consider all the options, resist making up our minds, and finally wait so long to decide that the opportunity passed us by. We weren’t certain trying a new way was the right thing, so we didn’t act.
But a few years ago, I discovered the power of the iterative approach and began working on my experimental mindset. That year, when decision time rolled around, we didn’t endlessly debate, nor did we once again make pros and cons lists, because we’d already thought about the issue plenty. I’d been overthinking this issue for years without realizing that’s what I was doing. This time I recognized the overthinking for what it was. And I knew what to do.
First, I did a reality check. There wasn’t one perfect answer to our driving dilemma. Either option got us to the beach.
Then I got moving. I quizzed a friend who always breaks long drives into multiple days about her experience, and then I made sure hotels were available for the night we needed.
Next, I explicitly gave myself permission to fail. I hadn’t wanted to act because I’d been afraid we wouldn’t like the new way—and it’s hard to act when you’re afraid of getting it wrong. When I could perceive it was unjustified fear holding me back, I felt free to move forward.
And finally, since we’d been thinking about this for ages, we decided to try it and see what happened. We’d consider it an experiment. If we preferred the new way, great. But if we tried it and didn’t like it, at least we’d stop wondering if another way might be better. We didn’t have to prefer the new way to the old to consider this little experiment a success.
In the end, we all preferred our two-day drive to the beach with the hotel stopover. But if it hadn’t gone well—if we swore we never wanted to do it again—it wouldn’t have been a mistake, because the goal was to get a result, not the best possible experience. No need to second-guess our decision for years to come.
What’s Happening in Your Life?
When we don’t recognize our overthinking behavior for what it is, it’s impossible to get over it. And as long as we rely on decision-making styles that encourage overthinking, we’re going to spend a lot of time overthinking. But once we see what’s really going on, we can begin to change. It will feel like a battle at first—especially if we’ve been analyzing things to death our whole lives—but with time, it will feel like a habit.
Next Steps
With fresh eyes, take a look at your own behavior.
1. Where are you experiencing analysis paralysis right now?
2. Where are you experiencing perfectionism?
3. What factors are keeping you stuck?
4. What mini-experiments can you implement in order to move forward?
4
Decide What Matters
“Would you tell me, please, which way I ought to go from here?”
“That depends a good deal on where you want to get to,” said the Cat.
Lewis Carroll
I hate to fly. Whenever I’m presented with the opportunity to take a trip, big or small, that requires an airplane, I usually torture myself by debating about whether to go. I hardly ever give a quick yes, even if it’s something I—or at least part of me—really want to do. The utter discomfort of plane travel always makes me withhold my yes.
So I was surprised by my friend Ally’s own trip. The last time I saw Ally, she was suffering from brutal jet lag because she’d just returned from a quick trip to Thailand. She’d traveled thirty hours and flown literally halfway around the world to spend just four days on the ground. I’m always curious about what compels people to take those thirteen-hour flights. I’m not sure I could do it myself, so whatever awaits them on the other end must be really worth it.
At the time, Will and I were debating whether to take a long trip of our own. Long for us, that is. We were considering a December trip to Scotland, and though our longest flight would “only” be nine hours, that was still far too long by my standards. By the time I saw Ally, we’d already been waffling for a while. I wanted to go, but I did not want to get on that plane, and that had kept me from saying yes. I knew I was overthinking it, because instead of working on solving the problem, I was obsessing about the unpleasantness of the flight and the inconvenience of the timing. The