That’s a reality of all hand pumps—it’s really hard to get a tire up to pressure with these things. So another reason Lezyne pumps are so good is because you can actually keep pumping longer than any other brand we tested. With excruciating effort, we could get the Sport Drive HP to pump tires to 90 or 100 psi. It still wasn’t easy, but it wasn’t impossible the way it was with some other models.
In addition to the Rema patches, put a new tire tube in your kit. The best method for dealing with a flat roadside is to swap out the tube and save the task of patching for later. If you’re not sure what size your tires are, it’s printed on the sidewall of the tire. This inner-tube buying guide has some photos of where to look. What brand is almost irrelevant as many tubes get manufactured in the same place, so whatever your local shop has behind the counter for under $10 will work fine. The only reason to spend more would be to save weight.
Now you might be wondering: “I’m carrying a tube; why carry patches at all?” As insurance for the unforeseeable. Wirecutter senior editor Christine Ryan admits she didn’t use to pack them, but said, “I’ve regretted that decision when I’ve had a flat on a ride, used my spare tube, and then, half an hour later, had a second flat. Also, lots of people aren’t very good at figuring out—or don’t take the time to figure out—what caused their flat and remove the cause: thorn, eensy bit of glass, whatever. Then they promptly have a second flat, and everyone else laughs at them.”
This is the shop I hoped to find when I began commuting two years ago. I'm a daily commuter and I love knowing that these guys will help me almost anytime that I need it. Andy, Jake and Brad listen and make sure to help me as best they can and are always speedy about it. Additionally, they encourage me to do my own work on my bikes when I have the time/when they know I'm capable and I really appreciate that encouragement. 

Change and a $20 bill:   In case your cell phone’s battery dies, it’s nice to still be able to use a payphone if you need to.   Also, the $20 is a great thing to have in case you lose your wallet or have some other mishap.   I’d rather be able to sit in a coffee shop or fast food restaurant when it starts raining while I’m waiting for my friend or cab ride, and a hot cup of tea or coffee or the beverage of your choice and a snack makes it all the more pleasant.  Just try to remember, this is for emergencies, and if you use it, replace it ASAP!

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).
Maintenance is the best prevention. “Prevention is the best medicine, and if you’re taking care of your equipment it’s super key. Bikes don’t just fail. If they’re in really good working condition and you clean them at night, and you’re religious about it, bikes are kind of like cars — they’ll start talking to you if something is getting worn or getting creaky or needs to be replaced.”
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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?
Modern bottom brackets use a sealed bearing type construction that keeps water and debris locked out, so they seldom go wrong. Maintenance is impossible so they need replacing when they do wear out. Older style cup bottom brackets need to be re-greased every now and again, and occasionally will need to have their bearings replaced. There are a lot more teeth on the chainring cogs than those on the rear cassette, so need changing less regularly. Cranks usually a solid one piece construction so there is not much to go wrong.
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