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

The true reason smart, creative, and motivated people spend time on low-value busywork at the expense of the big-picture stuff.

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.


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.


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.

[Image: Flickr user Stephen Coles]

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  • Guest

    At the end of the day and week, we all have our own priorities to meet, so sometimes time management is just a matter of getting to know ourselves a little better. If we use some resources like time recording software, task management tools, etc., which helps to achieve our goals with a little more creativity.

    To develop effective time management skills, I would suggest to use Replicon time recording software ( ). We’ve been using it at our office for more than a year now and its capabilities are simply superb. Try this application and you’d see it for yourself.

  • John Walles

    Howard, great job on this life HAIKU.  Much more than just time management is going on in your story.  You have crystalized the issue that many people spend tens of thousands of dollars trying to resolve.  All those people charging $125 to $200 an hour are shaking in their boots, though as we all know they have nothing to fear.

  • Michael P. Dolan

    Howard,  I was struck by how much your insights in this article resonated with the approach I use with many of my clients.  In my coaching practice I help leaders develop what I call "Truly Productive Leadership," which essentially means, focusing on what matters most in any given moment or day, in a way that maintains or builds presence, rather than destroys it.  

    I was actually a David Allen Company Senior Coach for over five years - and still love David's GTD approach.  But as I worked with hundreds of clients helping them apply the GTD approach, I often saw the same productivity breakdowns still bubbling up for clients, even after they took on the GTD habits. Your article nails what I've experienced in my own private practice:  that without a path of building inner awareness, taking on new productivity practices can actually serve to just deepen the unconscious protective or avoidance patterns we already have.

    In a way, your prescription for developing in this arena is really a broad prescription for opening further to our shadow, opening further to the deeper fears which are the engines that drive our personality patterns.  This work of inquiring into our resistances is about making the unconscious conscious, and can open up levels of presence and engagement way beyond what might be possible through productivity practices alone.

    Great work!

  • Nick A

    This could not be a more timely read as I found myself sifting through tons of aggregated blog posts and stories under the false impression that consuming all of that information was going to somehow move me forward in my true desire for creative endeavors. It was nice to stop reading headlines for a moment, absorb your story, and realize how closely it describes the issues I am facing right now. Having spent a lot of time with no time management at all I am inspired to put an action plan in place keeping this article in mind. The tools used for time management are not the answer but part of the answer and I was wondering if anyone has had success with any? I think a big barrier to good habits is not having the right tools that facilitate making change in a way that fits you. Thanks for the motivation.

  • John C.S. Hansen

    Having a "Not to do" list is just as important as a "to do" list.

    Delegating or allocating tasks to someone else is necessary at times for all of us.

    Some tasks should be struck off the list altogether and others done less frequently. A weekly task can be turned into into a bi-weekly or monthly task sometimes with increased efficiency and no significant loss of effect. 

  • Howard Jacobson

    Yes, and the "not to do" list is a place where a lot of my strong feelings come up. "Who am I if I don't do this?" "Who will I be disappointing?" "Who am I if I make someone else do this?"

    It's a great discipline to say no. I read somewhere that saying "yes" to one thing actually means saying "no" to everything else at that moment. But it takes more courage to give an active, present "no" than to just default to the easiest position.

  • Marco Makanyaga

    This is very interesting one especially in this lovely world. Why this, this is because a lot of people do progress positively at the same time while others got a negative progress due to the fact that using a lot of times to find a solution on them selves while might be possible to get the solution(s) through others advices. For any fruitful results time managements should be given a higher priorities in doing things positively.


  • Jacki Whitford

    Howard - great article. When you deal with your fear and the feelings associated with what is holding you back, it is like taking the brake off. You start to fly with confidence. Your brain stops freezing and your creativity starts to flow again. I have posted this article on my LINKEDIN account. I hope it brings you more readers.

  • Howard Jacobson

    Many thanks for the share, Jacki! I'm discovering that my fear is the great edge of my life. I read a quote this morning from a Mexican shaman to that effect, that what's inside us will either save us or haunt us, depending on whether we embrace it or push it deeper inside.

  • Gautham Nautiyal

    quite relative to what I have been experiencing for some time :) thanks Howard, it was subtle yet thought provoking. nice read

  • Howard Jacobson

    Hi Gautham, I'm not often accused of subtlety, so I very much appreciate hearing it ;)

    Love to hear more about your recent experiences...

  • Mwood1216

    This is a great article. I get that way more often than not. I try to get things accomplished but the draw of trying something new or avoiding what I have to do gets in the way and I loose my purpose or momentum (sometimes both). I make lists every day and follow them, but I am going to try to adjust to what feelings I have too. Thanks so much! 

  • Howard Jacobson

    So glad this was helpful. Check back in here and let us know how it's going.

  • Kattroester

    If you are still living (and working)  like feliz you have not been working long or you are not very efficient

  • Dallas McMillan

    Thanks for this article, I'm procrastinating about doing a big job and this was the perfect avoidance strategy. I guess sometimes we really do need to just get things done, before we are even close to seeing the underlying issues :-)

  • Howard Jacobson

    Yes, we definitely have times where we can't navel-gaze, but just have to roll up our sleeves and act despite all our internal messes. 

    The trouble is, that mode of being is exhausting, not much fun, and unsustainable. 

    Unless we can use those times to create a new, more empowered, more in touch self-perception that can smash through some of our constricted thinking.

  • Austin Bene.

    Wow! Thank you. I am Felix. That's how it hit me. I've started applying it.

  • Thanneermalai Narayanan

    It's very easy to read but it takes real dedication. This article has answered one of the mysteries on how to master your fun part of the brain and not show resistance. I am very fond of martial arts and Tai Chi is one of the skill to respond to the resistance and not react. I would also like to share a TED video about procastination which explains why we do.