When the Wind Derails a Win

Two weeks of wins, then one gust of wind doubled the cost of a video shoot and shattered my gear. Why I am sharing the failure, and what it taught me about pricing, producing, and authenticity.

Last week, I shared that I was stepping out in faith, leaving the security of a guaranteed paycheck and a role I'd held for ten years. And if you've been following along, the last two weeks have offered some genuinely extraordinary moments to celebrate.

A sold-out show at Red Rocks. A new consulting project born out of a recent keynote. And a glowing endorsement from Caroline Duffy, someone I deeply admire, which has already generated a speaking inquiry.

Those are real. I'm grateful for every one of them.

But life isn't all wins. Sometimes there are winds. Read on.

The Shoot

A few days after that sold-out show at the Bridgestone Arena in Nashville, I spoke at the Hall County Chamber of Commerce on behalf of UNG Evergreen Learning. The talk landed the way I'd hoped it would. It connected with the audience and unlocked the imagination of someone in the room who reached out afterward. They wanted my help leveraging AI tools for something I genuinely believe in: more human connection.

So when I headed out solo to my first independent video shoot in 10 years, about an hour from home, the wins were stacking up. At least before the wind had a say in the matter.

One of the quiet benefits of working inside a corporation is access to resources and teammates. When you're setting out on your own, it can be a lonely journey. I'd priced the project in a way that made it accessible to the client, which meant going alone, no extra set of hands.

The goal was to create AI avatars in front of a green screen that could be placed throughout their beautiful property. Real people in real locations to create avatars for welcome videos. Customer touchpoints. Personalized moments. With AI, we'd be able to create future content from the footage I captured on the shoot. The challenge with most green screen content, think of the local weather report in a small market, is that studio lighting rarely matches the environment you're keying in behind it. I'd never tried shooting green screen outside before, but I was eager to see if capturing it in natural light might actually deliver something that felt more real, even if the AI avatars weren't.

When I arrived on site, I saw something beautiful. A perfect overcast sky. Even lighting. Ideal conditions. I scrambled to set up my green screen, teleprompter, cameras, and microphones, knowing from experience that outdoor conditions can shift the moment you look away.

I headed inside to go over the plan with the talent.

By the time I walked back out, the eagerness I'd felt was replaced by a sick feeling in my stomach.

One Gust of Wind

One gust of wind had caught my green screen like a sail. With no one standing guard, it had toppled the entire rig. The teleprompter glass was shattered. The gimbal on my secondary camera was destroyed. The cost of the damage doubled the fee I'd agreed upon for the shoot. In fact, there's little hope of even breaking even on the initial stage of the entire project. Ouch!

With only a minimal burst of profanity, I resolved to pivot. I moved the green screen inside and captured what I could without a prompter.

On the drive home, I gave myself five minutes to vent to my wife. I spent some time in prayer. Something like, "God, why have you forsaken me?" Then I asked myself: how do I make this a lesson?

Producers and Engineers

Here's what I landed on. In music, we work with both producers and engineers. Producers coach great performances out of talent. Engineers handle the technical. Even the best in the business, producers like Brendan O'Brien who genuinely can do it all, know they're at their best with the right support around them. That's where I excel: in the producer role, drawing out great performances, putting talent at ease, fostering human communication. Not managing gear solo in the wind. I know how to do all of the technical things, but as I've shared before: "Just because you can, doesn't mean you should."

So going forward, my rate will reflect that. I'll always have at least one extra set of hands. It might price me out of reach for some clients, but it will unlock better work.

Why Share a Failure?

The old adage is "Fake it till you make it." So why am I sharing this failure?

I'm sharing this because authenticity matters deeply to me. My public speaking mentor, Melissa Gordon, instilled one principle above all others: Authenticity is the North Star of communication.

When THIRD DAY was starting out, we played shows with more people on stage than in the audience. Shows where the sound was so bad we couldn't hear the vocals over the drums. We experienced broken-down vans and stolen equipment. Failure was part of the foundation. It made us better. But there's a difference between failing at seventeen and failing at fifty, when the money you're billing has already been spoken for by the expenses of life. But, is there really?

If you're scrolling through your feed right now, you're seeing everyone's victory laps. The awards. The peak moments. The new job. The highlight reel. We tend to keep the harder moments to ourselves, and maybe that's sometimes the right call. But, if you're in a moment of uncertainty or experiencing some genuine professional struggle, other people's success might feel a bit like salt in the wound. Take heart!

As I step into this next chapter as an author, speaker, musician, and marketing consultant, my plan is to share not just the highs but some of the honest, costly, uncertain moments in between. Because I believe that's what actually encourages people.

I'm venturing into the great unknown with transparency, determined to fail forward. Committed to doing whatever I do with authenticity and integrity, and hoping it just might encourage someone along the way.

So I have a question for you

Do you have a failure you're willing to name? Not in the abstract. A tangible one. One that cost you money, or shook your confidence in your path.

If your team is navigating a season of change and needs a reminder that failing forward is part of the work, that is exactly what my keynotes, workshops, and leadership sessions are built for. Learn more at taianderson.live/keynotes.

Originally published on LinkedIn, June 26, 2026.