Rhett Butler and in part from one of my favorite articles from last year, by Mark Manson. I grew up giving too much of a shit about people liking me, too much of a shit about doing what people wanted me to do, too much of a shit about being successful by the world’s standards, and so on. And at age 27 I had recently lost my dream job, lost all of my post-college friends, lost a marriage, and was working as a video store clerk (and it wasn’t even at Blockbuster). I had given a damn about what everyone else felt, believed, and thought about me, that I didn’t have any belief or thought in myself. So against other peoples’ advice, I finally went with my gut, and started my own business, sold and gave away everything I owned, and traveled for a year. It’s my best decision to date, and I’m now more comfortable in my skin than ever. I both care a lot (for the things in my life worth caring for, like loving myself, friends, family, purpose) and don’t care at all (namely, other’s people’s business and what they have to project onto me).

There's absolutely nothing admirable or confident about indifference. Not giving a fuck does not mean being indifferent; it means being comfortable with being different.

5. It’s not so much how far I go, as much as how deep I go. I used to dream about traveling every inch of the world, envious of people who had country counts in the triple digits. But then I realized that I’d rather see less, but experience more, then see a lot, and not experience enough. Travel is a means to an end, not an end in itself.

6. Home isn’t just a place where you lay your head, but it’s where you stand. You guys, I actually have a home that really is a home. Yes, a home as in a house, but more importantly a place, marked by the people and experiences that make it so. This isn’t something I’ve ever had as an adult. And I think the last few years have in some ways been a journey toward this. I used to say that I would continue traveling until I found some place I never wanted to leave. It seems as if I found that place (and people), and I particularly like how Pico Iyer sums up home.

Home isn’t just a place where you lay your head, but it’s where you stand.

7. Only by risking going too far, could I possibly discover how far I can actually go. T.S. Eliot put it much more eloquently, but how could I possibly know who I am and who I’m not, and just how far I really can go, if I don’t try new things and push my limits to see how far I can actually go? I wouldn’t be spending my time on half the things I am now if I hadn’t made a decision to constantly try new things and take on new challenges.

Exhibit A: Bro or snowboarder (Photo by Bobby Christian).
Exhibit A: Bro or snowboarder (Photo by Bobby Christian).

8. The greater risk is risking nothing at all. Life is scary as shit. It really is, but what I’ve found is that the hardest part often isn’t doing the thing, but deciding to do the thing and making the jump, because many of the greatest risks have so little certainty and guarantees. But then if they did, they wouldn’t be risks. But at the end of my life I’d rather say that I risked too much then not risked enough.

9. Brick walls are not there to keep us out, but to show us how bad we want it. This again takes from Randy Pausch’s The Last Lecture. This year I took what were probably more uncalculated risks then I’ve ever taken. And I’m just going to go ahead and say that it was the most special year of my life and yielded the greatest returns. But I also worked harder than I ever have, spending many an all-nighter up working toward returns from the risks that I had taken. Passion is misguided if there isn’t hard work and purpose that supports it.

The brick walls are there for a reason. The brick walls are not there to keep us out. The brick walls are there to give us a chance to show how badly we want something. Because the brick walls are there to stop the people who don’t want it badly enough. They’re there to stop the other people.

10. There is no failure, only the wisdom of the past, hope for the future, and the courage to continue on in the present. Yes, I’ve most certainly fallen the last few years. And I’ve most certainly embarrassed myself. I’ve made mistakes. And sometimes, I’ve done it all simultaneously, such as falling for the first three hours of learning to paddleboard (and learning to surf, and snowboard, and just about anything else I've tried to learn). But there have been no failures. I’ve learned, I’ve grown, I’ve evolved, and I’ve become a better person. It stands to reason then, that I’m not going to stop taking risks now. Alright, so perhaps I won’t bet on the no. 16 seed at March Madness this year.