Going From Expert to Idiot: Starting Over in a New Field

I like to toot my own horn. I think I’m pretty damn smart, and I’ve got the receipts to back it up: top grades, a stint living abroad, an executive MBA from Georgia Tech, over a decade as a trusted advisor to serious organizations in consulting, then another decade practicing those same skills in industry. I’m good at what I do. That confidence, or cockiness, the truth is probably somewhere in between, existed because every one of those experiences built on the last one in a logical progression. Grades led to a decade of consulting. Consulting led to an executive MBA from Georgia Tech. That combination led to the industry job that followed. Each step was earned by the step before it.

That was all true. Until it wasn’t.

The two piles

When Chrissy and I started building Celeste Naturals, I started sorting every new task into one of two piles almost without meaning to.

Pile one is transferable skills, and it’s a bigger pile than I expected. P&L, logistics, standing up the website and its backend, paying suppliers, downstream planning, market and competitor research, understanding why trademarks matter, calculating and paying sales tax. None of that required a real leap. Even where I hadn’t done the exact task before, I had enough adjacent exposure from my risk management background that none of it felt far outside my comfort zone. I could bluff my way to competent fast, because I was really just applying an old skill to a new label.

Pile two is net new, and it’s where all the pain lives.

Being a risk practitioner is, underneath the jargon, the same risk math I’ve written about before: assess the situation, find where it can go wrong, minimize the odds of the bad outcome. Even when I hit something unfamiliar, it followed a loose, repeatable script that told me I could figure it out. I’ve spent a career being nimble inside ambiguity. It turns out that is not the same skill as being creative.

Running this business is full of chances to be creative, and none of my old training touched them. Seasonal scent choices. Label fonts. Vessel sizes and how they actually feel in someone’s hand. Color theory, for the packaging and the product both. Building a retail space people actually want to stand in front of. Underneath that sits a second layer I’d also never touched: ingredient research and sourcing, figuring out the right combination of wax, wick, and vessel, making sure our scent lineup actually spans categories like ozonic, gourmand, floral, and herbaceous so a customer has a real chance of finding something that speaks to them.

I had done none of this. I was not good at any of it. Nothing about it was obvious. I found myself clawing at a rock face, grabbing for any handhold that seemed like it might not crumble under me. These are problems a middle schooler in an art class solves without thinking, and I was burning hours on YouTube trying to understand the minutiae. And here’s the part that made it worse: I’m also my own harshest critic. The failing came bundled with a running commentary reminding me exactly how much of an idiot I was being.

What actually got me through it

Not a mindset. Stubbornness, and the muscle memory of having pushed through pain before.

In 2019 I did the Ironman 70.3 in Florida. About 50 miles into the bike leg, I went down and landed on a patch of rocks that were doing an excellent impression of being soft. Torn rotator cuff. Torn labrum. Road rash and blood doing their thing. I lay there staring at the sky for a minute, genuinely wondering what sequence of life decisions had put me on the ground in that exact spot. Then I got up, got back on the bike, and finished the last six miles slowly and in real pain.

At the transition to the run, quitting never entered my head. I was still ambulatory, and I’d promised my daughter a medal. The run leg was less a run than a walk, shuffle, cry rotation, but I finished it, at whatever pace that took.

Here’s the correction I need to make to my own story, because it matters: I didn’t finish that race on stubbornness alone. Stubbornness got me off the ground. What actually carried me the last six miles was every training rep I’d banked before that day, the mental and physical account I could draw down when things went sideways. Stubbornness without the reps is just refusing to quit at something you were never prepared for. Stubbornness with the reps is resilience.

That’s the exact mechanism I’ve leaned on for every net-new, middle-schoolers-could-do-this-in-their-sleep task this business has thrown at me. Try. Fail badly. Learn the specific thing that made it fail. Try again. Every rep gets banked, the same way a training block gets banked before a race, until eventually I have enough of them to draw on when a new problem shows up that looks a lot like an old one.

Where I push back on “embrace the beginner’s mind”

I don’t lean into that phrase, and I think it’s a little bit of a trap.

The beginner’s mind framing grants you a lot of forgiveness for mistakes, which sounds healthy and mostly is, but it also gives you permission to stay comfortable inside those mistakes longer than you should. It’s very easy to tell yourself “I’m just a beginner” as a permanent identity rather than a temporary phase you are actively trying to exit.

My version of it: I give myself grace for being in the idiot phase while I’m actually in it, learning the wax-and-wick chemistry or fumbling a color palette for the fortieth time. What I don’t give myself is permission to stay there. Mediocrity doesn’t get to be the resting state just because I’m new at something. The idiot phase is allowed to exist. It is not allowed to become a personality.

The progression starts over, it doesn’t disappear

Here’s what I didn’t understand at the start of this: the same mechanism that built my old expertise, one earned step logically stacking on the last, still works here. It’s just starting from a lower floor, and the reps look like burnt candle wax and unreadable font choices instead of client decks.

I spent a career being the person in the room with the answers. I’m now, on a fairly regular basis, the guy Googling how wick size interacts with fragrance load at 11pm. Both of those things are true, and only one of them used to embarrass me. The other one is just what it looks like to be building the next set of reps.

I’ll take slow and shuffling over not finishing at all. I did it once with a torn rotator cuff and a promise to keep. I can do it again with a hot glue gun and a hundred discarded scent tests behind me.