I tend to take shakedown trips before taking long trips. For example, prior to bicycling across Canada in 1997, the year before I cycled the Dempster Highway (Dawson City to Inuvik). Before cycling around Australia in 2001, I cycled a week in Tasmania the year before. Before cycling across Russia in 2007, I cycled five weeks through Ukraine/Russia in 2006.

I don't really take shakedown trips before a small week long trip. I've chosen to not own an automobile and hence bicycle everywhere and also do weekend rides all year long. I've developed a fine-tuned checklist and so can pack most things the night before. However, when doing a long cross-continent type ride, I'll do several things including a week or two shakedown the year before and also plan my trip with enough "slack" so I can do some training on the ride - and also get a chance to mail things home and/or buy new things if necessary.