“Every year, hundreds of New Yorkers congregate on Tax Day at the 24-hour post office at 34th and 8th Avenue, polishing off their 1040s, filling out their registered mail slips, and sealing their envelopes. The lines snake up and down the cavernous interior of the building and most of the people are more tired than anxious. (With the exception of the few still filling out their forms.)”

Photo and description by Amit Gupta.

Last weekend I had the unenviable (yet unfortunately inevitable) task of getting our 2009 taxes prepared.  I stopped actually doing our taxes about 10 years ago, but that doesn’t mean I’m completely off the hook here.  There’s still just as much preparation involved to make sure everything is tracked and reported, and that my accountant has all the information he needs in order to file.

There are far worse things in the world, I know.  But I definitely don’t look forward to this time of year.  In fact, it’s probably the most postponed thing on my to-do list.

Let’s see… I could play with my daughter or sit in my home office surrounded by arcane forms.  We could go for a walk down by the waterfront as a family or I could scan and shred documents instead.  My wife and I could watch an episode of Friday Night Lights or read in bed… or I could sit at a computer adding up real estate taxes and 1099/W-2 forms.  You get the picture.

I decided to take a different approach this year.  Instead of dreading and postponing the project from week to week, I’d learn from it.  I knew I didn’t want to do this, but I knew I had to.  So I decided to use it as a sort of test for overcoming procrastination – how would I get myself to move forward despite knowing it wouldn’t be any fun?  At the very least, I could write up my experience on Refocuser and see if the process helps others.

So I documented my thoughts throughout the week in my online notebook – and simplified it down to a pretty straightforward process for powering through unpleasant things.  Just like everything else, this may not work for everyone, but now that I can articulate the steps I followed, I recognize it as a pattern that’s worked for me for a long time.

But before going further, it may help to figure out what kind of procrastinator you are.  The type that puts things off and never does them – or does them super poorly – or the type that does eventually get things done, albeit with a bunch of unnecessary anxiety.

This article (thanks Steve!) does a great job of describing the difference between a “procrastinator” (the first type) and an “incubator” (the second):

Incubators were the only students who had superior-quality work but who also worked at the last moment, under pressure, motivated by a looming deadline.

This set them apart from the classic "good students," the planners who strategically start working long before assignments are due, and from the procrastinators, who wait until the last minute but then hand in shoddy work or hand it in late.

For most incubators, having a label that is less pejorative than "procrastinator" can be a breath of fresh air.

Everyone has the list of boring things they dread need to do.  Clean the gutters, do your homework, write your dissertation.  If you’re a true procrastinator, you may never get these things done – so this process may help you quite a bit (although you should also consider some more radical change). 

If you’re an “incubator” then you know you’ll eventually get them done, though you’ll beat yourself up every step of the way.  This process may help you structure the way you respond to a looming deadline.  Regardless of which type you are, there’s an easier way.

Here’s the simplest way I’ve found to overcome procrastination, step-by-step:

1. Get into the right mindset

If you think you’re doing something forced upon you, you’re not going to want to do it.  But if you feel like it’s something you’ve chosen – or something you can benefit from – you may find yourself a little more motivated to get through it.

For me, it was helpful to reframe the task in my mind from something I had to do (mundane busy work) to something I wanted to do.  I reminded myself throughout the week that the sooner I get it done, the sooner we’ll have a tax refund deposited.  In other words, I was training myself to think about the outcome first and the process second.  It helped motivate me… ever so slightly. 

So try thinking about things a little differently – no more “have to”, more “want to”.

2. Give yourself enough time to get it done easily

This of course is important – this practice won’t work if you have a deadline tomorrow.

I knew I had some time to get it done because I started thinking about this project well in advance of the deadline.  It was only the first week of February and I had until April 1st (or so) to get this project finished.  In other words, I had enough time to break up the project into tasks I could actually imagine myself doing easily. 

If you aren’t the type of person to plan ahead, you’re going to need to try and become one.  At least to the point that you aren’t putting planning off until you no longer feel comfortable with the time you have left.  Just a little bit of upfront planning makes the entire project a ton easier.

Anxiety may help motivate you, but there’s still a better way.  Zero anxiety beats even the smallest bit of anxiety any day.

3. Break out everything you have to do into a bulleted list

A common theme in a lot of the things I write about (see 12 Goals) is to get specific.  If you don’t know exactly what you need to do to finish the project, you’re going to look at it as an amorphous blob of face-eating hell.

“Finish my taxes” is a lot scarier to your psyche than “Collect all the forms from the filing cabinet and kitchen counter”.  So break the project into logical chunks: collect all the forms, sort them, scan them, figure out which to keep and shred the others, and so on.  All the way down to “Put it into an envelope and walk to the post office”. 

Keep the tasks relatively small (30-60 minutes of actual focused work) and put the list somewhere you can reference it easily.

4. Commit to a single task for the first day, not to exceed 60 minutes

Commit to just one task for the first day.  Something small and easy, realizing that most of your project is probably small and easy when looked at in 30-60 minute chunks.  As David Allen describes, you want to reduce everything to a “crank the widget” sized thing so you don’t even have to think about it when the time comes to do it.

So just do the single task… start to finish.  If you don’t want to continue once that task is finished, you don’t have to… because you have time for the rest.  But no matter what, you’re going to get this one, simple, easy, widget-cranking task finished.  And when you do, you’re going to check it off the list and give yourself a nice little “task completion high”.

If you still find yourself trying to talk yourself out of it, try combining the task with something you actually enjoy doing.  For me it’s listening to music or watching a movie.  Since I don’t usually sit around listening to music by myself very often, it’s something I can look forward to – even if I’m sorting documents or doing research at the same time.

5. Allow yourself to continue.  Or just do the next thing tomorrow!

This is where things usually get interesting, thanks in part to that Flow state.  You’ve gotten yourself to start, but you aren’t forcing yourself to finish it all right now.  You’re setting yourself up pretty nicely to get into a zone where you lose track of time and just move easily from step to step.  Now that you’ve gotten yourself going, give yourself time to continue on.  Allow yourself to get the next task done if you’re motivated at that point to do so.

Success breeds success.  If you finish step 1, you’re more likely to do step 2.  Especially since it’s been broken down into its smallest possible form, and is presumably something that builds on the first step.  In  my case, if the tasks are small enough, I can usually get myself to move onto the next thing right away because I’m happy to be making progress, and feel good about what I’d just accomplished.

The more you do, the easier it is to picture yourself finishing the project.  The finish line isn’t off in the distance anymore.  It’s amazing how motivating checking things off can be – you can make a lot of progress just by starting!

If you find yourself anxious about continuing onto the next step right away, don’t!  You always have tomorrow.  Put it off – you can afford to since you just got a critical piece done.  There’s something freeing in knowing that you don’t have to do anything at this point – you may choose to, but that’s entirely up to you.  This alone can help beat that feeling of dread away.

In short: start early, break things down, commit to a small single thing, continue if you find yourself in the zone to continue, or move onto something else and continue tomorrow.

Have fun!  Even though I know this post is really about doing things that aren’t necessarily fun :)  If you’re still having trouble getting started, you may want to read Just Do Something: 6 Ways to Unblock Yourself & Get Moving.

Something to keep in mind: February is a short month.  It’s over next week.  Which means you have just over a month to get those taxes done!  53 days from today to be exact.  Now’s the perfect time to attack that specific project if you haven’t already.  And if you have, what are you doing still reading this anyway?