Running the Dipsea and Finding My Strength

This past weekend, I ran a legendary race called the Dipsea. It’s just over seven miles of treacherous trails, going from the center of my adopted hometown of Mill Valley to the blue oceanside of Stinson Beach. The first mile alone includes 700 uneven stairs built into the mountains.

Training for a race like this and incorporating strenuous exercise into my life has been transformative for me. I learn over and over again that obstacles are meant to be overcome. That struggle is something that propels me forward, making me stronger and better.

Trail races are a terrific metaphor for life as the leader of a company. Slogging up a steep incline where your legs feel like lead is not all that much different from getting through a month (or months) where profits are in the red. Any CEO could regale you with tales of the characters who make their corporate journey more of a battle: the ultra-conservative banker who doesn’t want to fund necessary growth; the client who wants a four star program for the price of a Motel 8. At various times in the race, I found myself dealing with runners who made the journey more challenging as well: the annoying lady wearing road shoes with no tread who barreled past me and then fell on “Steep Ravine;” the old dude behind me who let out a very loud and unpleasant moan with every exhale; the guy sitting along the side of the trail bleeding profusely with a tooth sticking out of his cheek… Shall I go on?

One of the (many) crazy things about the Dipsea Race is that you can pretty much get to the finish line any way you like. There are multiple shortcuts that the seasoned runners take in order to get a better time. On all of my training runs this season, I avoided the shortcuts, sticking to the main trail and just logging my elevation and miles. This meant that I approached race day with some mysteries ahead of me.

The first shortcut is the only one that is marked. A race volunteer stood at the trail intersection under two giant signs. One was marked “Suicide,” while the other said, “Safer.” Feeling a bit like Alice in Wonderland, I confirmed my suspicions that I am a giant wimp and I went right, avoiding the treacherous plunge and obeying my mother, who on Saturday forbid me from running any trail segment with a name derived from a form of death.

The “Doors” shortcut was rather tame in comparison so I took it, along with nearly everyone else in my vicinity. The only challenge on that one was that it was so narrow, it was impossible to pass. This didn’t stop the young teen girl behind me who was yelling, “On your left!” over and over. As she attempted to get past the guy on my rear, they both went tumbling into the poison oak that lined the trail. I plowed ahead.

As I approached the final 1/2 mile, where the trail hits Shoreline Highway and racers barrel down a street lined with beach bungalows to get to the finish line, I realized that the end of the trail on race day is very different from the end of the trail on my practice runs. I was faced with a short but crazy steep decline. My brain immediately flashed back to famous photos of Dipsea Race days past showing folks sprawling down that hill and face planting on the street.

I took a deep breath and muttered, “OK, I guess we’re doing this,” and I half ran, half leapt onto Shoreline Highway. It was then time to sprint to the finish where I happily discovered that despite the heat wave, I hit my time goal. I’m already planning my strategy for next year’s race.

When I was a kid, gym class felt like emotional warfare. I was always picked last. I’d stand as far back as possible, trying to melt into the cushioned wall, hoping against hope that a disaster would strike and class would be canceled. Once I DID get picked, the mental onslaught would start all over again, as I’d ponder why sports like dodgeball were even legal. I mean… how is it OK for kids to play a sport in which the goal is nailing someone with a ball?

All of this to say, I was never the sporty, athletic kid. I stuck to drama and choir and only occasionally wondered why I didn’t inherit any hand/eye coordination from my dad. I also never exercised. In my mind, sports and exercise were all the same thing. And that thing was distinctly not MY thing.

At the ripe age of 45, I am as shocked as anyone that physical activity is such a huge piece of my life. I have been thinking about this a lot lately, in the context of my role as CEO. I often say that I am an accidental CEO. I never saw myself as a business leader. As I reflect on this now, it’s not surprising that I didn’t see myself as an athlete or a leader. These roles weren’t modeled for me. I had no knowledge of athletes who weren’t coordinated. I didn’t know a single female CEO.

I want to apologize to that little girl standing against the wall in gym class. I’m so sorry she had no idea what was possible for her. I’d love to go back and tell her that she can (and will) be CEO of a successful company. She can (and will) run a badass race and earn a shirt with the word “survivor” on it. There are so many other little girls like that today who need to see examples of a stronger way forward and I just want to say that I am here for it.