How To Develop Strong Time-Management Habits, Even If You've Failed In The Past

My client Felix (not his real name) was complaining to me about wasting huge amounts of time during his work week. An energetic, goal-oriented entrepreneur, he found himself doing technical and administrative tasks rather than the high-value activities that move his business forward.

This was true despite the fact that he has a staff and a reliable cadre of vendors whom he pays to perform exactly those technical and administrative functions. What is he thinking? Why is he engaging in low-value activities at the expense of the big-picture stuff he loves, and only he can do?

And how can we get him back to his sweet spot?

The Get It Done Industry

There’s an entire industry devoted to helping Felix and you and me be productive. Software, advice blogs, workshops, hardware, apps, books--you name it.

All this stuff is generally organized around a few sound principles, which I’m sure you’ve come across:

1. Make lists
2. Prioritize the actions on those lists
3. Tackle the most important items first

So given Felix’s strong desire to be productive, and his knowledge of these principles, and his familiarity with all the tools and techniques of the Getting Things Done industry, why isn’t it helping?

Self-Sabotage, And How Productivity Is Like Dieting

Things become a bit clearer when we replace “be productive” with another very popular resolution: losing weight.

While there are debates within that community about which is the best diet strategy, I don’t know of many health coaches or diet writers who recommend sodas, candy, cookies, donuts, bagels, and greasy burgers on white buns.

And yet most dieters, who certainly “know better,” keep cheating and sneaking and rationalizing food choices that conflict with their big goal. Just like Felix, their minute-by-minute decisions undermine their desired outcome.

Why?

What Motivates Behavior?

In The Power of Habit, Charles Duhigg describes the inexorable pull of the “habit loop.” Something in our environment happens that triggers our desire for a “reward.” We are then compelled to take the actions that we think will get us that reward.

The reward can be a burst of energy, or a moment of connection with another person, or a positive emotion like happiness. It can also be avoidance of a negative, as when we distract ourselves to avoid feeling feelings or thinking thoughts that we are unwilling to entertain.

As long as we are unconscious of the environmental trigger and the compelling reward, we literally have no choice but to follow the pattern habit. And every time we comply, we dig the habit groove deeper and more automatically into our nervous system’s hard wiring.

We can try to override that habit loop, which is another way of saying “New Years Resolution.” But as studies have shown, willpower is a finite resource. It’s a muscle that tires quickly, much quicker than the death of the habit we want to be rid of.

In other words, in the battle between short- and long-term thinking, short term always wins.

The Futility of Time Manipulation

Virtually all the strategies of the get-it-done industry consist of some form of time manipulation. Meaning, some way to trick ourselves into doing what, in that moment, we really don’t want to do.

Trying to build new habits on top of dysfunctional old ones works about as well as putting a new car body on top of a rusty old engine. If we don’t deal with the fundamental issue, no amount of time blocking or beepers beeping or context-based task lists will overcome the pull of the habit mind.

So I could tell Felix to block out two hours every morning to get the big stuff done. To set a timer, maybe even a ticking kitchen timer, on his desk to remind him not to check email, code a web page, pay bills, or check Facebook.

And that would probably work for a while.

But eventually, something unacceptable would happen: Felix would find himself with nothing to do.

He’d get all his high-level work done. And he’d sit there, pleased with himself, for about four seconds.

And then he’d start to feel those feelings.

Which feelings, I don’t exactly know. Possibly feelings of “If I’m not busy, then I’m not worthy.” Or maybe, “Now that I have nothing to do, I could start feeling this deep sadness about how my father left when I was 6.” Or even, “I don’t like myself.”

The content of the thought or feeling doesn’t really matter. We all have thoughts and feelings like this (or we would, if we didn’t keep ourselves perpetually busy). They don’t necessarily mean anything is wrong with us. We’ve all been wounded by life, and those wounds all leave scars.

Resistance

The problem is not the thoughts and feelings themselves, but our resistance to them. If we simply allowed ourselves to feel the feelings, and entertain the thoughts without believing them, they would lose their power over us.

My own fear of abandonment used to absolutely own me. Whenever I was less than perfect, I would feel this tug of fear in my gut. If it could speak, it would have said, “Nobody’s going to want to be with you unless you’re flawless. You’d better hide or fix this mess before anybody finds out.”

I so didn’t want to feel that fear of abandonment, that I pushed aside all situations in which it could arise. I distracted myself, not with busy work, but with “good work.” I would fill so much of my time with pro bono work that I wasn’t making enough to live on. I would say yes to every client request, whether it was reasonable or not, whether it was something I wanted to do or not, because I didn’t want to experience the fear of abandonment.

There was no time management technique that could have released me from this curse. At best, time tracking brought awareness of the problem, so that I could see the vast mountains of unbillable hours and start to wonder about them.

But only a willingness to explore what happened when I consciously refused to indulge the habit brought me to freedom.

Freedom From Bad Habits

I learned how to sit with feelings that I had assumed would annihilate me. By experiencing them, I learned how to make peace with them. To discover that they were just feelings. That I could feel them and my world would not end.

At that point, I still had a bunch of “bad” work habits. They didn’t go away simply because I understood their purpose.

But at that point, the time manipulation strategies started working. Now when I block four hours for writing, I am much less tempted to bug out mentally and go on a Youtube binge. Now I can complete unpleasant tasks like calling back unhappy clients without going through paroxysms of avoidance. Now I can sit and meditate for 20 minutes every morning without finding a new daily excuse to avoid it.

When we try to apply the quick fix of tactical manipulation to behaviors whose roots are unseen, we not only fail, but we tend to reinforce the very thoughts and feelings that are causing the problem in the first place. Our failure becomes more tangible proof of our unworthiness, and like a yo-yo dieter, we careen between irrational hope and dark despair, always ready to buy another self-help productivity book, another to-do list app, another personal organizer.

I don’t know what Felix will discover when he allows himself to be bored, to be empty. I do know that when he realizes it’s OK, he will free himself to pursue his biggest goals and dreams.

FastCompany