What Admitting Failure Taught Me About Advertising
About irrational honesty, the past two years & the future of this blog
This blog is a failure!
It’s been more than two years since my last post.
In the meantime, I got sidetracked by getting a job, losing it again, following leads to nowhere, getting hit by depression, and starting over.
And to make matters worse…
If you were once a regular reader, I failed you.
Now I beg your forgiveness.
But if you read on, you have my word (1,925 of them to be exact) that I’ll make it up to you.
There’s even a musical surprise!
Here’s the story of my latest misadventures and what they taught me.
I’m a Loser, Baby, so… What else is new?
What happened in the past two years?
All the way back in 2022, the last time this blog was updated, I was negotiating with Bang & Olufsen about joining their design team.
The Danish audio brand was looking for a “conversation designer” — what sounded like a sound designer who could write a bit.
Having tried (and failed at) both, I wrote them a cheeky mail, arguing that what they really needed was the opposite: a writer who could sound design a bit.
To be perfectly honest, I wasn’t even sure I wanted the job.
I just wanted to see if I could challenge the premise.
My parents’ B&O radio in the 80s, Beolab 1900, was cooler than Transformers and Knight Rider combined.
I had been a lifelong fan of the iconic Danish brand but was afraid the company was simply too old-fashioned and rigid.
After 10 years of working with video games, I had grown weary of the power dynamics between creativity and engineering in the tech industry (you can read about it here, here, and here).
However, my fears were put to shame by the passion and mission of the new design team.
The Chief Design Officer had come from Apple and brought a clear vision for the future.
The team managers were dedicated, knowledgeable, and in it for all the right reasons.
New winds were blowing at the ol’ radio factory and soon I was sold.
Somehow they were sold too.
I’d like to tell you I’m just that good of a salesman.
I’d like to say it’s easy to persuade a big company that what it wants is wrong and what it needs is me.
But it speaks to the true character of an organization when it can take a step back and reconsider its priorities. It’s hard to find something you’re not looking for — even more so if you’re a company with multiple stakeholders.
I reckon it was 15% salesmanship, 25% unearned confidence from not being serious, and 60% B&O Design being smarter than me.
If nothing else, they were smart enough to win me over and make me actually want the job.
After six rounds of interviews, the position of Conversation Designer was taken down, and I became the first “Design Writer” in company history. Together, we would figure out what the hell it meant as we went along.
“We’ve never hired anyone like you. You’re gonna be the tip of the spear.”
I figured a speartip might meet obstacles and get headaches… yet I jumped in headfirst.
“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”
Oh boy, did I fail.
Even now, I don’t know what a Design Writer is supposed to do.
Over the following months, I served as a UX writer, copywriter, deck builder, presenter, translator, ice breaker, bartender, truth whisperer, and spin doctor.
What a ride!
Then a series of unrelated events happened and priorities changed. Even if I wanted to, I couldn’t tell you about it.
When the dust settled, all but one of the design leaders and managers had left.
The hard-to-define Design Writer role was shut down and I was offered to move to internal communication… to help explain why the design department was no longer there.
Being a nostalgic softy, I wish I could have stayed. I loved the brand and soon my colleagues too. Still do.
But the people I had come to work for were all gone.
If I moved to internal communication, it would now be my job to argue why my old job was never important in the first place.
I could appreciate the irony, it sounded morbidly funny… but not fun.
I declined and left B&O in October 2023.
The last product I worked on just came out. Shoutout to the team!
Diving, floating or freefalling back into uncertainty, I spent the better part of the autumn and winter wooing an international consultancy — only to discover they were never actually interested.
I briefly accepted a job as creative director for an upstart agency — only to find out it had no clients and was little more than one person’s pipedream.
And finally, I wrote, recorded, and released an indie rock EP as an allegorical year-in-review — only to remember that music is for young people with hopes and dreams.
I succumbed to winter depression and it carried over into spring.
Failure upon failure got to me.
Summer was spent crawling back out of my shell and then…
Well, then is now. We’re here. Today.
I promised you a musical surprise. It’s available on on Spotify, Apple Music and everywhere.
A History of Failure
Why am I telling you this?
Real weakness is the inability to admit weakness.
The more fragile the ego, the tougher the facade.
It’s why narcissistic machomen and gurus on social media can build quick followings — but have trouble retaining trust once the act falls apart.
And acknowledging failure isn’t just cathartic — it’s strategic.
“Confession is good for the soul and for copy too.”
Every copywriting icon from David Ogilvy to Bill Bernbach to Dave Abbott has a quote about the importance of truth in advertising. In fact, I started the very first essay on this blog with one of them.
Many classic campaigns have stood out and made people talk with brutal, self-deprecating honesty.
When KFC ran out of chicken in the UK in 2018, their apology went viral and became their most effective campaign in recent memory.
