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Why You Shouldn't Feel Guilty If Your To-Do List Only Gets Longer

It's normal to aspire to do more than you could ever get done. Don't beat yourself up about it.
Why You Shouldn't Feel Guilty If Your To-Do List Only Gets Longer
Image credit: Prasit photo | Getty Images
Entrepreneur Staff
5 min read

Regardless of the intentions you set for your work day or week, it can be difficult to complete all of the tasks you plan on checking off your to-do list in a set amount of time. Little things come up, from emails that require responses to troubleshooting requests from colleagues to personal matters.

Pretty soon, you’ve gotten a lot done, but not necessarily what you set out to do. That, or the opposite is true: You ignored those incidentals initially, but now, you’ve got to address them. Well, at least at some point. Eventually. Until eventually turns into a question of, “Will I ever?”

There are so many things in the world we would ideally do, if we could clone ourselves, but time is finite. Entrepreneurs especially have the odds stacked against them when it comes to time management and prioritization.

Related: How to Allocate Resources When Everything Is 'Priority 1'

It can be counterintuitive to let pending items on your to-do list -- or a growing to-do list -- make you feel guilty. That might be your involuntary reaction when you see the tasks looming, but in many cases, guilt, or even shame, can paralyze you, University of Texas at Austin Professor Art Markman writes for Harvard Business Review.

Generally, guilt is motivating. It incentivizes you to get things done, because you anticipate negative consequences or don’t want to let someone down. Think of it as a form of fear. There are various types of fear that entrepreneurs specifically face, according to researchers at Warwick Business School in the U.K. When there are financial risks involved with making a certain decision (or in this context, prioritizing certain tasks), or when there’s an opportunity cost to assess (the idea that if you drop the ball, all you’ve work toward thus far will have been for naught), fear can motivate.

However, Markman notes, if you’re sitting around feeling guilty, say, during a concert, family dinner or in another setting when you can’t actually do anything about the incomplete tasks, it’s only eating at you, making you resent your work.

Fear and guilt are less motivating when your decisions and their outcomes are intertwined with your self-esteem, or that failing to get something done translates, in your mind, to a larger character flaw. Markman explains that guilt morphs into shame, or “feeling like a bad person,” in many cases, and that when you’re ashamed that you haven’t gotten something done, you’ll be too down on yourself to feel motivated to finish it.

Markman cites research by Gabriele Oettingen, a psychology professor at the New York University and the University of Hamburg, who has a simple tip for boosting your motivation: Focus on your accomplishments, rather than dwell on all of the things you don’t have done yet. This will propel you to do more, so you can replicate the feelings of satisfaction you have with what you’ve done, rather than risk untimely guilt or crippling shame.

He also advises practicing self-compassion, a.k.a. giving yourself a break. Maybe it’s time you put a reminder on your to-do list to tell yourself periodically that it’s normal to have lingering tasks. You’re only one person, and there’s always tomorrow.

Prepare yourself so that when you inevitably find yourself in a fear-induced negative headspace that drives you to inaction, you’ll be ready to help yourself. Brad DeWees, a U.S. Air Force captain and doctoral student of public policy at the Harvard Kennedy School of Government who specializes in judgment and decision-making, told Entrepreneur earlier this year that creating a step-by-step plan can help you overcome something daunting.

In the Air Force, he says, “the prospect of jumping out of a plane would inevitably induce anxiety. We’d deal with it by reviewing, alone or as a group, the steps we were supposed to follow throughout the mission. Going through that review was a way of reminding ourselves that we had some measure of control over the situation.”

You might do the same with your to-do list: Enumerate what you need to do first, second, third, but think through each task one at a time, and what is required to complete it -- that is, if it’s something non-routine that requires careful execution.

Related: How to Figure Out What Your Time Is Worth

Whatever you do, avoid “completion bias” -- the desire to check off a greater quantity of easy-to-do, perhaps mindless tasks than tackle a more time-consuming or challenging objective. As the Warwick Business School researchers found, fear drives people to set easily attainable benchmarks but not necessarily prioritize the most important tasks, so that they don’t fall short of their goals. On the other hand, people set lofty goals (or create a mile-long to-do list) so they have an excuse for why they didn’t finish. These are all common traps to be aware of so you can avoid them.

If all of these mindset shifts aren’t enough, you can always take the Jason Feifer approach: Entrepreneur’s editor in chief got brutal with his schedule around the time when his son was born and he took over leadership of the print magazine, forgoing his longtime hobby of watching basketball and keeping tabs on the teams -- cold turkey.

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