There’s magic in youth. Unaware of the tensions, trade-offs, and struggles of adulthood, we’re lighter. We laugh more easily. We play more freely. We dream bigger. Then “real life” steps in. The first disappointment. The first failure. The first break up. We start to realize that life is pretty tough. These letdowns happen again and…
If we listen to the chatter in our heads long enough we hear signals. Steady beacons in a sea of whimsical, transient ideas. I should do this. I should build this. I should try this. They keep pulsing, simultaneously inspiring us and pissing us off because we’re not pursuing them. We get good at excusing…
When I was 24 years old, I fell into a position as the business development director at a small New York advertising agency. I had met the agency owner, Bill Markel, two weeks earlier at an advertising award show. I happened to be attending the event with a friend for the free food and drinks.…
I watch Jerry Seinfeld’s web series Comedians in Cars Getting Coffee weekly. I love the behind-the-scenes banter of comedians talking about their personal histories. It’s a rare glimpse of show-person as real person. This week’s guest was Garry Shandling, a long-time and close friend of Seinfeld’s. Shot in LA, they visited The Comedy Story where…
At least once a week I read a strategic plan that feels like it was written by a random-corporate-buzzword generator. The lingo sounds fancy, but there’s no substance behind it. Give it a little push and it falls apart. Here are few recent offenders: We’re going to utilize a best-practice project management methodology to accelerate cost cutting.…
Of all the jobs on a leader’s plate these days, perhaps none is more important than sensemaker. We’re all confronted with too much data and too many choices on a daily basis. We see countless potentially-valuable things we could do while only having time for a limited few. We’re so busy that we can’t see…
There’s a moment, when you’re trying to do something big or new, that you realize that logical analysis has taken you as far as it can. It’s never going to convince you to take that final step. Too much still feels uncertain. You realize that if you’re going to take that final step, it’s going to…
There’s one piece of advice I’ve found all long-term successful risk takers follow. Stay humble. The Greek philosopher Heraclitus famously said, “No man ever steps in the same river twice.” No matter what river we stepped in yesterday, today brings different water, different currents, and different conditions—in essence, a different river. The smartest risk takers have…
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