The Dumbest Question to Ask a Female Entrepreneur



As a female entrepreneur, I am frequently stumped by the following question:

“How is it different from being a man?”

Firstly – I want to immediately ask, is that really the most interesting thing you’d like to know about me, now that we’re here together? Now that we are both choosing this conversation over every other conversation on earth, this is what we most want to discuss? Not – how did I get the company started, what is my favorite cheese, what have I been the most surprised about in going from zero to over three hundred enterprise clients in just a few years? Sigh.
Secondly - while I understand the curiosity and I truly wish I could help (even if it’s just so I stop hearing the same question over and over!), I am never sure how the questioner hopes I will respond. What possible personal experience can I draw from, having never actually been a man? It’s almost impossible to walk in someone else’s shoes and know what they’re up against, what they’ve had to overcome, and I think it’s dangerous to look at how easy someone might make something look from the outside, and assume that their success therefore has been easy.
Thirdly – low quality questions create low quality responses – and likely, low quality results. Worse – the wrong questions can psyche people who might want to try to be a company-builder, from even getting started. The question is designed to paint women into a corner, listing out all the ways that it’s harder to be a female entrepreneur and for us all to go ‘boohoo, it’s super unfair, let’s not even try’.

Maybe it is harder, maybe it isn’t – surely, there’s some crazy stuff that happens that maybe wouldn’t happen the same way to a man, some power struggles perhaps that go down differently and maybe you’re judged a little more for stuff that men wouldn’t be judged the same way for. One difference that’s stuck out to me over the years, is the more narrow band of acceptable leadership behaviors for women, that simply don’t apply to men. You can be confident but not arrogant, forceful but not aggressive, caring but not wishy washy or too agreeable. The line between the extremities, can be a fine one indeed.
I don’t know the answer. But what I do know is, asking this question is designed to keep women stuck, and to make anyone reading the answer feel like the odds are going to be unfairly stacked against them, because they’re a woman.
The truth is actually far worse – the odds will be stacked against them, but not for that reason. They’re stacked sky-high because building a high growth, technologically innovative, valuable organization staffed with humans is incredibly hard, and most companies despite their founders best efforts, fail. Dwelling on disadvantages, real or perceived, is simply making a hard thing, harder – and it’s a waste of your precious time when you need to be putting your energy into building, growing, creating.

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