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What if the key to networking isn't your success, but sharing your biggest screw-up?
A blend of laughter, vulnerability, and courage—something you couldn't find anywhere else in the city—was what inspired Tamar Gaffin-Cahn to bring FUN to Boston
By:
Blanca Smith
Overcoming the shame and stigma associated with making mistakes requires a direct and forthright approach.
Everyone makes mistakes, without exception, but when there is a safe space to talk about them with people who are willing to listen and have good intentions, both our professional and personal lives improve.
That revelation was what motivated Tamar Gaffin-Cahn and Sam Feldman to take the movement to Boston. Their goal was clear: to eliminate the shame and stigma surrounding making mistakes through a direct and authentic approach.
They set out to build a welcoming community where people could set aside corporate facades and connect through real, unfiltered experiences. Over the course of five events, the Boston chapter has reached 270 attendees across seven different industries.
Laughter as a tension release
For Tamar and Sam, leading the chapter on Boston has shown that the preparation process is just as crucial as the event itself. One of the most rewarding aspects of co-leading the chapter is working directly with the speakers to help them process where their shame originally came from. Most of the time, the feeling of failure stems from unmet expectations and the fear of disappointing others or oneself.
Professional settings are often dominated by anxiety and shame. On stage, humor serves as an immediate release from tension. In Vol. II, that emotional honesty reached a point where the entire audience was in tears as a speaker shared what it was like to work at a terrible job while staying by the bedside of the woman who had raised her and who was dying.
Do you want to be a leader in your community?
Organize " Fuckup Nights " events in your city
Create a space where people can connect, share their failures, and grow—whether you run a coworking space, a community space, a business, or a conference.
Build your community and generate income while you’re at it!
Real connections happen organically at Fuckup Nights. During Vol. V at Fuckup Nights Boston, an employee from the venue’s brewery joined the audience without any expectations. At the end of the night, he approached Tamar and Sam to share that it had been one of the best events he’d ever attended, praising how naturally the format guided attendees toward vulnerable and meaningful conversations.
One of the most memorable stories shared on stage was that of a film director who received a government grant and hired her friends to make a movie. Along the way, she restructured the project, ignored her team’s advice, and ultimately lost most of those friendships. The film received no awards or recognition. The story served as a stark reminder of how easy it is to become consumed by one’s own vision to the point of losing sight of the relationships around us.
Radical collaboration in the community
After a year of leading Fuckup Nights Boston, both co-directors feel more connected to the community. As a third-generation Bostonian, Tamar sees the chapter as a direct way to contribute to her city, while Sam notices a simple change in everyday interactions: “When I say I co-organize ‘ Fuckup Nights,’ absolutely everyone is interested.” At home with the kids, however, they refer to the event strictly as “Mistake Night.”
The advice for anyone looking to get a license for their own city is simple: collaborate wholeheartedly with others. Starting a chapter isn’t something you can do alone; it requires a collective effort from the community. Finding an excellent co-organizer is essential, and local bars are often happy to offer their space for free to support real community growth.
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