Which Version of Me for Dinner Tonight?

“I’ve got dinner tonight with my friends… I wonder which version of me should attend?”

• Do they want to hear about the version that’s stressed out and can’t sleep?
• Or do they want the version that still makes it sound like my startup is doing better than it is?
• Maybe I’ll bring the version that pretends this startup isn’t that important to me and that, instead, I’m just focused on living my best life.

Ah, to hell with it, I’ll just pour myself a vodka gimlet and see which one shows up!
Sound familiar?

It’s because every Founder constantly goes through this battle as to which version of themselves they need to bring into the world. And that world has lots of audiences, from spouses and family to friends and colleagues to investors and customers. All of them want a different version of us, and we’re stuck deciding which one they get.

Why so Many Faces?

Founders tend to become actors, whether we like it or not. Funny enough, I was a theater major before I became a Founder, so maybe it goes the other way around, too. The acting isn’t incidental, though — it’s almost a requirement.

Our job is to turn something amorphous and improbable into something real and obvious. Which means we fundamentally have to start off delusional.

It starts innocently enough. An investor asks if we think this will be a big idea, and we tell them “YES!” and collect that sweet, sweet funding dough. But we were acting. We have no goddam idea if this idea is going to be big or fail completely (nor do they!).

We’re then forced to keep using those play faces in countless contexts. Our first customer asks if our product works — we use our sales face to say “Yes” (and hope that it does). Our spouse asks if all that debt we’ve created is going to be paid back with this startup, and we put on our “family protector” face and assure them.

At some point, we get so used to employing faces to reassure someone about something that we’re not even sure which face is ours. It’s weird.

That is the Job

Now, it might be weird, but that is the job of a Founder.

Our job requires us to put our own needs second, not because we’re so altruistic, but because our own real needs simply aren’t compatible. We don’t just get to cry because we’re so upset that we didn’t raise capital. We have to be out there putting on a fresh face to get that check.

While everyone at the office is freaking out about a new competitor that is likely going to crush us, we don’t get to join the anxiety party. We have to be the ones showing a bright face for a better future.

This job requires us to be a version of ourselves we aren’t, because the real emotion that comes with this job would involve a person absolutely no one would work with!
This isn’t to say we’re some emotionless robots; it’s to say we don’t always have the luxury of letting our true feelings dictate the words coming out of our mouths. It’s not pretty, but that is the job.

Who am I?

All of this theater and masquerading doesn’t change who we are inside. If this job didn’t exist, a lot fewer of those faces would be required — if any.

We’re stuck between a few different slabs.

The first is that defaulting to unrivaled honesty has consequences. If an employee came to us and said, “How certain are you that we’ll raise another round?” there would be no possible way to provide complete assurance. Well, that person is paying their mortgage with that assurance, so you'd better have a better answer!

The second is that we’re paid (hopefully) to be unreasonably optimistic for a living. When there are almost no signs that things will work, we have to believe they will. All day long. In front of every person in our lives.

The last is our damn sanity. If we sat around all day and really thought about how crazy this situation we’ve gotten ourselves into is, we’d go mad. So we have to revert to this delusional version of ourselves to make it through another day. It’s a survival mechanism.

So, Well, Who do I Bring to Dinner?

It’s a balancing act — we bring the version of us that brings us the most joy with the least amount of consequences.

If it wasn’t obvious, the emphasis there isn’t on “joy,” it’s on “consequences.” If our joy involves being brutally honest about how stressed we are so that we can let it all out, but we did it in front of our spouse (who is relying on us to support the family), those consequences pretty much determine who comes home.

Over time, this calculus becomes second nature, so much so that we start to not even notice it’s happening. We just adjust instinctively.

So, we’ll understand if the person you bring to dinner tonight isn’t really who you want to be. Because, as Founders, we know you brought the person you had to be.

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