EP 033: When Safety Becomes Suffocating: A Career Pivot with DJ and Producer Jonathan Amar
Feb 13, 2026
Essential listening for anyone who's achieved what they thought they wanted but can't shake the feeling that something needs to shift.
What happens when the stability you worked so hard to build starts to feel like a cage?
Jonathan Amar was a successful videographer before he could legally drink. By his early twenties, he had steady clients, consistent income, and a skill set people valued. From the outside, he'd figured it out.
Somewhere along the way, Jonathan started feeling uninspired and he had to decide whether to stay in the safe lane or risk it all to follow what felt truer.
This conversation is about what it takes to add something new without abandoning what works, why "one step at a time" is the only way forward when you can't see the whole path, and what becomes possible when you stop treating security like the end goal.
This isn't a story about burning it all down. It's about expansion, integration, and trusting that your body is trying to tell you something worth listening to.
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Covered In This Episode
- Why early success doesn't mean you have it all figured out (and how Jonathan is still "figuring it out day by day")
- The moment Jonathan realized that security and suffocation can coexist—when you have consistent clients, steady income, and a respected skill set, but still feel unfulfilled
- What Jonathan calls the "partition approach" to pivoting— and why you don't have to burn it all down to begin again
- Why depression might actually be your body's messenger telling you you're in the wrong place—and how recognizing this shifted Jonathan's entire relationship with his own restlessness
- The five-year question that creates instant clarity, and why this helped Jonathan finally take the leap
- How focusing on the final stage guarantees you'll never get there, and why one step at a time is the only way forward when you can't see the whole path
- What happened when Jonathan broke free from a consistent income that didn't align, and why the "safety" of staying put can actually be the riskiest choice
- The truth about why it's so easy to forget your dreams when you're feeling secure—and how that comfortable protection of a steady job becomes the exact thing keeping you from what you really want
- Why following your heart isn't selfish but actually a service to the world
- The reframe that makes staying put feel more dangerous than leaping
Chapters
00:00 Welcome to the Courageous Pivot Podcast
02:38 The Early Days: Meeting and Working Together
03:27 Challenges and Growth in Filmmaking
19:17 Transitioning to Music and DJing
34:42 Facing Criticism and Embracing Gifts
37:20 Starting Free Events and Overcoming Challenges
40:10 Balancing Film and Music Ventures
50:00 Advice on Following Your Passion
57:21 Reflecting on Business and Personal Lessons
01:07:23 Future Plans and Final Thoughts
Special Offers
-
Free Heart Coherence Masterclass – A complimentary session with Meghan Telpner exploring how to create alignment between your heart and mind, access inner calm, and live from your most authentic self.
- Click here to get 30% off Rise & Shine: A Guided Approach To Heart-led Living and Leadership. (Click here if you reside in Canada)
Related Episodes
- EP 016: What About the Money? The Hard Truth About Financial Security and Life Pivots — Because sometimes the "safe" income is actually the riskiest choice you can make.
- EP 021: A Creative Pivot: Why Being Good at Something Isn't Enough with Textile Artist Jen Arron — When skill and success aren't the same thing as soul alignment.
- EP 023: Learning How to Listen: When Your Story Requires An Unexpected Pivot with AI Expert Tiago Forte — What it looks like to walk away from something you built when your heart says it's time.
More About Jonathan Amar
Jonathan Amar's platform
Jonathan Amar is a Toronto-based filmmaker with over 15 years of experience behind the camera. Known for his cinematic storytelling and eye for detail, he has worked across music videos, branded content, and documentaries, capturing authentic moments with style and intention. His years of filming artists around the world eventually sparked a deeper connection to sound, leading him to explore music production and DJing as a creative extension of his visual work.