Keep Your Expectations Small

When your skills evolve, so does your fear. Here’s what you can do 

Image: Eunice De Guzman/Unsplash

“Failure is the condiment that gives success its flavor,” Truman Capote’s saying goes. The inversion is equally true; even just a sample of sweet success provides failure with its bitterness. 

Three weeks ago, I decided to make a screencast, film it, and sell it for money. It was an idea my friends and I’ve had for years; some of us run ecommerce businesses, some of us run studios, but none of us have actually tried selling information products. Almost immediately I decided, the thoughts came into my head… 

What an Evolved Fear of Failure Sounds Like

Eight years ago, I got takeout sushi with my friends, went upstairs to the Xtreme Labs office, and worked from sunset till dark to write and launch an ebook. I didn’t have a worry in the world; I was with friends, and even if I launched to a beautiful, round, zero, I would just figure it out after that. Hell, I was supposed to fail. I was a student. When else was I going to experiment?

But this time, I heard myself harshly critiquing the idea from the start. All those things I didn’t know eight years ago — the joys of ignorance — stood up and spoke out.

“Your audience isn’t big enough.” 

“You haven’t validated this idea.” 

“There’s not enough time to promote.”

The truth is, these voices weren’t even wrong. They all had valid points. But they were also just sophisticated ways of saying the same thing:

“I’m scared. Don’t do it!”

In accumulating my own expertise, I realized that my own fear of failure had evolved as well; I could point out flaws and reasons why things wouldn’t work much easier than I could eight years ago. 

My fear knew all the right, logical, things to say to talk me out of this. And in many ways, it was what I’d say to a friend or client in my situation.

As I worked throughout the week, I realized that I had lost agility compared to eight years ago, when I was a beginner. I was a student, and I’d never tasted success; I’d gotten used to the taste of failure. At least I was doing something

But now, my career, client list, and body of work grew, and I developed what I call.. 

The Intermediate’s Fear of Failure

As we get better at what we do, we expect to fail at it less and less often. We lose our connection with failure. The more work experiences a person accumulates, the stronger their reputation, and the greater their own expectations for the things they work on. The more we learn, the more we earn, the more we feel like it’s normal

For example, in the few weeks I focused on this experiment, I know the amount of money I could have made, if I wanted to get a job. A month not making that money can feel like I lost it. It’s tempting to expect my hourly rate to be the quantity I need to get back from my projects to justify my earning. Opportunity cost forces me to realize I’m investing all the potential earnings into my own life and learning experiences. 

Outside comparisons play a part, too. But now, eight years after my student side project, things seem scarier. People take on corporate VP titles. (I didn’t realize Goldman Sachs had 12,000 VPs in 2012.) They’re flexing on LinkedIn. They’re making down payments.

The fear of failure kept me doing the things I know I was good at, and didn’t support me in exploring the things I could be great at. Plus, it wasn’t real; nothing bad would actually happen if this project didn’t make a single dollar. Rather than enable me to develop new skills, it was keeping me in a silo. I needed to break out.

It really took this project to really encourage me to apply what I knew. I’ve watched Gary Vaynerchuk yell at 30- and 40-year-olds, “You’re a kid!” I think it’s an admonishment to return back to the mindset of a student. Like Amazon, everyday is day one. 

Return to the Beginner’s Mindset

A beginner’s mindset has no expectations. It is, by default, loosened up. It doesn’t worry about how the work or experience will turn out. 

The beginner’s mindset is about being okay with zero. Zero Likes. Zero views. Zero sales. Zero expectations. It’s purely about the experience, and zero results. You are a student again; you are a beginner again. 

In conventional linear progression, beginners accumulate experience. Other people may see them becoming intermediates, and then experts. But with the beginner’s mindset, even the most veteran experts are humble. They know that there are so many things they don’t know; so they’re always open to exploring, or re-exploring, an old idea. 

A beginner’s mindset can’t be read about; it takes practice. This experience meant a lot to me; it wasn’t the same as reading a book about the beginner’s mindset, it was a lot better

Keep Your Expectations Small

Paul Graham once wrote about keeping your identity small. I think it’s important that as we start excelling at the things we do, that we not throw away our experimental and playful side to preserve our reputations and expectations. In short, make something just for the hell of it, and ship it. 

It might not help your legacy; Andre 3000’s meticulous body of work is an example of that. But it will keep you creative; in his podcast with Rick Rubin, Andre talks about the pains of his legacy and how he feels stifled by external expectations.

The solution is to do something new, even if you think it might suck. Adopt a beginner’s mindset to overcome your intermediate fear of failure. What you’re working on today will limit or expand the things you can work on in the future. Keep your expectations small, and build the skill sets you need to do the things you want to do.