By Kerry Frank
October 24, 2025
Have you ever failed forward? If you haven’t, you should try it.
Failing forward is humbling. And then it’s rewarding.
I’ve talked about owning my mistakes with my friends, but I’ve also owned my mistakes in business. When I built my company, I built it on trust. I looked people in the eye and said, “If you sign this contract with me, I guarantee I’ll do my best.”
Notice, I didn’t say I’d be perfect. I’m not.
As our company grew, the weight of that promise grew too. I’ll never forget one day, driving toward O’Hare, stuck in traffic. Planes were flying overhead on their final approach, and the aviation geek in me couldn’t help but smile. I started recognizing tail logos, one after another.
That airline’s a client.
So is that one.
And that one, too.
It was a “pinch me moment” The realization that something I started in my basement had now touched the skies around the world.
But it also hit me that if my software failed, a large portion of the aviation industry could be grounded. My phone was always on. We ran 24/7 operations. We had emergency protocols for everything.
Then one morning, as I was pulling out of my driveway to drop my daughter off at school, my phone rang.
It was Aimee from the office.
“You know the software is down, right?”
What?!
Within minutes, I was on the phone with my lead architect and realized no one on call knew. The emergency line hadn’t rung. The alert system hadn’t triggered. Within ten minutes, we were in full emergency mode, hunting people down at the YMCA, pulling everyone to the office, launching stand up protocols.
As we dug in, we found the issue wasn’t our software at all. It was our cloud provider’s servers. Their failovers had failed. But my clients didn’t care about the technicalities. All they knew was that their system was down.
And that’s when I realized something important. The trust I had built was now on the line.
We spent the next few hours giving live updates to clients while our vendor did the same for us. Once the crisis passed, we immediately held a full review. Every team presented what broke down and how we would fix it.
Still, I could feel it. The defensiveness in the conference calls, the frustration, the loss of confidence. It didn’t matter whose fault it was. The buck stopped with me.
The next morning, I booked flights to visit the two clients most affected.
I didn’t bring a lawyer or a PR spin. I brought donuts.
I walked into their offices, passed out donut holes, and said, “I’m sorry there were holes in our service, but rest assured, we’re filling those holes right now.”
They laughed. Not because it was funny, but because it was real. No one in aviation did that. Most vendors blamed someone else. I showed up and owned it.
My vendor, the one who actually failed, never took responsibility. But my clients didn’t need to know that. They signed with me, and that meant accountability stopped with me.
That’s what it means to fail forward.
You face the hard things head on. You take responsibility when it’s uncomfortable. And you turn failure into trust.
Because in the end, failing forward isn’t falling down. It’s getting up faster, stronger, and more respected than before.
With Gratitude,
~ Kerry
#FromFailureToForward #GrowthMindset #LessonsLearned #GritAndGrace #OwnYourStory
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