How I Magically Transformed My Financial To-Do List Into Something I Actually Look Forward To

A few weeks ago, I noticed my car needed an oil change and tire rotation, and that the state inspection was due by the end of the month. I usually dread the rigmarole of finding an auto service center and scheduling when the work can get done, and this time wasn’t any different.

When I looked at my calendar, I couldn’t find a weekday that had an open block of time for the services, and I started feeling overwhelmed with the “too much to do, no time to do it” frenzy. But at that moment I remembered the perfect advice from motivation and efficiency guru Tim Ferriss. When faced with a task or obligation, he often asks himself, “What would this look like if it were easy?”

Inspired by that question, I added a spin of my own. I thought: What would this look like if it were fun?

To make my car maintenance errand “easy,” I picked the most wide-open day, even though it was one I usually try to avoid planning chores for: Saturday.

Then to make the errand "fun," I considered how I like to spend time. My ideal weekend kicks off early and outdoors. How could I add that to the required chore? Solution: I found a nearby town with a Mavis service station located near one of my favorite bike paths. Then I called up a friend I hadn’t seen in almost a year to make a biking date. Now the tedious to-do had an incentive: I would see an old friend and revisit my beloved rail trail at the same time.

Suddenly, I was no longer dreading the task; I looked forward to it. And when the Saturday rolled around, all I could think about was the upcoming fun. The chore was just a small part of the day, even though it had started as the focus.

I call this activity "strategic pairing."

Pairing a not-so-fun activity with another I enjoy is one way I’m able to knock out my to-do list without feeling too drained or grumpy. This works for both big and small items. For instance, at the end of the month I always comb through my expenses and tally my budget spreadsheet. Sounds pretty dry, right? Except I always do this at a bar or cafe, sipping a glass of wine or a latte. This turns the task into a treat, not a burden. I get to escape the desk where I work all day to enjoy a beverage — and my budget gets up-to-date.

How to make your own strategic pairing.

It's a little bit like matchmaking. First, think about all the tedious tasks you need to complete. Then, list activities and environments you enjoy. Finally, find ways to match your to-dos with things that bring you pleasure — think of this as your recipe for joyful productivity.

Here’s a list for inspiration.

You could try to link up grocery shopping and seeing friends, especially if one or both of you have limited free time. Perhaps you could hang out and chat (in person or on the phone) while getting food for the week. (There's a good chance your friend has limited free time, too.) Laundry and dancing work well together. Folding can't be boring and repetitive when you're moving to Lizzo while matching your fitted sheet corners.

The to-dos that require you to be online, like checking your credit score, setting up deductions, comparing phone plans, and canceling meal delivery, can be bunched together and completed at a cafe where you can sip on that matcha latte. Alternatively, you can find a friend who has their own life admin to work on, and make a date of it. Spend the first hour checking off all your items, and reserve the second hour for catching up.

A small word of warning before you begin.

While pairing can make chores fun and increases the likelihood they get done, this method doesn’t come risk-free. Say, for instance, one of your goals is to spend less money on dining out — something you really enjoy — and that includes coffee shops and bars. To stay on track, you probably shouldn't use my classic pairings: wine and budgeting, or lattes and a credit check. But you could use another, more budget-friendly match, like a library visit, where you can browse the new titles section, and use the free WiFi to work on comparing cell phone plans and completing other items on your list.

It takes a bit more creativity to find strategic options that hit all three criteria: fun, easy, and aligned with your goals, but once you do, you'll not only feel excited to get those tedious tasks completed, you'll do it knowing you stayed true to your goals.

So the next time you're faced with a money errand, ask yourself: What would this look like if it were fun?