How I trick myself into doing things I don’t want to do

The line between work and play is highly individual. (Image by valenaammon)

It’s no exaggeration to say that I used to be terrible at bookkeeping.

I would do months’ worth of it in just a few days, generally when I had to send everything off to my accountant for tax time.

My lack of consistent bookkeeping also made me a poor CFO, since I lacked the information necessary to make financial decisions for my business. I drifted along in a state of non-peaceful ignorance, nervously monitoring my bank account balance and hoping that I wouldn’t run out of money.

I kept myself so busy with service delivery that I would neglect to ensure that I got paid for my work. This, in turn, made me feel so bad that I didn’t want to look at the numbers, which perpetuated the problem of giving my finances short shrift.

What finally turned things around? I decided to get obsessed. I treated the work like a hobby and got the best tools (web apps for bookkeeping and budgeting). I returned to it every day to make a game out of budgeting and tracking, carefully earmarking funds for each category of expenditure.

Even when there was bad news, I rolled with it and figured out what I could do to make the numbers work. This led me to realize that I had to make some personnel changes and close one of my businesses.

Without my obsessive attention to my profit and loss statements, cash flow, and budget, I might have carried on indefinitely until I ran aground financially. Because of my CFO efforts, however, I knew ahead of time that we were headed for the shallows and was able to steer away.

When I’m bad at something or uncertain that I’m doing it the right way, I struggle to engage. When I go all in, I teach myself best practices and gain the confidence to know that I’m doing the work correctly and well. As a result, I start to feel good about what I’m doing and even start to enjoy activities that I used to dread.

This is exactly what happened with the financial management of my businesses. I’ve also applied this same approach to washing and folding laundry, cooking, yard work, nutrition, and note-taking. Whatever the thing is that I’m struggling to engage with, I pretend it’s a new hobby that I’m excited about. By investing in the right tools, giving myself adequate time to practice and learn, and obsessing about details, I develop a sense of mastery that causes me to be motivated to do something that I once avoided.

As a teacher, I’ve observed that people enjoy doing what they’re good at. I doesn’t matter whether someone starts off as a “music person” or a “math person” — anyone can become enthusiastic about what they’re doing if they have the right support and tools.

I don’t see myself as particularly organized or financially savvy. I’m good at math, but otherwise I have no real head start in that area. However, I’m getting great results because of the effort that I put in — and the effort that I put in has allowed me to find increasing satisfaction in the work, which makes it easier to continue.

If I look for the opposite — if I wait until I’m inspired to do the work to put in the effort — I’ll be waiting a long time. But somehow, putting in the effort first, the way I would do with something I really enjoyed, makes me inspired to continue. That’s my surest weapon in the battle of self-management.