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That's a very good point, Luke!

This is a great idea for a challenge, and I love that it seems to 'reverse' the typical direction of mentorship.

I have two examples where I've seen this kind of cross-generational mentoring work.

1. My local council set up a "youth mentoring seniors in computer skills" program over a series of weeks. I think it was run at the local library (or maybe through a school, I can't remember). I read about it in the newspaper, and I recall that both the seniors and the youth found it very useful.

I think for this to work, there needs to be clear boundaries around time commitment -- a short, intensive spurt of interaction would appeal more to the youth (say 4 consecutive weeks) rather than an open-ended, ongoing arrangement. Having a curriculum set out would also be helpful, so the youth don't need to reinvent the wheel.

2. Another example recently went viral: Students in Brazil being paired with retirees in the USA for English classes. This is a perfect example of the synergy that happens when a mentoring situation can be mutually beneficial.

(Every time I watch this video, I cry -- it is such an elegant solution to two complementary needs):

http://www.dailymail.co.uk/femail/article-2622691/Lonely-American-retirees-help-Brazilian-students-practice-English-video-chat-make-unexpected-new-friends-process.html

NB: Both these examples involve retirees, rather than people in their 50s seeking work, but I still feel that the examples give something concrete to work with and discuss :)