When the server walked past our table, my hand shot upward like a high-schooler eager to answer their teacher’s question.
“Can we get two more of the same, please?” I asked upon getting his attention.
“Another round of espresso martinis? I got you, boss.”
Leona grinned and nodded in approval, as expected. We go back like four flats on a Cadillac. From study buddies back at the G.O.A.T. HBCU to marketing professionals putting in work for thriving companies, we’ve remained a two-person support system. It’s a celebration every time we link up. So it’s only right that we throw back a few cocktails while getting our yap on.
Sipping a boozy, caffeinated concoction at 2 p.m. on a Tuesday has a way of making me chatty. It also makes me wonder why more of my peers don’t observe the same tradition. Weeks before this rendezvous, Leona and I both planned to burn a day of PTO, coordinating our schedules like a couple of executives setting off for a retreat. Except the only agenda on this outing was tacos and real talk. We call it the Skip Day.
The premise is simple: You and a friend both call out from your respective gigs for a workday hangout. This is not earmarked time for errands or spent couch rotting in solitude. It’s two (or more!) friends sharing a mental health day while the rest of Corporate America clocks in. Skip Day is the adult version of faking sick in grade school, except you don't have to fake anything. You just make sure you’re anywhere but your workplace.
The Skip Day didn't start as a formal thing. It evolved—the way most good traditions do—out of necessity. After weeks of failed meet-ups and playing calendar tag, we decided to multitask by co-working from a local Seattle café. We locked in, knocked off to-do lists, and squeezed in some kikis between tasks. It became a regular thing every few weeks. Eventually, we decided to cut the work part out altogether.
For Leona and me, it has become a seasonal ritual, and this latest Skip Day reminded me why it’s so important. It’s a moment to mute Slack messages and email notifications, while pouring into each other (and each other’s glasses). There, at that trendy Mexican restaurant, we traded career updates and inside jokes. Leona vented about her condescending-ass manager and celebrated the large-scale project she recently headed, wondering aloud what future opportunities it could unlock. My updates were familiar: the steady, sustaining drip of contractor work and the draining hunt for a full-time role. These topics are difficult to explain for people who haven’t lived it, but require no translation between us.
We started with drinks and guacamole, but Skip Days have a way of extending themselves. One spot becomes two, two becomes three. By the time we sat down for dessert, the conversation had shifted from light stuff like weekend plans and what we'd been watching to the real stuff: politics, family, the future, the past. It was the kind of conversation that makes you feel like yourself again, without the need for corporate speak or code-switching. And something about doing that when you would otherwise be on your fourth Zoom meeting of the day makes it feel even more fulfilling.
Skip Day doesn’t have to be spent eating or drinking. Take a hike or a day trip. Go see a matinee. Do some window shopping. Hit up a botanical garden. The only limits are your imagination or budget. The magic is as much about where you're not as where you are.
Long ago, United Negro College Fund commercials taught me that a mind is a terrible thing to waste. The same could be said for PTO days spent on obligation or isolation (or even worse, not taken at all). Find that person who you vibe with like no other, someone who gets it, someone who fills you up. Pick a day you're both free, outside of intense deadlines or work duties. And just show up for each other. You probably need it more than you think.