Disaster Confessions: When creative workflow goes horribly, hilariously wrong

There are minor professional slip-ups – like putting a kiss at the end of an email to your boss – and then there are career-defining, folklore-level disasters. The kind that makes you break out into a cold sweat and feel a biblical wave of nausea, the kind that gets referenced in meetings for years, the kind that, if you’re lucky, happened to someone else – and if you’re not, will haunt you forever.

Welcome to Disaster Confessions – a collection of real, spectacularly painful creative workflow horror stories. The ones that often start amidst a busy, messy process and spin out into full-scale chaos. We’ve gathered the best (or worst?) from across the industry, and to make sure no one ever has to suffer like this again, we’ve brought them to life with illustrations by Simon Landrein – because sometimes, the only way to deal with workflow disasters is to laugh through the pain.

And if any of these stories hit a little too close to home, it might be time for a workflow intervention with the Air team of experts.

The Reply-All Apocalypse

“I had spent the better part of an afternoon trawling through an endless email chain, searching for proof that the client had, in fact, asked for the changes we were now being asked to take out of the work. I don’t even know why I wanted to find it. I was going to have to make the changes anyway, but for my own sanity, I wanted evidence. Finally buried somewhere in the 100th reply, there it was: the approval note I’d been looking for.

Feeling slightly smug, I hit Forward to a small group of colleagues and wrote something along the lines of:

‘See? I knew they’d already approved this. Idiots.’

Only, I didn’t hit Forward.

I hit Reply All. And, the client was very much included in ‘All.’

The instant I realised, my soul left my body.

I felt sick for days, but we made the changes, and everyone pretended the email had never happened. I styled it out at the next meeting but felt ill in the car going over there. Now, I always log approvals and changes in a separate doc and have a delay on my email.”

The Link Has Expired

“We needed to send final high-res assets to an external partner – nothing complicated, just a quick file transfer. Someone dropped a file transfer link into the email thread, and we all moved on with our lives.

Fast forward a week later, and the partner comes back with: ‘The link has expired. Can you resend?’

Except by then, the files had been moved, renamed, and (somehow) duplicated across multiple storage systems. No one could remember who had the final version, and after an hour of frantic searching, we had to re-export and re-upload everything from scratch.

We lost hours over something that should have taken minutes. Lesson learned? If your assets are scattered across half the internet, expect chaos.”

The Auto-Sync Nightmare

“We were putting together a client presentation in Google Slides – still mid-project, but polished enough for a check-in. The designer was still making tweaks, so I saved a separate version for the client and sent them a different link to continue working in. Or so I thought.

We all log on, exchange the usual small talk about the weather and someone’s cat, and I start talking through the presentation. Then, as the creative director is explaining the design rationale, we watch in real-time as the deck starts changing on screen.

A headline suddenly shifts position.
A text box appears that just says, ‘DO WE EVEN LIKE THIS??’
And then – an image gets swapped for a meme someone had uploaded as a joke.

Cue frantic side messages to get everyone out of the deck while we awkwardly skip past the slides. Now, we never present from live files. Lesson learned.”

The M.I.A. Freelancer

“We’d hired a freelancer for a big campaign. Everything was going smoothly – weekly check-ins, clear deadlines, assets trickling in on time. Then, two days before launch, we realised we were missing one crucial final file.

We sent an email. No response. Called. No answer. A Slack message. Still nothing. A polite-but-slightly-panicked follow-up. Radio silence.

Hours later, we found out they were on a plane to Bali, completely off-grid, having assumed we had everything we needed.

We did not.

Cue an all-nighter recreating the missing asset from scratch, a last-minute export that made the deadline by minutes, and a team-wide mandatory debrief on never letting this happen again.

Final check-in means nothing if you haven’t actually received the files.”

The One-Man Server

“Our design director had one fatal flaw – he could never connect to the server. Rather than fixing the issue (he always said he’d sort it when he had time), he saved everything to his own hard drive, convinced it was the safer, more reliable option.

That was, until a major editorial project was in full swing, and he took a trip to Munich. He packed his laptop and every master file stored exclusively on his precious, offline hard drive.

Then he said his bag got stolen at the airport, and with it, days of work completely gone.

We scrambled to recreate everything from older files, knowing full well we’d never match it exactly. A day before the deadline, the airline got in touch to say they had his bag and his laptop – I think he lost it and made up a story about it being stolen – but we’d already redone half the work, lost hours of sleep, and collectively decided we hated him.”

The Asset That Time Forgot

“Halfway through a major rebrand rollout, we discovered a tiny but horrifying issue – our new logo wasn’t consistent across all files. Some versions had a slightly thicker stroke, others had a misaligned baseline, and one file had a random shadow effect that absolutely should not have been there.

It turned out the design team had accidentally been pulling assets from multiple folders, each containing slightly different iterations. By the time we caught it, the inconsistency had already made it onto brand guidelines, packaging artwork, and a live client deck.

Cue several hours of damage control, a panicked rush to fix everything, and a styled-out conversation with the client where we said we were trying out different versions.

Now, everything is filed following a rigid central system, and we have a ninja naming protocol.”

Has this happened to you? It might be time for an intervention.

These stories are funny because they didn’t happen to us. But for every file that goes missing, approval chain that spirals out of control, and asset that mysteriously duplicates itself, there’s a team losing valuable time, money, and sanity.

That’s where the Air It Out Hotline comes in. If any of these disasters feel painfully familiar, it might be time to fix the cracks in your workflow before they become full-blown catastrophes.