The Crossroads: A Pivotal Career Shift
For years, Olivia climbed the corporate ladder, reaching a VP role that represented everything she had worked toward. She was ambitious, successful, and deeply invested in her career.
But two weeks after returning from maternity leave with her second daughter, everything changed.
"I was laid off."
It wasn’t just a job loss—it was an identity shift.
✔ She had spent years excelling in a corporate environment.
✔ She had just returned from maternity leave, trying to find her rhythm again.
✔ Now, she was forced to re-evaluate everything.
The severance was excellent, but it didn’t soften the emotional impact.
"My ego took a huge hit."
For someone who had always tied success to professional achievement, stepping away from the corporate world felt unsettling. But as she processed the transition, she saw an opportunity:
Instead of jumping back into another demanding corporate role, she bought a business and began consulting—creating a career that fit her life, rather than the other way around.
She also made a geographic shift, moving from the Bay Area to Granite Bay, where her family could afford a more balanced lifestyle.
"I realized that my drive at work had changed, but I hadn’t really changed my choices. I was still on the treadmill—chasing the next promotion, thinking the money would make me happier."
It took getting laid off to force her to pause and ask: What do I really want?
The Challenges: Ego, Money & Identity
- Letting Go of Ego
"My biggest challenge was my ego—figuring out who I was without the big title."
Success had always been measured in promotions, recognition, and professional validation. Now, she had to redefine what success looked like on her own terms.
- Figuring Out How to Make Money with Flexibility
Corporate roles provided a clear salary, benefits, and a predictable career path. Running a business and consulting came with freedom—but also financial uncertainty.
"I had to figure out how to make money while also keeping the flexibility I wanted."
- Reevaluating What Actually Made Her Happy
Before, she was commuting long hours, grinding for the next title, assuming that more money meant more happiness.
But after stepping back, she realized:
"At some point, the money wasn’t making me happier, and I was spending too much time commuting instead of with my kids."
What Worked: Aligning Career Choices with Core Values
- Taking Time for Deep Self-Reflection
"Really working on myself and finding my core values made all the difference. I had to realign my choices with those values."
She stopped chasing what she thought she was supposed to want and focused on what actually mattered to her.
- A Supportive Partner
"My husband was a huge source of support throughout this transition."
Having someone to remind her of why she made the shift helped during moments of doubt.
- What She Would Have Done Differently: Start a Side Hustle First
"If you can start a side hustle while working, I think this is ideal."
She acknowledges that transitioning into entrepreneurship would have been easier if she had already been building something on the side before stepping away from corporate life.
The Tools & Resources That Helped
📌 LegalZoom – Helped with the logistics of setting up her business.
📌 The Pivot Book & Podcast – Provided guidance on navigating major career changes.
She sought both practical tools and mindset shifts to help her transition successfully.
Advice for Other Parents Considering a Career Shift
✔ Align Your Values with Your Career Choices
"I was still chasing the next job title and money, thinking it was the key to happiness. But when I really examined my life, I realized I wanted something different."
✔ Don’t Just Follow the Career Treadmill—Ask What Actually Makes You Happy
"At some point, the money wasn’t making me happier, but I was spending too much time away from my kids."
✔ Know That Every Choice Has a Tradeoff
"I do still doubt whether I should have taken that big job offer. But I remind myself why I made this choice and what my values are."
✔ If Possible, Test the Waters First
"If you can start a side hustle while working, that’s ideal. It gives you time to transition and see if it’s really the right path."
Olivia’s Both& Moment
Olivia’s story is about both stepping away from corporate life and continuing to build a career on her own terms.
✔ She experienced both an ego hit and the freedom to redefine success.
✔ She had both moments of doubt and deep alignment with her values.
✔ She found both financial independence and a career that allowed for the flexibility she wanted.
This wasn’t about giving up ambition. It was about redirecting it toward something that truly fit her life.