When Avis Rent a Car launched its famous "We Try Harder” campaign in 1962, it ran for 50 years because the hero’s journey and admission of only being number 2 was believable, while their boasting competitors had the trust of… well, car rentals.
When Volkswagen broke into the American market with the “Think Small” campaign, they did so with self-deprecating taglines like “Ugly is only skin-deep” and created advertising history.
Admission and confession build trust.
It’s probably why Warren Buffet begins his annual letter to the Berkshire Hathaway shareholders by admitting his biggest mistake of the past year.
And it’s definitely why the first essay I ever wrote for this blog was What Failing At Music Taught Me About Advertising. And why I later wrote about some pretty painful and personal stuff, like ADHD and losing everything in a fire.
A nuanced expression of character will last longer than a shallow brand persona claiming perfection.
We’re all flawed, broken apes with childhood trauma and systemic biases.
Supermen are for the comic books.
And even the Superman brand was failing until it got kryptonite*.
“A small admission gains a large acceptance.”
* In 1943 the voice actor on the Superman radio show went on vacation, and the writers needed to explain how the Man of Steel could be absent (stuck in a cave) while Lois Lane investigated. Until then Superman had been invincible and fairly boring. The writers invented kryptonite and the story took flight. The brand took off once Superman couldn’t.
A Theory of Failure
Why confession is divine and stupid is sexy
Behavioral psychology only really moved into the business world when Daniel Kahneman won the Nobel Prize in Economics in 2002 and a new school of thought gave theories to explain why a coherent brand persona is important.
22 years later, there’s still a long way to go.
Storytellers have known it for centuries, ad-people for decades, and economists are finally getting around to it.
Call it purpose, authenticity, storydoing… really, it’s a matter of character. A trustworthy brand is coherent, aligned, and humanly plausible.
Our brains can’t emotionally distinguish a rational, economic construct from an evolutionary organism. We know the brand is made-up nonsense yet we expect it to behave like it’s not.
Frankensteined brands are hard to maintain and grow because the parts don’t fit, the values are disjointed, and the stories fall apart — even if the strategy made perfect logical sense in isolation.
“Purpose marketing” might be dead (it was a dumb name to begin with), but Character Branding (trademark pending) lives in the minds of the audience — where it’s been since humankind started telling stories.
While the blog was on hiatus, Richard Shotton put out a new book. Like its predecessor (The Choice Factory), it’s one of the best guides to applied behavioral science.
The reason nuanced characters gain more trust than cheap supermen is found in behavioral biases:
The Pratfall Effect (identified by psychologist Elliot Aronson) shows that vulnerability makes people more likable — so long as competence is clear. Aronson’s study found that competent job applicants who spilled coffee on themselves at the end of the interview did better than the test group. More human = more trustworthy.
Costly Signalling is the theory from biology and economics that explains why we are evolutionarily primed to believe in organisms that spend resources on their message and why irrational bravery is sexy. In advertising, it’s often “the big commercial” where the extravagance itself is proof of commitment. But the appearance of brand courage (through admission or otherwise) can have the same effect at a much lower price point.
“All powerful messages must contain an element of absurdity, illogicality, costliness, disproportion, inefficiency, scarcity, difficulty or extravagance. Male strippers dress as firemen, not accountants; bravery is sexy, but rationality isn’t.”
The Reciprocity Norm is the social expectation of returning favors. According to Robert Cialdini (psychologist and author of “Influence — The Power of Persuasion”), there must be an element of surprise to it. If someone admits vulnerability when they don’t have to, it can trigger reciprocity.
The Ben Franklin Effect is similar to reciprocity… but opposite. The theory suggests you’re even more likely to have sympathy for someone after doing them a favor than if they did one for you. It sounds paradoxical but humans aren’t rational, we’re post-rational. We base our perceptions on our actions, not vice versa. When we invest in another organism through action or choice, we connect with it.
By admitting failure in this essay, I have implicitly asked you to make an admission on my behalf. If you’ve read this far, it might have worked.
The Beautiful Truth
What now?
I didn’t want to write this.
I took a job, closed down shop, and it all blew up in my face.
I spent a year trying to build up the courage to put it into words.
And now that I have, I don’t feel any better.
I feel naked and raw.
But courage is not the absence of fear.
Courage is to be afraid and then do the damn thing anyway.
“The most powerful element of advertising is the truth.”
Now, I will fail my way to new adventures.
I have no idea what the future will bring other than change. It usually does.
But the blog is back — until I get swept away by my next spectacular fiasco. I will not publish weekly to please the SEO gods — only when I have something to say or something needs saying.
And I’m back in work mode, exploring the landscape, and searching for new clients and good fits (hit me up if you’re curious and/or courageous).
I’ve even written a mission statement for the next time I get side-tracked:
