How To Fail At Anything: 8 Lessons From An Adventure Gone Awry

Remember that one time you went all-in on a shiny new marketing strategy, only to watch your site activity plummet? Or the year you decided to start your own blog, perhaps? You know, the one that’s still languishing as a perpetual embarrassment in some dark corner of the internet?

Well, I’ve just walked through the proverbial flames of failure and I’m here to give you a little bit of advice about how to fail at anything, in case this ever happens to you.



Welcome to Colorado. (Photo credit: Jonathan Hinderliter Photography


This summer, my partner Jonathan and I planned an epic adventure for ourselves. With several thousand miles of long-distance backpacking under our belts and a few seasons in the wild world of ultrarunning, we decided to attempt a 14-day thru-hike of the 500-mile-long Colorado Trail.

Spoiler: We failed.

I know, I know: people like to talk about failure in the introduction to their talks. They love to tell about how they rise from those sorry ashes to conquer the world by the time they reach the conclusion. 

Don’t worry. This is definitely not one of those stories.

Actually, this story is about how I failed at something important to me and a lesson about how to fail at anything. Most importantly, it’s about the importance of defining failure and how to recognize when it’s happening to you and take action accordingly.


Jonathan and me at the Southern Terminus of the Colorado Trail. (Photo credit: Reji Rajeshwari)


Here’s the thing about this trip: we made a really good plan. And even though just about everything went horribly wrong, I still think it was a pretty good plan, given the experience we had.

But now, for the lessons learned.

1. You can’t always know the right course of action in advance.

This is especially true when you’re entering uncharted waters.

We had several huge unknowns on this trip: the super-variable weather we’d face at elevation, the impact on our bodies of spending several days above 12,000 ft, and the wilderness, with all of its hidden challenges (wildlife, rockfall, etc.).



Jonathan prepares for a thunder-hail-storm, a mere five hours into our trip.


2. You have to simply make the best possible plan with the information that you have.

This was what I call a “reach adventure,” but it was definitely not a fool’s quest. We researched the terrain and weather, put extra food in our resupplies, tested gear in advance, and followed an extensive training plan in the months leading up to our trip.

Basically, we worked our butts off doing everything we could to prepare.

Sometimes, that’s just not enough.

Over the first few days of our trip, we planned to hike slightly less than the 35-mile-per-day average needed to complete our trip at our goal pace. We knew that this part of the trail would be (by far) the hardest and the highest terrain that we would face over the whole trip. 



The San Juans. (Photo credit: Jonathan Hinderliter Photography


Heading northbound from Durango to Denver, the first 130 miles of our trip would take us up a brutal 26,000 ft of elevation gain at an average elevation of about 11,500 ft. The high point of the section (and the whole trail) sits at 13,271 ft. 

To give you some perspective here, the total elevation gain from Mt. Everest’s basecamp to the summit via the popular South Ridge Route is about 11,560 ft.

Our first mistake was underestimating the total effect of elevation.   

While we did do a great deal of elevation training, neither of us had ever spent so much consecutive time, slept so many nights, or done so much climbing at such a high elevation. Working full-time meant that most of our training was done on the weekends, which was somewhat of a limiting factor.

3. The reality is that, as any marathoner will tell you, you don’t run the race until race day.



Me, running the race on race day.


When I qualified for the Boston Marathon this year, I had never beforeand I repeat, neverrun 26.2 consecutive miles at my race pace. I didn’t know, per se, that I would be able to sustain it.

But that doesn’t mean I was going in blind, either.

I had done speed training, long runs, short runs, and strength training. A few weeks before, I had run, albeit at a slightly slower pace, 22 miles with over 4,000 ft of elevation gain more than the race course, while carrying my own food and water.

4. If you want to test your real limits, there will come a time when, having estimated your potential, you simply have to dive in and give it your best go.

And this time, having estimated our potential, we were still just… wrong. 

