19: Case Study: Should I Leave My Secure Job for a Risky Business Venture?

Balancing stability, passion, and strategic transitions in career decisions

Stacy wrote to me with a classic dilemma many of us face: she has a well-paying corporate job that pays the bills but leaves her feeling empty, while her side business idea keeps her up at night with excitement. She's torn between the safety of a regular paycheck and the allure of building something of her own.

"How do you leave a job that is lucrative but doesn't bring you true fulfilment?" she asked. "How do you take time away from the lucrative business to work on the new business? How do you serve two masters while you are transitioning?"

This is a tension I've navigated personally and seen countless others struggle with. The challenge isn't just about weighing income against passion - it's about managing risk, designing transitions, and creating pathways that don't force unnecessary binary choices.