n 2013, Gustavo left Microsoft for what he planned as a six-month break to help his wife’s real estate team. He never went back. He became a top-performing agent, kept the career change secret for two years in case he needed a way back, then moved his family to Mexico and built a service business for U.S. real estate agents. It nearly failed in 2019, until a brother-in-law with a pencil and a P&L showed him what he couldn’t see.

Gustavo was G’s first manager at Microsoft, Redmond. In this conversation, they talk about leaving the security of a corporate job, why it took ten years to get where he expected to be in three, the two days a month he still misses Microsoft, and why the exploration phase is seductive, but giving up too soon is the real mistake.

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After five months away, I went back to work with a written plan. The boundaries held. The freedom didn't. A solo episode on what returning really costs, and why slow doesn't mean not growing.

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Rekha turned down a job at the IBM lab that built the computer that beat Jeopardy — and she's never called it a mistake. Twenty-five years into her career, she's asked herself three different questions about what to do next. This episode is about how you know when the one you're using has expired.

Rekha Raghu is a fractional executive, a coach, and my co-founder at Climbon Coaching.

Contact Rekha: linkedin.com/in/rekharaghu

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