As the major car accounts switched more to photography for their magazine advertising instead of illustrations, Linwood's parents bought a cottage resort and trailer park in the Kawartha Lakes region of Ontario. But when Linwood was 16, his father died, and he essentially took over running the family business (an experience he wrote about in his memoir, Last Resort).
At the age of 22, Linwood left the resort and got his first newspaper job, at the Peterborough Examiner.