Failing with Purpose

Note: This post generated some great discussion, which led to The Goldilocks Difficulty as a follow-up post. Also related: Component Goals – Lessons from a 5K, Look How Tough I Am!.


This isn’t a Western States post, but it’s one that it inspired. This also steals almost entirely from a talk I gave a couple of months back for my high school’s honors night (if you really want to see the video, it’s at the bottom). I hadn’t planned on posting it, but with some of the discussion I’ve seen this week I felt like I should.

First, I want to congratulate Ryan Sandes and Cat Bradley on their incredible Western States performances, as well as the rest of the runners out there who turned in solid performances and achieved their goals. The planning, mental toughness, and endurance they showed to achieve those results in those conditions is absolutely remarkable. When I’m running I start to complain when it’s over 70 degrees. Going that far and that strong in triple digits is unbelievable to me. I encourage you to check out Ryan’s and Cat’s post-race interviews below if you haven’t yet.

Now, a lot of attention has been placed on Jim Walmsley’s failure at Western States. I’m not going to say anything about that in particular, and I empathize with Ryan and Cat for focus being placed on someone else’s shortfall rather than their own achievements. I will say that Jim is a standup guy. Regardless of how you feel about his “confidence” in interviews, he’s a great person. I had the chance to hang out with him for a while after JFK 50 last year, and he was as nice and down to earth as could be. One of the things that I really love about ultrarunning is how awesome nearly every single person in the community is regardless of their ability level.

Waiting around after JFK 50. Photo: Gary Kelly

Now, I also empathize quite a bit with Jim because of his two failures, and even the way in which he failed. In 2015 I was stopped by stomach issues at Barkley, and in 2016 I lost too much time to a wrong turn. I hope that he comes back and gets things done in his 3rd year as well.

I may have kept going, but I was already gone by this point at the 2016 Barkley. Photo: Leon Lutz

I honestly envy him a little in that he still has that ultimate goal to reach for. I’ve been a bit listless the past few months not sure what my next big goal would be. Sure, I have goals. My next race that I’m focusing all my training around is Kona in October. But I don’t really have that one goal that puts an unquenchable fire in my stomach and gets me out of bed to do hill repeats in the rain at 6 AM. My training, and especially my nutrition, have suffered a bit because of that. Honestly, if it weren’t for the motivation provided by my Team Every Man Jack teammates, and the support from great partners like Hammer Nutrition and Chopt, and some pointers from fANNEtastic food, I might be back in “grad school shape” by this point.

Can I get some maple syrup and ice cream on my KrispyBo please?

But, before I get hungry, back to the point of this post. The rest below is basically a transcript from the video at the bottom.

Setting Stretch Goals

When I say failing with purpose I don’t mean failing on purpose, or failing just for the sake of failing. You’ll hear some people talk about how you should just experience failure. “It builds character.” Well, maybe sometimes, but not always. Sometimes failing is just failing and nothing good really comes from it, or at least not enough good to outweigh the bad. You might fail because you didn’t try hard enough, or due to bad luck, or even because the endeavor was truly impossible. In those cases the best action is to take what lessons you can from it, and move forward.

The failures where you reached just a bit too far, though, the ones where you set a stretch goal and came up short, those are the ones I want to talk about. Those are the ones that help you discover what you’re capable of, push your limits, and ultimately lead you to successes you may have never thought possible.

When I was in high school I ran cross country and track. If you ask my old coach, he’ll probably tell you that I was good, but by no means great. I didn’t always succeed, but I put it all out there every single race and became the best possible runner that my natural abilities allowed.

After finishing grad school and spending my time in college going the intramural hero route, I decided to give running one more go for the sole purpose of again becoming the best possible runner I could be and finding out what I was truly capable of in my prime. Naturally, I immediately signed up for a marathon, after a decade with no racing and having never raced further than 10K. It was a spectacular, miserable failure. At mile 18 it felt like someone wrapped two live electrical wires around my legs and I might as well have crawled to the finish.

The motion you see in this video accurately captures the speed I felt I was moving at. Photo: Jessi Kelly

Continuous Improvement

My time and place themselves were not my failure; my failure was that I had not found out what I was truly capable of. I could do better. So I tried again. And then again. On the third attempt I cut 49 minutes off that initial time and gained a coveted spot in the Boston Marathon.

