For the budding mechanic:  A good pocket sized repair guide.   One good option is the “Pocket Guide to Emergency Bicycle Repair”  by Ron Cordes and Eric Grove.   It’s only 3.5×4.5 inches and a half inch thick.   I don’t carry this myself, but for someone who’s new to this whole bike repair business, it’s really helpful to have. A future blog post will cover this book in detail.
Based on what we found, we chose the most relevant items and used them all. To test patches, I repaired holes using four different types of patches, from Novara (REI’s now-discontinued house brand), Park Tool, and Rema. Patching a tube isn’t hard but there are a few tricks, and the key was attention to detail and patience. I was extremely diligent in following proper patch procedure, which includes a thorough sanding of the entire area to be patched (for max stickiness) and properly letting the vulcanizer dry on both surfaces before applying. For the peel-and-stick patches, I went so far as to prep the area with canned air to ensure as tight a seal as we could possibly muster.

If you own a bike, you need a flat-fixing kit. It’s really that simple. Sure, maybe you’ll get lucky and get a flat close to a shop, or the buses will be running on time for once, but even with all that going for you, getting stranded across town will cost you time, money, and precious sanity. You can put together a great kit in less time than it takes to read this guide.
A pair of disposable latex gloves:  Not absolutely necessary, but good for keeping grease and grime off your hands during a repair.  Also, nice to have in an emergency when it starts raining and the temperature drops 20 degrees and you don’t have a pair of regular gloves.   Just keeping your hands dry and the wind from directly blowing on them makes a huge difference in comfort.
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As you mentioned, it is surprising how often you can get multiple flat tires on while riding, particularly on longer sprints. The tip about bringing a patch kit in your bike repair kit can be incredibly helpful if you’ve already had one flat tire. I agree that all you listed seems like an awful lot to carry, but it’s always better to be safe than sorry, isn’t it?
Pedals are important because the serve as the contact point between the rider and the bike’s transmission. Clip-less pedals systems come in a variety of designs favoured by individual manufacturers, but the mechanics of all styles are roughly the same. Tiny adjustments in the position of the show cleat – that snaps into position on the pedal – can make a big difference to the comfort and health of the rider.
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