Prioritizing Joy in the Entrepreneurial Journey- Looks Like Work, Season 3, Ep 6

We don’t talk enough about the moment when the dream job starts to taste like cardboard.

When the pitch is polished, the company’s been acquired (twice!), and your LinkedIn could make an angel investor weep—but you look around and realize that somewhere between scaling and raising and pivoting… you forgot to feel anything.

This is where I met Lee Rotenberg.

In this episode, Lee—a serial entrepreneur who’s built, sold, and raised more companies than most of us have houseplants—pulls back the curtain on what happens after the success. The real stuff. The part where joy doesn’t just get deprioritized—it disappears. And how, slowly but surely, she’s choosing to bring it back.

We talk about the sneaky grief of letting go of an identity that once felt exciting. The difference between building for validation and building for resonance. And what it looks like to make fun a business priority—not as a bonus, but as a non-negotiable.

We dive into:

• Why fun is a serious career strategy

• The difference between chasing success and actually feeling it

• The weird grief of closing a chapter that "should" make you happy

• Early-stage energy vs. scale-stage stress

• Fundraising fatigue (it’s real and it’s spectacularly underdiscussed)

• How presence beats perfection — in business and beyond

• And why your best ideas might only arrive when you stop white-knuckling the plan

Lee’s powerful reframe:
👉 “What’s the why behind what you’re doing?”
Not the pitch-deck version. The quiet one. The one you whisper to yourself when no one’s looking.

This episode is a love letter to the creative misfits who build businesses from intuition, then get caught in the spreadsheets. The ones who crave delight, but forget to schedule it. Who believe that success should feel better — and are willing to experiment until it does.

If you’ve been feeling like your calendar is full but your cup is not… come listen.

"Being successful is being happy... being very present and not trying to think about what is next."

Resources & Mentions:

1. "Let Them" by Mel Robbins - described as "the most life-changing book" Lee has recently read

2. "How to Be a No Limit Person" by Dr. Wayne Dyer - recommended as motivational and energizing

3. "You Are a Badass" by Jen Sincero - endorsed as an excellent read

4. Lee's podcast with Alex called "Unfinished Business" - interviews with inspiring entrepreneurs

5. Follow Lee on LinkedIn for authentic insights on entrepreneurship

6. Book recommendations from this season of LLW

7. Catch up on previous seasons of Looks Like Work wherever you get your podcasts: Spotify | Apple | Podbean

8. Subscribe to the newsletter: chedva.substack.com

9. Check out The Curiosity Lab and CuriosityGPT