I still felt I could do more, though, so I branched out into triathlon and ultrarunning. I could barely swim a lap and couldn’t change a bike tire, but my end goal was to test myself in an Ironman, so naturally that’s what I first signed up for. In ultrarunning my end target was the Barkley Marathons.

My first Barkley, in 2015, I had absolutely no idea what I was doing, and despite my goal of finishing 5 loops I quit after three. The following year I returned, making it to the 5th loop before succumbing to the course and being forced to quit. Many people told me that year, “John you had the most inspiring race.” Frankly, I would have much rather had a perfectly uninspiring race and achieved my goal and finished.

This year I returned for the 3rd time, and despite bad, highly variable weather and a 1:42 AM race start, I became the 15th finisher. In four years I had gone from out of shape recent graduate, to a Boston qualifier, to a Kona Ironman World Championship qualifier, to a finish at what many consider the most difficult race in the world.

DONE. Photo: Thomas Gathman

The Value of Failure

I had plenty of failures along the way, though, and I consider those an irreplaceable part of my success. These failures occurred from me trying to push myself too far, from choosing to put myself in situations where failure was not just possible, but highly likely. laz likes to say that you can’t accomplish anything without the possibility of failure. Well, I’d like to take that one step further and say that oftentimes accomplishing something great has failure along the shortest route.

That first marathon taught me more and prepared me more for my ultimate goal than successes in multiple shorter races ever could have done. And yes, those failures did build character too and helped me improve in ways that extend far more broadly than running arbitrary races. Now I’m also at the point where even my failures are beyond my original wildest dreams of success. Four years ago, while I was eating Doritos and writing my dissertation in between playing intramural softball and World of Warcraft, I’d have thought winning the lottery was more likely than me finishing the Barkley Marathons. The difference, though, is that I could actually affect the likelihood of one of those two things.

One of these days Homonza. One of these days we’ll conquer the World… of Warcraft

Achieving Success

At some point you have to ask yourself: which would you rather do? Would you rather enjoy a string of mildly fulfilling successes, or would you rather reach for something greater, knowing you might fall short and fail but at the very least knowing you got as close as possible and became the best version of yourself in the process? And don’t get me wrong, setting and achieving smaller goals is fun, rewarding, and can even be necessary to measure progress and stay motivated. During my journey towards a Barkley finish I ran smaller races, and I set a Guinness World Record for Fastest Marathon Dressed as a Videogame Character while dressed as Link from the Zelda series. I had a blast doing that and it gave me some much needed positive reinforcement. But the end goal, the carrot on the stick that kept me pushing forward was always Barkley.

Professionally, I’m an engineer, and I like to always have a system and process for doing things. So how can you put what I’ve said into action?

  1. Choose a goal that is deeply meaningful to you. No one else can define this part for you. You have to have strong internal motivation to overcome any difficult obstacles you encounter and to be able to truly appreciate your achievement if you do reach success. Without that strong personal motivation, there’s absolutely no way I would have pushed through the challenges I faced this year at Barkley.
  2. Discuss your goal with friends and family. Gather their input on your perspective and approach. Ultimately the decision is still yours, but few great things can be achieved without support from those around you. Again, there’s no way whatsoever I could have finished Barkley without support from my wife and other friends and family.
  3. Evaluate the likely outcomes of your endeavor. How likely are you to succeed? If you fail will it help you on your next attempt or teach you other valuable lessons? If you’re likely to succeed, what will you gain from that success and what is your next main goal likely to be? For me, Barkley was right on that edge of impossible: highly improbable, but you’re sayin there’s a chance.

Remember this is about failing with purpose, not on purpose. If your ultimate goal ultimately isn’t hard, there’s nothing wrong with that. On the other hand, if your ultimate goal is undeniably impossible, then failure isn’t necessarily a good thing. I’m not here to paint some picture of unicorns and rainbows where everyone will get anything they want as long as they really put their mind to it. Remember that bravery is steadfastness in the face of likely failure, while foolishness is the ignorance of its possibility.

But if success is even remotely possibly, then be brave. Reach for that stretch goal. No matter the outcome, I can promise you that you’ll come closer than you would have had you aimed for and achieved something smaller. In the end that’s the ultimate measure of success: how close did we come to reaching our farthest, to becoming the best possible versions of ourselves? Barkley gave me that opportunity to measure myself, and I hope that as you all move forward from here you’re able to discover your own Barkley and pursue it with passion and purpose.

