Designers learn to have lots of wild ideas because they know that the number one enemy of

creativity is judgment. Our brains are so tightly wired to be critical, find problems, and leap to judgment that it’s a wonder any ideas ever make it out! We have to defer judgment and silence the inner critic if we want to get all our ideas out. If we don’t, we may have a few good ideas, but the majority will have been lost—silently imprisoned behind the wall of judgment our prefrontal cortex has erected to safeguard us from making mistakes or looking foolish.

Life design brainstorming has four steps, and a very structured approach to coming up with lots of prototypable ideas. Typically, if you are the facilitator who brings the group together, you might have already framed the brainstorming topic. You want a team of no fewer than three and rarely more than six people who have all volunteered to help. Once the group is convened, the session proceeds as follows.

Most of the time when people tell us “our brainstorm didn’t work,” we find out that they framed a poor question—either one that already assumed a solution or one that was so vague they couldn’t get any traction for generating ideas. Watch out for this when you start to brainstorm with our four-step method.

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.

Chapter 20: Back to Basics

“Too many people approach creative brainstorming by taking what’s practical into consideration way too early in the process. Working with Jonathan and Dan reinforced what I’d always believed: Start with what you want to achieve, instead of limiting yourself to what’s realistic or sustainable. Or, as I like to say, don’t ruin a story with the facts. Eventually, you’ll reverse engineer your great idea and figure out what’s possible and cost-effective and all the other boring grown-up stuff. But you should start with what you want to achieve.