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Becoming a Leader

I worked 80-hour weeks. Now I keep the Sabbath.

I worked myself to burnout at 80 hours a week. The fix wasn't a productivity system – it was one full day of rest, and it made the work better.

3 min read
Team work, work colleagues, working together
Becoming a Leader

Triple your team's productivity with a glossary

More meetings won't fix a team that talks past itself. The fix is a shared language – and if you build software, you already know how to make one.

3 min read
Tree tunnel
Becoming a Leader

The Friction Between You and the Work

Most of your week is friction around the few things that actually grow you and your team. A short piece on clearing it — plus a free copy of Calstead.

2 min read
Sunlight through the trees
Becoming a Leader

You Don't Know Their Heart

In conflict we invent stories about people's motives. Assuming the worst rarely makes us kinder, and most slights are imagined. A calmer way to respond.

4 min read
Road thru fields at the golden hour
Becoming a Leader

You're Not the Main Character

Good leaders don't outsource the call to a spreadsheet, a P&L, or an AI trained on someone else's worldview. They do the foundation work first. Here's what

6 min read
Woman rock climbing inside building
Becoming a Leader

I Got to the Top of the Wall and Couldn't Jump

I climbed thirty-five feet up, looked down, and couldn't make myself jump. What that taught me about the mental work leaders skip before a hard transition.

5 min read
Forking forest path
Becoming a Leader

How I Killed a Startup Idea in an Afternoon for $44

It was a morning in late May, and I was at the desk in my basement office in Springfield with a cold cup of coffee I'd forgotten about, reading about a standard

13 min read
Empty brown leather chairs lined up against a wall in a corporate setting
Becoming a Leader

AI Layoffs Are a Leadership Failure

When companies like Meta and Atlassian cut thousands of people to fund AI bets, it's not innovation — it's a failure of the obligations leaders owe their teams.

5 min read
A craftsman working in a workshop, demonstrating skill through active work
Becoming a Leader

Some Expertise Has a Shelf Life

Some skills don't scale. The question is whether you'll adapt—or whether you're building capabilities that actually compound.

4 min read
Two women sitting together at a table, engaged in open and candid conversation
Trust & Culture

The Two Ways to Tell Your Team You're Not Perfect

Remote teams need deliberate vulnerability to build trust. Most leaders know one mode. The second is what makes the difference.

4 min read
A person walking alone on a quiet path through a wooded forest
Becoming a Leader

The routine you were actually made for

When the to-do list stress feels bigger than it should, it's usually not about the tasks. On routine, identity, and what we're actually made for.

3 min read
A calendar with multiple meeting blocks crossed out in red, leaving open white space
Trust & Culture

The week that tells you whether you have a product job

Take a week. Block the calendar. Decline every meeting. One of two things happens—and either outcome tells you exactly what kind of job you have.

4 min read
A chord diagram showing complex multi-directional relationships between interconnected nodes
Becoming a Leader

Step Zero

Before the linear work of product management begins, there's a step zero – the work of becoming the type of leader your team needs.

5 min read