Most of the meaningful things in my life didn’t come from a plan.
They came from moments where I honestly didn’t know what I was doing. These events remind me of walking out in the deep snow this week on the trail in zero degree weather. There were no footsteps to follow. Was I going to make it all the way and then make it back before freezing? I didn’t know, I just went for it!
I didn’t have a blueprint. I wasn’t confident these things would work. Sometimes I wasn’t even sure it was a good idea. I just took a step, said yes, or kept moving—and somehow, things worked out.
Looking back, that’s been true more often than not.
We tend to overestimate how much clarity we need before we act. In reality, clarity usually shows up after we move, not before. At the time, these decisions felt messy, uncertain, and unfinished. Now, they look like turning points.
So in this episode, I want to share ten times I didn’t know what I was doing—but it worked anyway. Not because I was smart or strategic… but because I was willing to keep going without all the answers.
10 Times I Didn’t Know What I Was Doing — But It Worked
When I look back, none of these moments felt brave or strategic at the time. They felt uncertain. Awkward. Sometimes impulsive. In most cases, I had no idea where things would lead.
But every one of them led somewhere.
1. Switching majors in the car on the way to enroll at OSU
I changed my major while literally driving to enroll. No long-term plan. No confidence it would work. That decision didn’t pan out the way I thought—but it led to two years of graphic design school in 1983, which quietly shaped everything that came after.
2. Submitting a design to the KATT calendar contest
I sent in a design without any real expectations—and ended up winning the KATT calendar contest not once, but twice, in 1989 and 1991. It was one of the first times I realized: maybe I can do this.
3. Applying for an Advertising Director job without the experience
In 1989, I applied anyway. I didn’t check all the boxes. I didn’t have the résumé. But I showed up. That leap put me on a path I wouldn’t have landed on if I’d waited until I felt “qualified.”
4. Asking Denise to get a beer
This one was simple—and huge.
In 1997, while buying a birthday card at a party, I asked Denise if she wanted to get a beer. No overthinking. No big speech. Just a moment that changed my entire life.
5. Quitting a 13-year job to work from home on the Internet
In 2003, I walked away from a stable job to work online—when working online wasn’t exactly normal. I started designing cartoon logos and slowly figuring out how to make money on the Internet. I didn’t know if it would work. I just knew I had to try.
6. Turning Enid Buzz into a full-time business
In 2013, I decided to make Enid Buzz my full-time job without knowing if anyone would keep reading or following. There were no guarantees—just a gut feeling and a lot of showing up.
7. Trading advertising for a vehicle
Around 2018, I approached a car dealership with an idea: trade a vehicle for advertising. No precedent. No script. It worked. I ended up driving a free SUV for three years.
8. Driving to Nebraska to see a total solar eclipse
In 2016, I hopped in my SUV and drove to Nebraska on a whim to see a total solar eclipse. No hotel. No perfect plan. Just the sense that I didn’t want to miss it. I’m glad I listened.
9. Interviewing Garth Brooks
In 2015 I received an invite to interview Garth Brooks alongside all the state TV reporters. It was my first celebrity interview ever. I didn’t feel ready—but I did it anyway.
10. Throwing my name in the hat for the 2017 Presidential Inauguration
On a whim, I decided to put my name in for free tickets to the 2017 Presidential inauguration—without thinking through the logistics. I ended up getting picked, which meant I suddenly had a new problem: I had to fly myself there and find a place to stay.
I did a small crowdfunding campaign to cover airfare and started calling old friends to see if we could crash with them. None of it was planned. It was all figured out on the fly. But it worked—and I ended up experiencing something I never would’ve seen if I hadn’t taken that first, impulsive step.
The Real Lesson
Looking back, none of these moments came from having a perfect plan. They came from movement. From curiosity. From being willing to act before everything made sense.
At the time, these decisions didn’t feel bold. They felt uncertain. But uncertainty didn’t stop them from working—it was part of the process.
If there’s one thing I’ve learned, it’s this: you don’t need clarity to move forward. You get clarity by moving forward.
So if you’re standing in that uncomfortable space where you don’t quite know what you’re doing, you might not be lost at all. You might just be early.
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