How To Transition Out Of An Advertising Career? With Rachel and Lynette
Nearly 200 episodes in, The Overthinkers is turning a page. This is Rachel Mercer's final episode as co-host — and the debut of Lynette, a former global strategy lead at Ogilvy, ethnographic researcher, insect farm co-founder, and current Vermont transplant who consults for small businesses at what she calls her "community rate" (sometimes paid in sausage). To mark the moment, the three of us tackle mid-career transitions out of advertising: how to actually make the jump, why transferable skills are almost too broad to be useful, and what question you should be asking yourself before any of the rest of it matters. Rachel shares how client relationships built over 20 years quietly become your best career infrastructure. Lynette makes the case for low-stakes pilots before big leaps. And Shann is, characteristically, the most pessimistic person in the room about where AI leaves the advertising industry — and what that means if you're thinking about waiting before making a move. A proper goodbye, a warm welcome, and genuinely useful career advice in between.
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