Why It Is Good To Be Bad at Estimation

If you knew how long it would take, would you even get started?

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I am bad at many things, but I am easily the worst at estimation. Ask me how long something will take and you’ll get a wrong answer every time. Not just wrong, hilariously incorrect. I’ll microwave something for 15 seconds that really needs a minute, and leave things in the toaster until they are on fire. If I need to meet you somewhere I’ll either be really early or really late, never in the middle. 

Years ago I thought this was a weakness, and I marveled at the people who seemed to be able to estimate everything. They were so quick and accurate in knowing how long something would take. It wasn’t hard to be better than me, but they were just so good.  

Eventually, I realized that my weakness for estimation was a strength in disguise. 

When I was starting my first company (Flurry), I remember believing that we would be working on it for a long time. At least 2-3 years! I even spoke to a financial planner about how to handle the windfall I expected in two years. I was hopelessly naive. 

Nine years later, when we finally sold Flurry, I looked back at the journey. Those nine years were some of the hardest of my professional life, as the company has struggled for most of them. That included being insolvent not once, but twice! I got paid minimum wage for 3 of those 9 years. While it was a big success at the end, it certainly didn’t feel that way on the journey. 

Nine years was also a really long time for me as a person. Over those nine years I got divorced, got married again, had a child and moved more than once. The person I was at the end of those nine years was very different from the person that started out on that journey with his naive optimism. 

I don’t regret any of that journey, or any of my startup journeys since. However, I am sure that if the young, naive version of me knew exactly what was ahead he likely would not have even attempted it. My inability to estimate or even understand how long it would take, and how hard it would be, was an asset that let me start on a harder path than any reasonable person would undertake. 

This is true of almost anything ambitious. If you spend too much time understanding exactly how hard it will be, you’ll never get started. The most ambitious things require someone to jump in and force themselves to figure it out along the way. You need to commit to unreasonable goals, with the confidence that you can figure it out along the way. 

There is, obviously, a flaw with all of this as you can easily waste years of your life on something that was never going to work. However, how would you know before you try? Still, you need to balance this kind of naive expectation with ruthless evaluation of your progress along the way. It’s fine to embark on an impossible journey without understanding how long/difficult it will be, but there is no excuse for not evaluating new information along the way to decide if you should continue. 

Starting isn’t the only hurdle to achieving ambitious goals, but it is one of the highest. In my experience, most people fail to ever even start. If that’s you, then it helps to not fully understand what you are getting yourself into.

It worked for me.  

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For more on Company Culture and Leadership, see:

• The Downside of Optimism and how it holds you back.

• The Art of Being Unreasonable

• How Company Culture is a management tool. 

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