
25 Things I’d Tell My 20-Year-Old Self About Comedy, Creativity, and Life
A letter from my older, scarred, still-standing self to the kid who thought sleeping in his car was a strategy.
They say, “Youth is wasted on the young.”
Maybe that’s true — or maybe it just takes a few decades of bombing, writing, rewriting, and rebuilding to figure out what really matters.
What follows isn’t theory; it’s earned wisdom from a lifetime in stand-up, comedy writing, and creative reinvention.
I can't tell you exactly how to succeed. I can only tell you what I learned from my 30-plus years as a comedian, joke writer, author, and screenwriter.
These are lessons about craft, confidence, and staying true to your voice — insights that can save you years of trial, error, and self-doubt in your own creative career.
If my 20-year-old self had known these things, he could’ve skipped a lot of headaches, anxiety… and at least a few trips to the free clinic.
1. Don’t Listen to “Practical” Voices
I bumped in to my high school career counselor at a Target store, 3 years into writing for The Tonight Show. I said, "Mr. Campbell?"
He said, "Who's askin'?" He was always blustery and would often toss out jabs and insults. One time when I was trying to ask a girl to the prom he blurted out, "Mr. Corley, She'll never date you, you have a cowlick."
But here he was in the Target.
I said, "My name's Jerry Corley. You were my high school guidance counselor. I'll never forget the advice you gave me, Mr. Campbell. You said, "Mr. Corley, you can't joke your way through life."
He said, "Sounds like something I might say. So what have you been doin' with yourself?"
I said, "I write jokes for a living."
My point here is, if someone’s imagination fits neatly inside a cubicle, their advice won’t help you live a creative life.
“Practical” is just the polite word for surrender. If they’ve never bombed on stage or bet on a dream, they can’t tell you how to live one.
2. Bet on Your Obsessions
The thing you can’t shut off — that constant itch to write, perform, create — that’s your compass.
If you chase “security,” you’ll always feel unsafe. If you chase curiosity, you might not always feel secure, but you’ll always feel alive.
3. Talent Matters Less Than Tenacity
This is a known fact. Polite persistence and an unrelenting drive will be your push to success. You’ll always meet people who are funnier, luckier, prettier, taller. Let them be.
Comedian Nate Bargatze was grinding for more than 20 years before he made household name for himself and last year, 2024, he broke a record as a comedian at the box office earning 82.5 million dollars and selling 1.1 million tickets.
You’ll win because you kept showing up after they went home.
4. Study the Science Behind the Art
Everyone else will guess at what’s funny. You’ll know.
Study structure, rhythm, psychology. It’s not magic — it’s math disguised as laughter.
You can learn the science behind writing comedy and writing jokes on demand. Check out Breaking Comedy's DNA a book that breaks down why people laugh and how to make it happen consistently and on-demand. There's not another book like it. Oh, and it's written by me.
5. Stage Time Is Only Part of Your Learning
Stage time is the proving ground — not the whole school.
Just as a concert pianist or tennis champion doesn’t reach greatness only on center court or Carnegie Hall, it’s the hours of deliberate practice and coaching that build the skills to rip past the pack — and to develop the resilience and confidence to do it on demand.
Perform to test; practice to transform.
6. Be Able to Work Clean
When I do clubs, I work blue. When I do corporate or TV, I work clean. Working clean increases where you can work. It also increases your revenue streams. Working clean makes you ready for TV and...
As of last year the top box office comedian, Nate Bargatze made 82.5 million dollars working clean.
That set a record in stand-up comedy live performance. So work the way you want to work, but be able to work clean.
7. Build Systems, Not Just Dreams
Dreams get you started. Systems keep you going.
Create habits and your own plan to get out and work. Don't wait for the phone to ring or to get an email or have someone reach out on social media.
Build your own plan. Find the open mics using some of the aggregating sites like The Comedy Bureau, Bad Slava, and the online magazine Dead-Frog. These resources will fill you with creativity, excitement, and stage-time opportunities.
