The Long Game

The whole point of playing the long game is understanding that ridiculous goals are ridiculous right now—not forever. When we force ourselves to take our goals to extremes—What would ultimate success look like?—we can create an honest road map for ourselves. It might take five years, or ten, or twenty. But that time will pass anyway.

If a goal is worth pursuing, it’s worth pursuing the version of it we actually want—not one that’s watered down to protect our ego. Big goals on their own might feel paralyzing. How do you even start to write that novel? But big goals coupled with small, consistent efforts can be exactly the galvanizing force we need to achieve something powerful,

“Yes” is easy in the moment, for so many reasons: We don’t want to disappoint others or let them down. (She was counting on me!) We’re worried about negative judgments. (Will she think that I think I’m too good for her?) We don’t want to have hard conversations, and it’s easier to avoid them. (What will I even say?) We like feeling important and th

There’s a great quote by Henry Wadsworth Longfellow that goes something like: we measure ourselves by what we feel capable of doing, while others measure us based on what we’ve done. This makes sense, of course. But it’s awfully frustrating when there’s a gap between what we know we can accomplish and what we’ve done up to that point.

for everyone else, the next time they suggest “hopping on a call” or “grabbing coffee” for no clear reason, it’s useful—before agreeing to anything—to ask some questions to slow down the process, force them to think about what they want out of the encounter, and weed out people who aren’t willing to make an effort. For instance, you could say, “I’d

I’ve come to understand what few recognize: the rate of payoff for persevering during those dark days isn’t linear. It’s exponential.

The key is to make yourself “findable” by the people you’d most like to do business with.

I wrote these questions out: What should I spend my time doing? What are the 20% of my activities that will yield 80% of the results? What can I stop doing? How can I use constraints to my advantage? What are my hypotheses about the future—and how do they inform my actions today? Over the next hour, I wrote pages of notes with answers to those ques

Jeff Bezos, in his 2018 letter to Amazon shareholders, tells an unusual story about handstands. “A close friend recently decided to learn to do a perfect free-standing handstand,” he recounted.4 She took a handstand workshop at a yoga studio, but wasn’t progressing as fast as she wanted, so she hired—yes!—a handstand coach. Bezos recounts what the