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How To Lose Like A Winner

“You can’t succeed if you don’t know what losing is.”

— Garth Brooks

As I write this, I’m thinking for the millionth time about how I’ll restart my transcontinental run yet again. Because make no mistake, I plan to finish that run as soon as it’s possible to do safely.

But there have been times in the past when no matter what I did, I wasn’t able to finish, and those are the times I’ve learned the most.

Dealing With a DNF

Losing hurts

In 2014, I entered my first Ironman event, Ironman Galveston 70.3.

I had trained extensively for the swim, bike, and run. I knew I’d need every minute allowed, so I practiced swimming faster so I knew I could finish the swim on time, had trained with and without a wetsuit so I’d be ready no matter what the water temperature was, practiced full-length “bricks’ (bike, then run), and even put fresh tires on my bike and stocked extra CO2 cartridges in my bike bag in case of a flat.

When the day of the race came, I had a flat on the bike at Mile 6. I wasn’t that experienced at changing tires and lost a good 15 minutes trying before the event’s bike mechanic showed up and replaced the tube for me.

By the time I got from Galveston Island to the turnaround past Jamaica Beach, I ran into strong headwinds that further slowed me down.

I ran out of time a mere 1.7 miles from the bike finish and was pulled off the course.

I was heartbroken. It was a big deal to me—my first official Ironman event, and it had been expensive to enter. A lot of my ego was tied up in it. I knew friends were watching online and cheering me on. I called my wife from the van that brought all of us DNF (Did Not Finish) cyclists back and then let my friends know I hadn’t managed to finish even the second part of the race.

Accepting the unacceptable

It took me the better part of half an hour to realize that if I had been exactly seven minutes faster, I’d have crossed the cutoff in time to keep going. It depressed me even more when the judges corrected my swim start by 7 minutes due to a timing error, meaning that if I had not been pulled off the course, I would have just barely made it and could have kept going.

But what hurt the most was having to admit to myself that I had not, in fact, adequately prepared for eventualities. I had not thoroughly worked the failure calculus and done enough to mitigate risk.

Sorting it all out

For weeks afterward, I kept circling back in my mind to what had gone wrong that day in Galveston. After some time kicking myself and feeling exposed and ashamed of being a loser, I managed to sort the questions into two types:

  • Fanciful wonderings that were out of my control: What if the timing error had been discovered earlier? What if there had been a back-current during the swim that got me out of the water faster? What if there hadn’t been headwind near Jamaica Beach?
  • Practical questions I could address: Would a can of Fix-A-Flat have helped? What about a class on how to change tires fast? What about practicing shorter transition times between sports–for instance, pre-tying my running shoes or pre-stuffing my bike jersey with electrolyte gels?

I gradually realized that I had to let go of the things that were out of my control in order to focus on what I could change.

Going Forward From Failure

Accepting the Results

There’s no question about it. I didn’t finish Ironman Galveston.

All denial does is make your failure not your fault, and while that feels good in the moment, the truth is that it also puts your success out of your control. You are no longer in charge of your destiny. You are a victim.

Accept that it was windy. Learn to ride into wind.


It’s been said that failure is a tough teacher: it gives the test first, then the lesson. In my experience, failure, while painful, tells you where your effort is lacking. It’s a gift. It’s a chance to learn.

Sometimes, no matter what you do, things will go badly. The most you can do is be prepared, chart out how you might fail next time, and prepare an alternate plan for that eventuality.

Doing something different next time

To this day, I carry Fix-A-Flat in my bike bag. I also switched to Gatorskin tires and a new wheelset with durable rims that resist spoke strip punctures, a lesson I learned from failure at another event.

When I trained for my first full Ironman 140.6, I incorporated those changes and practiced shortening transition times along with other improvements.

To Quit or Not to Quit

Sometimes it makes more sense to quit than to keep pressing on. A lot depends on the consequences of continuing.

When everything goes south at once

“DNF also means ‘Did Nothing Fatal’.”

— Anonymous

In 2016 I attempted my first full 140.6 “full iron distance” triathlon, the HITS Waconia 140.6, just west of Minneapolis.

As before, I had trained hard. I had researched the race. I had driven out to the site the day before and swam in the water around the same time of day that the race was to be held. Skies were clear, and I was optimistic.

The morning of the race was another story. I stood in the water, shivering in the rain and wind with other swimmers as heavy clouds hung just above. We saw lightning and braced ourselves against 30-40 mile gusts while race officials weighed whether to cancel the race. Heavy chop lifted us up and dropped us back down hard on the sandy bottom as one of the two rescue vessels, a paddleboard (!), kept repeatedly dumping its rider just feet from shore. The only other rescue vessel, a small motorboat, was nowhere to be seen. Visibility was almost zero.

In the end, they started the race.

I was 400 meters out when I caught a good-sized wave in the face and coughed it out. Then I met another one that rolled me and left me nauseated and disoriented. I caught sight of the motorboat and signaled to be pulled out of the water. But the boat sped off, unable to see me because visibility was so bad.

I decided in that moment that I had seen enough. I turned around, swam back the 400 meters I had come, walked up to the judge’s desk and declared myself a DNF.

Once I got back to the parking lot, I met another swimmer who had dropped out during the swim. Later I found out that over half the people who had entered dropped out during the swim.

Yes, some others chose to swim on, rode their bikes down rain-slicked roads (there were at least two bad crashes), and finished the event.

But for me, the math just wasn’t there.

When not to quit

  • If the challenge doesn’t make the situation more dangerous. If the weather on your bike ride has gotten windier and is slowing you down, sure, keep going. But don’t run in Iowa cornfields during tornado warnings like I did once and will never do again. And don’t swim during marine safety advisories.
  • If continuing doesn’t make the situation more injurious. If you know that you’ll hurt probably yourself in a significant but non-life-threatening-way, it’s not worth it. Things don’t always heal right or return to normal.
  • If you won’t accumulate risk by continuing. If it’s not making things worse to continue, and you have the resources and ability to do so, it’s probably okay to keep going. Just be sure you know what the risks actually are.

When to quit

  • If continuing puts your life in danger, don’t push on. Don’t be that guy stranded on the mountainside sleeping under the body of his dead climbing partner in an effort to keep warm.
  • If everything must go perfectly for you to finish, it won’t. Sure, take a chance if it’s safe–you might just barely make the bike cutoff for your Ironman; but if the situation has changed to one where you’re depending on hope alone, call it a day.

Why to quit

  • Quit for a rational reason. Saving your own life is a good one! Keep in mind what while many swimmers continued during the storm at Waconia, spectators had to rescue a guy who pressed ahead when the risk of drowning was actually very high.
  • Don’t quit to avoid losing. If your main reason for quitting is so that nobody can see you lose, that’s taking your toys and going home because you can’t stand losing. You may have retained control over your destiny in that event—but you will never improve until and unless you can get over your own ego issues.

How to quit

  • Give advance thought to “go-no go” conditions. Any time you ignore personal safety you’re taking a risk. When you repeatedly ignore risks, they grow up into disasters. Fate does not smile on the foolhardy, and you won’t be able to trust your judgment in a crisis unless you’ve had experience dealing with it. Your only substitute for experience is a plan.
  • Gather as much data afterwards as possible. You can learn something, even if it’s what not to do or where not to be.
  • Go back to the drawing board. Make plans for the next time, perhaps for a different race, different season, or different location.

Quitting isn’t “quitting” unless you abandon your goal. Get up, dust yourself off, make a plan and get back out there!