But here's the thing. Not all of the mics will suit you and some will be a waste of time.
That's where you build your own system. If some other comic can build an open-mic event, why can't you? Build your own system, dictate your own stage time, pave your own road.
8. Don’t Compete — Be 100% You
When you compete with others, you risk becoming just good enough to beat them.
Focus on being fully you — because no one’s ever seen that before.
Competition makes you a copy. Authenticity makes you unforgettable.
This doesn't mean you shouldn't do festivals and Comedy Competitions. They are terrific for exposure and developing relationships.
9. Be Curious About Everything
The funnier you want to be, the more you need to know.
Learn history, psychology, philosophy, weird trivia, the chemistry of fart jokes — whatever. It all becomes material someday.
10. Edit Like a Sculptor, Not a Surgeon
Don’t cut just to make it shorter — cut to make it stronger.
Editing isn’t about slicing words; it’s about chiseling marble until the punchline pops like a vein in George Carlin’s forehead.
Keep what’s vivid, real, and visceral — the smell, the shape, the sting.
A good joke paints an image so sharp the audience feels it before they even process it.
11. Learn to Translate Funny Into Value
Humor is currency. It buys attention, trust, and connection.
Whether it’s a boardroom or a bar gig, people will pay you for the ability to make them feel good about themselves while laughing at the truth.
12. Start Sooner, Fail Faster
Every day you wait to start, someone dumber than you already did.
You’ll get better faster by failing forward — bombing is just growth.
Dr. Wayne Dyer said, “Fear does not exist anywhere except in the mind.”
And he’s right — fear isn’t real, it’s imagination running in the wrong direction.
The cure for fear isn’t confidence; it’s action.
Because once you move, fear has to chase you — and it’s terrible at keeping up.
Start before you’re ready.
Do it messy. Do it scared. But do it now.
13. Ignore the Path — Blaze One
There’s no blueprint for “comedian, writer, screenwriter, entrepreneur.”
You’ll build it brick by brick — out of late nights, small wins, relationships, and an alarming amount of caffeine.
Don't let anyone tell you that you can't do something because of some arbitrary or made up rule.
When I originally wrote my movie Stretch. Lots of people told me that I couldn't sell a screenplay as an unknown writer. I grabbed my writing partner, we punched it up, then found a way to meet a director that we liked. He loved the concept. And we got a movie made.
14. Protect the Flame
There’s always someone ready to piss on your fire — some do it out of jealousy, some do it out of love. Nothing worse than to have a family member love you into failure by trying to have you to the "safe" thing.
Comedian is no less safe than accountant or factory worker. Every day in the news we hear about layoffs.
You know who I never hear getting laid off?
Comedians.
15. Never Stop Learning the Craft
Talent peaks. But skill compounds.
Every day that I write I learn something new. A new approach a new application of a structure to build a solid joke.
Study structure until it’s second nature.
The better you know the rules, the funnier your “rule-breaking” becomes.
16. Build Ownership Early
Performing for others pays once. Creating what you own pays forever.
Books, courses, IP — build shows, scripts, books, that make money while you’re sleeping or bombing.
17. Humor Heals
When life sucker-punches you, don’t cry — write.
Pain is potential energy. Turn it into punchlines before it turns you into poison. I can't tell you have many jokes I have about break-ups or a death in the family.
Write it down to tell the story, then come back to it and use your knowledge of joke structure to make it funny.
My friend had a near tragic event happen to him and his wife. So I wrote a joke around that event:
"I was in Vegas having lunch with a friend when he spilled ketchup on his shirt because he got a text that his wife was being rushed to the hospital and they lost the baby. He started crying right there... and I get it man, that was his favorite shirt."
The truth was he did get a text that his wife was being rushed to the hospital, but the baby was fine. For the sake of adding a little darkness to the joke, my version, kills the baby.
