Look for patterns or themes within the tips. A hundred million years ago (ok, maybe 10-15 years) when I did long(ish) papers for school, I found that themes evolved naturally as I wrote them. Even when I was starting out with only a vague idea, as I put the million tidbits down, I could usually start to find overarching themes. In your case, perhaps you’ve got 4 themes, for example:

Quality of Life Via Technology
Defending Quality of Life from Technology
People Skills Via Technology
People Skills In Spite of Technology

And after seeing those 4, maybe you find the can all be summarized by something like: “Good Tech, Bad Tech, and How to Un-uglify Your Life.”

Or, maybe not.

Perhaps my examples should be ignored. Or burnt. At the stake. But anyone as organized as you HAS natural subdivisions in how they do things, even if you don’t know it. Possibly this is one of those things where you look to your value system and see what’s important to you personally and how you look at the world, and thus notice where/how all your tips fit in.

On a different note – I *love* your podcast. I sincerely hope your sense of humor translates to the printed medium, because it truly makes your podcasts come to life.

Okay… so when will we be able to pre-order?

But it’ll still be pretty much a tips book, something to jump in and out of, that way. Is there a way to place some comments on happiness, success, and productivity among the tips? Sort of a bread-crumb trail through the book to keep people moving through it and expand on the big picture (really selling readers who aren’t sure they to improve themselves)?

I like the idea of a reference section, though tech can become outdated quickly, as Chris mentioned. Consider ways to make the reference evergreen: in addition to tech solutions, offer non-tech solutions (which reminds me of your podcast on your notebook solution for keeping tasks organized). Also, will you house the references on your site, which you can keep updated? Not only does that allow you to offer readers the most updated references, it brings readers to your site.

HTH. And if you need a good editor (perhaps Grammar Girl is busy?), I’d love to work with you.

I would add one more theme to the concept: as you are explaining “how”, focus almost exclusively on the process as opposed to the tools. If you want a truly timeless book, go with your own advice and stick to concepts and implementations that can be performed with low-tech solutions like pen and paper. Technologies come and go.

When you mentioned your wiki, my thoughts quickly jumped from “I want to help Stever with his book” to “There are tool many information management tools to learn!” I may be an anomaly but I’m actually one of those early-adopter types, so I wasn’t intimidated by the new technology thought. However, I’d bet that 75% of people everywhere stop _thinking_ about the core concept when they run across mention of a technology that they’re not familiar with.

So, my convoluted advice is to stick to core concepts and low-tech tools so that you can avoid minimizing your potential audience, the Luddites.

What if you created an Internet forum/community for people to share their own ideas for which tools they use and how they use them, branded as the book’s companion? Then you reference the community in the book for people who want “HOW-TO-TOOL” as opposed to “HOW-TO-GID”? Then you add community, stick, detail, and viral without having to make your book be about technologies? You do a great job with that in the podcasts.

Advice is usually worth what you paid for it. No, I don’t expect a check!