I Won a Stand-Up Comedy Competition… Then Slowly Lost My Sense of Humor
- Jun 3
- 3 min read
What happens when you win a stand-up comedy competition… and then slowly lose your sense of humor?
In this solo episode of Laugh or Death, I’m sharing the story behind the two framed comedy posters hanging in my studio. They’re from two stand-up competitions I won 23 years apart.
But honestly, this episode isn’t really about winning.
It’s about everything that happened in between.
When I was 23, I was in graduate school, stressed out, overworked, and taking life way too seriously. Comedy became one of the things that helped me get through it. I tried stand-up for the first time at a house party, started doing open mics, and eventually won a local comedy competition in Denver.
And then I made the mistake of deciding I needed to take comedy VERY seriously.
Which, looking back, is kind of the fastest way to ruin comedy.
I started overthinking every joke. A bad set could completely derail me. I stopped enjoying the process. Eventually, I quit doing comedy altogether… and I even stopped watching it because I couldn’t stop comparing myself to other people.
I had completely lost the plot.
Over the years, I started realizing that humor wasn’t just something I enjoyed. It was actually an important part of my mental health and wellbeing. Through therapy, research, improv, working with students, and a few ridiculous real-life moments — including spilling an entire Dr Pepper on my pants before a serious meeting — I learned that carrying yourself a little more lightly can change everything.
In this episode, I also talk about the way humor helped me through hard seasons, including COVID, losing most of what we owned in a house fire, and moving somewhere new without an established community.
Eventually, I found my way back to improv, stand-up comedy, and a much healthier relationship with laughter.
This time, I wasn’t trying to prove anything.
I close the episode with a few lessons I wish I could go back and give my 23-year-old self:
Your competition may actually be your community.
Stop comparing your insides to other people’s outsides.
Don’t live your life like an actor in a drama only to reach the end and realize you were the director… and it could have been a comedy.
If you’ve ever taken life, work, or even something you love way too seriously… this episode is for you.
And here’s a line I keep coming back to:
“You don’t stop laughing because you get old. You get old because you stop laughing.”
Links:
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To learn more about Paul’s work, book him for speaking engagements, or explore the science behind humor and resilience, visit: 👉 https://www.paulosincup.com You can also dive deeper into the tools discussed in this episode in Paul’s book: 👉 The Humor Habit
All Links For Paul: https://stan.store/PaulOsincup
Episode Minute-By-Minute:
00:00 – Winning two comedy competitions 23 years apart
01:15 – Why Paul hates stand-up comedy competitions
02:15 – Graduate school, stress & discovering stand-up
03:45 – Paul’s first stand-up set at a house party
05:20 – The Crocodile Hunter joke that somehow worked
06:15 – When comedy became too serious
07:15 – Bombing at a pizza-place open mic
08:00 – Quitting comedy and losing the plot
09:00 – Why even watching comedy became difficult
10:00 – Therapy, Colorado & rediscovering levity
11:00 – The science behind humor and wellbeing
12:00 – Why humor is like exercise
13:30 – How improv helped Paul stop overthinking
14:15 – Taking another serious job too seriously
15:15 – Realizing he could not bottle up who he was
16:00 – Becoming better at work by becoming lighter
18:00 – Humor as an olive branch
19:45 – Fake tattoos, eyeliner & staying sane
20:30 – Finding community through comedy in Montana
21:30 – Returning to stand-up without taking it too seriously
22:15 – Winning Montana’s Funniest Person
24:00 – Three lessons for his 23-year-old self
24:30 – Your competition might be your community
26:00 – Stop comparing your insides to other people’s outsides
27:00 – Chronic seriousness & the comedy IV drip
28:30 – You do not stop laughing because you get old
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