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.

Prototyping the life design way is all about asking good questions, outing our hidden biases and assumptions, iterating rapidly, and creating momentum for a path we’d like to try out.

Prototypes should be designed to ask a question and get some data about something that you’re interested in. Good prototypes isolate one aspect of a problem and design an experience that allows you to “try out” some version of a potentially interesting future. Prototypes help you visualize alternatives in a very experiential way. That allows you to imagine your future as if you are already living it. Creating new experiences through prototyping will give you an opportunity to understand what a new career path might feel like, even if only for an hour or a day. And prototyping helps you involve others early and helps build a community of folks who are interested in your journey and your life design. Prototypes are a great way to start a conversation, and, more often than not, one thing typically leads to another. Prototypes frequently turn into unexpected opportunities—they help serendipity happen. Finally, prototypes allow you to try and fail rapidly without overinvesting in a path before you have any data.

Our philosophy is that it is always possible to prototype something you are interested in. The best way to get started is to keep your first few prototypes very low-resolution and very simple. You want to isolate one variable and design a prototype to answer that one question.

Once you’ve committed yourself to life design prototyping, how do you do it? The simplest and easiest form of prototyping is a conversation. We’re going to describe a specific form of prototype conversation that we call a Life Design Interview.

A Life Design Interview is incredibly simple. It just means getting someone’s story. Not just anyone and not just any story, of course. You want to talk to someone who is either doing and living what you’re contemplating, or has real experience and expertise in an area about which you have questions. And the story you’re after is the personal story of how that person got to be doing that thing he or she does, or got the expertise he has and what it’s really like to do what she does.

You want to hear what the person who does what you might someday want to do loves and hates about his job. You want to know what her days look like, and then you want to see if you can imagine yourself doing that job—and loving it—for months and years on end. In addition to asking people about their work and life, you will also be able to find out how they got there—their career path.

It goes back to curiosity—one of the most important life design mind-sets. Whether you are seeking your first job, changing careers, or choosing an encore career, you need to be genuinely curious. That’s what prototyping conversations and prototyping experiences are all about: being open and curious about the possibilities. We call it pursuing latent wonderfulness. What this means is that you ask yourself, “Is there a 20 percent chance there’s something interesting to me going on somewhere in this organization? Is there a 10 percent chance?

Do yourself the favor of getting lots of options, then culling the list down to a short and manageable size (five max); then make the best choice that you can, given the time and resources available to you, get on with it, and build your way forward. Note that if you’re doing this with prototype iteration, you don’t have too much at stake, and you will be able to adjust as you go, before you really reach a significant investment. And once you make a choice—then embrace your choice and go with it. When the questions that lead to agonizing creep into your head, evict the thoughts, and direct your energy into living well the decisions you’ve made. Pay attention and learn as you go, of course, but don’t get caught with your eyes fixated on the rearview mirror of decision regret.

This letting-go step relies primarily on personal discipline. Keep your reframed understanding of decision making handy, and be sure to win the internal argument with yourself when you’re tempted to rehash and ruminate. Put in place the support you need to stick with it—find a life design collaborator or team to help remind you why you made the choice or choices you did; make a journal entry about your decision, and reread it when you get confused. Find what works to enable yourself to enjoy your choices fully.