🎗️You Winning Life🎗️
Most people know something is holding them back. They just can't quite name it.
You Winning Life is the podcast for high-functioning people who are done settling for "fine" — hosted by Jason Wasser, LMFT, Certified NET Practitioner, and Entrepreneur Coach based in South Florida.
With 20 years working with entrepreneurs, athletes (MLB, NBA, USTA), and everyday high-achievers, Jason brings a rare blend of clinical depth and straight talk to the conversations most podcasts are too polished to have.
Each episode pulls back the curtain on the patterns, beliefs, and nervous system responses that drive your decisions — at work, in your relationships, and in your own head. Guests include psychologists, performance coaches, wellness experts, and people who've navigated real transformation.
No jargon. No toxic positivity. Just the kind of honest conversation that actually moves the needle.
Work with Jason → thefamilyroomsfl.com
🎗️You Winning Life🎗️
Ep. 197-Quiet Cracking: Why We Ignore Red Flags in Careers (and How to Stop) w/Eliana Goldstein
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In this episode, Jason sits down with Eliana Goldstein, a certified career and executive coach, the resident Career Coach for CBS New York Morning News, and a member of the Forbes Coaches Council. Eliana’s coaching strategies have been featured on MSNBC, Business Insider, and Fast Company, and she has spoken at leading companies including Peloton and LinkedIn.
Together, Jason and Eliana explore the growing workplace trend of “quiet cracking”—when professionals, overwhelmed by today’s tough job market, settle for roles that don’t align with their values or strengths, ignoring obvious red flags along the way.
This powerful conversation uncovers the mindset shifts, strategies, and frameworks that can help you navigate career transitions with confidence, advocate for yourself in the workplace, and embrace change without fear.
🧭 What You’ll Learn in This Episode
- Why “quiet cracking” is becoming the new workplace trap—and how it mirrors relationship dynamics
- Red flags to look for (and stop ignoring) when evaluating career opportunities
- The role of self-advocacy in building fulfilling, financially rewarding careers
- How to align your work with your strengths and values through self-audits and strategic career planning
- Eliana’s journey from corporate marketing to career coaching, and how her personal growth shaped her mission
- Practical tools for career clarity: journaling, asking the right interview questions, and building authentic networks
- How to confidently frame career pivots, even when they don’t follow a “traditional” path
- Why evolving your definition of success matters—and how to embrace transitions from technician → manager → entrepreneur
🚀 Episode Highlights
- Quiet Cracking vs. Quiet Quitting — how fear, desperation, and uncertainty push people to take the wrong roles.
- Mindset Shifts — breaking free from imposter syndrome and cultural narratives that keep you stuck.
- Career Fulfillment — Jason and Eliana share stories of how small shifts in perspective can transform both work and relationships.
- Self-Advocacy & Growth — strategies for negotiating roles, realigning job responsibilities, and prioritizing satisfaction over short-term paychecks.
- Career Evolution — embracing change with confidence and redefining what success looks like at each stage.
⚡ Rapid-Fire Takeaways
- One career myth you should stop believing
- The best question to ask before accepting a new job
- One thing to stop doing on LinkedIn right now
- The first action to take in the next 24 hours if you feel stuck
- The career advice Eliana lives by, no matter what
🎧 Listen Now
This episode is for anyone feeling stuck, burnt out, or overwhelmed in today’s job market. If you’re ready to stop ignoring the red flags, advocate for yourself, and design a career that truly excites you and pays you well — this conversation is your roadmap.
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