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This started as an accident. Here’s what it’s becoming.
A small update on how Lessons works — why I’m adding a paid tier, what stays public, and how I’m thinking about conversation and community.
Dec 22
5
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
9
1
1
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
24
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Most Popular
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Time is emphasis: planning your calendar as a leader
Apr 14, 2023
57
11
8
Founder Mode: A Liar’s Perspective
Sep 10, 2024
78
9
6
There’s No Such Thing as a Generalist
Feb 28
70
8
8
J-Curves vs Stairs: Two Approaches to Career Growth
May 10, 2023
76
4
8
Choosing your next job
Feb 22, 2022
66
3
4
How to take time off and use it well
Sep 14, 2023
52
8
5
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"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
26
2
3
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
32
3
2
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
3
2
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
1
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
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
44
1
3
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
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Lessons
Things I’ve learned from years inside startups and scaling companies — about work, leadership, and building a career that actually fits.
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CJ Gustafson
Redefining Work
Lars Schmidt
The Beautiful Mess
John Cutler
General Practitioner
Sean Twersky
Bursts of Color
Geoff Donaker
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