The Earned Life: Lose Regret, Choose Fulfillment

“We tremble before making our choice in life,” wrote Isak Dinesen, “and having made it again tremble in fear of having chosen wrong.”

If there is no market for what you’re offering (and you don’t happen to be the rare visionary who creates a new industry out of thin air), all your skill, confidence, and support will not overcome that hurdle. As Yogi Berra said, “If the fans don’t want to come out to the ballpark, no one can stop them.”

Begin with a basic question. “What do I want to do for the rest of my life?” “What can I do that’s meaningful?” “What would make me happy?” These are not basic. They are deep, multifaceted questions that should be asked throughout your life (but don’t expect an easy or quick answer). Basic questions address one factor only—because for nearly all of

It forces you to regard your well-intentioned efforts today as an investment in the people you are most responsible for raising into productive, happy human beings: yourself and those you love most. It is not a gift; you’re expecting a return.

We all need help. Accepting that fact is an act of wisdom, not a sign of weakness.

If an earned life is one of productive overkill—of going all in on what matters—accompanied by sacrifice and trade-offs, that was the moment I got serious about earning my life. I had no other choice.

Being a creative director at an advertising agency may not seem at first like the perfect training for becoming a screenwriter, but it makes perfect sense when you appreciate the two roles’ adjacency: They both require a gift for storytelling.

Letter Two: Now write a letter from the present you to a future you, one year, five years, ten years down the road. Spell out the investment—in the currency of sacrifice, effort, education, relationships, discipline—that you are making now to benefit the person the letter is addressed to.

Letter One: First, write a letter to a previous you expressing gratitude for that previous self’s specific act of creativity or hard work or discipline—preferably something earned rather than given—that has made you better today in some way. It can be recent or long ago. The only criterion is that you single out this action as a difference maker in