Be Seriously Unserious

Aloha Flow Riders!

Ready for some real talk? This week Doc Rock sat down with Ecamm's Caleb Dempsey to break down why being "seriously unserious" might be the creative breakthrough you've been waiting for.

The Flow: Episode 123 - Get... Nov 11 · The Flow 65:21   ​

"I really believe that what you do from five to nine is what makes your nine to five great. The more people try to fill their five to nine with side hustles instead of fun and play, it actively impacts and drags down the work that they do." - Caleb

The Problem: "I don't want to be on camera" (sound familiar?)

The Solution: Start where you're comfortable. For Caleb, that meant writing newsletters for 30 people every Saturday morning.

The Evolution:

• Started with a newsletter focused on personal updates + slowly shifted to comedy writing.
• Eventually moved to video when writing felt like something they could do in their sleep
• Now they’ve built "Seriously Unserious" - a newsletter focused on fighting off the Sunday scaries

Remember: Your brain doesn't have to start with "let me record this." It can start with "that's so funny, let me write that down."

Seriously Unserious written by Cleb and never AI Seriously Unserious is a weekly newsletter exploring the goofy ideas that live inside my head, bad business ideas, and a few videos for those who don't love reading that much. Delivered direct to your inbox every Sunday, this newsletter is designed to help you connect with your inner unserious before you clock into your work week. Subscribe​

1. Reconnect with Your Inner Child

Write down 10 things you wanted to be when you grew up. Pick one action item per week for the next 10 weeks to take a step toward each goal.

Want to be a rock star? Buy Guitar Hero. Take a voice lesson. Hit up karaoke. The point isn't perfection - it's play.

2. Get Comfortable with Failure

• Every SNL episode records 40 sketches but only airs 11
• Unsubscribes don't mean your content is bad - they mean your list is more aligned
• That comedian who "bombed"? They might have been testing new material

Failure isn't the end of your story - it's research for your next chapter.

3. Generate Ideas Daily

Stop using AI to brainstorm for you (at least for a month). Instead:

• Come up with 20 podcast ideas before recording
• Call a friend and talk it about them - choose the best one
• Write 10 ideas for content segments for the best one
• Call a friend and talk it about them - Choose the strongest three

Quality comes from quantity. Take 100 shots, hit 10 - that's an incredible percentage.

The Social Media Reset:

• Comment real comments (not just emojis)
• Reply to Instagram stories
• DM smaller creators with genuine engagement
• Save content that inspires you for later reference

Remember: AI can't replace your humanity. When you show up authentically, the algorithm notices - and so do real people.

Caleb organizes their creative life with three simple categories:

MAKE: What content will you create this week?

PLAY: How will you recharge your creativity?

RELEASE: What will you share with your audience?

Keep this gameplan where you'll see it daily. Add a personal mantra at the bottom to keep you focused.

When you shift from "I have to work" to "how can I make this fun?" everything changes. As Caleb shared:

"When I stopped distrusting the world around me, things opened up. When I stopped believing that my failures would derail my success, failure became more fun."

1. Try Caleb's Make-Play-Release framework - Create your own sticky note categorizing what you'll create, how you'll recharge, and what you'll share this week.
2. Connect with fellow creators - Leave three meaningful comments on videos that inspire you this week.
3. Embrace the unserious - Schedule one hour this week for pure play.

Reply to this email and tell Caleb how it went — they will read every response!

Mahalo,
Doc Rock & Caleb

Want to find Caleb's newsletter? Check out seriously.unserious.club​