A few weeks ago, my friend Skyler, Director of Communications for Longview ISD, asked if I would speak to students at their “LoboTalks” (think TedTalks) event.
When he told me the topic he thought fit me best was “Failing Forward,” I couldn’t help but smirk. There’s something amusing about being the guy who comes to mind when “failure” comes up.
Our friendship started back in 2019 when we recorded a podcast I titled “Staying Passionate, Failing Gracefully, and Building Brand.” Skyler made sure he wrote down the phrase “Stay Passionate and Fail Gracefully” so he’d remember to say it while we were recording. Some things really do come full circle.
It’s always an honor to be asked to speak, and I’m excited to share how Failing Forward has become a guiding theme in my personal and professional life.
Failure as a Guide
Matthew McConaughey (Longview Native) is making the rounds on the podcast circuit to promote his new book and recently chatted with Joe Rogan. The topic of posting the Ten Commandments in Texas classrooms came up. I’m less interested in that debate and more intrigued by McConaughey’s deeper question:
“What can I rely on that will stand with me — a time-tested truth that I can go to in the storm, when I need to catch my breath? What can I lean on in the dark, or when the crowd says, ‘Do this, do this’? What is that simple sheet, ingrained in me, that our youth can say, ‘Yeah… I can rely on that’ — regardless of who the author is?” — Matthew McConaughey
That question stuck with me. What could I offer students—or anyone—that serves as a framework for decision-making and character-building, something to help us stay on track when life gets hard?
That’s a question I hope to answer with my talk, and this series.
Failing Forward through the Piney Woods🌲
This past Saturday, I ran my first ultramarathon: the Piney Woods 50k. I’ve had my eye on this race for years. I ran the 25k last year, so I knew it would be tough, but after months of training, I felt ready for the challenge.
Four loops, roughly 7.75 miles each. The course is technical. By the end of loop three, my legs were screaming at me with every step to stop. The race-day buzz had faded, the trail had thinned out, and I was alone with the pain in my legs and feet and the noise in my head. My body wanted to stop. My mind was tired of the constant forward motion. I started justifying why it would be okay to quit.
My wife and her sister Callie were my crew, cheering each time I came through. I sat down while they refilled my bottles and encouraged me, but I could barely say more than “I don’t want to go back out there.”
Chelsey could see how serious I was—but she didn’t accept quitting as an option. She knows me at a values level. She’s watched my love for running grow, the discipline I’ve built, and how much I’d invested in this day. She knew I’d regret a DNF (Did Not Finish) if she placated how I felt in the moment and started packing up.
Without hesitation, she decided to go with me on the final loop. Only a few hundred yards in did she realize she’d just volunteered for a 7.75-mile hike. But she never complained and encouraged me throughout the final miles, following me and leading me as we navigated through the piney woods.
She didn’t do it for herself—she believed in me.
And that belief carried me to the finish.
Failure is Foundational
Failing Forward is about learning from mistakes, not just success.
And while it may seem like the only success is the specific version you have in your mind - that job, that relationship, that level of income, that trip, that house…fill in the blank…
That mistake or failure doesn’t mean your turn is over.
Sometimes you just need to get out of your chair and start walking.
Every step you take may feel like failing in the moment, but you can also find ways you are actually succeeding.
I believe you can find those ways through a commitment to values and people who share those values, so they can help identify the growth opportunities for us when we’re stuck.
So to me, this is the essence of Failing Forward:
Seeing mistakes or setbacks as opportunities for growth
Living by values, not moods.
Building relationships with people who share those values.
Recognizing and celebrating those values in others.
Making values visible in everyday actions.
Remember: Your First Attempt Isn’t Last
Here’s a Power Acronym I wrote to help remind myself what it means to FAIL. You can read the original post here.
Our First Attempt Isn’t Last.
F irst
A ttempt
I sn’t
L ast
Here’s to committing it not only to memory, but to action!
That’s why I’m writing this series on Failing Forward: to introduce young people (and anyone willing to read) to resources, frameworks, and real stories that build leaders—not headlines, controversy, or spin.
This is just the start. Over the next several weeks, I’ll share more reflections on how setbacks can shape us into better leaders if we keep moving forward—and surround ourselves with the right principles and people.
Thanks for reading!