Tim Brown and Roger Martin provide a really nice description of how you might do this in their article “Design for Action.” In particular, the idea of throwing out multiple possible strategies and consciously debating them rather than incrementally working from strategies that are already in place is excellent.

The five mind-sets you are going to learn in order to design your life are curiosity, bias to action, reframing, awareness, and radical collaboration. These are your design tools, and with them you can build anything, including a life you love.

Be Curious. Curiosity makes everything new. It invites exploration. It makes everything play. Most of all, curiosity is going to help you “get good at being lucky.” It’s the reason some people see opportunities everywhere.

Try Stuff. When you have a bias to action, you are committed to building your way forward. There is no sitting on the bench just thinking about what you are going to do. There is only getting in the game. Designers try things. They test things out. They create prototype after prototype, failing often, until they find what works and what solves the problem. Sometimes they find the problem is entirely different from what they first thought it was. Designers embrace change. They are not attached to a particular outcome, because they are always focused on what will happen next—not what the final result will be.

Reframe Problems. Reframing is how designers get unstuck. Reframing also makes sure that we are working on the right problem. Life design involves key reframes that allow you to step back, examine your biases, and open up new solution spaces. Throughout the book, we will be reframing dysfunctional beliefs that prevent people from finding the careers and the lives they want. Reframing is essential to finding the right problems and the right solutions.

Know It’s a Process. We know that life gets messy. For every step forward, it can sometimes seem you are moving two steps back. Mistakes will be made, prototypes thrown away. An important part of the process is letting go—of your first idea and of a good-but-not-great solution. And sometimes amazing designs can emerge from the mess. The Slinky was invented this way. Teflon was created this way. Super Glue. Play-Doh. None of these things would exist if a designer somewhere hadn’t screwed up. When you learn to think like a designer you learn to be aware of the process. Life design is a journey; let go of the end goal and focus on the process and see what happens next.

Ask for Help. The last mind-set of design thinking is perhaps the most important, especially when it comes to designing your life: radical collaboration. What this means is simple—you are not alone. The best designers know that great design requires radical collaboration. It takes a team. A painter can create an artistic masterpiece alone on a windswept coast, but a designer cannot create the iPhone alone, windswept beach or not. And your life is more like a great design than a work of art, so you cannot create it alone, either. You do not have to come up with a brilliant life design by yourself. Design is a collaborative process, and many of the best ideas are going to come from other people. You just need to ask. And know the right questions to ask. In this book, you will learn how to use mentors and a supportive community to help with your life design. When you reach out to the world, the world reaches right back. And this changes everything. In other words, life design, like all design, is a team sport.

The moral to the stories of Dave, Melanie, and John is this: Don’t make a doable problem into an anchor problem by wedding yourself irretrievably to a solution that just isn’t working. Reframe the solution to some other possibilities, prototype those ideas (take some test hikes), and get yourself unstuck. Anchor problems keep us stuck because we can only see one solution—the one we already have that doesn’t work. Anchor problems are not only about our current, failed approach. They are really about the fear that, no matter what else we try, that won’t work either, and then we’ll have to admit that we’re permanently stuck—meaning we’re screwed—and we’d rather be stuck than screwed. Sometimes it is more comfortable to hold on to our familiar, failed approach to the problem than to risk a worse failure by attempting the big changes that we think will be required to eliminate it. This is a pretty common but paradoxical human behavior. Change is always uncertain, and there is no guarantee of success, no matter how hard you try. It makes sense to be fearful. The way forward is to reduce the risk (and the fear) of failure by designing a series of small prototypes to test the waters. It is okay for prototypes to fail—they are supposed to—but well-designed prototypes teach you something about the future.

Prototypes lower your anxiety, ask interesting questions, and get you data about the potential of the change that you are trying to accomplish. One of the principles of design thinking is that you want to “fail fast and fail forward,” into your next step. When you’re stuck with an anchor problem, try reframing the challenge as an exploration of possibilities (instead of trying to solve your huge problem in one miraculous leap), then decide to try a series of small, safe prototypes of the change you’d like to see happen. It should result in getting unstuck and finding a more creative approach to your problem. We will talk a lot more about prototyping in chapter 6.

One of the most powerful ways to design your life is to design your lives. No, we haven’t hit our heads and that isn’t a typo. We’re going to ask you to imagine and write up three different versions of the next five years of your life. We call these Odyssey Plans. Whether or not three interesting variations of your next five years immediately leap onto the screens in the multiplex movie theater in your head or not, we know you’ve got at least three viable and substantially different possibilities in you. We all do. Every single one of the thousands of people we’ve worked with has proved us correct in this. We all have lots of lives within us.

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.