Basic first aid supplies:  A few bandages of varying sizes.   6 Aspirin, or other OTC painkiller of choice.   A few alcohol pads in sealed foil packs, useful for cleaning grease off grease and grit off of the bike, and also cleaning cuts on yourself if you take a spill.  1 day supply of any prescription drugs you need to take regularly.   Wrap these up in tinfoil and tuck away.   It might just save your day.
But before I get started, let me share with you a few tips. OK, one tip: Get a work stand. Because putting your bike upside down isn’t good for it—yes, I said it. When I first started fixing my own bikes, I couldn’t afford a fancy $300, folding, magnetic, fixes-the-bike-for-you stand. I tried piecing together a “DIY $30 Stand.” I followed all the directions that the Internet demanded, and once I’d bought all the clamps and pipes, this thing cost really more in the neighborhood of $60—but it only stayed upright with a rope tied to something sturdy in the garage. It was one word: junk. So I bit the veritable chainring and charged a decent stand on my credit card (I hate debt, folks).
The retractable tube is stored inside the body of the pump when not in use, and it can attach to either a Schrader or a Presta valve, the two types of valves you’ll see. Some pumps can accommodate only one type, making them less universal. Toggling between the two is simple, which can’t be said of other models with itty parts that require nerves of steel to handle on a good day, let alone while wearing gloves, crouching in the wind, oblivious to the sewer grate a few feet away.
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?
The Pedro’s lever slipped only once throughout testing, though that may have been my fault because I was spaced out after changing 16 different tires. So they’re not foolproof, but they are far and away more reliable than the next closest competitor, from Park Tool, because the small, rounded tip on that one is hard to keep seated under the tire. Not impossible, but I wouldn’t choose it over Pedro’s.
Be organized. “I like having everything be really small and super organized. I put all of my tools in CamelBak’s Tool Roll. It’s got little compartments, and I can separate tire changing stuff in one place, stuff like extra pedal cleats or an extra derailleur hanger in another, and it all rolls up into this tidy pouch. If I do have a repair, I can pull that one thing out and lay it out on the ground and it’s easy to work.”
Friction gear systems are a lot simpler to adjust, because the movement of the derailer cable can be modulated as you ride, every time you change the gear- they require less cycle maintenance. Modern index shifting systems are a little more complicated because each ‘click’ must release the exact right amount of cable to allow the derailer to move the correct distance to move the chain from one gear to another. Setting up and adjusting a derailer is not difficult and requires only basic tools, but there is a methodical procedure to follow.
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