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On Thursday night, San Antonians have a chance to learn about some major mess-ups by well-known residents of the city they share.

Chef Tim McDiarmid, fashion icon and on-air personality Leighton W., and realtor and “world-traveling superconnector” Jessica Conrad will deliver concise, Pecha Kucha-style presentations for “F—Up Nights Vol. 1” Thursday evening at Ivy Hall.

The franchise began in Mexico City in 2014, and has since spread to 300 cities throughout the world, including La Paz, Bolivia; Brussels; and Taiwan. Through the efforts of Anne Wolfe-Andersen, San Antonio is now on that list.

“When I lived in Mexico, I attended a F—Up Nights, and I thought it was such a brilliant concept,” Wolfe-Andersen said of her first experience four years ago.

“I believe this world is in a lot of ways moving towards being far too sensitive and simultaneously, not nearly sensitive enough,” she said. “To me, F—Up Nights is about inspiring both more radical empathy and humble bravery in every aspect of life.”

After observing many cities as a business consultant, she recognized something missing in San Antonio’s ability to reckon with its shortcomings as a city.

“Embracing failure is necessary, I think, for a lot of communities to grow and develop, for business to grow and develop, for people to be able to move the needle in a lot of the more disadvantaged areas of our community,” she said. “In very successful communities, like startup communities, people talk about these things.”

McDiarmid is not recognized in San Antonio for failure, but for her success as “Tim the Girl,” guiding The Good Kind restaurant on South St. Mary’s Street through the pandemic, while also leading a philanthropic effort to feed frontline health care workers called “Be the Good Kind.”

But such unexpected revelations are part of the point, Wolfe-Andersen said, “because it’s just so important to know that we all fail so often. People who try to do something get discouraged because they think people are successful immediately, and most often they’re not.”

Early on, the main organization posted an explanation of its goals and purposes on its blog. Among its chief messages is, “we don’t celebrate the failure, we celebrate the resilience.”

The point is “trying to understand the failure, to see what we can learn from it, and ultimately, celebrate the resilience of the people who have failed and lived to tell the tale,” according to the accompanying explanation.

Leighton W. said he feels he is too often seen as “perfect” when he’s out in public, a perception he would like to shed. His successful career as a beauty and wellness entreprenuer has not been without its flaws, he explained, including a recent pandemic-related dispute with his main funder behind the Loma de Vida Spa & Wellness center at La Cantera, which resulted in the loss of his contract.

Though some who know him might see that as a failure, Leighton said he would not have risked the health and safety of his customers and co-workers to reopen too early, as was asked of him.

But that episode is not in fact what he intends to speak about on Thursday evening, he said. Nor will he be talking about deciding not to push toward releasing a new skin-care line people had been expecting, and he won’t be talking about a general perception that he’s “ousted” himself from the San Antonio fashion community.

Instead, he’ll be talking about the personal evolution that failure can inspire if met with resilience, well in keeping with the aims of Wolfe-Anderson and the community in general. Without giving away the subject of his talk, he allowed that he would address a realization brought on by the invitation to speak.

“I realized that my biggest [mess-up] really wasn’t anything that I necessarily did in the motions of my everyday professional life,” Leighton said, but in how he made decisions.

And he hopes his story and those of his fellow speakers will help others understand how to accept their own failures.

“When you find the people that are actually willing to talk about how they they had a perceived failure of their own … it’s really empowering. You feel a little bit less alone,” he said.

Wolfe-Andersen said she hopes the first event will be successful and become a regular fixture in San Antonio, and will help inspire her community.

“My goal is for people to feel inspired and to leave having had a really good time,” she said. “And with any luck, they’ll feel like their scary dream is a little closer or a little easier to obtain than maybe they thought.”

Tickets for in-person and online-only attendance are available on the F—Up Nights San Antonio website. A free dance party will follow the presentations.

Nicholas Frank

Nicholas Frank moved from Milwaukee to San Antonio following a 2017 Artpace residency. Prior to that he taught college fine arts, curated a university contemporary art program, toured with an indie rock...