What I learned at my first Fuck-Up Night (#51)

Three people stood on stage and told the truth about their failures.

Not the polished LinkedIn version. The real one.

And somehow, all three stories landed on the same lesson: you already knew what you had to do. You just didn’t trust yourself enough to do it sooner.

On February 25th 2026 I was invited by Dejan Stojanovic to my first #FuckupNight Fuckup Nights Vienna, — an event format where founders and executives get 10 minutes to talk about their biggest failures, followed by open Q&A from the audience. No slides. No spin. Just the story.

It was Vol. 51 here in Vienna, held at The Social Hub Vienna. Full house. Great energy.

Here’s what stayed with me.

Ingrid Wick grew up knowing she would run the family business.

She literally wrote it in her high school yearbook — dream job: Chefin. Boss. Not a vague aspiration. A conviction. The company was Wick Norm Fenster, a window manufacturer that had been in her family for four generations.

She spent years working toward that role, navigating family dynamics, internal politics, and the slow-motion collision that happens when multiple generations and multiple egos all claim ownership of the same thing. Eventually the conflict became unsustainable. The company went insolvent.

Her fuckup, as she framed it: she stayed too long. She kept believing it could be saved, kept absorbing the stress, kept showing up — long past the point where leaving would have been the right call.

What finally shifted things was her father. He looked at her and said: do what’s right for you.

That was enough.

Today she works with family businesses going through exactly this kind of transition. She didn’t leave the topic — she went deeper into it, this time on her own terms.

Klaus Buchroithner co-founded Vresh GmbH , a streetwear brand. Now running Das Merch.

At some point, the team had an idea: Mark Zuckerberg always wears the same grey shirt. What if they sold that shirt? Simple, iconic, a little bit cheeky.

They talked to two lawyers. Both said: don’t do it.

They found a third lawyer — recommended by an investor, someone with a reputation for being bold. He also told them not to do it.

They did it anyway.

The campaign went viral. The domain was

https://zuckerbergshirt.com

. Marks photo was on the website. Within a short time, a cease-and-desist arrived from a major law firm acting on behalf of Zuckerberg.

Klaus said he aged seven years in that period.

But here’s the real fuckup — and it wasn’t the legal risk. It was that they had no Plan B. No fallback domain ready to redirect traffic. No alternative product name queued up. No press samples to send out when the attention hit. They hadn’t produced a single shirt. All that viral momentum, and nothing to catch it with.

After they shut everything down, the law firm went quiet. No further action. The whole thing cost them lot of sleepless nights — but also became one of the best marketing stories they’ve ever told.

The lesson isn’t “don’t be bold.” It’s: if you’re going to be bold, at least know what you’ll do when it works.

Claudia Reiterer spent 27 years at ORF.

She was one of the most recognizable faces in Austrian journalism. She knew how to dissect political situations with precision — live, on camera, under pressure. Analysis was her craft.

Then something happened internally. She was careful about the details on stage — there were clearly things she couldn’t or didn’t want to say publicly — but the outline was visible: a political shift, a change in who held power, and suddenly someone who had been a fixture for nearly three decades found herself being offered a desk job. A room somewhere. Some Excel spreadsheets.

She stayed. For a while. Because the job meant security, and leaving meant uncertainty, and that felt like a lot.

Eventually she did what she probably should have done earlier: she made a simple flipchart. Two columns. Reasons to stay. Reasons to go. Financial security was the only thing in the left column. Everything else — freedom, new challenges, reclaiming her identity, not spending her days in a back office — was on the right.

She left. Without a single word from management. Not a thank you, not an acknowledgment of 27 years. Her colleagues organized a small goodbye — Tarek Leitner and others — and that was it.

In the audience Q&A, she mentioned that at a women-only event, she shared her story and seven women immediately said it had happened to them too. Same pattern, different organizations.

Her reflection: at 24, she was braver than she was at the end of those 27 years. Somewhere along the way, security had quietly replaced courage as her default setting.

The audience answered a couple of live question. The most revealing: What’s your biggest takeaway?

The answers came in from across the room: Mut (Courage). Bauchgefühl (gut instinct). Einfach machen (just do it). Bauch hat immer Recht (the gut is always right).

Same ideas, over and over. In German, in English — same answer. A truly inspiring community.

It was my first Fuckup Night. It won’t be my last.

And at some point, I might be the one standing on that stage.

I’ve got enough material. 😅

Thanks to Dejan for organizing, and to Ingrid, Klaus, and Claudia for having the guts to go first.