My New Strategy for Managing Multiple Skill Sets and Habits

A long time ago, in an era of my life filled with hard work, stress, and lack of sleep, I was a big procrastinator.  In my late twenties,  a good friend introduced me to Leo Babauta‘s idea that habits are more important than willpower and that robust habits are formed by starting very small, working every day, and slowly building up.  (James Clear also posted about this very same topic today.)  This “habits over willpower” idea started me down the road to developing desired habits; eventually, I crowded out undesired habits.  By my early thirties, I had finally slain the demon of procrastination that had plagued me for so long.  Good riddance!

However, like most people, I still had trouble doing more than a few things outside of work each day, and, since I wanted to devote substantial time to any skill set or habit–and by “substantial” I mean at least thirty minutes–I still wasn’t able to do everything I wanted to do.  Each day, after leaving work, I would do the following in some order and would then run out of time for anything else: socialize, prepare dinner, draw/paint, and run or lift weights.

If you had asked me, say, a year ago, if it’s possible to achieve high levels of skill in multiple endeavors, while keeping each of them active in your life, I would easily have said no.  I would have pointed to the case of Rhodes Scholars, who, despite a high level of achievement in multiple endeavors, seem to achieve things linearly instead of in parallel.

That all changed very recently when I changed my time management strategy to make it more flexible and more capable of handling multiple skill sets/habits.  Although I’m still testing it, I’ve implemented it daily for a few weeks now and it’s been much more effective than any organizational strategy I’ve used before.  (For most of my life, if I neglected anything for several days, it was at high risk of being neglected for weeks and then months, which was terrible because I ended up spending a lot of time regaining lost skill/knowledge.)  It also requires much less overhead in terms of tracking activities and finding time for them.  For the first time in forever, I’m making consistent progress along each skill set/habit without neglecting anything.

I work full-time and work out every day, but I also want to make progress along the following skill sets: rheumatology, presentations, drawing/painting, writing, classical guitar, and computer programming.  Another requirement is the ability to stay flexible, so that I can, say, attend social events or explore new opportunities.

My new strategy is very simple:  devote at least five minutes to each skill set every single day.

It’s not possible to devote a significant amount of time to every skill set or habit every day, because this will push everything else out of your life and render your days rigid and brittle.  However, it is possible to rotate “significant” time amongst your various desired skill sets, and the best way to do this is to spend some time on each skill set every day, so that you don’t drop any of them.  This has an interesting and useful side effect:  by spending some time on each skill set every day, you have a feel for which skill sets have been neglected over the past few days and need to be pushed to the front (e.g., these will get thirty minutes or more of dedicated time), and also for which skill sets have been getting too much attention and need to be pushed to the back (e.g., these will get, say, five minutes of dedicated time).

If I’m very busy in a given week and don’t have much time to spend on activities outside of work, or if I’m working on a big presentation and have to dedicate most of my time to that, I might take very small steps along the other skill sets, such as adding a few lines to a blog entry, or just a few strokes to a digital painting, or spending a few minutes on a classical guitar exercise that’s giving me particular trouble.

My theory is that it’s better to spend a tiny amount of time on any desired skill set each day than to let it go completely unpracticed for an entire busy week.  These daily “microsteps”, punctuated regularly (such as every few days) by significant steps, seem to be ideal.

Additionally, there’s much less pressure to be very serious about any of these skill sets, because they can be compressed at any time to make room for novel opportunities or special events.  I’ve finally relinquished the stress that comes with deep commitment to a ton of stuff all the time.

With this new approach, everything in my life gets sufficient attention over time.  Of course, this strategy (and any strategy, quite frankly) will fail if one attempts to do too many things, but I think that this is the best approach I’ve used so far for managing many skill sets/habits without abandoning any of them.

Update 2/1/16: I’m still using this strategy!  What I realized is that one must exercise good judgment about which activities get the most attention.  The correct priority of activities is important.  This can be difficult to know at first.  For example, I realized I’d rather become a better writer than a better artist.  So, I now spend more time on writing than on drawing.  I also realized that programming is too low of a priority to keep stringing it along.  So, I ditched programming altogether.  While I was studying seriously for my rheumatology boards, studying and my significant other were my first priorities outside of work.  Etc.

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