That, in sum, is the process for choosing between possibilities for where to play and how to win. First, frame a choice. Second, explore possibilities to broaden the set of mutually exclusive possibilities. Third, for each possibility, ask, what would have to be true for this to be a great idea, using the logic flow framework to structure your thinking. Fourth, determine which of the conditions is the least likely to actually hold true. Fifth, design tests against those crucial barriers to choice. Six, conduct tests. Finally, in light of the outcome of the tests and how those outcomes stack up against predetermined standards of proof, select the best strategic choice possibility. This process broadens the possibilities up front and then systematically narrows the field. It leverages different perspectives to enrich the discussion, rather than bogging it down.

A team led by Professor Dan Schwartz evaluated two groups. One started with three ideas in parallel, then subsequently had two more ideas on the way to their final idea. The second team started with one idea and then iterated four more times. Each team generated five rounds of ideas, but the parallel team did much better—generating more ideas and clearly better final solutions. The serial team—who started with just one idea—tended to keep refining the same idea over and over, never really innovating. The conclusion is that if your mind starts with multiple ideas in parallel, it is not prematurely committed to one path and stays more open and able to receive and conceive more novel innovations. Designers have known this all along—you don’t want to start with just one idea, or you’re likely to get stuck with it. Try not to think of your Odyssey Plans as “Plan A, Plan B, and Plan C”—where A is the really good plan and B is the okay plan and C is the plan that you really hope you don’t get stuck with but that you would accept as tolerable if absolutely necessary. Every Odyssey Plan is a Plan A, because it’s really you and it’s really possible.

The key is to remember that imagined choices don’t actually exist, because they’re not actionable. We’re not trying to live a fantasy life; we’re trying to design a real and livable life. If we burdened ourselves with knowing everything about our decisions and discovering every option possible (which, of course, you should do if you’re going to make “the best choice”), we’d never decide. In life design we know that there are countless possibilities but aren’t stymied by that fact. We revel in exploring a few possibilities, then taking action by starting with a choice.

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.

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?