From Hollywood Dreams to a Life of Impact | J.R Orenstein | Episode #82
What do you do when the career you’ve worked so hard for suddenly no longer feels aligned?
In this powerful episode, we sit down with J.R. Orenstein, who went from working behind the scenes on major Hollywood productions like NYPD Blue and The Day After Tomorrow, to becoming a respected leader in the insurance industry and content creator with purpose.
J.R. shares the truth behind walking away from the entertainment world, what it took to build his own agency from the ground up, and how tools like ChatGPT are now helping him work smarter, serve clients better, and lead with intention.
This is more than a career pivot—it’s a masterclass in listening to your gut, embracing reinvention, and building a life rooted in impact.
In This Episode, You’ll Learn:
– Why career pivots often lead to purpose
– How to build confidence in uncertain seasons
– Ways to leverage storytelling in business
– Simple strategies to use AI tools like ChatGPT more effectively
– How showing up online can transform your brand—and your mindset
Timestamps – Key Moments
00:00 – When the Path You’re On No Longer Feels Right
01:05 – Finding Creative Fire in Unlikely Places
02:24 – What They Don’t Tell You About “Making It”
07:34 – Listening to the Inner Voice That Says, “There’s More”
11:27 – The Career Shift That Was Never in the Plan
14:09 – Building a Business Before You Feel Ready
18:54 – From Film Scripts to Instagram Reels
21:05 – The Fear of Being Seen (and Why It’s Worth It)
23:40 – AI Isn’t Replacing You—It’s Unlocking You
26:38 – How to Ask Better Questions (and Get Better Answers)
Resources & Mentions:
Follow J.R. Orenstein on Instagram: @j.r.orenstein
ChatGPT by OpenAI: openai.com/chatgpt
Stay tuned for the upcoming AI Masterclass (details coming soon!)
Follow the Host: Ben Lavender @benmtvg
Connect with Us:
Subscribe, leave a review, and share this episode with someone who’s on the edge of a pivot or needs a reminder of what’s possible when you trust yourself.
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