Why can’t I be OK with where I am?

As a Founder, no matter what I've ever accomplished I've never been OK with where I am. It's weird, too, because I started out with so little that accomplishing anything was a huge win. And yet, I find that my anxiety exists in nearly ever Founder I meet.

It almost seems like the very drive and ambition that makes us great Founders also makes it very difficult for us to just kick back and enjoy the status quo. It's as if we're Kevin Arnold constantly reaching for the car door handle of accomplishment while our asshole older brother Wayne keeps hitting the gas pedal when we try.

"Why wasn't my last accomplishment enough?”

When we had nothing but a dumb idea and a dream, the idea that this could turn into our day job was a massive milestone. Then one day that actually happened. Then we wished we could just make enough to pay our bills. And then that happened. Each time, we just thought that if we hit that one milestone, we'd finally have "made it." But then we got there (usually with zero fanfare) and it felt like nothing actually changed.

The problem is that at some point, we start to realize that no matter what we accomplish, it won't be enough. We set new goals (because that's what we do) and we dutifully crush them. Rinse. Repeat. The only thing that changes are the bags under our eyes and the rolls around our sides.

At some point, we have to realize that the "next goal" actually doesn't matter. It's the fact that we haven't been able to stop and enjoy the last 10 goals or (heaven forbid) realize that what we've accomplished is enough. Or, dare I say it, we are where we were trying to get all along, we just forgot about it.

Balancing Complacency with Sanity

For many of us, the fear of being OK with the status quo is tantamount to complacency, the dreaded spectre of failure that we save for people less capable than us.

Or, just maybe — and let's just get crazy here — we might actually enjoy ourselves for once. We might actually take the time to appreciate what we've done and give ourselves the internal validation that we should have earned way too long ago.

Imagine for a moment there are two versions of ourselves — one that is running on an endless treadmill, looking super fit and healthy but doomed to die because we can never get off the treadmill. The other is this lazy sloth watching our Carl Lewis self, slowly dying from doing nothing but eating E.L Fudge cookies (so good..).

We don't want to be either of those people. We don't want to become the sloth version of ourselves any more than we want to die on the treadmill. We have to balance complacency with maintaining our sanity.

Being OK with where we are IS the Actual Challenge

What we're missing in the middle is being OK with who we are and where we are right now (which isn't always great).

We have to realize that while there may be a bigger/better version of ourselves that we can visualize, we already ARE the bigger better version of us from our last milestone. We have to be able to celebrate our victories (be OK with where we are) as a reflection of our past goals, or we won't be able to make our next goals mean squat.

Our goals shouldn't be about what we don't have. They should be about celebrating what we do have.

In Case You Missed It

Fat, Sick, and Nearly Startup (podcast). Join Wil and Ryan as they break down the ways Founders can learn to deal with personal hardships that are often a result of our own Startups — while we're still running them.

Optimizing for Happiness. We do something in our planning at Startups.com that is relatively unheard of in the startup business: we optimize for happiness. Here’s how we do it.

How I Harness My Insane Startup Anxiety. There are two types of Founders: those that admit they are wracked with anxiety, and those that are lying about it. We’re all going to deal with it for the rest of our lives — so why not use it as a superpower, instead of reacting like it’s kryptonite?