What to Do if You’re Procrastinating on Your Taxes (Or Another Crucial Deadline)

Like money, time can be used for either investments or expenses.

As you probably know, investments are activities that bring a return. The major time investments include: planning and management, relationships, self-care, health and fitness, education, a spiritual or meditative practice, community work, and what I call “replenishing recreation” (e.g., socializing or a passionate hobby).

taxcatExpenses are everything else, including household chores, “busy work” at the office, and escapist recreation like television or video games. (A little escapism is fine, but don’t go overboard. Most of your recreation should be replenishing.)

Perhaps THE key to a productive, happy life is to maximize the amount of time you devote to investments relative to expenses.

Of course, the line isn’t always clear. Different people might have different investments–you might have kids, I might love gardening. And the same activity could be either an investment or an expense depending on one’s preferences and circumstances.

There are, however, a few crucial differences between investments and expenses:

1. Investments tend to be active, expenses passive.

2. Investments tend to connect you–to others or nature, or to your senses, intellect, creativity, or other capacities. Expenses isolate you. And,

3. Investments tend to be fun. They tend to be complex (in a good way), creative, engaging, and diverting, if not outright enthralling. Expenses are boring.

Now about your taxes…

You probably don’t find tax prep much fun. Maybe you find it boring or tedious. Or, maybe you’re ambivalent about the role of money in your life, or in society at large. Or, maybe doing an annual sum-up of your financial situation freaks you out.

And yet you must do your taxes, and personal finance (of which tax prep is part) is definitely an investment.

Here’s how to cope:

1) Do it in community. We are such powerfully social creatures that for many of us simply working alone feels like a punishment. If a task you’re trying to do also feels like a punishment, as tax prep might for you, then that’s two simultaneous punishments! (No wonder you’re demotivated!)

In Cambridge, MA, there’s a group of writers who meet regularly in the lobby of a public building. There’s no chitchat or discussion: everyone simply sits down and starts writing. Even writers who are usually blocked manage to write during those meetings! Community is THAT powerful. So, if you can’t stand working on your taxes (or writing, schoolwork, or another project), get a friend to join you. Maybe he can assist with the tedious chore of sorting receipts. Or, maybe he can provide cups of tea and occasional gentle support. Or, maybe he will simply sit alongside you and do his own work, so that the two of you help each other alleviate your mutual loneliness. Any of these approaches is fine.

2) Delegate it. If you have the means to hire an accountant, do it. If you have the means to pay someone a few bucks an hour to sort through the receipts, do it. If software will help and you have the means to purchase it, do so.

You’re not Calvinist, I hope, and so you shouldn’t see any virtue in suffering. Your time is too precious to waste on unpleasantness and tedium, even important tedium. If you can delegate all or most of the tax prep do so.

If you don’t have the means then perhaps you can barter. Or, take your information to a VITA site and get free help and honest advice. (Call first to make sure you qualify, and for an appointment, if needed.)

The main technique, though, is to:

3) Slow way down. Dig deeper. Start really focusing in on, and reveling in, the details of the work.

This is the opposite of what most people do with an icky project, which is to try to blast through it as quickly as possible. This pretty much guarantees a disappointing result, and (unless they’re doing it at the very last minute), a long, distracted, wasteful process filled with procrastination and self-recrimination.

By slowing down, however, you can magically make a chore become more interesting.

This advice isn’t as weird as it seems–after all, there are plenty of people out there who actually enjoy managing their money. And the slowing technique also works with more daunting projects than taxes. People with serious illnesses, for instance, often find that when they take an active, creative role in their maintenance or recovery they not only get a better result, but are better able to tolerate their illness.

The “slowing down” advice doesn’t conflict with the “delegate” advice, by the way. Whatever parts of the project you can delegate you should. But by slowing down on the parts you retain, you’ll get a better result.

Here are two subsidiary techniques, both discussed at length in my book The 7 Secrets of the Prolific:

4) Journal about your block. Journaling itself relieves stress, and as you use it to illuminate the details of your ambivalence to doing taxes, you will probably come up with strategies for overcoming them. And,

5) Reward yourself abundantly during and after the tax prep process, both to maintain your motivation and because you earned it.

Good luck!

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