randy and jacqueline walking away on a path in a park toward trees and grass

Ideation, Evaluation, and Iteration: How We Plan Our Lives

The importance of making options, trying things out, and changing what doesn't work.

Whether you are working on a new product, project, business, or simply the next steps in your own life, the key to success is to generate a lot of ideas before evaluating and investing in any of them. Don't discount an idea before it's explored.

"[T]he number one enemy of creativity is judgment."

- Bill Burnett and Dave Evans, Designing Your Life

When I read Designing Your Life by Bill Burnett and Dave Evans recently (here's my review!), I was struck by the chapter on unsticking yourself from what the authors called "anchor problems"—problems that do have solutions, but solutions you're not seeing because you've anchored yourself to a particular solution that can't work.

By way of illustration, a local group is considering forming a new education co-op. But they got stuck talking about fundraisers and forming a nonprofit…. even before they have a regular group of families who show up, before they know what they need the money for, when their minimum viable product requires neither a fundraiser nor a nonprofit! They latched onto the ideas because one woman happened to be very excited about organizing fundraisers, and because someone else mentioned that nonprofits are good for education groups.

This is incredibly common. People get stuck on the first somewhat reasonable idea, instead of ranging farther to see it's actually the best option. They get anchored.

How do you get unstuck?

To get unstuck, Burnett and Evans recommend a designer's favorite tool: ideation. Come up with idea after idea—good, bad, wild, weird, and maybe even some beautiful, shiny gems. There are tons of ideation techniques, just do an online search. The critical aspect of all of them is that your aim is to consider all angles before committing. Generate as many ideas as possible, as many ways of solving your problem or reaching your goal as you can.

Burnett and Evans also brought up the idea of prototypes in that chapter—i.e., try things out, learn from them, iterate on them. The idea of prototyping and iterating comes up again and again in my reading, whether it's Charles Marohn making little bets to build strong towns or Bruce Feiler iterating on family traditions to make happy families. Anytime you're messing with a complex system—a town, a family, a life—it behooves you to try small changes, test them, evaluate, and iterate.

In How Children Succeed (read my review!), Paul Tough wrote about a method of getting unstuck and building discipline, resilience, and motivation called mental contrasting. First, think about all the obstacles you may face on the way to your goal. Then, consider how, specifically, you might overcome each obstacle. Be optimistic, but also plan how you'll tackle inevitable setbacks. Consider alternative paths.

Ideation, evaluation and iteration: How we plan our lives

The ideation, evaluation, and iteration approach is exactly how Randy and I plan much of our lives. I enjoy planning—all the adaptation, flexibility, scheduling, forward thinking, and timelines that feed into it. The fact that we take the same approach to life planning is a significant boon to our marriage.

During the ideation and evaluation stages, we go for long walks. Whether hiking a mountain together or breaking out the double stroller and the baby backpack to cruise the neighborhood, it's been a tradition ever since we started dating—long walks and lots of talking.

First, we check in on our goals. We make sure we're heading in the right direction, and whether that direction is still where we want to be headed. Then, we talk over possibilities, directions, and five-year plans. We toss out ideas. We question. Eventually, we'll settle on something—with the intention to keep iterating if it doesn't work out.

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We're Jacqueline and Randy, a blogging duo with backgrounds in tech, robots, art, and writing, now raising our family in northern Idaho.

Our goal is to encourage deliberate choices, individual responsibility, and lifelong curiosity by sharing stories about our adventures in living, loving, and learning.

Learn more about us.



Start here

Curious about our life and journey? Here are some good places to start reading:

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