What I Learned from Meeting Chuck Woolery and Winning $5000

Nathan & Kat on LingoExactly five years ago, I was on a game show. Lingo was its name, and spelling was its game. It starred one of the smoothest customers of them all: Chuck Woolery.

How this all happened is rather simple: I, an actor (though working at an insurance agency by day), submitted my picture to an online casting notice for the game show, was called in, auditioned for the show by “playing” it (with my friend Kat), and a few weeks later, received a call that Kat and I would be contestants. Now Kat and I thought our audition had gone dreadfully; we didn’t even guess our word “camps” correctly! (In a last ditch effort, I had guessed “carps.” Sigh)

Somehow they had seen fit to include us and now we had the chance to play an actual game show with the face of “Love Connection” – and we could win money!

I’ve edited the best bits of the show together below (less than 5 minutes!), so you can see for yourself how it went. Five years later, here are the two biggest lessons I take away from that experience.


After the first commercial break, Chuck comes over to “get to know you better.” Just like with late-night talk shows, this conversation is a bit rehearsed. Prior to the show, all of the contestants for that day (about 10 of us) were gathered in a room as one of the producers asked us what we’d talk about with Chuck.

It’s natural to feel like you want to talk about something awesome or exciting, so that Chuck and everyone watching (I’d like to assume millions) will remember you. What’s ironic, though, is that our memory often works exactly the opposite – it’s the little details we hang onto: instead of all the grand story, perhaps we’ll retain what color shirt someone was wearing, where they grew up, or what their mother did for work. Strange, isn’t it?

Nathan on Lingo

It takes years as an actor to master this...

So there I was, sitting on this couch, listening to those around me share something about a hobby or accomplishment in my life, and what immediately occurred to me? My plant.

See, I had this Japanese Aralia (bought from Home Depot!) that had at one point absolutely thrived, growing to about six feet tall. Well that was all in the past. I made the mistake of leaving it on a porch over one particularly hot Van Nuys summer and the plant almost died. I say “almost,” because it retained three large leaves, yet would not do anything else, regardless of how I cared for it.

Now, I knew they’d never let me go on-air and talk to Chuck about my plant. I mean, who am I – Johnny Depp?? I’m just not one of those “eccentric types.” Yet what happened? The producer turned to me, I said, “I have this Japanese Aralia that won’t grow and it won’t die. I’m not sure what to do,” and she said, “ok, great.” Whaaaaaa?????

Here’s the kicker – the plant was a hit! I had watched dozens and dozens of episodes prior to my taping to prepare and practice. Never did I hear Chuck or his co-host Shandi ever mention anything a contestant brought up; they barely even spoke to the people during the show. Yet during my taping, the two of them referenced my plant at least five times!

Shandi also had a few interactions with me personally. I’d like to think she was genuinely interested, and not just being really nice :-) . Chuck and Shandi were probably hungry for something different; they taped fives shows per day, and much of the show is repetitive. Like anyone, I’m sure their brains enjoy new information, a challenge, and the unusual.

Be authentic with people; even if we can’t articulate it, we know when someone is putting on a front or being fake. Speak what’s truly going on with you: what’s important, what are your concerns, what are you passionate about, what do you love? No need to try and impress anyone with a tale (tall or otherwise). We’ll remember you more for what came from your heart.



You know when you’re watching a game show and you think, “why are they taking so long? it’s so obvious!” Well, add in an 8-second clock, needing to spell slowly, remembering to be visibly animated after a win, the knowledge that money is on the line, and you get panic, brain freeze and temporary paralysis.

Nathan & Kat - Bonus Round

what words start with "S"????

One thing that Kat and I never did, though, was give up. We always went down swinging: whether it was accidentally guessing a 6-letter word, picking out red balls and losing our turn (happened multiple times), or running out of chances to guess. I knew Kat is a fighter; it’s one of the reasons she was the person I thought of for a partner.  With all the opportunities the other team had to take control and dominate, they never did. Kat and I remained positive and were always ready for another shot at the game. It’s why we ended up almost 400 points ahead by the end of it all!

Even in the bonus round, when time mattered all the more, I can see myself getting frustrated that the words weren’t coming to my brain. Did I just quit and run away? No, thoughI did quickly consider that. We had to keep guessing, even when we knew we were way off, hoping that we’d hit on the right letters eventually.

If you believe in what you’re doing, keep at it. You never know what’s around the corner; just when you think it’s impossible or makes no sense to keep going, you may see the end or come across something that lines it all up and makes everything easier. But you won’t find that if you stop. True success is never handed to anyone.


Even if we hadn’t won, these lessons are still true. The prize just makes the wisdom that much sweeter.

And here’s all the fun…


How about you –  what lessons have you learned from a specific experience (winning cash optional)?

I’d love to hear your answer along with any other comments you have below.

Until next time,



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Former life: actor/office worker/virtual assistant; lived in Los Angeles for 11 years. Since then: sold nearly everything, took a $5 flight to Hawaii, lived there for 3 months, wrote an eGuide about all of it, and still traveling. Currently: digital nomad - looking to improve myself, have fun and serve others.