I doubt that I am wiser, but I have a few thoughts (caution: long-winded :-).

First of all, the old model of retire-at-65-on-a-pension has pretty well gone the way of the Dodo. Full pensions are increasingly a rare breed, so many people will work part time for walking around money even if they have the basic essentials covered.

People reaching 65 these days are healthier and more active, and may in fact want to keep working until 70, especially if they can negotiate more flexibility into their job situations. Or maybe they want to take lower-paying but more satisfying positions in not-for-profit or community organizations.

With the coming mass retirement of baby boomers, there will actually be a shortage of skilled people in many areas. All that right-sizing in the '90s means that companies killed off a lot of young up-and-comers who would now be ready to fill these positions. This means there will be an increased opportunities for those who keep up-to-date in their fields. Age-ism may be less of an issue than it is now.

Regarding money, some people try a "material fast" for one month, where they try to cut their non-essential spending to zero. This gives them a benchmark of what really matters. It's also an opportunity to step off the consumerism treadmill and cultivate interests that are very inexpensive and yet highly satisfying. Once you start thinking this way, it can ripple through many areas of your life and save you untold thousands.

For casual income, consider starting one or several Saturday micro-businesses. Ideally, choose something that meshes with your hobbies, so it's interesting, and so you can write off all that gear so you don't pay tax. For example, I'm testing the waters with a micro-business that does basic sharpening and minor repair to knives, axes, pruning shears, gardening tools and so on. A couple of afternoons a week at farmers' markets should tell the tale. Free advertising through Craigslist and Kijiji and bulletin boards. I have every indication that the demand is huge; and the overhead is stuff I buy anyway.

My 2 cents (and then some).