Undertaking a challenge to do something—anything—every day for 365 days straight means that you get to enjoy amazing opportunities that you may never have embraced before, but that at other times, you’ll need to buckle down and grunt out some truly difficult efforts. This maxim is no less true with the Outside 365 Challenge.

Some days, my daily time moving outside is spent walking along a beach in perfect weather—the waves crashing on the shore warm against my feet, the breeze cool against my face. And other times, I have to ask myself, “why am I doing this again?”

One of the latter took place on the morning of a travel day in which I was headed to warmer climes, but as I slapped my alarm into quietness at 5am, well before the sun arose, I looked out the window and realized that not only was it well before dawn, pitch black and cold, but Central Colorado had been consumed by a snowstorm.

I added extra layers and a thick pair of boots to my planned attire, strapped on my headlamp, and headed out into the depths of the early morning hours. 

With the snow whipping into my face, the light of my headlamp bounced back into my eyes, blinding me with light instead of darkness. The only thing I could see was the blank snow in front of me. As I walked a route that I’ve walked dozens of times during this challenge, I navigated the few curves in the road almost by feel, turning around at a place that I’d predetermined as one of my minimum destinations.

Thankfully on the return I had my tracks to follow, but I initially had planned to spend my walk sipping coffee and waking up for the day. Now, having one hand (sans glove) out of my pocket holding my coffee mug turned out to be the complete opposite of relaxing. Almost no part of this experience was redeemable. 

And yet.

And yet I was out walking in a snowstorm at 5am, and the absolute peace and quiet and utter solitude, even in my own neighborhood, was magnificent. Choosing to get out and move turned out to be well-worth it after all.

It always is.

Outside Day 173

Today was my first day of skiing in two years!! In addition to two surgeries, I’ve spent months and months in physical therapy and thousands of dollars on medical bills as I’ve prepared for today. 

Is it OK to be honest when our outdoor experiences aren’t actually amazing? Hope so, because here goes nuthin'.

While it was an absolutely gorgeous day to be out in the mountains and the views from the Continental Divide were to die for, I can’t help but be terrified of adding a fourth or fifth year onto this absolute mess of ACL surgeries and subsequent recoveries. Despite wearing a brand new knee brace, I could still feel the weakness in my knee during every single turn I made. 

Was it just pain from my patellar tendon that’s still ornery a full year after the most recent surgery? Was it my ACL groaning under the strain? Ultimately, does it even matter what the root cause is?

It’s no exaggeration to say that downhill skiing has been one of the most important and defining aspects of my life, but when is enough enough? Do I keep working on strengthening, struggling slowly forward? Or do I raise the white flag?

If yesterday clarified one thing to me, it’s that I can easily head up into the high alpine and enjoy the beauty of the snowy mountains from the seat of my bike. We have so many different types of adventure available to us here in Colorado, that I don’t feel like I have to sacrifice what modicum of health I do have on the altar of powder skiing.

I don’t have any answers yet about what the future holds. But maybe it’s time to finally buy a snowboard.

Outside Day 163.



Fat biking in Fourmile. Photo: Scott Anderson


I have this problem where I unwittingly try to make everything I do more difficult for myself. This is evident even in my original Outside 365 Manifesto. In that manifesto, I created a well-defined rule for what it meant to get outside and be active. 

The more years that roll on, the more I become convinced that living life doesn’t have to consist of yearning for what you do not have and struggling to achieve it. Rather, living life well is more closely tied to doing the best that you can with what the resources that you have at your disposal.

Instead of setting my Outside 365 bar at one mile of walking, 30 minutes of biking, etc., I removed the bar entirely and simply said, “if I intentionally get outside and move, that is enough.” 

Early on in my challenge, many of my outside days didn’t even consist of taking the dog for a one-mile walk. It may have been eight tenths, a half a mile, or even on one or two days 0.4 miles—paltry in comparison to many other days where I’d spend hours in the saddle, covering dozens of miles of singletrack.

Along the way, here’s something I realized: even if I only walk a half a mile, that half a mile is infinitely better than nothing. There’s a common saying that “no matter how slow you’re going, you’re beating everyone on the couch.” Actually, I’d upgrade that statement to say you’re moving infinitely faster and infinitely further than the person on the couch. The rate of increase, of a half a mile compared to 0 miles, isn’t 50% of 1 mile or 100% of 0, no—it is infinitely better

Of course, that revelation isn’t groundbreaking or even original, but here’s the upshot: removing unnecessary rules, lowering my standards, and simply choosing to go outside and move my body has resulted in me actually succeeding in getting outside. While perhaps some days are still only 0.8 miles, others are 30 miles of mountain biking, two hours of paddleboarding, and so much more.

Sometimes if you lower your expectations, you end up accomplishing so much more than you’d ever have dreamed!

Outside day 143.


CDT on the way to Tank Seven. Rider: Greg Heil. Photo: Marcel Slootheer

Early on in the year it occurred to me that I was unlikely to meet my Outside 365 goal in 2018. Here’s one reason why: so often when we set goals like this one, goals where we seek to change our lives on an ongoing basis, we begin from ground zero. From a standing start, we intend to launch full-speed into our life change projects. 

In reality, that never works out quite the way I wish it would. Exploding off the starting blocks is a tactic for a sprint race, not for a marathon.

If there’s one skill you must learn to become a better-than-average mountain biker, it’s this: how to conserve momentum. Momentum is the key to riding a bike well. Carrying your momentum will take you up and over obstacles without requiring you to put in a lot—or any—work. Instead of looking at the steep upslope off in the distance as requiring a bunch of pedaling to climb up, if you can instead conserve your momentum from the previous downhill, you’ll sail straight up the next climb.

So before I started logging my Outside 365 days again—instead of sprinting off the starting blocks for a marathon race—I waited until I had a little momentum built up. At some point, I realized that I had inadvertently been active almost every day for a full month without even trying and in that moment, I realized I finally had the momentum required to launch back into this project. 




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. 
Trail: Tank Seven. Rider: Yours Truly. Photo: Marcel Slootheer

I had the opportunity recently to sit down and chat with Ben Welnak of Mountain Bike Radio. We spoke a bit about my history, but ended up doing a bit of a deep dive into what could--for lack of a better term--be called the philosophy of mountain bike media. I may have gotten a touch overly philosophical, but hey--that's par for the course. If you're interested, check out the recording here:

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