Failure

Living, Dying and Being Reborn

I’ve seen failure in the workplace take many shapes, from sudden exits to lateral “promotions” to demotions and more.

Failure on the job comes in a variety of forms—sometimes obvious, sometimes less so. There’s one experience that sticks with me from early on in my career. For context, you have to understand that the early days of digital agencies, where I cut my teeth, were serious bastions of innovation during the Web's foundational days, attracting some of the best and brightest.

Many of my peers from former employers like Agency.com, Digitas, Critical Mass, and Edelman have gone on to prominent roles at established companies, in startups, or even by building their own thing…

One of my Agency.com colleagues went on to co-found Kickstarter, and one of my Edelman colleagues, whom I had the pleasure of working on a high-profile partnership deal, started the successful Cauliflower Crust Pizza brand, Caulipower. If I had to list the amazing things so many of my former colleagues have done and are doing in their careers, it would be a never-ending exercise.

And several of these highly successful folks failed along the way believe it or not. When it comes to failure, I’ve seen it—and lived it too.

I digress.

A gifted colleague at one of those agencies was rapidly promoted to president of the growing Chicago office. I was happy for her—she was one of the smartest people I’d gotten to see in action during those early years.

At that time, I wasn’t very senior and was pretty heads-down in client work, so I had very little exposure to the company's leadership dynamics and office politics. But then one day, an office meeting was called, and the president, who had not been in the role very long, rose before the entire office and tearfully announced that she was stepping down.

I literally felt the humiliation that she must have been feeling at that moment. She was wearing it on her face.

You could tell that the choice was not hers, and that she was being put in a position to signal to the office that a smooth transition had been planned and she was on board with it. One thing I liked about this person was her authenticity. And in that moment, I could sense how devastating it was for her to get up in front of the office she once led, do her best to keep her composure, and then announce her transition. It was difficult to witness.

On a human level, I simply felt terrible for her, regardless of how legitimate or not, the reasons were for her sudden transition. The story, however, has a happy ending. Not surprisingly, she went on to bigger and better opportunities. I was glad to see this.

What I could not foresee at the time was that, years later, I’d go through an almost identical experience.

I was promoted to lead a practice and P&L worth around 15M with a 70-person staff. It was the most direct operational role in my career.

I was not successful.

I could get into all the reasons. When I reflect on it, I occasionally play back where I fell short vs. where things were simply out of my control. In column A, I felt short on some leadership basics, even though I also did some things right. In column B, there were three successors to that role who also did not succeed. That was validating to some extent, but I still owned what I could have done better.

It really doesn’t matter because, at the end of the day, it was a failure, despite what I learned in the process. I created the cover art for this piece on a business flight around that time. It is the phoenix, rising from flames and ash—the same one we know from mythology and a myth that always resonated with me. My crude iPad art represented an intuition that I knew to be true—that I was going through a process of life, death, and rebirth, and my professional “failure” was the catalyst.

Living
I believe there’s some variation of the saying “if you aren’t failing, you aren’t living,” and I think, while cliché, it’s also true. Living means taking chances. To love anything is to take a chance knowing that the love may not last the test of time (been there, done that, and paid for it in more ways than one). In my case, when I accepted the promotion that ultimately ended in “failure”, I remember feeling it was a chance to rectify a previous mistake: I had once been offered an opportunity with more formal responsibility but declined it.

To live is to take the risk that we might fail at something. If we’re not failing, we are limiting what we learn and limiting life itself.

Dying
As I alluded to earlier, I found myself in the same position as the executive who had to announce her own transition to the office. I thought about her when I did it. When it came time for me to do the same, for whatever reason, I showed no vulnerability on the outside. In fact, I literally threw my shoulders back, stood tall, and declared that I was shifting my role from playing “defense to offense.”

Clever David.

In reality, I was dying. Or parts of me were, metaphorically speaking.

While I have never died physically (obviously), I imagine if, and when it comes suddenly, it involves some shock, pain, and then a mourning process from others if you’re fortunate. But when you fail, it is you who must go through the mourning process—something I was doing while finger painting this phoenix on an airplane at 30k feet. Failing is painful. Don’t be fooled by the hustle culture LinkedIn influencers who talk about failing performatively.

Most of them skip over the grief that comes with failure. It’s real, and it can take time to recover from. My advice is if you’re dealing with failure right now, sit with the grief for a while. Move past the denial. Give yourself the space to grieve the loss and transition that comes with failing at anything. You’ll know when you are ready for the next step.

Rebirth
To this day, I still remember something I wrote in one of my Moleskine notebooks as I began to work my way past the dying part of failure.

”Be so good, they can’t ignore you.”

With apologies, another cliché, but it was the only way I could see how to claw my way back to how I wanted to feel after my failure. This is the part where the phoenix begins to rise from the flames—only think of it happening in slow motion, over weeks, months, and even years. I had a reputation to rebuild within the company, and I wasn’t going to do it superficially—that is not me. Any assignment I was on… any person I worked with… any opportunity… I gave it my all.

There were some stumbles. There were also successes. Client wins, partnerships. And even notes of kudos from respected stakeholders, both colleagues and clients alike.

It was a process. I made some mistakes early on… too eager, too insecure, too immature.

But I forced that fire to reforge me and strip those things away in time. And I made peace with my failure as I moved forward.

Today, my fiery phoenix rising from the flames and ashes is the wallpaper on my iPad, and it’s been there for well over a decade. It is my daily reminder of the live, die, rebirth cycle that comes with failing, which comes with living…

I think I’ll keep it there for the next decade and beyond.

Visually yours,

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David Armano is a futurist, strategist, and Enterprise AI transformation leader who helps his colleagues, clients, and community solve intricate business challenges and see a clear path forward.

He’s known for his unique approach to visual thinking and for insightful yet grounded takes on intelligent experiences, culture, and leadership. In addition to his day job, he writes David by Design to translate complex shifts into actionable ideas.