Some years ago, I set a goal for myself to go outside and be active every day, for 365 days straight. I embarked on the mission (again) in late 2017, and at the beginning of 2018 I wrote a manifesto about this idea

The beginning of the Outside 365 project in late 2017 wasn’t the first time I’ve begun this project. And it wasn’t to be the last. As I wrote in mid-January, if I fail, I have a very simply plan: start again.

And as it turned out… I did fail, or at least, I had to stop and take a break. I’m not quite sure how many false starts the Outside 365 project has been through over the years… but it’s been several.

Despite those numerous false starts, my commitment hasn’t wavered, and the goal has stayed (mostly) the same. Then sometime last week, I checked my logs and realized that I had been active for over 100 days in a row. In fact, today is Day 108.

Achievement—It Feels GOOD

I still have a long ways to go to reach 365 days of activity in a row, but reaching the 100-day mark feels monumental because, through perhaps half a dozen false starts, not once have I passed 100 days in a row. 

75+? Yes. 100? No… at least, not until last week.

Also within the past week, I have ticked over another milestone: moving from 29 years old to 30. By most standards, turning 30 (or any decade birthday) is a pretty big deal, and if my Instagram feed is any indication, it tends to be the cause for much celebration and pseudo-insightful musings.

As I reflected on both of these milestones, I realized something interesting: I’m much prouder of and I feel much more accomplished by reaching 100 days in my Outside 365 journey than I do reaching 30 years of age.

Here’s the thing: in order to reach 30 years of age, all I have to do is not die and I’ll have succeeded. Sadly, numerous people still don’t reach this milestone—but billions others do. 

But in order to reach 100 days of outside activity, I had to actually put in some effort. I had to try and apply myself in order to achieve that goal. I had to pull on my clothes and head outside to move my body, even if that meant walking in the pouring rain down a dark, unknown road after sunset in Norway after 30+ hours straight of traveling. 

So this week, if I’m going to truly celebrate any achievement, it won’t be turning 30 (despite the excellent party last night—thanks friends!). It will be reaching 100 days in my Outside 365 journey. 


Over the next couple of days, I’ll share a few insights and changes that I made to my approach that have allowed me to reach this milestone for the first time. 


Hogback Trail, Canon City, CO. Photo: Philip Sterling

Possibly the most important Over a Beer column that I wrote for Singletracks was titled, “How do you define success?” In it, I was earnestly seeking to understand how Singletracks readers define success in their own lives, but the piece fell pretty flat with the audience.

It has struck me more than once that earnestness doesn’t necessarily go over well with most mountain bikers, and this particular column only drove that point home. Ok, there were a handful of great responses—some from friends that I respect and admire—and for those, I am immensely grateful.

This idea of success has been stuck in my craw ever since then (almost a year now), because it strikes me as an interesting and critically important question. It is a question that each and every one of us must answer for ourselves. We must choose how we define success.

Of course, you could choose to abdicate your decision and let someone else define success for you. Perhaps you listen to a news pundit that defines success along their political or ideological lines, and you buy in wholeheartedly. Perhaps you listen to a politician and buy their definition of success. Or perhaps you’re convinced by a rich businessman or famous author. Or maybe you read a religious text that espouses a definition of success and because everyone in your circle of influence subscribes to it, you buy into that definition instead.

If we adopt someone else’s definition of success, I’m afraid that it will never hold the same kind of core foundational power, motivation, or become the driving force in our lives that it could be if we instead chose to do the work to define success for ourselves. In order to form some sort of core belief on this topic, I personally believe that we should all sit down and think about success and say, “Ok, all of these people define success in these various ways. What do I believe, and most importantly, why?” 

At the end of the day, whether or not we become “successful,” whether or not we are happy with our lives and the progress we’re making—these evaluations come down to the metrics that we’re using, the goalposts and mile markers that we’re measuring against. If we’ve chosen the wrong goalposts, the wrong definition of success, we’ll never be successful.


Or perhaps worse: we’ll be “successful” at completely wrong and ultimately, utterly meaningless things. 
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