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10.15.2020 Talking Tech

What Failing Often Means to Me

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We’ve all heard the mantra “Fail Fast, Fail Often” popularized by Ryan Babineaux and John Krumboltz. You’ve probably seen a dozen posts daily on LinkedIn about people miraculously failing their way to the top.

“At 18 I was living on the streets, by 19 my first Fortune 500 company had gone bankrupt, at 24 I was on my 8th company, and now I’m rich!” - so on and so forth.

I have a problem with this understanding of failing, persistence and progress.

It’s the insta-dramatized life of the entrepreneur “hustling” their way to the top. It’s unapproachable, outlandish and atypical. When we distort reality, life’s lessons become less applicable in the day to day and success begins to look like failure.

FFFO (Fail fast, fail often) does not have to be catastrophic, failing is not the goal - learning is.

When FFFO is distorted, we:

  • feel like failures if we haven’t raised $100 million and then blown it all rather than feeling like successes for raising $250,000 and spending it wisely

  • feel like our next business will not be successful because we haven’t bankrupted 5 others yet.

  • pitch customers outsized contracts well beyond our capabilities rather than stretching to new, yet achievable capabilities.

FFFO in reality is smaller and more frequent. It encourages us to try new things and make big bets, but to not always go all in. It teaches us to learn from every “failure” and apply it to our next swing. Most importantly, it teaches us to keep swinging.

FFFO in reality is:

  • I tried five new CTAs (calls to action) on my ads and only one worked

  • I tried to upsell with a new widget for a month and people didn’t bite

  • we tried to switch the team to a new organization software and it didn’t take right away

  • I tried a new subject line on a sales email today and no one responded

  • we tried presenting our pricing in a new format and it only worked 30% of the time

  • I thought I could pull off bow ties and got mocked relentlessly

You don’t need to cause a catastrophe to “fail,” and you can learn from small things every day. FFFO is still a healthy exercise, but let’s lower the stakes. Every day, look at what went well, what could go better, and learn instead to fail fast but learn often.




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