The Bigger Picture: Expect to Fail

In a world where positive thinking and optimism rule, advising people to “expect to fail” seems doomed…to fail.

Allow me to explain.

A few years ago, my daughter was part of a Brownie Troop. Friends and family purchased cookies, but that was not enough. She wanted to walk through the neighborhood, knocking on strangers’ doors and offering them Thin Mints and Tagalongs. My heart melted; that was a such a sweet, almost old-fashioned idea. I reflected back on several poorly attended lemonade stands, when neighbor after neighbor zipped by without even a glance. I reminded her that our neighbors are not always the most friendly, “neighborly” people, and she should not be surprised when she gets turned down. My little eight-year old, oh so wise, scoffed that she did not expect EVERYONE to buy. But if she went down our entire block, surely SOMEONE would want to buy. So, she and my husband took off down the block and knocked on every door. The results surprised me. Most of our neighbors were kind and generous, and my daughter made a killing. Still, she took her failures in stride, and delighted in the successes. After every failure, she kept going until she hit the end of the block. She was prepared to fail, and being prepared and unafraid empowered her to cruise through those rejections instead of feeling crushed and embarrassed.

When I launched my first company, WebWisher, my partners and I expected to fail. We realized that we were young, still in school and knew very little. But we were excited about starting a business, we were having a ton of fun and we truly believed in our concept.  We failed over and over again. I lost track of the numbers of VCs that just stood up and walked out of the room mid-pitch. Trying to be kind, teachers, friends, parents and experts were blunt: they told us point blank that they did not believe in our idea and that it was not going to work. As three young women, we faced another level of skepticism; we didn’t look like sharks. We were introduced in a business plan competition as “The Spice Girls”. We were told to act demure in meetings. Yes, we were beaten down countless times, but we did not expect an immediate homerun. We expected the failures, and that removed a lot of the sting.

I am not advising anyone to aimlessly chase ambitious goals without believing in them. Knowing that you will eventually succeed is what propels you out of bed and pushes you to keep chasing the dreams. In the big picture, you pursue your goals with determination because you know you can make them happen. But day to day, challenge to challenge you should expect to fail, and fail spectacularly, over and over and over again.

Chances are, you are going to be rejected much more than you are accepted; you are going to fail much more than you succeed. Plan to succeed but expect to fail.

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