Sam Feldman almost got fired from a job at TripAdvisor before his first day. Tamar Gaffin-Cahn unleashed technological chaos after changing her company’s Facebook information.
These may seem like off-color introductions for two leaders of a networking event to make to a sold-out crowd, but the gathering held at Boston’s Trident Booksellers last week called for nothing less. The event series — whose name is similar to “screwup nights,” with a certain expletive twist on the first word — celebrates the shared rite of workplace errors as a way to go deeper than the elbow-rubbing and sowhatdoyoudo? chatter of typical professional get-togethers.
And it all starts, said Gaffin-Cahn, with the gathering’s not-fit-to-print title.
“Even the name itself is in your face, and it’s authentic,” said Gaffin-Cahn, who works in the career development center at Emerson College and has a side-gig as a life, leadership, and career coach. “I think that that’s what people are craving when it comes to building professional relationships.”
The arrival of the event series to Boston, after more than a decade taking root in hundreds of cities globally, comes at time of widespread stress among workers as the job market wobbles. The nights, its organizers hope, serve as an antidote to this anxiety, offering a chance to shed corporate veneers, laugh over cringeworthy faux pas, and maybe even walk away with a business card or two.
“I don’t want to do an elevator pitch of myself,” said Feldman, a job search coach who is working to relaunch Impact Hub Boston, a coworking space. “But when I have conversations with people about just how [bad] my week is going, or the thing that I messed up, or all the things that I still feel, after doing this for a while, that I’m still stuck at — that’s where the bonds happen.”
Feldman and Gaffin-Cahn launched the Boston chapter last year, with a November event at Somerville’s Aeronaut Brewing Company; the Trident event was the sophomore gathering. The concept has been around since 2012 — the product of a booze-filled night out with friends in Mexico, said cofounder Pepe Villatoro.
“We complained a lot about the simplistic success stories” common at conferences and other professional events, said Villatoro. “We said, ‘Okay, stop. Instead of complaining, let’s try to lead by example and share our biggest failure.’”
At the Trident event, three speakers each got seven minutes and 10 slides to accomplish that mission. The crowd was not spared the mortification; in between each speaker, Gaffin-Cahn read aloud a failure written anonymously by attendees on sticky notes and pasted on the back wall.
The entries ranged from the harmless — “I drove around Indianapolis for an hour thinking it was Bloomington (pre-GPS!)” — to the regrettable — “I got caught making a plan to get my boss demoted” — to the downright frightening — “I gave the wrong address to a school bus full of kids on a field trip.”
After Gaffin-Cahn led the crowd in three deep breaths, requesting a collective F-bomb on the final exhale — “who feels better? I feel better,” she said — the speakers took the stage. Camille Clark, the senior vice president of operations at The Possible Zone, a Boston nonprofit, talked about spending years hustling in the corporate world, seeking the validation of the “cool kids” after growing up in poverty. Sharon Topper, who teaches at Emerson and Boston University, recounted being unceremoniously let go from a startup that printed images on coffee foam. Ben Shown, the head of design at the Seattle-based consulting firm Blink UX, described being taken off a project after his ego got in the way of listening to proposed changes from his boss.
Once the speakers concluded, Gaffin-Cahn and Feldman presented each of them with a ball cap emblazoned with the words “Embrace Failure” on the front — with ‘failure’ aptly misspelled on each.
After presenting, Clark, 51, said the experience was cathartic — even after her decision to bring her iPad up on stage so she could be sure to remember her lines required an extra dose of humility.
“People who I don’t know know these things that I thought were shameful, but actually made me a better person, better leader, all that stuff,” she said.
Many attendees jumped at the chance to unburden themselves of their professional snafus. Gloria Xiao, 24, a financial analyst, recalled a slip-up involving the central repository her company uses to store all its data.
“I submitted wrong information and overwrote all the correct information,” she said, a story that earned a big laugh and high-five from her friend James Chang-Davidson, who runs a software consultancy at Northeastern University.
Though Xiao’s error produced a string of panicked Microsoft Teams messages from her boss, she said she didn’t sweat it too much.
“If you’re successful at something, you must have failed many times,” she said. “Anyone who says they haven’t is lying.”
Maura Vogel, another attendee, who works as the director of graduate student recruitment and strategic partnerships at Tufts University’s Gordon Institute, said the prospective students she interacts with “need to know this stuff.”
“It’s cool to hear that it happens all the time, every single day, everywhere,” said Vogel, who added that her biggest failure was accidentally sending out admission decision letters that shouldn’t have gone out.
Gaffin-Cahn and Feldman said they hope to host events about every two months — the next one is scheduled for March 25, at a to-be-determined location — and eventually bring the concept to offices. They’re starting to be on the lookout for new speakers, who in addition to sharing their tales of workplace woe must also reflect on “lessons learned,” Gaffin-Cahn said — the values reassessed, the career changed, or ego checked in the wake of failure.
That seemed to be the main takeaway for attendee Ariel Lowinsky, 29. His biggest failure? “I got fired from my job, I got embarrassed in front of everybody, my whole company.” But it’s also what led him to starting his own venture.
“It was the best thing that ever happened to me,” he said.
Dana Gerber can be reached at dana.gerber@globe.com. Follow her @danagerber6.