Lessons

Why Startup Leadership Feels So Lonely

Startup leadership is lonelier than anyone admits. Here’s why it feels that way, and the three supports every leader needs to make it feel lighter.

Dec 9

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Lessons for new leaders

Every new leader wrestles with the same tension: move fast or listen first? Here’s how to get the timing right so people actually follow you.

Dec 2

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November 2025

"Disagree and Let’s See"

An alternative to "Disagree and Commit." A practical way to handle decisions you disagree with by treating them as experiments, not battles to be won.

Nov 18

24

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October 2025

The Sandwich Metaphor

A way to think about the impact that feeds you. Not everyone’s built to “fund the groceries.” Some of us come alive handing out sandwiches. The work…

Oct 21

31

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September 2025

Who’s driving your car?

What if your career choices were being made by the wrong part of yourself? In this essay, I share a powerful metaphor from my coach: picturing your…

Sep 15

39

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Letter Bombs

We’ve all been tempted to promise a title or guarantee someone they’ll always be the most senior person -- just to close the candidate. But those…

Sep 3

15

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July 2025

Happy Friction

Happy friction is like a speed bump. It’s something you add on purpose to make people pause. Ideally, not because you’re afraid to delegate, but because…

Jul 15

14

June 2025

Leavers vs. Stayers

Over the years, I’ve come to see that many of us fall loosely into two career archetypes: the leavers and the stayers.

Jun 26

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May 2025

Make It Easy to Draw the Elephant

Great communication is simple if you think about it as “connect the dots”. It isn’t about talking more—it’s about creating clarity and alignment. Your…

May 13

45

April 2025

10x the Problem

When you're stuck—when you're agonizing over a decision, or when it feels like there’s no obvious answer—I have a simple tool I use with founders and…

Apr 30

18

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February 2025

There’s No Such Thing as a Generalist

Generalists vs. specialists — which is better and why? You’ve probably come across at least one think-piece or thread on this topic. It’s everywhere…

Feb 28

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December 2024

Molly's TED talk: Jumping Off Career Cliffs

Applications are now open for the next cohort of Glue Club! Glue Club is a leadership development community that helps you be better and feel better at…

Dec 3, 2024

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