Office Shenanigans: The Out of Office Message Side Hustle
Taking time off work makes me paranoid. Let’s say I take a few days off, and the proverbial shit hits the fan: I’m saddling my coworkers with extra work, and they have to put in extra hours to make sure I can have a few carefree days of rest and relaxation. Even worse, what if I take all that time off and nobody notices I’m gone? Did I just vacation my way out of a job?
This is an incredibly unhealthy way of looking at work, and it’s taken me years to actually take my allocated time off without going through an emotional roller coaster of doubt and recriminations. My solution? Going to extreme lengths in composing out-of-office messages. If I could convince myself that coworkers looked forward to my out-of-office messages, I’d feel better about the extra work they had to put in on my behalf. And so, I started taking advantage of how Outlook lets you set different out-of-office responses for internal messages.
The Basic Formula: Fun Fact, Bad Pun, Cute Critter
Most of my out of office messages followed a basic formula: share a fun fact, inflict a terrible pun, and share a cute critter picture in between essential facts about who to contact for what reasons. Here’s an example:
Fun Fact of the Day: Google has a custom error page: Error 418. I’m a Teapot. This is a ridiculously obscure joke based on the initial request for comments on Berners-Lee’s proposal to establish HTTP (hyper-text transfer protocol) as the standard for the internet. Larry Masinter at the Xerox PARC replied with the “Hyper Text Coffee Pot Control Protocol for Tea Efflux Appliances”, or HTCPCP-TEA. The protocol called for replying to attempts to brew coffee with a teapot with “ERROR 418: I’M A TEAPOT.”
Now that teapots are connected devices, Error 418s are theoretically possible. Google’s Error page, though? A practical fact. (source: Now I Know)
Fun Joke of the Day: Every morning I wake up and think about cooking up a batch of pancakes, but I keep waffling.
Cute Animals of the Day: Did you know that some cat afficionados refer to their habit of kneading as “makin’ biscuits”? Here is a cat makin’ biscuits.
By sticking to that basic framework, creating a new out-of-office message became a fairly procedural thing. But that got boring, so I started getting a little more creative with the formula. When I had to miss the company’s 90s Prom party, I filmed an apology video to include in my out-of-office message. And then I filmed another apology video for missing an evening of axe throwing. Heck, when I missed the office holiday party one year, I created an office-wide scavenger hunt that started with my out-of-office.
That’s when the consulting gigs started.
Birth of a Side Hustle: Out of Office Messages For Hire
Eventually, coworkers started asking me to write out of office messages for their vacations, as well. And how could I turn down the opportunity to take over other peoples’ inboxes, especially when they’d let me use their inboxes for product placement, like the following message?
Hi, you’ve reached [coworker]’s inbox.
They’re going to be out of office until DATE, and auctioned off control of their auto-responder to the highest bidder. So now you get to learn about the wonders of Casper brand mattresses — they’re like regular mattresses, only sold through affiliate codes! Buy a mattress with code CHERRYBLOSSOM for a 10% discount on your perfectly ordinary mattress purchase!
For urgent concerns, please reach out to [coworker’s boss]. For any Mattress Purchases, go to CASPER with affiliate code CHERRYBLOSSOM.
Fun Fact of the Day: [coworker] is going to DC to enjoy the cherry blossom festival. Because cherry trees only bloom for a week or two, they have come to represent the concept of “mono no aware”, the wistful realization that nothing lasts forever.
…just like our deal with Casper Mattresses, using affiliate code CHERRYBLOSSOM. Sleep sound knowing you got a great deal, because we’ll all be dead eventually.
Joke of the Day: Why are rivers lazy? Because they never get off their beds!
…and if you take advantage of our Casper Mattress promotion, you’ll never get out of bed either! Use affiliate code CHERRYBLOSSOM for 10% off.
I shouldn’t need to explain that Casper did not sponsor this out of office message and the affiliate code didn’t work…but my coworker did actually use that message when they were out! Which only made me bolder for future sponsortunities…like the time I made set up an email triage system for someone I didn’t even work with any more.
Hi! This is [former coworker]’s email address.
Unfortunately, [former coworker] is out of office, and can’t get back to you. Luckily, they outsourced the following triage system to handle your request accordingly. Please follow the instructions below.
