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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Eighteen years at Microsoft, all in engineering. Natasha made it to M2 — and then went back to M1, because that's the work that fills her up.

A conversation about building a network before you need it, the mistakes worth making, and what she calls balance. On taking your shot, learning what fulfillment actually feels like for you, and slow ambition.

Find Natasha @ inkedin.com/in/natasha-gaitonde-7035512

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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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Earlier this year I stopped working for five months. Ten years ago I couldn't have done that — and this episode is about why.

Next episode: Rekha Raghu, fractional executive and my co-founder at Climbon Coaching.

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When Microsoft laid me off in 2014, it felt like being jilted by a lover. There were no boundaries between me and my work — I didn't have a job at Microsoft, I was my job at Microsoft. So when the job ended, I couldn't tell you what was left.

In this first episode I tell the story of the two coaches who split my career in half. The first one, in 2014, was handed to me after the layoff. She worked on my strengths and told me something I'd known my whole working life without ever saying out loud.

The second one, in 2022, I found and paid for myself — while I still had the job, the title, and the stock package. She worked on my values. That conversation is why I walked away from two million dollars at Broadcom before the golden handcuffs closed.

Strengths tell you what you're good at. Values tell you what to do when the good option and the right option aren't the same option.

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