Tim Ferriss, author of The Four-Hour Workweek, provides an interesting thinking exercise in an interview with the 37 Signals blog. In short: What if you hated the work you have right now? What would that compel you to do?
Ferriss suggests that it's OK to love your work, or really loathe what it's doing to you. But if you're "comfortable" in your day-to-day gig, you might never do actual thinking ahead:
So how do you break out of a comfort rut? Ferriss says, "It's very valuable to amplify the pain. If your job is mediocre, sit down and do an exercise on paper to really run through what your life is going to look like in two, three, five years if you continue to do what you're doing. What options are you going to have? If you don't have kids now, but you're going to have kids in five years, do you want to be in the same job at that point? What are your options going to be then? What is your risk tolerance going to be then?
The whole interview is worth a read, and it clarifies a point about Ferriss' and other seemingly time-freeing productivity methods: the end goal is not idleness.
Tim Ferriss on tolerable mediocrity, false idols, diversifying your identity, and the advice he gives startups [37signals/Signal v. Noise]