Anna Mackenzie: Redefining Plan A

Are you a regular listener of the show? Do you want to shape the conversation for season 2? Fill out this quick survey and help me and the production team ideate for next season's guests and episode lineup. (And if you can, leave a review of the show on Apple or Spotify too!) 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.