How do you do a task you absolutely do not want to do?

4 Tips on how to do the dang thang.

How do you convince yourself to do that one thing that keeps showing up on your to-do list? You know the one—it’s not huge, but it’s not going away, either.

Maybe it’s filing your taxes, updating your CV or calling your in-laws, I mean it’s only a quick chat, right?

What is your thing? The one thing you keep postponing?

For me, it’s sending out some past due invoices and reconciling some expenses in my accounting software that I’ve been putting off for… let me check… 4 months!!

That’s right, I delivered events 1/3rd of a year ago but my brain apparently decided I don’t need to be paid for them.

I intellectually know it’s something I have to do and it’s not the hardest thing in the world, yet, everyday, I magically discover seventeen other things to do instead.

A psychologist would probably say I should explore the deep-rooted issues of where that block comes from. Maybe I feel a bit of anxiety remembering the ups and downs of our family’s finances and so I have an issue with money. Maybe I have a bit of undiagnosed ADHD or some other neurological roadblock. Maybe I just lack discipline.

(Note to self: I still need to find a good therapist.)

An engineer (aka me) would say what’s needed to make this happen? Here are four ways to get that stubborn task off your todo list (that I’m totally going to follow this week, I promise):

1. Delete

The first way to get the task off your todo list is to just delete it. Decide you’re simply not going to do it. This may not be the best decision long term, but it may be best for your short term mental well-being.

Though I’m saying this somewhat facetiously, I think there is tremendous power in knowing that this is an option. It’s not always the best option, but taking a moment to reflect on what would happen if you didn’t do the thing can help you reframe how important it actually is. 

Sometimes, you find that you don’t have to do the thing. For example, did you know that you don’t have to finish every book you start? You’re no longer in school, if you start a book that isn’t great, you can just…never pick it up again (except to donate it). 

So, what happens if I just don’t send the invoices? Well first of all, we eventually run out of money. And money is important, it’s how I buy Legos (and food, etc). And second, the IRS will probably have a lot of questions at the end of the year.

So, in this case, deleting the task is more of a hassle than just doing it, so then it’s time for step two.

2. Delegate it.

Can I have someone else do it? Can someone else send these invoices?

Yes. If only I could shed this DIY mentality. 

The clear challenge with delegating tasks is finding the right incentive—be it money, chocolates, or a heartfelt plea. By passing duties onto others, you not only check off your to-do list but you also gain extra time and peace of mind. Clearly, whoever claimed you can’t buy happiness never enjoyed the services of a skilled accountant.

The irony of delegation is that it can sometimes require just as much time to teach someone else how to do the task as it would to just do it yourself.

Case in point: this week's invoice debacle. By the time I explain the invoicing process to someone on my team, I could easily finish them myself.

However, I just realized this while typing: I could just record the process and have them follow that. Then, the next time invoices come around, I can delegate with the click of a button. Efficiency, meet your new best friend: Loom videos!

3. Defang it.

If you can’t delete or delegate the task, the next step is to defang it (can you tell I got too attached to starting each of these tips with a ‘D’?).

That simply means: find ways to make the task seem less daunting or overwhelming. Here’s how to shrink that mountain into a molehill:

1. Break it into smaller tasks. I know this is cliche advice at this point, but it absolutely does work. Instead of thinking about the entirely completed project (being completely caught up on my finances), think about the individual tasks it takes (sending invoices, reconciling expenses, etc). 

2. Embrace the 80/20 rule. Sometimes the intimidating part of a task is thinking about what it will take to get it all the way to 100% completion. The reality is that not all tasks really have to be done 100% (at least not right now). After all, “done is better than perfct.” It turns out, I don’t actually need to completely revamp the design of my invoices, the current version is good enough, I could just hit send. 

3. Start at the beginning. Overcoming the inertia of NOT doing a task is sometimes the hardest part of doing it. Reframe what success for the moment looks like, not by saying everything is completed, but rather that you at least started. I don’t actually have to send every single invoice out today, all I have to do is send out the most outstanding ones that clients have asked about. Then I can either ride that momentum and keep sending them along, or at least be a step closer the next day.

4. Make it fun, d’uh! If a task feels like a chore, jazz it up. I’ve been meaning to check out the new Eminem album. It’s not exactly toddler-friendly carpool music, but it could be perfect for crunching numbers.

4. Deadline it.

Again, to keep with the D theme, let’s use deadline as a verb. I often joke that I don’t procrastinate but I do believe in just-in-time productivity. 

My tendency to procrastinate has successfully guided me through high school, university, a career at P&G, and entrepreneurship. About the only thing I didn’t procrastinate on was my birth, since I was born three weeks early. The challenge arises when there’s no clear, external deadline for a task (like those sneaky invoices that don’t demand immediate attention).

Creating deadlines when none exist is an art form, especially when your tasks lack inherent urgency. Here’s how I’ve managed to get things done:

1. Become accountable to someone. The most effective method I've found for making deadlines stick is by making them public. It's one thing to have a boss dictate your schedule; it's another to keep your email inbox pristine without oversight. I tackle this by looping others in—whether it’s hiring a coach, committing to a partner, finding an accountability buddy, or announcing to your newsletter that you’re going to finally send those invoices by the end of this week. 

2. Commit to completing it before enjoying personal activities. Without a set deadline, I motivate myself by linking task completion to leisure activities I enjoy. I’m a regular at NYTimes games like Wordle and Crossword, but I’m setting a new rule right now: no games until all outstanding invoices are sent. It’s my personal twist on the “eat the frog” strategy—tackle the biggest, ugliest task first to make the rest of your day smoother. Bianca takes the opposite approach—she tackles the easiest tasks first to build momentum. Do whatever works for you, as long as you…

Just Do It

I wish I had the discipline and willpower to follow Nike’s campaign slogan completely unprompted. I tried that method for ~4 months and it never got done. But with some of the tips above, I’m finally ready to cross that dreaded item off my todo list.

How about you? Do you find yourself wrestling with procrastination or are you a master of discipline? Share your strategies or seek advice in the comments below. I’d love to hear how you tackle your to-do list!

(an)drew

P.S. If this post tickled your productivity bone, why not spread the joy? Pass it along to someone who might enjoy a chuckle—and a nudge to get things done!