#36 - Leading Like I Don’t Matter (And Why That Matters)

I’m CTO of a small startup called Wednesday Waffles. We’ve got a scrappy dev team, and things are going pretty well—but I’m still holding the reins too tight.

I hoard mission-critical tasks and I don’t delegate enough. I've justified this by thinking, “I’m just doing the work that needs doing.” But that’s only half of the truth.

The other half? I’m scared.

I want to feel important. I want to feel needed. I want to feel safe. And building a team that doesn’t need me feels terrifying.

But I want to be a better leader—the kind that builds people up and helps them grow. The kind that shares critical tasks, delegates responsibility, and sets the team up to thrive, even without me.

Making that change stick isn't easy. I’ve learned that my most reliable strategy is finding selfish reasons to keep doing the right thing—even when it’s tough.

I don’t lie. Mostly because honesty matters deeply to me, but also because, selfishly, I'm terrified of ruining my reputation.

I try hard to be generous. Primarily because generosity feels good and meaningful—but also because, selfishly, I believe it comes back around.

Until recently, I didn’t have a selfish reason to be a truly selfless leader. Then I remembered something from a talk I hosted at Boston Dynamics.

I invited a respected leader to speak to a group of early-career engineers. Someone asked (as someone always does), “How do you get promoted?”

He replied:
"You need to do the job you want before you’re hired to do it. Eventually, higher ups will just make it official."

A fair pushback followed:
"But how can you do that if you’re already swamped with your current job?"

His answer stuck with me:
"If you don’t have time, you have to MAKE time. If you're an individual contributor, get so good at your job that you can finish it in half the time. And if you're a manager, make your team self-driving. Develop your people and systems to the point that neither need you. That's how you create space to work on other things."

That clicked for me.

I shouldn’t fear building a team that doesn’t need me. I should strive for it, selfishly, because it frees me to tackle bigger things—and ultimately become more valuable to the company.

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See you next week — Rayhan