At the end of those first 130 miles, Jonathan was limping down the trail on a knee injury and I had acquired a nasty case of Achilles tendonitis that soon became unbearably painful.

I also got really, really sick.



Off-trail, at a hostel in Lake City, CO, I sit and wallow in my sickness.


5. Once you’ve made a plan, there are times to stick to it and times when you need to make new decisions. 

For us, mistakes #2 and #3 were pushing through injury and pushing through sickness.

Dealing with sinus issues at 13,000 ft is kind of horrific. Not only does the sinus pressure worsen with every climb, but it also makes it really hard to sleep. Above 12,000 ft, sleep is challenging enough if you’re able to breathe fully out of your nose. I didn’t have that luxury.

The other thing about not sleeping is basically this: no sleep = no recovery.

At elevation, your body is working harder just to keep you alive, so recovery is already minimal. You get out of your tent in the morning feeling just as beat-up as when you climbed in the night before.



Home sweet tent on a foggy morning. 


Instead of dropping our mileage and listening to our bodies, we stuck to our plan. And instead of deciding to do that mileage at a slower, “below goal” pace, we ended up hiking ourselves into the ground.

After trying new strategies and fighting to save a dying project

6. There will be a moment when you simply have to decide that you’ve failed.

Both Jonathan and I had injuries with the potential to cause long-term damage, had we continued, and our usual joy in hiking was quickly vanishing. Still, after months of planning and excitement, the decision to get off trail was excruciating.

Failure sucks. And it beats you up emotionally. I felt like a failure as a person. I felt foolish. I questioned my training, my research, my goal, itself: “Why did I ever think that I could accomplish that?”

But what if I hadn’t trained so hard? What if I hadn’t done all that research? What if I hadn’t tried at all?

7. You only know what you can’t do—what your limits are—once you’ve thrown yourself at it with everything you have, and failed.



The High Point, or, the flattest part of the Colorado Trail.


I do not look back at my plan and think, “I could have trained harder,” or, “I could have done more to prepare.” I have no regrets about taking a trip through some of the most beautiful, remote terrain in Colorado.

And while I can’t say that the plan was flawless, I still look back and think that, given the information and experience I had at the time, “That was a damn fine plan and I just wasn’t good enough.”

This is the key to failure.

Astro Teller, “Captain of Moonshots” for Google X (that’s his real title, I promise), says in his TED Talk that,

“Real failure is the point at which you know what you’re working on is the wrong thing to be working on or that you’re working on it in the wrong way.”

He says that there is always a point at which giving up on a project—failingfrees you from the futility of continuing to try new strategies on something that is never going to work.

8. Failure is the moment when you realize that you’ve made the wrong plans. 

In hindsight, it’s easy for me to say that we should have done more strength training. Or that we should have made better decisions about our mileage. But that’s a monumental waste of time and energy.

The important thing is that we made a thorough plan, did our best to make it happen, and that we’re going to make a very different plan next time.

Once Jonathan and I knew that we’d been beaten, we decided to use the rest of our vacation time to hitchhike across Colorado. The time will come for another test of endurance, but this time… I’ll say that we found a whole different kind of adventure and leave it at that.



Finding the humor in the situation at the Cottonwood Hot Springs outside of Buena Vista.


Best of all, admitting your project is a failure allows you to stop spinning your wheels.

Jon Westenberg, failure evangelist of Medium, puts it this way:

“Throwing in the towel doesn’t mean you’re a loser… It means you’ve reset your priorities and your workload and your dreams, and you are about to get the f[***] over it and find a brand new challenge.”

I’m not saying that failing is fun or easy. But if you never really fail at the things that are most important to you, you might never know your own limits. Or, you might just miss an opportunity to move on to something better.

So get out there, and fail at anything.

Do it often, and do it with gusto, even when it hurts.



(Photo credit: Jonathan Hinderliter Photography)  


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Molly Michieli

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