Tip #1 — Portable Speakers Yes, Headphones No

Riding with music is the only way to fly. Portable speaker technology has come a long way, and every biker who wants a playlist to accompany their ride should have one. Riding with headphones happens, but you’re courting danger. Blasting beats, on the other hand, makes one more conspicuous, which is the single most important quality to have when biking in urban environments. Playing good music is vibe sharing and part of any healthy community.

JBL makes a great line of Bluetooth speakers with good sound and battery life.

Tip #2 — A Waterproof Bag is a Worthy Investment

You’re going to have to haul shit. There’s no shortage of bag options on the market, with plenty of great-looking bags out there that also happen to be uncomfortable or built like crap. When you’re carrying things everyday, when you have to haul heavy shit, or when it’s wet, a top tier bag will make all the difference. Messenger (single strap) style < Backpack (double strap) style. In my experience, messenger style single strap bags need a stabilizer strap to be secure. Even with one, messenger style bags rotate and slide, requiring constant readjustment. They are cute though.

My ride or die is the Ortlieb Waterproof Messenger Bag. Hurricane proof (Sandy tested). Many cargo bikes have the Ortlieb panniers; both styles are quality. When I bought my Ortlieb 15 years ago, it was more money than I had ever spent on a bag, more than a piece of luggage. Considering the tonnage I’ve carried in it since that has always come out dry, it was money well spent.

Tip #3 — In Cold Conditions, Ski Goggles Win

I don’t like flying dust in my eye, and clean wind isn’t too much better. Cold wind torments me. If you don’t wear corrective lenses and you’re not wearing sunglasses, some clear eyewear can be nice in windy conditions. You can get safety glasses from a hardware store if you don’t want hundred-dollar Oakleys. Cold weather (20 degrees Fahrenheit and below) adds a different dimension. It makes light wind uncomfortable and wind gusts hostile. My automatic response is to blink to keep the wind out, and biking is easier with your eyes open. Even regular corrective lenses can be uncomfortable in the cold, like keeping an ice cube on the bridge on your nose. Ski Goggles eliminate all those problems. People may judge you as a nonce wearing a luxury item, and you will lose a marginal bit of your peripheral vision, but otherwise they are a cold-weather game changer.

Tip #4 — Stop Flats At Their Source

This tip is mostly for 700c wheelsets. Puncture flats suck, obviously. For everyday city riding, I prefer Maxxis Re-Fuse to Gatorskin. (*I heard Maxxis Re-Fuse has changed their design post 2021, and it’s less good. I haven’t ridden the new ones — luckily I stocked up during 2020 lockdown and still have two fresh ones in the box.

When I first started riding 700s, most of my flats were pinch flats. I didn’t know it at the time; I hadn’t heard of a pinch flat. I was perplexed at how often I’d go to my bike about to head out only to find a flat tire with no visible puncture to the skin. I’d remove the tube and find little holes, like tears, usually in a pair at the sides. Snake bites. The solution to pinch flats isn’t a tougher skin, its stronger rims. I upgraded my wheelset a little, and pinch flats became a rarity. Upgrading to deep rims wiped pinch flats out.

Tip #5 — In Rain, A Lot of Water Comes From Below

And it’s the nastiest water. Short of downpour conditions, you’re likely to get more wet from road and tire splash than falling rain. Fenders are your friend. Most heavy bikes (and e-bikes) have some kind of built-in fender, but any fixed gear bike is will leave your wheels exposed. Front wheel fenders are nice; rear wheel fenders are necessary. Rooster Tails are the cycling phenomenon where water flies upward off the rear wheel. This water came from the street and hitched a ride on your tire. It is filthy and can permanently stain clothing. Without a fender, it will spray an area from your bike seat, around your ass, and up your back.

A lot of people will wear waterproof jackets and pants - maybe even a poncho - but their footwear is a shitshow. You can embark on a quest for waterproof footwear keeping in mind the critical danger area - the ankle region - where pant meets shoe/sock. It takes a certain level of bike dork to wear gators. (I say this without judgement; I own a pair of gators.) Don’t be shy about throwing some socks and shoes in a waterproof bag [SEE TIP #2]. One word of warning, some shoe soles like Converse do not get along with wet bike pedals. They’ll slip off mid stroke or when you’re standing, and that can be really bad.

Tip #6 — Quick Release = Quickly Stolen

I don’t know what the bike thievery numbers are like these days. I assume they stay consistent over the years but wouldn’t be surprised if these days thieves are targeting e-bikes more than the general population. My very first bike lesson in New York was if something has a quick release - wheel or seatpost - it’s only a matter of time until somebody steals it. You can have a chain or cable and lash your wheels when you lock it up. Most low-level opportunists aren’t rolling with a wrench, though. Invest in a good lock. The bike I brought to the city had a standard lock and got stolen. I spent more on a Kryptonite chain than I did on my next bike. Worth it.

Tip #7 — The Entropy of Bike Life Accrues More and More Tools

Don’t fight it. If you’re riding with any regularity, you will eventually buy a floor pump. You will have tire levers, some wrenches and Allen keys. You’ll start keeping a spare tube or two on hand just in case. Someday you’ll get a bike stand. With any luck you’ll only use it once or twice a year. Bike tools are good. Being able to do basic maintenance is liberating. That said, finding a bike shop you trust is absolutely necessary because you’re going to need a pro sometimes.