Getting painfully specific

I’m guessing this ship has a detailed manifest and itinerary. (Image by Pawel Grzegorz)

I’m guessing this ship has a detailed manifest and itinerary. (Image by Pawel Grzegorz)

It’s the moment of truth. We’ve clearly identified a problem, and it’s time to pivot to solutions.

“Now that you see this pattern, what will you do differently?”

“I guess I’ve just got to try harder to stay on top of my work,” she says.

It sounds right. It sounds virtuous. It sounds like a reasonable thing to say to get your teacher/boss/mom/coach off of your back. But of course, nothing really changes as a result of “trying harder.” If the way we’re doing it isn’t working, trying to do more of the same isn’t going to help.

In order to fix our problem, we have to let go of the idea that our failure is the result of a lack of virtue or work ethic. That allows us to come up with fresh strategies for solving our problem that aren’t rooted in the same muddled thinking that got us to this point. Then, we have to get incredibly, painfully specific about how we will implement the new solution.

For example, let’s take one of my longstanding weaknesses: being on time. It has been a struggle most of my life. When you’re late for things, it’s seen as selfish and rude, two things I definitely did not want to be. But from meetings to classes to work shifts to weddings, I was constantly showing up barely on time or just a hair late. And if something went wrong, I’d be really late.

Trying harder did not work. The only thing that worked was listing all of the things I had to do in order to get somewhere or meet a deadline, estimating the time required for each. Then, I added it all up, plus a buffer. Then, I worked backward to figure out what time I had to begin. In this way, I was finally able to start getting places on time or even early.

It wasn’t that difficult to execute my new strategy, but it did require a bit of discipline and patience. I had to overcome my tendency to prioritize action over planning. I had to build a new habit, thoughtfully and intentionally. I had to change.

How can we criticize someone for wanting to try harder? Well, it’s actually a bit lazy. It’s a way to avoid having to change. It might even be a way to hide behind our lack of ability. “I tried as hard as I could,” we might say, “And I still failed.” Then, we get to get out of doing the thing right—or doing it at all.  We never have to do the thinking that leads to growth. We get to stick with the pain we’re accustomed to instead of having to face new and unfamiliar discomfort.

In my case, being late is unpleasant, but it was what I was used to. On the other hand, being on time meant making sacrifices and prioritizing. It meant acknowledging my limitations and saying yes to fewer things. That has been an adjustment. What’s more, there has been a series of cascading changes that flowed from the initial shift in habits. This was no small thing. I can understand why a new approach might trigger fear or resistance. It’s safer to double down on the same old familiar moves, even if we know how ineffective they are.

However, getting painfully specific about how we will solve a problem carries a benefit that makes it more accessible: in effect, we’re identifying the pieces of a project, breaking it down into manageable tasks that can be experimented with. For instance, instead of saying that we’ll just try harder to stop gossiping, we might look at the triggers that lead to talking about other people. We can devise a plan for how we will address each trigger, and even include a reward for taking the new path. Instead of defeating a behavior through sheer force of will, which heretofore has been a failure anyway, we can decide in advance an array of alternative behaviors that doesn’t require us to “try harder” at all. All we have to do is follow the plan—conveniently, one that we designed with our own tendencies in mind, purposely making it easy to follow.

Success isn’t about willpower or determination. That’s like trying to walk from Boston to New York. It’s so much work with so little result that you’ll give up long before you get there. On the other hand, creating a highly specific plan is like taking a train, plane, or car. It requires some initial investment, whether time, money, or attention, but it pays off.

Even if we’ve failed in the past, we can learn the skill of specificity. And we don’t have to do it the old way, grimly going it alone and beating ourselves up when we struggle. Instead, we can ask others for ideas and support when we’re tapped out. We can test solutions and learn from them. We can celebrate each tiny step forward and continue to refine our approach. It’s more effective, and it’s more fun.