“At the time, people thought what I did was ridiculous,” recalls Sarah, who went on to work at Etsy for over nine years. Why give up a steady job? But safety and security weren’t what brought her to law; she’d studied it to help other artists. That’s what was interesting to her, and she was willing to fight for it.

What Are Your Fundamentals?

Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it.

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 effort we’ve invested over time, we’re ready to take full advantage of the opportunities life presents.

Play The Long Game

If you always do what interests you, at least one person is pleased.

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 Sarah decided to press her luck.She booked a plane ticket to NYC to pitch him for a job, but Kalin said he was busy. She persisted, and eventually he agreed to fit her in. When they met, he ended up hiring her on the spot.

Go Back To Your First Principles

Often, the truest test of what’s interesting to you is to look at how you’re spending time right now. For instance, if you can’t get enough of podcasts and are always recommending new ones to others, maybe you could raise your hand and offer to launch one for your company or seek a job working for a firm that produces them.Or if your Instagram feed is littered with close-ups of food, you might be a good candidate to become a food writer, start a catering company or head up branding for a food company.

1. Evaluate How You’re Spending Your Time

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 can shadow him at work for a day. By seeing if your curiosity sustains itself over time, you can weed out fleeting interests.

What Are You’re Constantly And Consistently Curious About?

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’s interesting for us, following that curiosity could spur us towards mastery and send us in useful directions — like new connections, a book project or a campaign to preserve local wetlands.

Not All Of Us Have “The” Career. But All Of Us Have Interests. 

If we want to play the long game, one of the first things we must do is identify [our most important] goals so we’re able to make the adjustments needed in our lives to move towards achieving them.

“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 she was learning a lot, she didn’t feel satisfied.What did bring her joy was making jewelry on the side, which she started selling on a then-new website called Etsy. Looking at the site, she had a revelation: “Etsy didn’t have an in-house attorney, and my goal to help artists could come true if I worked for them.”

2. Remember What Got You Started 

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 reality.But what if you’ve been working heads down for so long that you’re not even sure what you find interesting anymore? Or you’re stuck or bored in your professional life, or feel confused, or just aren’t sure where to start?

“Interesting” Is A Luxury, Elusive And Transient. Or Is It?

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 attainable.﻿There are a million reasons not to try something new. But playing the long game means ​​acknowledging we aren’t already experts at everything, and that it’s OK to sometimes look foolish in service of becoming the person we want to be.

3. Ask Yourself: What Kind Of Person Do I Want To Be?

What should we do if we’re still figuring out what feels meaningful to us or if we’re drawn to many different things? “Optimize for interesting”, says Dorie Clark, in her new book “The Long Game: How to Be a Long-Term Thinker in a Short-Term World”. 

Have you been working heads down for so long that you’re not sure what you find interesting anymore? Or are you bored in your work life, confused, or unsure where to even start? Here are three strategies to zoom in on what lights you up, from consultant and speaker Dorie Clark.

KATHARINE HEPBURN

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