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Storyteller-in-Chief: Last One Wins

The children’s playground rhyme — “First the worst, second the best, third the one with the hairy chest” — unfolds as a runner-up’s taunt, a reminder of inadequate achievement. And yet many successful people get their start in last place — and work their way up. There are times I’ve experienced being “the worst” at something and, with much effort, overcame obstacles to land a No. 1 ranking.

A case in point is my middle school orchestra. My starting position in that orchestra was third violin, last chair. But I was very passionate about learning violin. I practiced, rehearsed, got together with friends to play and joined a second orchestra, of which I was also last seat. I played in my spare time and wore out my family’s and neighbors’ ears. By the following September, I graduated to first section, first chair.

In just one year, I had gone from being the worst player to the best. What’s more: I ended up applying for and receiving a schorship to study violin at San Diego State University! That experience burned into my world outlook: If you apply hard work and effort, it is possible to succeed on an accelerated time frame.

Fast-forward to the beginning of my career in tech entrepreneurship. I had secured my dream job at a seed fund in Utah. I was on a team with 15 engineers and knew nothing about technology and little about entrepreneurship. My first day, the team gave me a video iPod for work, and I didn’t even know how to turn it on. The engineers not-so-subtly hid their laughs, then helped me learn Tech 101: e.g., web hosting, blogs, web development, RSS, domain names, open source, back end/front end development.

Three years later, I founded a tech startup accelerator. Just as I learned violin, I worked hard to absorb, practice, ask, observe and continue to learn about the tech industry. The accelerator has since enjoyed great success and recognition — we were selected as one of the top 15 U.S. accelerators by the Small Business Administration and have been featured in numerous local and national publications.

My third experience with failure is very personal. Although I went on two short flights as a child, in my teen years, I developed a paralyzing fear of airplanes. Because of this phobia, I missed weddings, funerals and career opportunities, and didn’t fly for more than 13 years. Finally in 2007, I decided to white-knuckle my way through three short flights. It was unbearable; I suffered during those flights with crippling anxiety. What’s more, the change didn’t stick. I went another five years without flying.

But I didn’t like it. As my career progressed, I became more aware of opportunities passing me by. I decided to try once again, but this time I wanted to work on the problem incrementally. So I went to airports to watch planes, took an online class about fear of flying and worked through my fears with a therapist.

I also started accepting opportunities outside of the Pacific Northwest, where I had been operating my business for the past three years. I drove 48 hours each way to attend SXSW in Texas and serve as a mentor for the White House initiative Startup America. As another event in Oakland approached, I realized I was too exhausted to drive. So I booked a flight instead. The next morning, as panic started to set in, another opportunity arose: I got an email inviting me to the White House Business Council Summit, to take place three days later.

Even if I skipped Oakland and began driving immediately, I still wouldn’t make it. Invitations from the White House don’t come every day, and I realized there were no good alternatives. The prior year’s preparation gave me the courage to book a new flight from Portland to D.C.

Needless to say, I arrived in the nation’s capital with fragile nerves. But I arrived. And in the two years that followed, I flew more and began flexing the muscles required to monitor and manage this anxiety.

In 2014 another opportunity came along, this time to go to Kenya, Africa — more than 20 hours of flight time each way. It was difficult, but I was able to do it. The next year, I flew twice more to Kenya and lived in Africa for seven months participating in humanitarian projects, something I could not have done without overcoming my fear of flying.

Again, first, the worst. I missed family events and critical life experiences, but slowly I “upgraded.” Since I flew to Africa in October 2014, I’ve logged more than 72,500 miles — a record I’ll break again in years ahead.

I share these experiences to highlight the journey. I can think of many more areas of life in which I have been “the worst.” But what I remember most is this: The worst is only the starting place. At any point in time, I can move toward a more advanced state if I so choose. And that opportunity is yours as well.

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Carolynn Duncan is the founding partner of the Northwest Social Venture Fund and TenX.


  • Gloria Shakespeare
    Gloria Shakespeare Wednesday, 02 March 2016 14:13 Comment Link

    A great article. We met Carolyn in Kenya and knew of the great work she did there. Love a success story.

  • Mandi
    Mandi Wednesday, 02 March 2016 06:50 Comment Link

    Great reminder about how quickly one can accomplish what they set out to. Great stories. Thanks for sharing.

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