Redefining Plan A

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In this final episode of the first season, I sit down with my friend Anna Mackenzie. Anna has built a portfolio career that blends digital products, global mentoring, writing, and fractional advisory work. We talk about how she transitioned out of her first business and into portfolio life post-COVID, the tension between freedom and burnout, and why structure is a non-negotiable for sustainable autonomy as a portfolio careerist.

We also dig into the emotional side of this path — the grief of leaving our old identities behind, how the global conversation around job security is shifting, and what it means to build a career that’s rooted in self-expression, not just monetization.