In this episode, we talked about:
- The courage it takes to quit a path that doesn’t align with you, from law school to PhD, and how to navigate guilt and external expectations.
- Pivoting in your career or business intentionally, including moving from side hustle coaching to thought leadership and content creation.
- Aligning your work with your strengths, passions, and values, rather than chasing validation or revenue alone.
- Building confidence through consistency, mentorship, and supportive communities while embracing the uncertainty of change.
- Mindset shifts for quitting and pivoting strategically: knowing the difference between fear and misalignment, planning thoughtfully, and evolving gradually.
Listen to the full episode now:
“There’s no right or wrong decision—what matters is alignment with who you are and what you value.”
Timestamp:
- 0:00 intro
- 1:43 quitting law school & PHD: overcoming asian parents’ expectations
- 6:39 Cheryl Lau’s side hustle coach journey
- 8:01 transitioning from side hustle coach to thought leader: reinventing your career
- 11:49 3 core values to embody when pivoting your career for growth
- 15:15 thought leader club: pivoting towards new business directions
- 18:39 making career decisions that align with business and financial growth
- 20:12 creating a business that breaks the mold: embracing entrepreneurship
- 21:04 embracing the identity of a podcaster over coach
- 23:38 break the stigma of tying your identity to your income source
- 25:46 join our community! building connections for personal and professional growth
- 30:04 committing to podcasting: earning the right to call yourself a podcaster
- 36:27 are you quitting out of fear or misalignment? understanding career transitions
- 38:07 mindset shifts for successful quitting and pivoting in your career
- 39:57 being practical about quitting or pivoting careers: making strategic decisions
- 41:29 taking your time to quit and pivot—it’s okay to evolve slowly
- 43:20 outro
“Quitting is not failure. It’s a courageous pivot toward something that truly resonates with you.”
Connect With Cheryl:
- Cheryl’s Podcast: https://www.youtube.com/@UCeKkylzVPyJyT_fRAoRc4XQ
- Cheryl’s Instagram: https://www.instagram.com/cheryltheory/
Detailed Summary:
Introduction
Welcome back to Small Girl Big Talk, part of the Foundations for a Fresh Start series. Wendy introduces Cheryl Lau, a seasoned entrepreneur, coach, and podcaster, to talk about the art of quitting and pivoting in your career, especially in content creation and entrepreneurship. The episode focuses on how to reinvent yourself, grow personally and professionally, and make courageous decisions when a current path doesn’t fully align with your goals.
Quitting Law School & PhD: Overcoming Expectations
Cheryl shares her first major career pivot: quitting law school in her first year after realizing it wasn’t the right path. She also discusses quitting her PhD, a decision that brought more emotional weight and guilt, especially considering her immigrant parents’ expectations. Cheryl emphasizes the importance of acknowledging these fears and pressures while still prioritizing personal alignment. Wendy and Cheryl reflect on the courage it takes to make such decisions, highlighting how external expectations can make quitting feel like failure, even when it’s an intentional pivot.
Side Hustle Coach Journey
Cheryl recounts starting her journey as a side hustle coach, the only path she knew at the time. She candidly admits that coaching side hustlers was not her ultimate strength but served as a necessary starting point to discover her skills, values, and what resonated most with her clients. Wendy shares how Cheryl coached her first personal branding business, noting Cheryl’s early influence and guidance.
Transitioning to Thought Leadership
After three years as a side hustle coach, Cheryl realized her true strength was in helping clients develop thought leadership—guiding them to articulate their unique stories and perspectives. The pivot from side hustle coach to thought leader coach required letting go of an identity that had been publicly successful, including her award-winning side hustle podcast. Cheryl shares three core values that guided her through the transition:
- Backing yourself – making decisions even if others don’t understand.
- Commitment – staying dedicated even if initial results are slow.
- No right or wrong decisions – focusing on alignment rather than external validation.
These values were consistent from her first pivot (law school) to her second (business identity), emphasizing that courage, clarity, and alignment are central to successful career transitions.
Thought Leader Club & New Business Directions
Cheryl discusses launching the Thought Leader Club and the strategic considerations behind pivoting her business to better match her strengths and client needs. She highlights the importance of using evidence from client results and market research to guide pivots. Cheryl also shares how adapting her business approach—including co-working with clients in real time—helped her refine her offering while staying true to her skill set.
Embracing Entrepreneurship & Identity Shifts
The conversation delves into the challenge of separating identity from income source. Cheryl explains how she transitioned from coaching to embracing the identity of a podcaster and content creator. Podcasting became a consistent, pride-filled anchor in her career, despite not being a major revenue driver. Wendy reflects on the importance of valuing your own work and achievements, even when external recognition or monetary gain is minimal. They emphasize that true career fulfillment comes from aligning work with strengths, passions, and personal values.
Community & Personal Growth
Cheryl encourages listeners to join communities of like-minded individuals to foster personal and professional growth. She shares how engagement with others and accountability can support pivots and reinforce confidence during transitions. The discussion highlights that building connections and mentorship networks is a critical part of evolving in any career.
Mindset Shifts for Quitting and Pivoting
Cheryl outlines practical considerations for career changes:
- Assessing fear vs. misalignment – understanding whether quitting is due to fear or genuine misalignment with your current path.
- Practical planning – evaluating potential financial or business impacts before making changes.
- Gradual evolution – recognizing that it’s okay to pivot slowly and test new directions before fully committing.
Wendy and Cheryl reinforce that mindset shifts, coupled with data and self-reflection, make quitting a strategic decision rather than a reactive one.
Podcaster Identity & Content Creation
Cheryl reflects on her growth as a podcaster and content creator, noting how consistent creation over years has solidified her identity in this space. Wendy draws parallels to her own experience, emphasizing that long-term commitment builds confidence and credibility. They explore the tension between revenue-focused identity (coaching) and passion-driven identity (podcasting/content creation), highlighting the importance of pride and ownership in one’s work.
Conclusion
Cheryl and Wendy close the conversation by emphasizing that quitting or pivoting is not a failure—it’s a strategic choice to realign with your strengths, values, and goals. Career and creative transitions often involve fear, external pressures, and identity shifts, but approaching them intentionally can open doors to new opportunities. Staying committed to your values, learning from experimentation, and embracing adaptability allows for growth that’s sustainable and authentic. The episode leaves listeners with the reassurance that evolving your career or creative pursuits is a courageous act, and each pivot moves you closer to a life and work that truly resonate with who you are.
