We’ll explain a few simple ways to do this, but first you need to understand one really big point: Designers don’t think their way forward. Designers build their way forward. What does that mean? It means you are not just going to be dreaming up a lot of fun fantasies that have no relationship to the real world—or the real you. You are going to build things (we call them prototypes), try stuff, and have a lot of fun in the process.

Want a career change? This book will help you make that change, but not by sitting around trying to decide what that change is going to be.

Life design is about generating options, and this exercise of designing multiple lives will guide you in whatever’s next for you. You aren’t designing the rest of your life; you are designing what’s next. Every possible version of you holds unknowns and compromises, each with its own identifiable and unintended consequences. You are not so much finding answers in this exercise as learning to embrace and explore the questions, and be curious about the possibilities.

Remember, there are multiple great lives within you.

You are legion.

And you get to choose which prototype to start working on next.

Designing your life is actually what life is, because life is a process, not an outcome.

If you can get that, you’ve got it all. We are always growing from the present into the future, and therefore always changing. With each change comes a new design. Life is not an outcome; it’s more like a dance. Life design is just a really good set of dance moves. Life is never done (until it is), and life design is never done (until you’re done).

Life designers don’t fight reality. They become tremendously empowered by designing their way forward no matter what. In life design, there are no wrong choices; there are no regrets. There are just prototypes, some that succeed and some that fail. Some of our greatest learning comes from a failed prototype, because then we know what to build differently next time. Life is not about winning and losing. It’s about learning and playing the infinite game, and when we approach our lives as designers, we are constantly curious to discover what will happen next.

The only question that remains is one we’ve all heard a time or two before: What would you do if you knew you could not fail?

What you do for a living shapes who you become. If you spend most of your day in paradigmatic mode, you’re likely to slip into depersonalized habits of thought; you may begin to regard storytelling as non-rigorous or childish, and if you do that, you will constantly misunderstand people. So when I’m in a conversation with someone now, I’m trying to push against that and get us into narrative mode. I’m no longer content to ask, “What do you think about X?” Instead, I ask, “How did you come to believe X?” This is a framing that invites people to tell a story about what events led them to think the way they do. Similarly, I don’t ask people to tell me about their values; I say, “Tell me about the

person who shaped your values most.” That prompts a story. Then there is the habit of taking people back in time: Where’d you grow up? When did you know that you wanted to spend your life this way? I’m not shy about asking people about their childhoods: What did you want to be when you were a kid? What did your parents want you to be? Finally, I try to ask about intentions and goals. When people are talking to you about their intentions, they are implicitly telling you about where they have been and where they hope to go. Recently, for example, my wife and I were sitting around with a brilliant woman who had retired from a job she’d held for many years. We asked her a simple question: How do you hope to spend the years ahead? All sorts of stuff spilled out: How she was coping with losing the identity that her job had given her.