Over the past decade I’ve completed a handful of bucket-list-type challenges that I really enjoyed. This post is about the characteristics of those challenges that I believe made them so engaging. I hope that by documenting them I can continue to find great challenges for myself in the future, and hopefully you can benefit from my experience as well.

Across a wide range of challenges, I’ve found that I have the most fun when they hit on most of these attributes:

1. A binary goal that can clearly be marked completed or not
2. Some amount of risk that I will fail, endure physical harm or need to be rescued
3. Unknown unknowns, things I don’t yet know I don’t know about
4. A new location to get to know
5. The need to learn some new skills in order to complete it
6. The need to train and get in some sort of peak shape in order to complete it
7. A high amount of required physical exertion
8. Some awe inspiring natural outdoor beauty
9. A competitive benchmark to compare my performance against
10. Good friends to plan, prepare, train and enjoy the adventure with

Not every challenge involves all of those, but thinking back on a few of my recent ones, they all have at least a handful of that list (as indicated by the numbers from the list above)

• won a marathon – 8 elements – #1, 2, 3, 4, 6, 7, 8, 9
• competed in an Ironman – 9 elements – #1, 2, 3, 4, 5, 6, 7, 9, 10
• surfed mavericks – 8 elements – #1, 2, 3, 4, 5, 6, 8, 9
• ran around Mt. Rainier – 9 elements – #1, 2, 3, 4, 5, 7, 8, 9, 10
• 135+ mile SUP adventure – 8 elements – #1, 2, 3, 4, 5, 7, 8, 10
• summited Mt. Whitney – 7 elements – #1, 3, 4, 5, 7, 8, 10
• went canyoneering in Zion National Park – 7 elements – #1, 2, 3, 4, 5, 8, 10

A key theme to all of this is growth. All of these adventures represented the first time I did something and a chance for me to grow, physically and mentally. That growth in myself is my favorite part of challenges. It is a chance for me to break through comfort barriers and expand my realm of competence.

Growth is also the reason I don’t think I would be happy striving for mastery at a single thing. For example the idea of trying to run a faster marathon every year, would only hit on four elements (binary goal, risk of failure, need to get in shape and physical exertion) and I’d eventually get tired of it. Essentially the challenge would come down to whether I was able to train more, train smarter and fend off injury. That is certainly challenging, but not robust enough for me to enjoy indefinitely.

Similarly, I can’t expand my challenges via elements #2 or 9. I am not looking to do new things simply by taking on more risk. There are far too many people that take on way more risk than I can justify as a father of four. Similarly, challenges that simply require more time to be competitive won’t work for me as my time is very limited these days.

Instead, as I look to future years, it seems obvious to me that the elements I should look to pivot on in order to find new exciting challenges are #3, 4 & 5. Finding new realms where I don’t know what I don’t know, new locations to explore and new skillsets to master.

For me the fun part is finding worn paths others have taken that I can follow and then finding new ways to follow them combining skills I’ve gained in the past with new ones I learn. Transitioning from running marathons to doing triathlons or ultramarathons is a pretty common story. Adding in SUPing feels new and draws on elements of kayak camping and surfing. Maybe next I’ll add in some skis and a paraglider to really help me nail those FKTs. The fun is in the growth and that comes from pushing limits not just in how you train, but in what you’re willing to take on as well.