It was June of 2000, (right after the hi-tech bubble burst! remember?) and I was in an orientation meeting for my first sprint triathlon. It was a Danskin Women’s Triathlon, and the Bay Area was one of dozens of locations across the US where women competed in 1/2 mile (750 meters) swim, biked for 12.4 miles (20 km), and ran for 3.1 miles (5 km).

I still couldn’t believe I had let my friend Alison drag me into it, and was quite certain that I would drown in the lake, despite the laps I was doing in a tiny local pool in my attempt to train properly. 

Triathlons were just starting to pick up back then, and the Danskin all-women series was the safest place to start. Still, there were some super-fit, beautifully attired pro racers on $10K bikes who were terribly intimidating. I was not comforted AT ALL by the fact that they were female! And it was scary to think I’d be sharing the same course with them.

Danskin encouraged first-timers to join the race orientation, which was given by Sally Edwards, the series’ national spokeswoman. Sally was 53 at the time, tan and sinewy. She famously held the Ironman masters (age 40+) record for both men and women. [An Ironman triathlon consists of a 2.4-mile/3.86 km swim, a 112-mile/180 km bicycle ride and a marathon 26-mile/42 km run, raced in that order. It is widely considered one of the most difficult one-day sporting events in the world.] 

But when she spoke, what impressed me more than her athletic record, was how smart and funny she was.

When Sally got on stage, she started by asking how many of us were afraid we’d finish last. 

Most hands shot up, mine included. Frankly, I figured I’d be dead last, as it would take the divers some time to locate my body at the bottom of the lake…. 

(Interestingly, Sally says that when she asks men, no one thinks they’re going to finish last – take a moment to think about this fact!) 

Then she said, “You don’t have to worry about it. I’ll be doing the race, and I took a pledge to finish last.” 

Since pledging, Sally Edwards has finished last in every single Danskin triathlon, so that no other woman would have to. 

Now the crazy thing is that Sally was a professional athlete, and these races counted toward her ranking, which meant that she went from being ranked at the top of the field to the very bottom. But she didn’t care. 

She told us that she was honored to race next to the women at the end, because they are the most inspiring. 

Now is where my memory gets fuzzy (forgive me, Sally!) so I can’t swear all the following details are 100% correct, but as far as I recall, Sally told us of the Danskin triathlon in Boston, where she had caught up with the woman at the end during the run part. The last woman was walking. She couldn’t run, and she was clearly struggling. 

As she had done in every race, Sally introduced herself and asked the woman who she was and why she was racing. The woman said she was married to a police officer, and they had 8 children, all or most of them adopted. Turns out that her husband would meet homeless children and runaways on his job. He couldn’t bear to leave them on the street, and would just bring them home. 

For her 40th birthday, the family gave her a gym membership. She had worked so hard to raise all the kids, that she had gained weight and neglected her health. To help her, the husband and kids also signed her up with a personal trainer. The trainer encouraged her to set a goal, and train for something specific in mind. He recommended the Danskin triathlon. 

The woman was having a really hard time, but what kept her going was knowing that her husband and 8 children were waiting at the end of the race with a cake they baked for her the night before. They decorated the cake with a little swimmer, a little cyclist, and a little runner. 

I can’t tell the Boston woman’s story without choking up. However, while it is incredibly heartwarming and endearing, what I find even more inspiring is Sally’s story.

In this interview, she shares that for the first couple of years as Danskin’s national spokeswoman, she raced as a professional triathlete, because she thought that’s what the sponsor expected. 

But then she got injured. 

During recovery, she still wanted to participate, so she said she’d finish last. Everyone laughed at her, because she’ds never finished last in her life! 

That first time, she was so inspired by the stories of the women at the end, that she decided to do it again. As triathlons were growing in popularity, she found out that there were more friends and family waiting to greet the final finisher, than there were supporting the top racers.

Sally Edwards ended up doing 150 Danskins; she never missed a race in 22 years.

And when she went from first to worst, Sally became the worst female triathlete in America, because no one consistently finishes last in every single race. The competitive folks she hung out with, mostly guys (as you’d expect) said, “what are you doing, finishing last??” and she said, “It’s the best place in the whole race.”

Her message, which became the series’ message, was that it doesn’t matter where you come in the race, it matters that you’re participating. As a result, over the years, 600,000 women completed the Danskin Triathlon.

And while daring to participate, and starting by participating without judging yourself are fantastic tools, I want to ask you: 

Where can you find freedom, or create better results, by intentionally attempting to “come in last”? 

I have found this to be truest in writing. Have you heard of the concept of a “shitty first draft”? The idea is to fully commit to writing something awful, just to get going. My terrible first drafts include actual “bla bla bla” bits where I get stuck, and obviously require reworking… But they get me so much further than staring at a blank screen or not even trying. Counterintuitively, attempting to do my worst effort, gets me much further than trying to succeed!

Sometimes, deciding to do a bad job on purpose is just freeing and fun. I experienced this at a company Karaoke night. I really wanted to sing, but also didn’t want to embarrass myself. But doing an intentional screamfest of “I Will Survive” with a couple of friends was all that was needed to enable us to try to properly sing other songs. Being somewhat off-tune felt ok, and not like a miserable failure.

Failing can also help by proving to yourself that you can get back up again

When she was in the 3rd grade, my daughter got herself into a panic over a school test scheduled for the following day. When I realized I could not calm her down, I told her that I really hoped that she failed. In fact, I said, I hoped her mind would go blank so she’d score a nice round 0, just so she could see that the sun would rise again. In retrospect, we did a minimal version of Tim Ferriss’s Fear Setting exercise, because that got us into talking about what would really happen if she failed, and she realized that it would just mean her teacher would work with her more. Not so scary.

In fact, whenever we’re learning anything new, we’re in “expansion mode” and teetering between failure and success. This is a delicate moment. Unless you have exceptional talent, when learning something new, everything you do is probaly inadequate. Knowing you will come in last, is a great way to look that reality in the eye. 

As a kid, I asked my uncle to teach me how to whistle with my fingers. He showed me how to fold my tongue with my fingers, how to position my lips, and said, “Now you’ll blow out air silently for a few days, but if you stick with it, you’ll figure it out!”

I stuck with it and figured it out. I always whistle the loudest at concerts and shows (my kids are equally awed and humiliated by this ability). But other times I’ve given up too soon, unable to deal with being the worst at least for a while. I ended up quitting swing dancing, playing guitar, and quite a few professional directions. Perhaps unnecessarily. Maybe I could have been more conscious of Sally Edwards’ lessons at the time.

I hope you will use this going forward. Embracing failure can help you get started, ,get unstuck, persevere, reduce fear, or simply encounter interesting people. Ask yourself, where can I intentionally fail to leap forward?

Photo by Jon Del Rivero on Unsplash

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