The Video

And finally, the video. I actually recorded this while in Malta, which was a good thing because the talk was actually given the following night when I was wandering homeless around London in the rain.

19 thoughts on “Failing with Purpose

  • 2017-06-28 at 7:40 PM

    Fastest Marathon Dressed as a Videogame Character??? X) You killed me with that one… Probably your ultimate goal could be finish Barkley dressed as Donkey Kong. Thanks a lot for this post. It’s kind of an inspiration to me at this moment. I just finished my first 10K couple months ago and right now I’m training for my first half-marathon. My mid term goal is to finish the “Cruel Jewel 50” ultra on May 2018. This goal is what motivate me everyday to keep pushing forward… slow but steady. Mentally I’m super ready but my main concern is more regarding staying healthy and injury free while training to my max. Any suggestions or comments will be highly appreciated!!!

    • 2017-09-27 at 8:22 PM

      Somehow I just now saw this; sorry about that! Donkey Kong would be tough… maybe Diddy, though haha. I’m glad you enjoyed the post, and I hope your training has been going well! On training, you definitely need to bump it up slowly one notch at a time. I’m a huge believer in 2-4 weeks hard, 1 week easy for recovery. Each week, gradually push forward a little, and then after the recovery week start a little further forward than the previous cycle (maybe start where you were in the 2nd week of the previous cycle). Always listen to your body, though, and if you need an unscheduled recovery week take it! You might also get to the point where you’re at the upper limit of training and can’t keep ramping up on volume alone – that’s where speed and intensity come in. Sorry again for the 3 month delay on the response, but I hope this still helps.

  • 2017-06-28 at 8:57 PM

    My new motto; if success is even remotely possibly, then be brave. Thanks for the great post.

  • 2017-06-29 at 5:38 AM

    Great stuff John, as always. I will forever be in awe of what you did at Barkley. You paid your dues, learned from your mistakes, respected the Barkley course and grew into it over time. Your success was a measured and beautiful thing achieved with humility and grace.

    • 2017-06-29 at 10:20 AM

      Thank you very much. It means a lot knowing people look deeper than the 2017 Barkley highlights. It didn’t just happen. Best of luck with your own challenges!

  • 2017-06-29 at 6:04 AM

    This is really interesting: “oftentimes accomplishing something great has failure along the shortest route”.

    I’ve been trying to run a sub-X marathon within a time-frame of a couple of years. To do that I’ve been running spring and autumn marathons, making incremental progress. Each time I succeed in taking another chunk off my time, I feel that sets me up to run closer to goal pace than I would have been ready for before. The main goal was too big for me, so I broke it down into smaller goals that I could succeed at.

    A clubmate has the same marathon goal, but is a bit more ready to embrace failure than I am. Each time he runs a marathon he sets off at goal pace and blows up before the end. But each time he gets a little closer to the end than the time before. Eventually he’ll go the full distance without cracking.

    How you frame your goals feeds into this: he and I could run the same times along the way to our end goals, with me seeing it as a series of successes and him seeing it as a series of failures. I think personality type comes into this too: I’m not sure that I could stay motivated with his approach, and I’m not sure that he could stay motivated with mine.

    Then again, I think we’re both ready to reframe our outcomes in whatever way is most useful to us. After each of my ‘successes’, I’m very quick to reframe it as a failure: “Yes, I got my time today, but I was only aiming for X so I still need to get faster.” And after each of his ‘failures’, he’s very quick to reframe it as a success: “I didn’t have it today, but I was still running at goal pace after X miles, so I’m getting there.”

    I guess we all need a mixture of successes and failures, and part of psychological challenge is knowing what mixture we need today and framing our experiences accordingly.

    • 2017-06-29 at 10:34 AM

      Thank you, that’s a really great perspective. Taking the “success” out of each failure so you can build upon it is extremely important, otherwise it’s just pointless failure. I think you’re right that the approach depends heavily on personality type, and I think it also depends on the goal itself. The key thing for me, though, is that any intermediate goal should be just out of reach of what you think you can do for the result (success or failure) to be most useful. Too easy and you’ll get bored and get nothing from it. Too hard (i.e. not even remotely possible) and you’ll get frustrated/hopeless and get nothing from it.

