How I Harness My Insane Startup Anxiety

I have insane anxiety. But I’m not supposed to tell you that.

I’m supposed to create a facade of confidence that says all of the decisions in my life and all of my outcomes materialize with full certainty. My career, résumé, awards and success should be nothing but a shining reflection of confidence and brilliance.

That’s all bullshit.

I wake up in the morning and I freak out. I go to bed at night and I freak out. It doesn’t end. It didn’t end after growing companies, selling companies, making money, or any of the other bazillion “final reasons” why we think it will all disappear someday.

My anxiety is here to stay. So I have to deal with it. And I’m guessing if you’re reading this, you do too.

Let’s Just Admit We’re All Freaked Out

Essentially there are two types of Founders: those that admit they are wracked with anxiety, and those that are lying about it.

By definition, a startup is a torrent of anxiety. We’re swan diving headlong into the abyss. We’re likely doing things we’ve never done before with products that have never existed before. There’s nothing about this process that should make us feel assured and certain.

So let’s just start off by admitting we’re all freaked out and it’s a big problem and we all need to figure this shit out.

Great. Moving on.

How I Harness the Force

A long time ago I realized that the core problem was never going to go away (it’s how I’m built), but my methods for dealing with it could be vastly improved. So I set out in my typical OCD fashion to find ways to wrangle this wily beast.

I found that anxiety is an emotional chess game of perception that I could challenge and, to some degree, conquer.

Our fears and anxieties are meant to help us avoid danger. But the days of living in caves and running from saber-toothed tigers are behind us. These days, the giant fanged creatures are silly inventions in our heads. Yet physiologically they still get our hearts pounding out of our chests like our Neanderthal ancestors.

Over the years, I’ve built a toolbox for my anxiety that includes four instruments. For those of you who don’t care about the details of the methods, here’s the short GTTFPoint Version:

1. Detail the consequences. Spend time figuring out exactly what will happen when things go south and what will likely occur after that. Be 100% sure you know precisely what you’re worrying about.

2. Don't believe the hype. Assume pretty much everything you read or hear about someone else or some other company doing amazingly well is a bunch of bullshit. Because it probably is. Don’t compare yourself to it, and learn how to filter it.

3. Focus on action. Take your anxiety and force yourself to use those cycles productively. The best way to prevent yourself from worrying is to burn up all of those available cycles doing productive stuff.

4. Take a long view. Put it all in perspective. Compare where things are now to the big picture and calibrate accordingly.

If this is the end of your attention span (I’m with you), then I’d recommend not using each of these tools by themselves, but using all of them in combination. While we can’t prevent anxiety from rising up (sadly it’s just not that simple), we can focus on becoming extra badass at dealing with it.

For those of you that are still interested, here’s exactly how I manage each method:

Method #1: Detail the consequences.

The most common enemy I’ve found within anxiety isn’t the anxiety itself – it’s the perceived consequences of the problem.

Early in my career, I had racked up over a hundred thousand dollars in personal debt. That’s a lot of money by anyone’s account, but I was 20, and given that my alternative was to get a job making less than 10 dollars per hour to pay that down, it was safe to say I was thoroughly effed.

I wasn’t sleeping. I was laying in bed every night staring at the ceiling saying “What the hell was I thinking? I’m so screwed. My life is over.” I’m sure we’ve all been there at some point.

Yet one night I distinctly remember rolling out of bed at some ungodly hour, walking over to my Commodore Amiga computer (re: “Wing Commander” console) and typing a list that looked something like this:

“Things that will happen when my life will inevitably be forever screwed”

1. I’m going to get kicked out of my apartment.

2. I will default on all of my credit cards and have awful credit forever.

3. I’m going to be embarrassed by my failure amongst all my friends.

4. I’m going to have to stay in school. (This last one was serious for me – I was always an awful student.)

The list went on, and I went into serious detail about what would be the outcome of each of those issues. Collectively they all felt pretty awful, and in the context of my world at the tender age of 20, it was all that I had. So it was pretty much my “end of days.”

Then I did something that changed my feeling entirely. I said, “OK, the apocalypse is awful and everything – but what happens after that?”

I then made another list that went something like this:

“My Mere Post-Apocalyptic Existence on Planet Earth”

1. I won’t ever have to think about this again.

2. I will get a crappy job but will actually be able to spend my money again.

3. Every human on the planet finds a place to live – inevitably so will I.

4. Embarrassment due to failure aside, my friends will probably enjoy my company once again.

5. I will have more time to play Wing Commander.

Suddenly I realized that “Post-apocalyptic life” actually sounded pretty good by comparison.

I found that when I could shift my anxiety from “going bankrupt” to “what happens after I’m bankrupt,” it was a far different concern. That exercise probably cut my anxiety in half that night – which, if you’re crippled by worry, is about the most amazing feeling of relief in the world.

It’s not that bad things won’t happen – it’s that we rarely force ourselves to truly play out the consequences beyond the painful part. Once I had this more complete perspective, my anxiety waned substantially. It was life-changing.

Method #2: Don’t believe the hype.

