As someone with, you know, a personality, the bane of my existence is what I call “business jokes.” You know what I mean: jokes that aren’t actually funny, because that would be inappropriate. Business jokes simply gesture at the possibility of a joke, at the concept of humor. For example, the last line of your official “professional” bio probably contains a business joke. (Mine: “I hold a Bachelor’s degree in Ancient Studies from Barnard College at Columbia University, and I continue to have strong opinions about the Trojan War.”)
Business jokes have their place in the workplace. Still, you want to be able to bring your authentic self to work. Doing anything else is depressing and sabotages your work relationships, because your colleagues lose track of the fact that you’re a real person. But making room for your personality in the cramped space of business interactions is tricky. That’s where jokes come in. Actual jokes. And all the earnestness that jokes require. Making a real joke is more vulnerable than making a business joke: You’re actually putting something on the line.
So I recommend OOO autoreplies as a place to audition a bit of your real personality for your coworkers. I know this sounds terrifying – you have no idea who will see that thing! – but that’s also what makes it liberating. Juxtaposing the rote automation of an autoreply with something as intimate as your actual personality is charming. It catches your reader off guard. It also gives you a little bit of distance from the audacity of the act. You’re arriving in someone’s inbox, but not because you dared to cold email them; no, it was the autoreply that did it.
Autoreplies are also a low-pressure environment. If the reader enjoys your autoreply, they can comment on it. If they hated it or were simply too busy to read it, they’ll just ignore it, because there’s no expectation that they reply. No harm done. Most email providers also let you share different replies based on whether someone is already in your contacts list and/or part of your organization, which also lowers the stakes.
Here are two suggestions to inspire you:
Shake up the format
I wrote this autoreply in the style of William Carlos Williams’ “This Is Just to Say.” I slyly included a link to the poem so that if someone didn’t recognize the reference they wouldn’t be horrified.
I am out of
on a Disney cruise
If you need help before I return on Tuesday 11/8,
please contact X (account)
or Y (account)
or Z (everything else)
this cruise is wonderful
with abundant food
and Donald Duck
Here’s one I did in the style of a text-based adventure game. This got the most praise of any OOO I’ve ever written:
CHOOSE YOUR OWN OOO ADVENTURE
You find yourself in a dark cave. On the floor is a note. It reads: “Hello! I am out of the office until Wednesday, December 13. I have no access to my phone and only occasional access to email.”
What do you do now?
TO REQUEST HELP WITH [CLIENT], email [address].
TO SLAY A CONTENT STRATEGY DRAGON, please reach out to kindly wizard [Colleague] at [address].
FOR OTHER INQUIRIES, including Wikipedia guidance, please make yourself comfortable in this cozy cave and I will get back to you ASAP. Together we can tackle any obstacles this RPG of life throws at us.
IF YOU ARE PANICKING THAT THIS WEIRD OOO EMAIL WENT TO A CLIENT: Fear not! External folks are getting a much more normal version of this missive.
I firmly believe regular, restful breaks are critical to doing great work. So thank you, sincerely, for the support that enables me to go on offline adventures now and then. I hope I can return the favor.
Stay strong and stay brave, fellow adventurer.
And here’s one I did as a goofy FAQ:
Hi! I’m out of the office until Tuesday, February 21. Here’s a handy FAQ for while I’m gone:
Are you on a Disney cruise again?
Yes. Yes, I am. If you saw how cute my nieces are, you’d understand.
I have a question about [Client]!
Stay calm, sir/ma’am. The friendly folks at [address] are here to help.
I have a question about [different Client]!
Reach out to [address]. He’s the best. And his doodles of Disney characters are downright inspired.
I need something else!
I’ll get back to you as soon as I can on Tuesday. It’s going to be OK!
How will I pass the time while you’re away? Can you please recommend a good podcast or TV show?
Have you tried Reply All? How about The Good Place? Or just rewatch Alien. It holds up.
What’s a style or format that’s entrancing or amusing you lately? Can you somehow Frankenstein it into an OOO autoreply? I’d like to see your attempt!
Invite conversation by sharing what you’re up to
One way to help colleagues get to know who you are outside of work is to…tell them what you do outside of work!
Here’s a nerdy email I wrote about seeing “Hamilton”:
Did you know that I have a lot of feelings about musical theater? Fun fact: I have a LOT of feelings about musical theater. I am a human vessel of Musical Theater Emotions.
I’m confessing this to you now because my heart has led me to Chicago to take in a performance of a little show called Hamilton, and as a result, I am out of the office until Thursday, 10/27, when I shall eagerly peruse your correspondence.
But don’t feel helpless!
If you have an urgent question related to [Client], [Colleague] ([address]) will make sure you’re satisfied.
If you need help with something related to [Client], you don’t need to wait for it: [Colleague] ([address]) has your back.
And if you need immediate assistance with anything else, please reach out to [Colleague] ([address]), my right hand man.
I have the honor to be
Your obedient servant,
Here’s another from when I went on yet another Disney vacation:
Hello! I’m out of the office from Friday, 10/13 through Monday, 10/16, for an emergency trip to Disneyland. You know, like what happens when you’re an adult. If you need anything while I’m away, please reach out to [address], or sit tight until I return. Unless you have recommendations for Disneyland snacks I need to try, in which case you can text me at [number]. Thanks!
Of course, with all of these, the usual caveats apply: Respect your company culture; provide the vital info up front for folks who are busy; and strike a positive, helpful tone.
I hope I get a chance to see what you come up with!