Are You Training Yourself to Fail?

“Did you get done what you wanted to get done today?” Eleanor, my wife, asked me.

“Not really,” I said.

She laughed. “Didn’t you write the book on getting done what you want to get done?”

Some people are naturally pre-disposed to being highly productive. They start their days with a clear and reasonable intention of what they plan to do, and then they work diligently throughout the day, sticking to their plans, focused on accomplishing their most important priorities, until the day ends and they’ve achieved precisely what they had expected. Each day moves them one day closer to what they intend to accomplish over the year.

I am, unfortunately, not one of those people. Left to my own devices, I rarely end my day with the satisfaction of a plan well executed. My natural inclination is to start my morning with a long and overly ambitious list of what I hope to accomplish and push myself with sheer will to accomplish it. I’m prone to be so busy — answering emails, multitasking, taking phone calls, taking care of errands — that, without intervention, I would get very little of importance done.

And then, exhausted by my busyness, but unsatisfied by how little of importance I’d accomplished, I would distract myself further by doing things that made me feel better in the moment, if not accomplished — like browsing the internet or eating something sweet.

I’ve created a quiz that you can access here to test how well you manage complexity. The quiz is based, in large part, on my own failures. In other words, left to my own devices, I would not score well.

Here’s the thing: the odds are against us getting our most important priorities accomplished. Our instincts most often drive us toward instant gratification. And the world around us conspires to lure us off task. Given total freedom, most of us would spend far too much time browsing websites and eating sweets. And being totally responsive to our environments would just have us running around like crazy catering to other people’s agendas.

For me, the allure of accomplishing lots of little details would often override my focus on the big things I value. Each morning I would try to change my natural tendency by exerting self-control. I would talk to myself about how, starting this morning, I would be more focused, psych myself up to have a productive day, and commit to myself that I wouldn’t do any errands until the important work was done.

It almost never worked. Certainly not reliably.

And so, without understanding it at the time, I was teaching myself to fail. People talk about failure — I talk about failure — as critical to learning. But what if we don’t learn? What if we do the same things, repeatedly, hoping for different results but not changing our behavior?

Then we are training ourselves to fail repeatedly.

Because the more we continue to make the same mistakes, the more we ingrain the ineffective behaviors into our lives. Our failures become our rituals, our rituals become our habits, and our habits become our identity. We no longer experience an unproductive day; we become unproductive people.

You can’t get out of this pattern by telling yourself you’re a productive person. You’re smarter than that; you won’t believe yourself and the data won’t support the illusion.

You have to climb out the same way you climbed in: with new rituals.

For me, the best way to discover the most effective rituals to help me achieve my most important priorities was though trial and error. Every evening I looked at what worked and repeated it the next. I looked at what didn’t and stopped it.

What I found is that rather than trying to develop super-human discipline and focus, I needed to rely on a process to make it more likely that I would be focused and productive and less likely that I would be scattered and ineffective.

Rituals like these: Spending five minutes in the morning to place my most important work onto my calendar, stopping every hour to ask myself whether I’m sticking to my plan, and spending five minutes in the evening to learn from my successes and failures. Answering my emails in chunks at predetermined times during the day instead of whenever they come in. And never letting anything stay on my to do list for more than three days (after which I either do it immediately, schedule it in my calendar, or delete it).

It doesn’t take long for these rituals to become habits and for the habits to become your identity. And then, you become a productive person.

The trick then is to stay productive. Once your identity changes, you are at risk of letting go of your rituals. You don’t need them anymore, you think to yourself, because you are now a productive person. You no longer suffer from the problem the rituals saved you from.

But that’s a mistake. Rituals don’t change us. They simply modify our behavior as long as we practice them. Once we stop, we lose their benefit. In other words, being productive — forever more — requires that you maintain the rituals that keep you productive — forever more.

I would love to say that I am now one of those people who is naturally pre-disposed to being highly productive. But I’m not. There’s nothing natural about productivity for me.

But when Eleanor joked about my writing the book on getting our most important priorities accomplished, she reminded me that, while it may not be natural to me, I could be highly productive.

And the next day, following a few simple rituals, I was.