STEP 1: If your request is urgent, please proceed to step 2. Otherwise, please proceed to step 15.
STEP 2: Are you sure it’s urgent? I mean, really really sure? If so, go to step 3. Otherwise, go to step 14.
STEP 3: Okay, fine. Is this a work thing, or do you have cute puppy pictures to share? If this is a work thing, please proceed to step 4. If you have cute puppy pictures, please proceed to step 13.
STEP 4: Still here, huh. Fine, we’ll get down to business. If this is something where a coworker might be able to help, please proceed to step 5. If you really need [former coworker], please proceed to step 6.
STEP 5: For questions regarding [client], please contact [Email A]. For questions regarding [other client], please contact [Email B]. For all other concerns, please proceed to step 13.
STEP 6: if this is an urgent work request that involves sending [former coworker] puppy pictures, please go to step 13. Otherwise, go to step 7.
STEP 7: [former coworker] will compromise and accept kitten pictures. If that works for you, please proceed to step 12. Otherwise, please go on to step 8.
STEP 8: Michael has given up all pretenses of using [former coworker] as an excuse to solicit cute animal pictures. Hedgehogs, bunnies, otters…whatever you have, he’ll take. Just send them over to [my personal email]. To handle your urgent request that doesn’t involve cute pictures, go on to step 9. This time, it’s for real.
STEP 9: Thank you for your patience. If this is something that absolutely requires [former coworker]’s immediate attention (see step 2), can’t be handled by their contacts (see step 5), and doesn’t involve cute animal pictures (see most of the listed steps), you can reach them at [emergency contact info].
STEP 10: This step intentionally left blank
STEP 11: There is no path to reach this step in [former coworker]’s email triage process. How are you reading this? The email triage system depends on compliance with instructions. Please return to step 1 and try again.
STEP 12: Cute kitten pictures should be sent to [my personal email]. He will not pass them on to [former coworker], but will be grateful for your assistance.
STEP 13: Please forward your cute puppy pictures to [my personal email], and he will ensure they reach [former coworker]. Probably. It’s possible this step is the payment he demanded in exchange for writing the out of office message.
STEP 14: [former coworker] is a little disappointed that they had to ask twice, but appreciates your candor. Please proceed to step 15.
STEP 15: Thank you for respecting [former coworker]’s vacation! They’ll get back to you when they return, and appreciate your patience.
So, yeah. I went a little overboard. But I got cute animal pictures out of the deal! Which, truth be told, is a bit of an ongoing theme with my out of office for hire gigs. Case in point? My most recent experiment in fake neural nets, for a friend’s ski trip.
Hi! You’ve reached the inbox of [friend].
She will be unavailable until [date], living out her dreams of belting out showtunes in a Frozen wonderland, but don’t worry: she fed the entirety of her email archives into a neural net, and generated the following prompts to address most of your concerns.
That’s a good question. I’ll have to circle back with the team before providing a formal response, but know that it’s my top priority.
Can you rephrase that question in the form of a cat picture?
Heck yeah I’m in for skydiving next Wednesday — did you really need to ask?
I think we need to think long and hard on that before moving forward — it’s a big decision and we don’t want to be hasty.
I’m worried not enough people are taking my request that all questions take the form of cat pictures seriously — do you think they need examples first?
Yes, of course I’ll share the video of me singing Let It Go on a mountaintop while wearing a flowing dress to YouTube. It’s the least I could do for Michael’s assistance in setting up the neural net email auto-responder system!
Sure, let’s tentatively approve a broader rollout of the neural net auto-responder project — what could go wrong?
If the above responses didn’t address your concerns, technology has failed us all and [friend] will get back to you by [date]. For inquiries of a more urgent nature, please reach out to [Person A], and they should be able to help. For true emergencies that require my attention, they have my contact information but you wouldn’t put them in a position to deal with that guilt, would you?
With one notable exception from a friend’s boss with no sense of humor, reviews of the messages have been positive, since the bar for amusing messages have been set so abysmally low. And maybe that’s the real moral of this story: compete in niches nobody cares about, and even half-baked ideas will look like innovative work.
