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Funnest job no doubt (but probably the worst $!) was running a ski shop. The shop was pretty specialist and only sold twintips. There was the challenge of running a small business, but also the fun side of chilling and just talking with other skiers, watching ski movies, getting stoked on peoples ski stories, helping people chose the right equipment for people - I made alot of friends with people who just came into the store.
Worst job - cleaning planes at an airport. 12 hour nightshifts 6pm - 6am. God that sucked. But I worked my ass off and saved money to go and spend a winter out in the French Alps when I was 18. So I guess it payed off.
The fun jobs are often the worst paid unfortunately!