Posts in Mental Models
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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Just Because You’re Certain, Doesn’t Make It True

How many times have you been 100% certain about something, only to find out you were wrong? For me, it’s probably five times a day. It wasn’t until I heard Joseph Goldstein articulate this idea in a lecture on the Waking Up app that it struck me how important an insight this is: “Certainty is not an indication of truth.” Many of the things you are certain about eventually prove to be wrong. And the faster you can rework your belief system in the face of contradicting evidence, the better off you’ll be.

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You Can’t Envy Someone’s Success Without Recognizing Their Suffering

When you see someone standing at the top of the mountain - at the pinnacle of success - you automatically ignore the treacherous path they took to get there. Why? Because you can’t see it! All you see is the victory. And what’s hidden are the thousands of failures they suffered along the way. You can’t envy someone’s success without recognizing the suffering (past and present) it took the person to get it.

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Excellence Is A Standard You Set For Yourself

There’s a familiar refrain among pro athletes: “No one puts more pressure on me than I do.” That’s because excellence is a standard you set for yourself. No one can make you “work hard.” No one can make you care. Unless you find something you’re intrinsically interested in and want to become the best in the world at, you will never be great at it.

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Learn To Listen To Your Gut

We are all drowning in information. When you have the entirety of human knowledge in your pocket, it’s not your brain that needs exercising, it’s your gut. Your instinct. That inexplicable feeling that tells you what you should do and when to do it. It’s not always right, but it’s always true for you. And it pushes you where you really want to go. And if you don’t spend time intentionally learning to listen to your gut, you’ll never escape the world’s noise.

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Creativity Is Messy, And It’s Supposed To Be

Creativity isn’t an exact science. When you start building something, you want it to be perfect from the very first spark. And nothing kills your momentum faster than realizing what you just made sucks. But it’s supposed to suck! It’s not fully formed yet - it’s just this delicate mass of ideas and features trying to find its form. It’s those who stick with their project through this early, ugly phase that come out the other side with something valuable. Stick with it.

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Compare Yourself Only To The Most Successful People You Know

Comparing yourself to others is a dangerous game. You have no idea what the other person has gone through to achieve the success you see from the outside. Very likely it’s more suffering and uncertainty than you could imagine. Still, there is a benefit to mapping progress against your industry peers. And if you do compare yourself to other people, compare yourself against the best.

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