How to Build a Portfolio Career Without Starting Over, with Kate Dillon

Episode 344 - Career change after 40 does not have to mean abandoning everything you have built. In this conversation with Kate Dillon, we explore portfolio careers, small career experiments, transferable career capital and how to create more professional options without making an unnecessary leap.

There is a particular kind of career dissatisfaction I see frequently among experienced professionals. They are successful by conventional measures. They have seniority, expertise, a respectable salary and two or three decades of professional history behind them. Yet increasingly, they feel uneasy about the idea that the next ten or fifteen years of their working life should look much like the last ten or fifteen.

The problem is that many people interpret this uneasiness as evidence that something dramatic needs to happen. They imagine leaving their employer, retraining completely, launching a consultancy, buying a business or finally pursuing the idea they have been quietly carrying around for years. Then reality intervenes. There is a mortgage, children at university, aging parents, a lifestyle built around a certain income, and a professional reputation that took a long time to establish.

This is where the conversation about career change can become unnecessarily binary. Stay or leave. Corporate career or entrepreneurship. Employment or consulting. Security or freedom.

My conversation with Australian lawyer, strategist and entrepreneur Kate Dillon offered a much more useful possibility: perhaps the next stage of an experienced professional's career does not require abandoning what came before. It may instead involve building outward from it.

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