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The Coached Model Coached Premium Coached Weekly PricingOn making decisions, understanding yourself,
and getting better at the things that matter to you.
Why practice doesn’t always make the nerves go away—and what helps instead.
I get nervous more than you'd think. I've sent about 350 of these newsletters and I often still get a knot in my stomach before each one goes out. I feel the same right before a big presentation, or a meeting with someone "important".
A way to make today’s decisions by asking what you’d regret later.
In 1994, Jeff was at a crossroads.
He’d recently been promoted to senior VP at an investment bank (the youngest in the firm's history), and was earning handsomely.
But something gnawed at him:
The internet was growing 2,000% a year, and he couldn’t stop thinking about quitting to start a virtual bookstore.
The opportunities you miss when people hesitate to start a conversation with you.
A huge part of your career (and life, honestly) depends on random conversations:
Airbnb started because after a design class, Joe Gebbia went up to speak to Brian Chesky, who became his co-founder.
A friend of mine struck up a conversation with someone at a mutual friend’s birthday party — they now have two kids.
Or even personally: One of my closest friends and collaborators today is someone I randomly started talking to at a coffee shop.
A few times a month, I share thoughts on life and career strategy—drawn from my own work and conversations with people I learn from.