The Fear of Regret

Fear of regret is a barrier to entry when trying to live a mindful and intentional life. During downsizing and organizing projects, hypothetical what-if scenarios create an obstacle between practical reflection and movement forward. They paralyze us in a subtle fear. When fearing regret, there’s an underlying assumption that our stuff is really important, because unimportant things don’t provoke regret, right?

Regret prevents us from letting go of an item because of it’s potential use or what we believe our emotional state may crave having around in the future. This may be the case with memorabilia related to a loved one or even something minor but irreplaceable like a yearbook. What-ifs are predicated on the idea that the future may hold terrible sadness of regret. We forget that regrets about objects, if they ever materialize, are not painful like regrets of actions/inactions. 

The fear of regret is often worse than the regret itself. After my parents downsized to a retirement community, I asked my Mom whether she regretted letting go of so much stuff. She said that, for example, she’d reach for a vase and then would realize she’d donated the one she would have chosen. When she realizes that she no longer has it, she’s bummed out for a moment and then moves on. A small price to pay to live in their new home and keep it well organized.

I think about this a lot: the emotional energy exerted to prevent a passing thought. I know she keenly considered those vases and their various styles, sizes, and quality. I recall her gathering them and trying to get my siblings and I to take some. She was an enthusiastic salesperson, like many others who resist giving their more precious stuff away without knowing exactly who will cherish it as much as they did. 

All of the effort had a partial payoff. She has a strong selection of vases that allow her to easily display various bouquets of flowers. It was worth some energy to be picky but probably not all of it. It was likely not worth any fear of regret or keeping a slighter larger collection than would suit her needs.

In Make It Feel Good, I discuss how we stress over the risk of not making the right decision. This is based on the idea that there is a right or wrong decision to be made. We believe the right/wrong mental construct is worth it, because we might make the right choice. The payoff of which would make everything perfect. But there is no perfect. A right or wrong decision doesn’t exist in the first place. There are too many external, unpredictable variables; too many ways in which a person may change and grow. By admitting to the flaw in the construct and therefore relinquishing the attachment to making the right decision, the fear of regret loosens. 

Decision fatigue, in a part, is caused by the need to make the right decision and is supported by these fears. Fatigue occurs when the weight of choice is too heavy to continue carrying it. So we give up, and keep the damned thing. It’s not worth regretting, as terrible as we’ve pictured regret to be. It’s this mental construct that makes the fear of regret even more powerful. 

We also like to hold on to regrets. Sometimes we choose to be painfully reminded of the important letter we forgot to send, the thing we bought accidentally but didn’t return in time, or the D-graded paper that made us give up on a dream of being a writer. We fear unrealized pain but sometimes we actively choose to hold onto existing pain.

While the lingering concern that one day you might want something that you gave away persists, ask yourself if that’s a world you can happily live in. What would you regret more: living a full, intentional life focused on your values or keeping all the things that you might regret one day not having? Because if you’d prefer the former, you’ve captured the more abundant side of the trade-off. Dismantling the fear of regret when downsizing and organizing allows you to avoid a regret of regrets.

For another take on regret, listen to my Words for Wednesday podcast, Ep. 77, To Live or Not To Live With Regret.