Clever People Rarely Fail. They Just Stay in the Hallway Too Long (An MIT Game Showed Why)

The Sunday night that started it

It was the last Sunday in October, the kitchen dark except for the laptop, and I was counting tabs. Twenty-two.

A novel stuck two chapters from the end. A spreadsheet for a product I’d sketched in August. Half an essay. Something about sourdough I can’t account for.… Read the rest “Clever People Rarely Fail. They Just Stay in the Hallway Too Long (An MIT Game Showed Why)”

The Hidden Maths of Midlife Income: What a Part-Time Job Really Pays After 50

Prefer the story? I told it on Medium: Why “Just Get a Job” Stopped Working for Me at 50. This is the maths underneath it.

Once you’re past fifty and the money looks thin, everyone hands you the same four answers. Get something part-time. Go freelance. Turn the hobby into a little side line.… Read the rest “The Hidden Maths of Midlife Income: What a Part-Time Job Really Pays After 50”

Prefer the story? I told it on Medium: Why “Just Get a Job” Stopped Working for Me at 50. This is the maths underneath it.

Once you’re past fifty and the money looks thin, everyone hands you the same four answers. Get something part-time. Go freelance. Turn the hobby into a little side line.… Read the rest “The Hidden Maths of Midlife Income: What a Part-Time Job Really Pays After 50”

The Quiet Life Is the Ultimate Leverage: How to Test Your Inherited Dreams Before They Steal a Decade

Quiet life. That’s the phrase I never once tested before nearly spending a decade chasing its opposite. It was 11:42 PM on a Tuesday, and I was doing arithmetic on a life I had never once sampled.

My laptop screen cast a cool blue glare across the desk. Open in front of me were three tabs: a real estate listing for a high-rise city apartment, a speculative financial model calculating the revenue needed to justify a London zip code, and a draft of a pitch deck for a business expansion I wasn’t even sure I wanted.… Read the rest “The Quiet Life Is the Ultimate Leverage: How to Test Your Inherited Dreams Before They Steal a Decade”

I Quit the 5 AM Club and My Career Moved Faster (Seneca Saw This Coming)

Watch the short companion video on YouTube, or read on for the full essay. This piece also lives on Medium.

I used to be a proud member of the 5 AM club. At 11:43 PM on a Tuesday, I was answering emails that could have waited until Thursday.… Read the rest “I Quit the 5 AM Club and My Career Moved Faster (Seneca Saw This Coming)”

The Conviction Gap: The Career Skill AI Cannot Replace (And Most Professionals Don’t Have)

Quick read: Most mid-career professionals plateau at the same spot — somewhere between senior individual contributor and director. They produce great analysis, structure problems beautifully, and write competent memos. But they never quite cross into leadership. This piece is about what’s actually going on, why it’s getting worse in the AI era, and the three habits that close the Conviction Gap.

… Read the rest “The Conviction Gap: The Career Skill AI Cannot Replace (And Most Professionals Don’t Have)”