What if Our Startup Anxiety Never Quits?

What if no matter what we do, our anxiety never goes away?

We all want to believe that the relief from whatever is stressing us out is just one milestone away. If we could just raise this next round, or get the product shipped, or get to profitability — we'd be able to breathe easy.

It doesn't stop there. We believe if we just make enough money, meet the right person, or finally buy that one thing then we'll be "satisfied" and all that anxiety will melt.

But what if it never does? What if all of our achievements keep bringing us right back to the same point — and we can never figure out why? Can we really "out achieve" our anxiety?

I Tried It — It Didn't Work!

Let me tell you Founder friends — I tried it. I started this game with a boatload of anxiety about life. I graduated high school at the bottom of my class, got rejected from every college I applied to, had $0 in the bank, and didn't even have a date to prom. Let's just say things weren't going really well for this guy.

Soon after I launched my startup, and by the time I was 22 I was a millionaire. I learned two things — that having a bunch of money didn't help my anxiety one bit, but it did make it 10% easier to find a date. So "yay" to that I guess…

From there I spent nearly 30 years checking boxes. Houses, cars, wife, kids — you name it. I started 9 startups because I was dumb enough to think that was a really good idea (it's not, don't do it). No matter what I did, no matter what boxes I checked, nothing changed. I still woke up at 2 a.m. in cold sweats worrying about something, no different than when I was graduating high school with zero boxes checked.

It's Not The Thing, It's The Anxiety

It turns out that those milestones were never my issue — it was the anxiety itself. What messes us up is that we all project that anxiety onto something real, and then pretend that if that thing gets fixed or achieved, then the anxiety will disappear with it. Spoiler alert — it won't.

It's really hard for us to believe this — REALLY hard. In fact, you're probably reading this right now saying "This guy is an idiot! If I had what he has I'd be golden and wouldn't be writing crying, self-pitying essays like this!" To be fair, you're probably right on both counts, but that doesn't mean the same anxiety you're feeling right now would magically disappear. You're falling for the trap.

The trap is that it's the anxiety that we're really battling. This feeling of not being safe, not being validated, not being heard. While we think our achievements will "solve" that anxiety, the real solution is recognizing what that anxiety really is and vanquishing the source of that feeling altogether.

How Do I Slay This Vile Demon?

Oof, now that's the real question. There's no one size fits all answer here because how we each got here is very different, even if the labels of our demons kind of look the same. The first step in my experience (your mileage may vary) is to recognize, often in disbelief, that no matter what you think you can "solve" by checking boxes, the anxiety actually won't change.

Instead, the key is to dig into the "why" of our anxiety. Why don't we feel safe? Have we always felt unsafe? Where does that come from? Are we actually not safe or do we just feel that way? By the way that last question is often the trickiest.

All together we need to find the psychology behind these feelings, not just the simple surface-level feelings. And now we're beyond where my lack of professional experience can take us. The road forward involves someone way more qualified than me, but my goal here is just to give you, my fellow Founder, just a little nudge to begin your own exploration. As always, you're not alone, and I'm here to listen.

In Case You Missed It

Why Can't I Be Happy Where I Am? (podcast) Why is it that as Founders, we feel like we must constantly be chasing something - otherwise we don't feel satisfied? Listen in to find peace within Startup chaos!

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?

We're All Afraid of Paper Demons (podcast) When you start to focus your attention on something that has not happened yet it will create growing anxiety that will hinder what you are truly capable of achieving. Stop worrying about the things that didn’t happen and start planning based on what’s happening now.