51: How to Know When It's Time to Leave the Job You Used to Love episode artwork

EPISODE · May 7, 2026 · 34 MIN

51: How to Know When It's Time to Leave the Job You Used to Love

from SisterSmart Leadership

Have you been at the same company for years, even decades, and suddenly the work that once excited you feels stale? You are not alone and there is a clear path forward.This is the question so many ambitious women face: how do you know when it is time to leave a job you have loved? When the culture shifts, when new leadership changes everything, when an outside force like a merger or a pandemic rewires the workplace, the thought of moving can feel daunting. You know you feel stuck but you do not know what the next steps are.In this episode of the SisterSmart Leadership Podcast, Jill Avey sits down with her client Rebecca H., a privacy specialist in the legal field who spent more than 15 years at the same organization before she made her move. Through the Sisters in Leadership program, Rebecca was able to recognize the leadership skills she had been quietly building for over a decade, develop the executive presence she needed to interview at a higher level and land a role at an established publicly traded mid-sized consumer products company where she leads a sizable team with a real mandate and the resources to deliver on it.Whether you are a woman leader who has outgrown your current role, a high performer wondering whether your complacency is really stagnation in disguise, or an in-house specialist who has never been told you are a leader, you will find inspiration and a roadmap in Rebecca's story.In this episode, you will learn:How to recognize the difference between contentment and complacency in your careerWhy a culture shift can quietly drain your enthusiasm for the work you used to loveHow leadership skills get built off the org chart, and why that matters when you are ready to move upThe executive presence work that helps women get hired into bigger leadership rolesA networking and resume strategy that opens doors without ever telling anyone you are lookingHow to step into a brand-new leadership role and build psychological safety from day oneWhy being a likeable badass is the sweet spot for women leaders who refuse to be trampled or seen as a pushoverHow a personal strategy retreat can reframe your whole career and create real long-term balanceMENTIONED IN THIS EPISODELikeable Badass by Alison FragaleABOUT REBECCA H.Rebecca H. is an experienced privacy specialist in the legal field with more than two decades in legal practice. After spending over 15 years building her career at her previous organization, she recently moved into a senior in-house leadership role at an established publicly traded mid-sized consumer products company, where she leads a sizable team and is responsible for redefining the company's privacy program. Because of the sensitive nature of her work, Rebecca is sharing her story on audio only and using her first name and last initial.—Register for the Free Executive Presence for Women Masterclass: The 3 keys to Increase Authority and Influence, happening live on Thursday, August 8 at 12 PST.A replay will be available for those that register! https://zoom.us/meeting/register/tJAkdOsrDItGdHchQv1BXFozsGRUjL74xlK#/registration —🌟 FREE MASTERCLASS: Achieve Your VP Promotion: 3 Steps to Success in the Next Yearhttps://sistersmart.com/register-sil—✈️ FREE PASSPORT TO PROMOTION PRIVATE PODCAST: 7 STEPS TO GET PROMOTED FROM DIRECTOR TO VP Get access to the Passport to Promotion Private Podcast—👩‍💻 APPLY FOR THE SISTERS IN LEADERSHIP PROGRAM An 12-month coaching program for women leaders who want to rise up and fulfill their career potential and get promoted from director to VPJoin Sisters in Leadership to Get Promoted to VP—💻 EXPLORE OUR LEADERSHIP COURSESWe offer a few leadership courses for you to begin sharpening your skills from meeting management to executive presence and productivity.Sign Up for a Leadership Course—👋 CONNECT WITH JILL 🌐 Website: https://sistersmart.com/ 🎥 YouTube: https://linktw.in/uWD3ko 💼 LinkedIn: https://www.linkedin.com/in/jillavey/

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