30 Lessons from a Year of Goal Setting and Risk Taking

It was about a year ago that I found myself at a crossroad. I had relocated from San Francisco to Seattle. I had recently lost the most important person in my life. I was working on a project I considered to be my most important work to date. And being two years since my one-year trip and a few months since my most recent long-term trip, I had this longing for more. All that as I came up on what friends were calling a “big birthday,” but what was just another number to me.┬áIt’s not that I wasn’t happy. I was as happy as I had ever been, yet felt this pull that there was more that I could be doing. Shortly after this, when a few friends and I all gathered in Hawaii to celebrate my 30th birthday during the second week of February, on a whim, I did something that I rarely do: wake up before the sun does. After an hour’s drive toward the top of Maui’s Upcountry near Haleakala, I strapped on a parachute, ran down the mountain, and paraglided over the Hawaii island of Maui. The next day, what I thought began as a joke about my friends and I getting tattoos (and me getting my first tattoo), ended with all of us doing just that. And so began the list.

The idea behind “bucket lists” always rubbed me the wrong way. It seemed to be so jaded, only for the rich or those confronted with illness. I had always thought of myself (at least for the last couple years) as having experienced a well-lived and well-traveled life, yet with what seemed like an ever-growing list of things I wanted to do, but that weren’t getting done. Sure, I had seen people do lists, like a “40 before 40″ list that stretched over a few years, and eventually wanted a list like Danny Dover’s multi-year bucket list to complete all of his goals by a specific deadline, or Akvile Harlow’s Listpiration, where she does one bucket list adventure per month. But I wanted to shake things up. I wanted life to be filled with a certain passion and urgency, and not simply wait until the end of my life or for personal tragedy to strike. And so after back-to-back days of some of my most spontaneous adventures that left me wanting more, the “30 at 30″ List was born: One year, to do at least 30 things I had never done, but with the intention of doing as many things as possible. Now with 8 days left, I’m on #36.

Here is some of what I’ve done, along with what I’ve learned along the way, some being lessons I’ve re-learned, and others being new revelations (broken up into two pages, that you can click at the bottom or here to access page two)

Paragliding over Hawaii's Maui

1. A bucket/life list like this is only as strong as my resolve (Paragliding over Maui). There's no way I would have experienced what I have this year if I hadn't attached a deadline. The items would have sat dormant on a (visible or invisible) list until there was an involuntary urgency, like personal tragedy, that thrust me into action.

Timshel tattoo

2. Life is both harder and easier than I think (My first tattoo, "timshel," from East of Eden and the Mumford & Sons song of the same name). I find that the greater the challenge, the more I have to dig deep to rise and confront it. What follows is a stronger tolerance of future challenges.

Fly aerobatic plane over Las Vegas

3. My greatest weaknesses, can be used to better myself and the world around me (Flying an aerobatic plane over Las Vegas). What is stubbornness sometimes, is determination other times. It may have been one of my father's less desirable traits, and it may have made me lose my lunch not once, not twice, but three times in flight; but I find that with each passing day I seem to have a greater zeal, resolve, and determination for life that I only wish inspires others.

Las Vegas Muscle Car

4. Bucket lists aren't the end, but rather a means to an end (Drive a muscle car). There was one point when I was on pace after the first three months to do 60 items. I realized if I kept up that pace that it would become about the list, and not about challenging myself, investing into experiences, and enriching my life. The moment it became about the list itself, and not about it being a vehicle for bettering my life, then it would've lost its purpose, and I would've lost the passion.

Las Vegas Strip

5. I am a blatant tourist (Experience March Madness in Las Vegas). And I'm completely secure in this. As much as I love the offbeat, nook and cranny parts of travel, I love just getting lost in the blatant touristy things of a destination. This is the only way some people travel, and that's alright.

Spring Training in Scottsdale

6. I'm not living "the dream," I'm living my dream (Attend Spring Training). I don't really know what "the dream" is. I just know that I'm trying to orchestrate a life that I want to live. I want to live life on my terms and this is how I've chosen to do it.

March Madness Staples Center in Los Angeles

7. I would rather be good at a few things then great at one thing (Go to the Big Dance a.k.a. a March Madness game, here at the Staples Center in Los Angeles for the Elite 8). I used to think I wanted to be a traditional travel writer and just write travel books and magazine articles. But then I realized that while that might be my passion, it wasn't where my purpose, passion, and skill all intersect. I'd rather tap into my full potential, which has meant trying to be as versatile as possible. Along the way, I've picked up some new work skills and hobbies, some of which, weren't possible without this one-year project.

