Posts in Mental Models
Embarrassment Is Temporary. But Regret Is Forever.

Everyone wants success. But most people aren’t willing to start down a path filled with unknowns unless they get a guarantee of success before they take that first step. The worst thing you can do is NOT start because you’re waiting for a guarantee your idea will work. The embarrassment of starting and failing is temporary. But the regret of not starting at all is forever.

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Don't Be Too Smart To ‘Borrow’ What Works

A common trap smart people fall into is to see something that works, but avoid “borrowing” it to use it themselves. Instead, they try to come up with something uniquely their own that could work even better. Don’t be one of those people. Don’t be too proud to take an execution you see working, and make it your own. Don’t be too smart to borrow what works.

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5 Life Lessons From My 90-Year-Old Grandma

My grandma just turned 90. I spent a week celebrating with her at a “cobbage” (as my 3yo niece would say) on Lake Michigan. It’s amazing what you can learn from someone who has lived 60 YEARS (basically another lifetime) longer than you! Here are a few of those lessons.

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The Rational Flâneur: Embracing Optionality

I once flew to Ireland for a weekend. My wife and I showed up at the airport in Toronto expecting to fly standby to Paris, but the flight was full. So we hopped on the only other flight with open seats - the flight to Dublin. I didn’t know it then, but I had become a Rational Flâneur. Unlike the tourist who’s stuck in a schedule, the flâneur embraces uncertainty. They alter their course easily based on new information. They keep their options open. And you can use this idea to embrace optionality and capture upside in your life and work.

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Nothing Good Can Happen Unless You Finish What You Start

“Start less, finish more.” This is something I repeat to myself regularly. No matter what I’m working on - an online product, a screenplay or pilot script, an article for Wealest, or even a Tweet I’ve been battling to get right - it’s almost always better to finish what I start and send it out into the world than abandon it. Because shipping is the only way you can get lucky. That’s the only way good things happen. You’ve got to finish what you start.

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The Dream-Chaser’s Milestone Dilemma

There’s a feeling I’ve had for the past year that I haven’t been able to articulate until now. I’m calling it the “dream chaser’s milestone dilemma.” It’s that feeling of ambivalence when you watch the people closest to you do normal things like get married, buy homes, and have kids. These milestones feel like a world away when you’re chasing a creative dream that takes a decade(+) to pay off. And it’s not a pleasant feeling. Here’s the good news though… I’ve also found the cure for it.

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