Topic
Tradeoffs
Essays on tradeoffs, decision-making, and the real cost of every choice. Every decision I make about my time, money, or work comes at the expense of something else. I used to pretend that wasn't true, or that I could find a way to avoid it. I can't, and neither can you. These essays are about choosing which cost you're willing to pay, and then living with that choice.
Give yourself a raise.
Making more money is great. Keeping what it buys you is harder.
What if it works?
Six rules I use to evaluate growth, protect my time, and decide when to leave money on the table.
Before you make the deal.
Dolly Parton turned down Elvis Presley to protect the publishing rights to her song. A lesson in conviction, ownership, and knowing what’s worth keeping.
People deserve bad news.
Avoiding a hard conversation can feel harmless in the moment. But sometimes waiting too long makes the truth useless
Unreasonable.
Why choices that look wrong build lives that feel right.
Synthetic purpose.
When problem-solvers run out of problems, they manufacture fake ones. I've been doing it every morning at 5:30 a.m. for a year.
The machine or the life.
Some mornings I wake up and think, what the hell did I just do?
I'm a crazy person.
The most successful people I know don't have better habits. They have something slightly wrong with them.
How much does your job actually cost?
A woman we met in a Paris cafe seemed to have the perfect corporate job. Then she told us what it actually cost her.
The money trap nobody warns you about.
She finally hit her income goal. Then she wrote to tell me she's more anxious about money than when she was broke.
I almost made a terrible mistake last week.
I almost automated the one thing that keeps me connected to my readers. I'm glad I caught myself.
The money-first trap
I walked away from guaranteed annual revenue last week. Two years ago, I would have jumped at it. Here's what changed.
Everything is Hard.
Everything worth doing is hard. The only question is which hard thing you're willing to choose.
9 Reasons You Should (Consider) Quitting Your Job
Nine signs it might be time to quit your job. You probably already know the answer.
Should I Quit This Business?
When should you quit a business idea? There's no perfect answer, but there are clear signals most people ignore.