#56 — Saying Yes

“People are effective because they say ‘no,’ because they say, ‘this isn’t for me.’”

— Peter Drucker.

There’s a lot written about saying “no.” Ruthless prioritization, clear goals, focus. Filter out anything that doesn’t fit. I often recommend Drucker’s Managing Oneself to young people entering the workforce. All those principles are key.

But taken the wrong way, it can mean shutting the door to possibility.

I learned a lot from this conversation with Jessica Eggert.

At 17 she was an extreme planner.

At 19 she was hiding her age to get a corporate job.

At 24 she was a manager.

At 29 she had checked off all her previously declared goals.

And then she realized she was confused about the definition of success. She described that moment as a way-too-early mid-life crisis.

She then got into a mode of saying “yes.”

With no intention of being an entrepreneur, she starting solving problems for her family. She was frustrated with her experience setting up childcare and summer camps for her young kids. She started helping herself and others.

There wasn’t a lightning strike moment. She put her work into the world and said "let's see what this can be" with each iteration.

Many many twists and turns later, she founded LegUp.

It was a very real story about the messiness, confusion, and work required to find a new direction.

Now she’s on a mission that was never in here life plan.

Jessica shared her stories about redefining success, navigating shades of grey in product market fit, and building a culture toward diversity.

I hope you enjoy the conversation.

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