      I’ll follow up on this, either by updating this post or making a new one, as this touches quite a bit on some of the design we had to put in to the tasks we gave our human research participants

  • 2017-06-29 at 6:42 AM

    Dear John,

    Inspiring post, just on time since during the WS100 weekend, I tried to accomplish the Olympus Marathon here in Greece, unfortunately without success!!

    As a result your post could not have been more suitable for the occasion. My only concern is how everyone, including me, defines the impossibility of a certain goal. Yes, ex post analysis of my goal, with 9.500 feet vertical, all of them during the first 21kms, proved a task that i was not fully prepared to accomplish. Was my goal impossible?

    In retrospect, when I was preparing for this race, I had times when my goal seemed impossible, but I kept going and I stand in front of the starting line hoping that by the end of the day I will be a totally different person for reaching my goal!

    I failed, and as you are describing above, I have already distilled all these things that I need to carry with me the following period, in order to become a “better” me!!

    Thanking you again for your post,

    All the best,


    • 2017-06-29 at 10:37 AM

      Thank you very much, and congratulations on the improvements you took from your race. The appropriate level of difficulty for a goal is a very fine line, and is different for each person. I’ll try to pull a few references and follow up on this a bit more. Best of luck in your next race!

      • 2017-06-30 at 4:01 AM

        Thank you very much John for taking the time replying to me. Looking forward for your new posts / activities!


  • 2017-06-29 at 9:22 AM

    John, really appreciate your thoughts on this one. I agree that flirting with failure can often lead to some of our greatest successes. I ran into Amy, the RD for VT100 at the Cayuga Trails races and mentioned I had some time goals for this year’s race. Her response was “Well what are they? You have to tell other folks what you’re racing for to make it real!” I was both nervous and excited in stating that I hoped to go sub-24 this year. While it may not be an extraordinary feat for some, it would be a significant improvement for me, and I’m excited to test it out in a couple weeks.
    Thanks for sharing this. I hope your training and racing continues to go well.

    • 2017-06-29 at 10:40 AM

      Thank you, and good luck at VT100! All goals are individual and personal, and I believe that internal motivation is much more effective than external. At the same time, the two aren’t mutually exclusive and sharing your goals can definitely provide some extra motivation on top of what you have internally.

  • 2017-06-30 at 11:44 AM

    Love this! I’m a cognitive science professor and attempting my first 100miler at VT100 in two weeks. This was exactly what I needed to read. My A-goal is a stretch, but I’ve done a lot of planning, training, and messing around with spreadsheets to create pace charts to make it a possibility (yay data science!), even if it’s a remote one.

    What I thought you might be interested in is that there is a term for what you’re describing in the cognitive science of teaching and learning literature called “desirable difficulty”. We often make the biggest gains and learn the most when we are right on the cusp of what we think is possible to grasp or achieve. We learn by figuring out what we don’t know and pushing limits. Here’s a really basic overview of the topic with some citations to primary sources (

    Thanks for putting this into words – I’ll be thinking about it a lot out on the course! Also, congrats on being a BAMF and getting it done at Barkleys.


    • 2017-06-30 at 12:48 PM

      Thank you! I had not heard that exact term before, but I dealt with quite similar concepts in grad school where we borrowed principles from gamification to design experimental tasks. What we used was called “gamer flow” (or I think “cognitive flow” in more generic terms). It’s an extremely interesting area for sure, and I think the most difficult thing to deal with is that everyone’s desirable difficulty or flow looks a bit different and depends on a lot of factors. I’ll probably follow this up with a short post next week. As you say, finding just that right level of hard is important.

      • 2017-06-30 at 3:09 PM

        Yeah! I think about this stuff all the time as I deign courses. I want things to be hard and challenging so that it’s meaningful and the learning is long-lasting, but I don’t want my students to be totally overwhelmed or overstretched and set up for failure. It’s neat how so many of these concepts can transfer to things like ultrarunning and pushing physical limits! Thanks again, and I look forward to your follow up post.

  • 2017-07-12 at 8:18 AM

    Great stuff, inspiring. I call this “Winning by Losing.” No matter the words, if one doesn’t toe the start, there will not be a finish.

    • 2017-07-13 at 2:56 PM

      Thank you. I’ve never been a huge fan of the “you miss 100% of the shots you don’t take” quote, because in team sports you could pass to someone else who could take a much better shot, but for individual efforts it definitely applies.


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