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Introducing Gloomsday, the Holiday for All the Things You Hate

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Yesterday in our Mastermind, I confessed to something I do that feels really silly, but that always works well for me: It’s a holiday I made up called Gloomsday that I “celebrate” a few times a year.

Gloomsday, essentially, is a day when I purposely do annoying tasks I’ve been putting off. It  doesn’t fall on a specific day of the year. I invoke it when I need it — when work is piling up, and I have a huge list of little things I’ve been avoiding. They’re things that don’t take that much time, but loom large in my mind anyway because I just really, really don’t want to do them.

Stuff that’s typically on my Gloomsday list:

  • Cancelling accounts to “free” trials
  • Totaling up my freelance hours and sending invoices
  • Returning emails, texts and DMs
  • Washing “handwash only” clothes
  • Writing podcast guest invites
  • Changing passwords

None of the things I listed above are particularly difficult, and none of them even take very long. That’s the point — Gloomsday isn’t a day to begin things that take days or weeks to complete. It’s a day when I take the small, random items that keep sticking to my to-do list and getting pushed from list to list, and I just do them. I “eat the frog,” as Mark Twain said. And then I just keep eating frogs all day.

Yesterday, someone asked if I reward myself on Gloomsday, but I don’t have to. Even doing a couple of things I’ve been avoiding gets rid of mental clutter and makes me feel so much better that it’s a motivator all on its own. But just because I don’t use rewards as a motivator, that doesn’t mean I deny myself, either. It’s not like I’ll turn down a cookie just because it’s Gloomsday — it’s about progress, not punishment.

Want to have your own personal Gloomsday? I invite you to try it! As the official Gloomsday founder and self-appointed officiant, here are my tips:

Declare a Gloomsday!

Sometimes I decide the night before that the next day will be Gloomsday, and sometimes I just wake up, look at my to do list, and declare it day-of. Sometimes I do it on a rainy day that “feels like a Gloomsday” to me. Sometimes it’s on a regular day. (Gloomsday isn’t weather dependent.) All you need to host a Gloomsday is a list of stuff you’ve been avoiding … and I always have one of those.

Start with a Few Tasks

I normally begin with five or so things on my Gloomsday list, but as I start knocking them out and feeling a major sense of accomplishment, I add more. It’s sometimes better to set out with a shorter list and add more throughout the day as you work through it; that way, you’re less likely to get overwhelmed.

Add Tasks As You Go

As long as you’ve checked off enough tasks already to get the warm feeling of accomplishment, it’s fine to add a few more. A few hours into my day, I usually find myself remembering other things I’ve been avoiding and adding them to the list. I actually get excited about doing them, because that’s what makes it Gloomsday. (I know, I know. I’m just weirdly into holidays, even those I’ve invented myself.)

Finish up in One Day

Don’t make every day Gloomsday — that’s not the point. I once had a Gloomsweek, and my husband would like to pass on his warning that, if you do that, the gloom won’t stop with you. I probably got a lot done that week, but it wasn’t fun. Weirdly enough, Gloomsdays usually become sort of fun for me, but keeping it contained to one day is key.

The Lasting Results

Gloomsday probably will make you a little more likely to take care of the small stuff, at least for a little while, because by tackling your list, you’ve reminded yourself that it’s sometimes better to face annoying tasks than to let them grow more powerful. (Insert Harry Potter “Howler” reference.) Don’t worry — you’ll be able to celebrate Gloomsday again. We’re human, and eventually we’ll have another long list of “someday” projects. And while someday may never come, we can make sure that Gloomsday does.


Carrie Rollwagen is host of the Localist podcast and cofounder of Church Street Coffee & Books. Currently, she works as Vice President of Strategic Planning at Infomedia, a web development company in Birmingham, Alabama. Find the Localist at @thinklocalist on Instagram and follow Carrie at @crollwagen.

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