If you were to scan the headlines of any major industry journal, from entertainment to business to politics, you would assume that everyone being featured has it all figured out. You’d be lead to believe that those captains of industry are just killing it while you sit around crying in your beer.

But like the great Flavor Flav said, “Don’t believe the hype.”

Headlines are meant to be sensational – to inspire you to read. Celebrities don’t lead glamorous lives (they are often pretty sad actually) and famous Founders don’t just happen to be killing it every day. More often than not, the stories you read highlight the polar opposite of the reality that exists.

I didn’t fully appreciate this fact until I started getting to know many of the Founders I once read about. I learned that every time you read a headline like “Company X Raised $50 Million in Venture Funding” there’s a Founder of that company thinking, “My god our burn rate is so insane. I hope this $50 million will last us before we go out of business!”

If you need even more proof, look no further than your Facebook feed. One might deduce that according to Facebook everyone in the world is having a blast. Their kids say the funniest things, their vacations are amazing, and they are always at the best events.

If the reality of people’s lives were actually on Facebook, it’d be pictures of baby vomit, crappy hotel rooms, and sitting at their cubicles doing work they hate. Calibrating your expectations to these incomplete, rose-tinted public images is masochism at its finest.

Method #3: Focus on action.

My mind is constantly racing. It’s like if you were to hold down the channel selector on a remote control and just watch the shows flash across the TV in no particular order, endlessly.

So instead of just saying, “Oh crap, my mind is racing,” I started writing down all of the stuff that was going through my mind – especially the anxious thoughts. What I learned was that while my mind was racing nonstop, I couldn’t actually have two thoughts at the very same time.

That was actually a huge discovery for me.

That meant if I were to simply focus on keeping my mind busy with positive actions, like building toward something, it would steal away from the cycles I would have for negative actions, like worrying about silly stuff.

I learned, in times of serious anxiety, to look for the most productive thing I can be doing, and throw myself at it with full abandon.

If our rowboat were sinking, instead of crying about it, I’d put all of my attention toward bailing water out of it. Would we still sink? Probably. But I know now that in times of crisis, that energy needs to be converted into positive action or it will turn into a horrible liability.

Now when I’m super anxious, the first thing I do is create a list of every productive thing I could possibly be doing. I’m writing this article right now, so I can tell you this is actually a response to some other anxious moment I’m dealing with.

Often the best ways for me to transfer this type of energy is to do something mindless, like cleaning or yard work or something that has a defined, positive outcome.

The way I see it, whether I’m anxious or not, I still have 18 waking hours per day to get something done. If I’m going to spend that time doing something, I may as well spend it in a way where I can get something out of it. Worrying doesn’t buy me anything.

Method #4: Take a long view.

I want to end with “taking a long view” because this one assumes you’ve been able to implement the previous three.

Early in my career, I lacked the experience and perspective to really understand the long view, so frankly it would have been lost on me anyhow. I never really understood the difference between urgency and crisis – and that lead to an ungodly amount of ridiculous self-imposed anxiety.

Think back to when you were in high school. Remember how many “crisis moments” you had back then? Back then it was whether you had a pimple, or you were cramming for the SATs, or you weren’t sure if you were going to prom.

If you had to go back and relive those moments you probably wouldn’t treat them with the same level of anxious tension that you had back then. You’d look at them and laugh. You’d say “OK, I have a pimple. It’ll go away. Who cares?”

The difference between then and now is that you’ve developed perspective, or as it would relate to your high school career, a long view. Once you realize that individual challenges don’t automatically translate to life or death crises, you save yourself a ton of anxiety.

I use this technique all of the time. Hell, I’m using it right now. I think about the fact that I’m 3 days behind on this writing assignment and realize “I’m going to have to write a thousand more articles in my lifetime. This is just one of them.” It helps reduce some of the anxiety about this particular crisis.

I then use the same technique in my career. I think about all the ways in which I want to help Founders build great startups and I zoom out. I say “OK, whether I do 30% or 300% of what I want to do for startups this year it doesn’t matter because I’m going to be working on the same problem next year and the year after. I have my whole life to make this contribution.”

Does that long view change my urgency? Hell no. I still want to get this article done as fast as possible. But it reduces the amount of anxiety I have about this particular “problem” that I’ve basically invented.

I’m finding more and more that this last method has become one of my most valuable assets. By zooming out above the noise and invented crisis of daily startup life, it allows me to stay focused around the big picture items that truly matter.

Summary: Does it ever end?

The obvious question after reading all of these methods is whether or not the anxiety itself can ever be put to rest.

I can only speak for myself, but in my experience, the answer is “no.”

But I have to say, I’m OK with that. While on its surface the idea of anxiety sounds horrible (…and it is), I’ve figured out how to channel that nervous energy in very positive ways.

I use it to think through problems beyond their consequences and onto their resolutions. I use it to translate the rosy facade that the world tries to present into a realistic picture of how things truly are. I use it to summon and channel my energy into wildly productive outcomes. And I use it to force myself into big-picture thinking versus minutiae.

We are all going to deal with this silly anxiety for the rest of our lives. Why not use it as a superpower, instead of reacting like it’s kryptonite?