The Entrepreneur's Hoax, and Why I Won't Play Along

March 2, 2013

It seems like such an innocuous question: “How’s business? Everything going well?” People just want to be encouraging. They really are rooting for you and they just want to hear that a company they like (and an entrepreneur they like) is doing well.

I’ve read that the standard reply in Silicon Valley is to say something like “We’re crushing it!” and all I can think is Thank God I don’t live in Silicon Valley. If someone in Chicago said that to me I would raise my eyebrows and think they had been watching too much Entourage.

But what do I say? And why does it matter?

It matters because you’re probably not crushing it. Hopefully, you’re not failing miserably, either. Most of us are somewhere in between. Or, more accurately, some days we’re crushing it and some days we’re…not.

But entrepreneurship can often feel like a performance. A non-stop performance—for customers, for investors, for employees, for peers. Perception matters, and startups need to create a perception of success. “Fake it till you make it,” right? Everybody's playing the game, right?

Lately, though, I’m hearing some concerning stories about how faking it without making it has led to entrepreneurs burning out, even to the point of committing suicide.

Comparing your own private reality with the polished and refined public image of your competitors and peers is like women comparing themselves to Hollywood actresses whose bodies have been professionally coifed, colon-cleansed, styled and Spanxed before walking the Oscars red carpet: It's an elaborate hoax. And the hoax gives all the rest of us a distorted perception of reality and it’s bad for our self-esteem.

Much like the excesses of Hollywood, we can all be complicit in creating an ecosystem that feeds on (and then eventually requires) bravado and exaggeration. Or we can refuse.

Personally, I vote for keeping it real in Chicago. For being a safe space. For sharing our ups and downs and making struggle normal.

I’m not saying that you should dump your shit on everybody who says, “how’s it going?” And if you don’t possess that bizarre combination of incredible confidence and willingness to be proven wrong then you probably shouldn’t be an entrepreneur. But I am saying that we need to help each other benchmark against reality instead of an airbrushed, Botoxed land of make-believe.

So what’s my response when someone casually asks, “How’s it going?” On good days and bad days alike, I say something like “It’s going, thanks. We’re chugging along, making progress every day.” And we are. Moxie Jean is a lot bigger, and we’re ten times smarter than we were just a few months ago. We’ve figured out so many pieces of the puzzle (some painfully and all through trial and error). But truthfully, we still have some big things to figure out, and I ask my friends, mentors and investors for help and advice all the time.

I also try to be candid in sharing lessons, wrong turns and times of struggle, mostly because turning events into coherent stories helps me process it all, but also with the hope that other people will know that their own doubts and disappointments are part of the normal life of a startup entrepreneur.