Make the boring task fun on purpose

Every business has them. The tasks nobody wants to do. Reconciling receipts. Updating the CRM. Scheduling a month of social posts. Cleaning up the shared drive. Following up on unpaid invoices. They aren't difficult tasks. They're just so boring that you'll do almost anything else first. You'll even do other work you don't like, just to avoid the one you like least.

Most productivity advice tells you to push through with discipline. Eat the frog. Do the hardest thing first. I want to offer you a better option, and it comes from a researcher at Wharton who had exactly this problem.

“Temptation Bundling”

Katherine Milkman had two problems as a grad student. She knew she should go to the gym, and she didn't want to. And she loved reading trashy page-turner novels, which she felt guilty spending her time on. So she combined them. She only let herself read the page-turners while she was at the gym.

Later, with Julia Minson and Kevin Volpp, she tested the idea in a real experiment and gave it a name: temptation bundling. You pair something you want to do with something you should do. In the study, published in 2014, some participants got iPods loaded with gripping audiobooks they could only listen to at the gym. The iPods literally stayed there.

At first, that group visited the gym 51% more often than the control group. A second group, who got the audiobooks with encouragement (but no rule) to listen only at the gym, went 29% more. Here's my favorite detail: when the study ended, 61% of participants chose to pay for continued gym-only access to the audiobooks. People liked the trap so much they wanted to keep it.

I want to make sure I give you the full picture though, because that's how I am.

The effect faded over time, especially after the Thanksgiving break disrupted everyone's routine. And a later, much larger study found that simply giving people audiobooks and suggesting they bundle had a smaller effect than the original results suggested.

So temptation bundling isn't magic. It's a nudge, a way to make a disliked task easier to start. It works best for things you mildly dislike, not things you truly dread. For those, you need different tools.

But "mildly dislike" describes most business admin, doesn't it?

Why it works

The tasks we avoid usually pay off later. Clean books help at tax time. An updated CRM helps next quarter. That delay is the problem, because your brain heavily favors rewards it can get now.

Temptation bundling moves some of the reward into the present. The task itself doesn't get more fun. But the time you spend on it now comes with something you actually look forward to. It also cures a bit of guilt on the other side. The show you'd feel bad binge-watching becomes something you've earned.

How to bundle your business tasks

1. List your "wants." What do you enjoy but ration or feel guilty about? A podcast, a true-crime audiobook, a fancy coffee order, a playlist, a favorite candle, working from the nice coffee shop instead of your kitchen table.

2. List your "shoulds." What tasks do you keep avoiding that don't need your full brain? Invoicing, data entry, inbox cleanup, filing, scheduling posts.

3. Pair them. "I only listen to my favorite podcast while I do bookkeeping." "I only get the fancy latte on admin Friday." "I only work from the coffee shop when I'm doing CRM updates."

4. Make the rule real. The study's strongest group had the audiobooks locked at the gym. The closer you get to that, the better it works. If you let yourself listen to the podcast anytime, the bundle falls apart.

5. Match the want to the task. Audio works great for tasks that don't need words: data entry, sorting, design busywork. It works badly for writing or anything that needs deep focus. For those, try a place or a treat instead.

I had a client once who really dreaded her weekly invoicing. She'd let it slide until she was chasing three weeks of unpaid work. So I had her pair it with the one thing she never let herself do during the workday: watch YouTube videos. Invoicing became her Friday afternoon YouTube time. She didn’t miss another invoicing session again.

Stop fighting yourself

Discipline is a finite resource, and you're already spending plenty of it running a business. You don't need to white-knuckle your way through every boring task. Sometimes the smartest move isn't to try harder. It's to make the thing you have to do come with the thing you want to do.

What's one boring task on your list this week? And what could you pair it with?

If you want help building systems that make follow-through easier instead of harder, let's talk.

Studies to link: Milkman, Minson & Volpp (2014) · Teaching temptation bundling, follow-up study