Episode 344
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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Timestamps to guide your listening:
- 00:00 The myth that you have to pick a lane
- 02:47 How she built a portfolio career (it wasn’t planned)
- 06:31 The loss and public failure that freed her
- 10:35 Planner or not? Vision without a rigid plan
- 14:34 Why she built a business without quitting her job
- 21:06 The smallest experiment before you leap
- 25:35 Who to talk to (and the boss conversation to have)
- 31:31 The money question no one warns you about
- 37:02 “What do people pay you for?” and why you never start from scratch
- 41:30 AI, and the hardest skill: unlearning
- 47:02 Your next 12 months: where to start
Links mentioned in this episode:
- Kate’s diagnostics
- Find my talents TalentPredix strenghts assessment
- Book Mentioned: Do the Work, by Steven Pressfield
- Episode 121 - Impostor Syndrome and Fear of Success
- Episode 242 - The Role of Business Intelligence (BQ), Emotional Intelligence (EQ), and Social Intelligence (SQ) in Career Advancement
- Episode 287 - Hiring Makes No Sense Anymore: Why Recruitment and Hiring Feel Like a Burden and How Leaders Can Fix Them
- Episode 288 - How to Job Hunt During the Mid-Year Slowdown
About the host, Renata Bernarde
Hello, I'm Renata Bernarde, the Host of The Job Hunting Podcast. I'm also an executive coach, job-hunting expert, and career strategist. I teach corporate, non-profit, and public professionals the steps and frameworks to help them find great jobs, change, and advance their careers with confidence and less stress.
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