Writing the joke was my way of celebrating that the baby and his wife were fine. If they really lost the baby, I don't know if my conscious would be able to write that joke.
18. Don’t Chase Fame, Chase Mastery
Fame is rented. Mastery is owned.
Let the fame chase you because your craft is undeniable.
19. Invest in Yourself — Relentlessly
Invest in your education, your craft, your consistency. Missing days or weeks kills momentum and dulls the fire.
Need to get started? Take a comedy class. If you look back at comedians, there are a ton who took a class to get started including two top comedians: Anthony Jeselnik and Nate Bargatze.
A good class can teach you more than comedy theory. It give you a safe space to get your feet wet. It can connect you with short cuts to stage time and the process of getting booked.
I took a stand-up class then got private coaching on joke writing with a top comedy writer in Hollywood. In less than two years I was writing for The Tonight Show.
That private coaching pushed me way past all the other comedians who started at the same time I did.
20. Surround Yourself with Mentors Who’ve Climbed the Mountain
Find passionate, capable mentors who’ve already been where you want to go.
You’ll reach the summit faster with a sherpa who’s been to the top of mountains — not one who just read about them in a brochure.
21. Always Bring Joy — Especially on the Dark Days
Even when everything feels heavy, be the light.
That energy doesn’t just lift others — it transforms you.
Joy keeps your creative engine running when the world feels like it’s grinding to a halt.
Because when the shit hits the fan, creativity is your lifeline — it’s how you find solutions, reframe chaos, and turn “I can’t” into “watch this.”
Bring joy, not because life is perfect, but because that’s what artists do: we light the room when the power goes out.
22. Be Kind on the Way Up — You’ll Meet Them Again on the Way Down
This business runs on relationships. Every gig, every break, every “lucky” moment — it all starts with a person who believed in you.
Be kind, be gracious, and remember: today’s intern could be tomorrow’s executive producer.
Kindness isn’t weakness; it’s compound interest.
And sure — there are people you’ll need to avoid. But you’ll never regret choosing to leave a room with your integrity and your reputation intact.
This business is small and you might need that person to be on your side to get a film made.
23. Don’t Play to the Back of the Room
Don’t worry about the comedians in the back — they’re not buying tickets.
Worrying about what they think while you’re on stage pulls you out of the moment and away from the people who are there for you.
Those comics might give you smirks, nods, or the occasional “nice set,” but they’re not your audience.
The crowd in front of you is.
You’re not on stage to impress peers — you’re there to connect with strangers, make them laugh, and remind them they’re human.
The comedians in the back can wait. The audience in front of you can’t.
24. The Audience Is There to Connect
The number one reason an audience shows up is to connect.
It’s not an “us versus them” dynamic — they’re not your opponents; they’re your partners in laughter.
If they’re not with you, it’s usually because you didn’t invite them in.
Talk with them, not at them.
Connection happens when you stop performing and start sharing.
When you open up, they lean in. When you speak truth, they laugh in recognition.
Comedy isn’t about showing how clever you are — it’s about revealing how human we all are.
25. You’re Not Following Anyone — You’re Just Next
When you step on stage after a killer act, it’s easy to think, “How the hell am I supposed to follow that?”
But here’s the truth: you’re not following them — you’re just next.
Every set resets. Every moment is a blank slate.
The audience doesn’t want you to outdo the last comic; they want you to be real with them right now.
Don’t compete with energy that’s already spent — create your own.
Comparison steals your confidence, but presence gives it back.
You’re not in a lineup; you’re in a moment. Own it.
Final Reflection
If there’s one through-line in all of this, it’s connection — to your craft, your audience, your curiosity, and your courage.
Everything else is noise.
Comedy isn’t about chasing approval or fame — it’s about chasing truth and having the guts to say it out loud in a room full of strangers.
So write, risk, bomb, rebuild, and repeat.
And when you finally look back, you’ll realize you weren’t just building a career… you were building you.