In this episode, I sit down with Jaspreet Gill, high-performance coach and founder of Piloted Performance, to talk about the moment she realized the career she built at Microsoft no longer felt aligned — even though everything looked successful on paper.
We talk about the pressure many high-achieving women feel to keep performing, people-pleasing, and following the “safe” path, even when something internally feels off. Jaspreet shares her journey of leaving corporate, rebuilding her identity, and creating a career that actually feels fulfilling.
We also dive into the “good girl” guilt, confidence, trusting yourself, career transitions, and how she now helps ambitious women make aligned decisions, lead with confidence, and step into bigger opportunities without second-guessing themselves.
If you’ve ever felt torn between the life you built and the life you actually want, this episode is for you.
You can also download Jaspreet’s free resource, the Aligned Language List, to help shift the way you speak to yourself and move with more confidence and clarity.
Connect with Jaspreet:
Instagram | Linkedin | Aligned Language List
Connect with Cindy:
Instagram | Book Recommendations | Book your profit strategy call | Linkedin