Reframing Failure through the Lens of Iteration

Confession time – last week, I experienced my personal equivalent of a ‘standing on stage in my underwear’ moment.

You know what I’m talking about… that nightmare we all share about standing alone, in the spotlight, everyone looking at you while you’re up there in your skivvies?

I wasn’t exactly on stage, but I was standing in front of a room full of people. Fifty very high-profile, senior leaders from across industries who’d come to participate in a day-long workshop I was facilitating – to be exact.

In the weeks leading up to this moment, I had designed a day’s worth of panels, discussion and interactive activities – all with the goal of building community and creating collaboration opportunities for attendees.

The first half of the day went beautifully. People were engaged, smiling, and (most tellingly) not on their devices. “This is going so great!,” I thought to myself smugly.

And then – it was time for the after-lunch breakout sessions. We split into two groups and I took the lead facilitating a prioritization exercise. This is an exercise I’ve run many times. So. Many. Times.

And yet – as soon as I explained the instructions and sent people off to their easels and post-its, I knew it was going to bomb.

Has this ever happened to you? Where – even with a strong plan – you start something or try something and immediately see all the ways it’s not going to work?

Now here’s the surprising part: this is not a bad thing. At least, not when you adopt the mindset of Iteration.

As I define it, Iteration is an approach to taking action that emphasizes experiments, trials and prototypes. It invites us to show and share our work early – not because we have to, but because it helps us learn quickly. 

Rather than waiting for perfection, iteration encourages us to try out our ideas as soon as possible. With Iteration, failure isn’t the enemy. It helps you learn.

When I put the prioritization exercise in front of those participants, I could tell almost instantly that I hadn’t accounted for a few important details – details that would undoubtedly impede their ability to be and feel successful with this activity.

Was it a mistake? Yes, absolutely.

Was it a failure? Absolutely not.

Because I facilitate (and coach, and generally live my life) with the mindset of Iteration, I know that every plan can be pivoted. Every choice can be tweaked. And every mistake is a chance to learn.

I could have let my frustration over “failing” in this moment overtake me. And for a moment, I did feel exposed, vulnerable, and unsure of how to fix my error. I could sense people’s frustration levels rising, with lots of confused eyeballs on me.

And then – my Iteration engine switched on, and we pivoted. I went around to each group, explained my mistake, and gave them updated, clearer instructions. They were understanding, we shared a giggle about it, and then we all moved on.

Imagine if, instead, I’d stuck to my plan because “I planned this plan, darn it, and we’re going to do it!” Imagine how that would have only led to more frustration, more anxiety, and maybe even a true “failure” (in the form of unfinished flip charts and unhappy participants).

Adopting the mindset of Iteration allows us to be gentle with ourselves, treat every misstep as a chance to learn, and – in my case – enable deeper, more human connection with the people I was guiding.

Where are you holding onto your plan a little too tightly? How might the mindset of Iteration support you to pivot when needed, seek out new learning, and bring a bit more humanity to your work or life?

Today, take a moment to think about one step you can take to Iterate. 

💡Maybe it’s telling a trusted friend about your idea for your next career chapter. 

💡Maybe it’s finally signing up for that standup comedy night you’ve been secretly wanting to join. 

💡Maybe it’s acknowledging that your original plan hasn’t worked out and you need to come up with something new.

What’s your next step? I’d love to hear.

Onward,

PS: Iteration truly is the superpower that no one talks about. Which is why I devoted an entire journal to it! In Volume 4 of “100 Days of Designing My Life: The Reflection Journal,” you’ll walk through 25 prompts, questions and ideas to help you bring more Iteration into your life. Give it a try!