#29 - Your CEO Should Stress You Out

My partner and I have been dating for 2 years, and living together for 1. This is easily the best relationship I’ve ever been in, with the greatest potential to go the distance.

But it’s also the hardest.

She doesn’t let me get away with bad habits or negative energy. We’re both super intentional about the life story we want to write for ourselves, and we’re constantly bumping elbows while doing so. It requires empathy and sacrifice to make it all gel.

I resented her for it early in our relationship. I questioned if she was the right person for me.

But I soon realized that I got exactly what I wanted all along. I wanted to be in a relationship that made me a better version of myself. I wanted to grow, and this what growth feels like.

My relationship with my co-founder & CEO is the same.

We’re working on a social app together, along with 4 other friends and, man, has it been fun. But it hasn’t come without its difficult moments, especially in the early stages when you’re still learning how to work with each other. Understanding each other’s strengths and weaknesses.

In the case of our CEO, he’s got a lot of strengths:

• He’s incredibly persuasive and rarely takes no for an answer.

• He’s got more ambition and “delusional optimism” than the remaining 5 of us combined.

• He has unparalleled speed and endurance, willing to sacrifice any semblance of work-life balance to move the ball forward.

But I’ve come to realize that all the reasons why you admire someone are also the reasons why they frustrate you. In the case of our CEO:

• His persuasiveness and indomitable will means it’s tough to nudge the ship in a different direction than the one he’s charted out.

• His ambition and optimism mean we’re constantly missing deadlines or cutting corners to meet them.

• His speed and endurance means the rest of us are panting just to keep up, often feeling tired and overwhelmed.

I resented him for all of these things when we first started working together. But once I got over myself, I realized that this isn’t all too different than my relationship with my girlfriend.

My CEO is giving us exactly what we all want and need: growth and our best chance at success.

• It’s great that he’s difficult to debate with. We’re all forced to improve at standing our ground and selling our arguments.

• It’s great that he sets goals too ambitious to meet on schedule. We’re playing out the age-old adage, “Shoot for the moon. Even if you miss, you’ll land among the stars.”

• It’s great that he’s forcing us to sprint on wobbly legs. That’s how we all build up the cardio to outpace everyone else.

In other words, he’s playing his role perfectly. As CTO, I have to learn to play mine. He sets the standard for speed and ambition. I need to set the standard for engineering excellence. That means sometimes being a countervailing force — ensuring corners are never cut in service of ambitious deadlines.

Now back to work…

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See you next week — Rayhan