In this episode of the YMyHealth podcast, Co-Host Julie Woon sits down with therapist and life-transition whisperer Rebekah Lipsky, LMHC, LPC, LCPC, to talk about the emotional chaos of “becoming an adult”—whatever that even means anymore.

From calling off an engagement and quitting her job to launching a private practice and moving to a new city—all in one year—Rebekah’s personal experience with transformation fuels her passion for helping others survive (and even thrive) through life's biggest shake-ups.

Whether you're wondering if it's normal to still feel lost in your 30s or trying to support a friend going through their own transition spiral, this episode covers it all: relationships, careers, mental health, boundary-setting, and why your parents' advice might not always land in a post-pandemic world.

They talk about why “you’re not behind” is more than just a self-help cliché, how to know when it's time for therapy, and what it really means to move forward—even if it’s uncomfortable. Because yes, it’s all uncomfortable—but one version gets you stuck, and the other version gets you somewhere.

Feeling stuck, anxious, or just tired of pretending you have it all figured out? Hit play now and hear why navigating transitions is messy, meaningful, and 100% manageable with the right support!

Highlights:

• (01:20) – Rebekah reflects on navigating three major life transitions at once
• (02:35) – Common life shifts millennials face: career pivots, aging parents, and cross-country moves
• (04:08) – How cultural and generational shifts have redefined how we approach fulfillment and stability
• (06:23) – The rise of nontraditional career paths and how they impact identity and purpose
• (07:41) – Using values-based therapy to guide meaningful career decisions
• (10:50) – Approaching relationship transitions: breakups, boundaries, and emotional safety
• (13:46) – Learning to identify unhealthy patterns and the importance of emotional consistency
• (17:48) – How to support loved ones going through transition—and what to say (or not say)
• (20:45) – Addressing the feeling of “being behind” in life and the role of societal messaging
• (23:29) – When to consider seeking therapy for support during change
• (26:17) – The value of accepting discomfort as a pathway to growth and healing

Links:
Are you a millennial interested in learning more about healthcare issues specifically related to your generation? Start here: https://www.ymyhealth.com/ and follow us on Instagram at: https://www.instagram.com/ymyhealth_/

Learn more about this episode's guest, Rebekah Lipsky, LMHC, LPC, LCPC, here: https://www.rebekahlipskycounseling.com/
You can also follow her on Instagram @rebekahstherapyroom
Have a question about today's episode? Email us at [email protected]. We will be answering your podcast episode questions in our next upcoming Q&A episode this summer.

Learn more about YMyHealth's Podcast Co-Host and Content Marketing Strategist, Julie Woon, here: https://www.ymyhealth.com/team/julie-woon

Thanks again to our sponsor Dr. Sarah Diekman, Director of Diekman Dysautonomia! If you’d like to learn more about our sponsor and her practice that provides care to patients with POTS and Long COVID, go to https://dysautonomiaexpert.com