What If “Making It” Isn’t Enough? (Patreon)

When you look at someone like Paul F. Tompkins, it’s easy to assume he’s got it all figured out. He’s been a comedy staple for decades, whether it’s TV, live shows, or podcasting. But in our first episode of Past Due, Paul pulls back the curtain on what it’s like to build a career when the ground keeps shifting under your feet.

The entertainment industry has changed drastically, and Paul’s story reflects a reality that a lot of creatives face: thinking you’ve “made it” only to find that your industry doesn’t work like it used to. The gigs you thought would always be there? Gone. The TV networks that used to take risks on new ideas? Now driven by algorithms and global appeal.

Can you even make it as a creative anymore?

Paul shares his insight on some key topics:

• Success Isn’t Stability. You can be beloved, acclaimed, and still feel like you’re hustling to keep the lights on. Paul talks about how it’s not enough to just be good—you also have to be visible, adaptable, and lucky.

• Podcasts Help, But Don’t Fix Everything. Paul was an early adopter of podcasting, and while it’s kept him afloat, it’s no replacement for the kind of consistent TV work he used to rely on.

• You’ve Gotta Make Your Own Luck. The hardest lesson? You can’t just wait for the next opportunity to show up. Paul reflects on how he used to think, “Something will come along.” Now, he knows that he has to be the thing that comes along. 

I went home for Thanksgiving one year and I had been working on "Mr. Show" on HBO for two years and had been nominated for an Emmy for writing, and we were sitting at dinner and my mother said, “you know, your uncle could teach you how to tune pianos.” And I said, “why would I want to learn how to tune pianos?” She said, “so you have something to fall back on.” — Paul F. Tompkins 

Why This Matters

Whether you’re a comedian, a writer, or any kind of creative, Paul’s story is a reality check wrapped in hard-earned wisdom. It’s a reminder that creative work has always been precarious, but today, it’s also about navigating constant change and figuring out how to make a life when your passion doesn’t come with a steady paycheck.

If you’re looking for a laugh, some perspective, and maybe a bit of comfort knowing that even the greats are hustling just like you, this episode is for you.

📣 See Paul live in a town near you: https://paulftompkins.com/live

We want to hear from you.

🗣️ Have you ever thought you “made it” only to realize you’d have to start over?

Let us know here, or on...

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A Thought to carry with you...

You’re not waiting for the thing to come along.
You are the thing.