Amsterdam Holland canal

8. If I want to change my life, I have to do just that, change my life (Begin writing a non-fiction book transcript). I remember wanting to change my life for so long, but approached life like if I waited long enough for the change to happen, that it would happen. If you want to change your life, you have to change your life. It was Walt Whitman who said, "Not I--not anyone else, can travel that road for you, You must travel it for yourself."

Oahu Diamond Head

9. As fulfilling as traveling solo is, there are moments that are meant to be shared with someone special (Learning to paddle board from a Hawaiian on Oahu). And I'm not talking about your best friend. I mean like someone really special. There's a long list of those things that I'd love to share with a belle by my side. I mean c'mon, it can't get that much more romantic than making out in a hot air balloon. I'm going to change the name of my blog to, "The Traveling Romantic Philosopher."

Bow and Arrow

10. I am my greatest obstacle (Shoot a bow and arrow...from a castle). There's no excuses and it's no one's responsibility. My success is on me. As Randy Pausch said, the brick walls are there for a reason. They are to keep the ones out who don't want it bad enough, and give us a chance to show how bad we want something.

Philly cheesesteak in Philadelphia

11. Spontaneity stretches my life's boundaries (Eat a Philly cheesesteak...in Philadelphia). Spontaneity often infuses a needed jolt of passion and energy into my life. It also pushes my limits and if I do something out of spontaneity that I previously feared, then I have a lower risk of talking myself out of it.

Floatplane Seattle, Washington

12. The more I go, the less I know (Fly in a seaplane). If I've said it once, I've said it a million times, traveling the world humbles me like no other experience. It accelerates the classroom of life, showing me how big the world is, and how little I am. In that way, I'm thankful.

Houseboat on Lake Powell

13. The greatest risk is not taking any risk at all (Piloting a houseboat on Lake Powell). I would rather go all in and take the risk, and lose, then go about life wondering what would have happened if I would have risked. Risks don't have to be win-lose.

Snuba diving in Hawaii

14. But risks should be calculated (Snuba diving in Hawaii). While I've made my share of split-second decisions, most major decisions I at the minimum sleep on, as well as confide in a friend about. I'll often take a small risk, and then after seeing a return, use the results to taker a greater risk.

Scuba diving Okinawa, Japan

15. My successes tomorrow will be marked by the goals I set today (Learning to scuba dive in Okinawa, Japan). I truly believe in the interconnectedness of the world and the timing of certain events for certain times in our life. This year would be all for naught if I didn't believe that the goals I set and reached this year will pay off days, weeks, and years from now.

4 Comments on “30 Lessons from a Year of Goal Setting and Risk Taking

  1. I love all of this. I love the writing style for this post. I love the simplicity of your list. It’s not a grand bucket list. I don’t like the idea of those, by the way, and I happen to be a big list maker in general. What are my top 30 things to do or see before I kick the bucket? I have no idea. As I come across it, I’ll know it’s a moment or place I want to experience. Then I’ll move to the next one. This list, to me, is about enjoying where you are in life, enjoying the great moments like learning to dive in Japan, but also cherishing that six-pack on the front porch. I think the multitude of blogs out there that talk about this grand life we should all be living on the road gets tiresome. It’s OK to sit on the porch with a six-pack, and it’s OK to be happy attending an MLS game. Sometimes we can take those simple things in life for granted, when they end up being just as grand as the great moments.

    • Lance,

      I love everything about this. That’s really one of the biggest takeaways I hope people would get from this. Sure, I’d love to climb Mt. Everest, but I’d also love to go to a MLB playoff game. And I’d love to learn to sail. Also, I want to pet a whale. And sometimes, I just want to sit on my porch and drink a beer. And those desires are going to be different for everyone. But that’s something that people have to find for themselves. But I think it’s often the simple moments that really strike a chord with me and leave the most profound effect. Thanks Lance. You really summed up what I was trying to get across perfectly!

  2. I couldn’t agree more with this post! I’ve also found myself making life about the list, which is not the healthiest way to go about crossing items off a bucket list, at least not for me. I also love the part about spontaneity or choosing between certain things. Although a lot of people were going to the Open in Australia while we were there, I knew it wouldn’t be a satisfying activity for me and wound up choosing something else that wound up being a great experience :) I think you’ve captured all these points perfectly!

  3. Pingback: What I Learned from a Year of Investing in Experiences | The Traveling Philosopher

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