The Double-Edged Sword of Entrepreneurial Perfectionism

Everybody wants to rule the world

Welcome to your life — There’s no turning back

Entrepreneur personalities have a tendency towards perfectionism. It is one of the single most important traits that continually drives us to build better and better things. But this can be a double-edged sword when you are knee deep in building a growth stage company.

I had to google what this was. Who knew the O.C. could be so spot on?

It’s my own design — It’s my own remorse

I know I am a perfectionist. I strive to be perfect in my personal and professional life and what I expect from myself, I also expect from other people.

This means that I sometimes put unattainable expectations on both myself and others. Hell, what is perfect anyway?

We define perfection as something completely free from faults or defects, or as close to such a condition as possible.

Unfortunately, to decide what qualifies as something completely free from faults or defects, we use a subjective set of attributes based on our projection of how we think the world works.

Take this a step further and the definition of perfect directly contradicts both what a growth stage company is and really, the very essence of humanity.

There is a saying that, “it is not what happens to you, but how you respond to it.” More than anything, this is a statement about control and how it affects your reality. We do not exist in a vacuum, and no matter how much we try to control the people and situations around us, we can neither predict nor control the outcome of everything.

Help me to decide — Help me make the most

For many of us entrepreneurs, this is a hard one to swallow because we pride ourselves on calculated risks. We will put everything on the line, and commit 1000% because we calculated all potential scenarios and outcomes. Right?


Me. Keeping it chill.

So when events do not go perfectly, how do we continue to keep our drive and persistence while maintaining our perfectionist worldview that keeps our passion fueled in the first place?

One of the most beautiful things about life is you can continually grow, learn, iterate, and improve — so looking at perfection as an end goal or a static state really does us a disservice.

I can’t stand this indecision — Married with a lack of vision

I’ve needed to learn to reframe my idea of perfection. A key example of how I am doing this is I’ve consciously learned how to become okay with making mistakes, because it is an integral part of life and unavoidable.

Being a first-time CEO, if I made a mistake and if I didn’t own up to it, there were consequences. At first, rather than apologize, I would immediately go into fix-it mode. My team would feel like they were always scrambling, our customers would feel bulldozed, our company suffered.

What I didn’t realize is that making it better isn’t the only issue. It’s also the grace in admitting I was wrong, the care taken for those around me that were affected (team members, clients, users), and the ability to objectively look at what happened to prevent it from happening again (process!).

More so than simply the action of making it better, apologizing and committing to do better in the future — and then doing better — is a valuable asset. It’s the response to making a mistake that makes someone a good person, rather than not making any mistakes at all.

Nothing ever lasts forever

Spoiler: Everyone dies.

After four years of grind, hustle, business loans, debt, ignoring my health, small enabling wins, and a shitload of customer discovery, I hit a point as CEO of SD6 where I realized that the company as it stood wouldn’t be a win for our team. I had become good at apologizing and troubleshooting things along the way, but what I had not done was become okay with failure. In that situation, I had to practice letting go and accept failure.

My worldview had to change to, “I have a failed company and I am still worthy of being an entrepreneur and a leader.”

But it takes more than logical realization to change behavior, and I recognized that I needed to truly believe that statement in order to let go of my current view on perfectionism and accept myself and situation. To believe it, I needed to get back on the horse.

So I did some sleuthing. I looked at career successful entrepreneurs and dug up what no one wants to talk about–their failures. Like the cliche, I read a business book–The Hard Thing About Hard Things, by Ben Horowitz–and I began to appreciate the people who were striving to be better, more than people who did it right the first time.

So glad we’ve almost made it — So sad they had to fade it

Then, I took on a new job as CEO of an already established blockchain technology company, Input Strategic Partners, currently rebranding to Totem. I was nervous to take on this role. I wasn’t sure that I was the right person for the job. There was a voice inside me that said, “you have an idea, but you don’t know it’s going to work.”

Also me.

Of course, I didn’t let that stop me. Screw you, self-mandated definition of perfection! I would get to work closely with six other incredible entrepreneurs whom I have accrued mad respect for over the last few years living in Vegas and are running partner companies (one of whom inspired this post).

Enter an industry that is new and exciting. Come in with business acumen that many in the current space lack. Run and continue to build off of the stellar team that was already in place. Hell, I felt like I won the lottery.

Everybody wants to rule the world

Eight months later, and many, many more lessons learned, here I am blogging again. I‘ve dissected one example of how I have modified my view on perfectionism to showcase the importance of understanding our subjective definitions of core principles that drive us.

Reframing like this is a powerful tool. It has enabled me to continue developing my skills to be a badass CEO, while also not directly coming into conflict with my desire to be perfect and have others around me be perfect.

And if you get too caught up being perfect just remember, nothing ever lasts forever. Everybody wants to rule the world.

Holding hands while the walls come tumbling down
When they do I’ll be right behind you