Many people think I love organization and managing my time because I’ve put a lot of effort into designing productivity tools. This isn’t entirely accurate; what I really like is the feeling that I’m on top of things, and for the past few months I’ve had much doubt about this.

The Procrastinator’s Battle

I’ve been particularly focused on the time management / time awareness aspect of my daily routine, particularly because I have more external commitments at the moment than usual for the coming six months. With this extra mental workload, I’ve been finding it difficult to put time into “creative independence” tasks like the blog, product maintenance, and household chores.

I’ve written before about my distaste for duplicate effort, particularly when it involves tasks that are mundane: fetching/returning tools, searching for information that is inconvenient to access, chores that never complete, and so on. When I force myself to do them, I find the effort draining, which makes me even less excited to do it again. It often takes the threat of a looming deadline to kick in that extra energy to overcome the resistance. These are not pretty truths, and I feel that I should have been more proactive for many reasons. I’m sure we’ve all had that thought, and there are many hypothetical “whys”; here’s a few that pop into my head:

• distaste for uncertainty
• desire for perfection
• lack of faith in the goal
• lack of an achievable goal that feels like a big win
• lack of feedback during the performance of the task
• lack of immediate payoff
• lack of detectable payoff
• ease of access to distracting consumables (media, food, other people’s problems)
• lack of confidence in starting
• biochemical imbalance / neurology / poor nutrition
• emotional baggage
• lack of self prioritization
• external stress / other people’s priorities
• lack of commitment / interest despite its value
• pursuit of goal based on other people’s values, not yours
• boredom
• philosophical crisis
• lack of resources / starvation of process

I’ve written about many of the stratagems I’ve come up with, from forgiving myself to identifying and constructing stand-ins for missing resources. I’ve staved-off philosophical crisis year after year by creating a solid working set of principles. At the end of 2014, after having peeled away all the above layers, I’m faced with just two truths:

• work is unavoidable
• the work will take a long time

I’ve been staring these truths down all year, and while I’ve made some progress I have not yet felt the BIG WIN I crave. I know it’s coming, and that faith has been buoyed by the trickle of success in 2013, but I’m exhausted. Am I going to have to fight my own resistance for all of 2014? What else am I missing?

Time Management to the Rescue…Not!

Saying that time management is a solution for procrastination is trivially-true, like saying the way to reverse a company’s slide into bankruptcy is to increase sales. This insight doesn’t help anyone. I hadn’t realized that I’d fallen into a similar time management trap because I learned them a long time ago, when they actually had some value.

In past lives, I’ve worked as a manager, self-managing employee, director, and freelancer. Common to all these roles has been the need to manage time as billable resources. Having been through more than a few kerfuffles with startups and small companies, I am keenly aware of time management as a big part of company management in a production setting, though I am not particularly fond of it. I became really good at estimating time. I became risk-averse to committing to projects that were not adequately scoped or budgeted, and learned to turn down work that had too much wishful thinking embedded in the prospectus. I took to this because I like knowing how things work, and the way I test my knowledge is by comparing what I think will happen with what does happen on an hour-by-hour basis. Efficiency pleases me, as does the machinery that helps harness energy more efficiently.

However, it is NOT good when it comes to excellence-driven personal productivity. Excellence takes repetitive work over time doing tasks new and unknown, as the path to creative excellence is through a tangled forest of uncertainty. This can not be made efficient or predictable on a minute-by-minute basis.

Reversing the Cost Mindset

The big insight I had this week as that I was assigning a cost to each step of every chore, and the act of assigning a cost was making me not want to do it. For example, going downstairs to retrieve a hammer, pound in a nail, then return it is simple enough, but in my mind I was thinking of this as three discrete tasks that had a set of uncertainties (e.g. where are the nails, anyway?) associated with it. Maybe it was two minutes. Maybe it was 15 minutes. It didn’t matter what the estimate was, it was that I was MAKING an estimate that was silly. I have been doing this with EVERYTHING that was goal-related in my life. And it has made me tired and weary of work. The same attitude was coloring the way I saw my creative independence goals, mentally calculating a cost with each tiny step. Counting is tiring, particularly when there’s no use for the data other than to make you aware of the cost of time instead of the good of taking a step. It’s said that people tend to be more averse to certain loss than to a possible gain; perhaps this is an example of that mindset in action.

So what I’ve been doing this past week is suppressing the habit of assigning cost to what I have to do. It is an automatic habit, so I have to pause for a second as I catch myself doing it, but I think it’s starting to help break through some resistances. It will take at least three more weeks of practice to determine if it’s a real improvement, or just a temporary novelty.