It’s valuable to notice what is holding your attention — but don’t rush to make a fascination your new mission until you’ve tested it out. Find ways to learn more, such as setting up interviews with people who work in the field, reading books about it or asking a friend if you ca...

When we make the choice to optimize for interesting, we’re investing in our future selves. We don’t know where it will lead, and that’s the whole point.

Playing the long game means preparing ourselves for an uncertain future, where, because of the effo...

When you’re unsure of where your interests lie, go back to your first principles.

One day, Etsy announced new policies. Sarah had questions and some legal insights. Since the company was still small, she got the CEO, Rob Kalin, on the phone. They had a short chat, and then ...

Too often, in our lives, we tend to look at where we are right now and say, “Where can I go from here?” But that’s asking the wrong question.

If you start with your present situation, you’re limiting yourself out of the gate to what seems...

“I’m an artist,” Sarah Feingold told Dorie Clark, “and I went to law school because I wanted to help artists like myself.”

But it didn’t turn out that way. She got a job at a small law firm in upstate New York. She drafted motions, drew up contracts, and so on. Even though...

Wherever we are in our lives, we may not know what exactly we want to do or what we’re good at. However, we all have things we’re interested in. But what should you do if they don’t seem “meaningful” enough to be a career? Let’s take a passion for photographing birds. Well, if it...

Some may question this advice of optimizing for interesting, that it’s a pipe dream or something only the wealthy can do. That’s fair enough — in the short term. But the whole premise of playing the long game is we’re not victims of circumstance. Our current reality isn’t our fixed, eternal r...