May 6, 2026
I’m Jenn, a technical writer and communications lead at Kittelson. You might recognize my name from the Streetwise newsletter you get in your inbox every other Thursday. I’m here today to talk to you about bike commuting. Specifically, how to become a bike commuter.
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Bike commuters. We’ve all seen ‘em. A line of riders zipping through downtown bike lanes, a blur of high-viz yellow and panniers. A dad powerfully pedaling the two small helmeted beings seated behind him on the e-bike. Perhaps you’ve even been lucky enough to encounter a Bike Bus, where gaggles of laughing children frantically pedal their way to school while rocking out to music. You’ve almost certainly watched them struggle up a hill in the pouring rain from your window seat on the bus or driver’s seat of your car (with more than a little smugness). And maybe, just maybe, you’ve watched a bike commuter coast gracefully down a tree-lined neighborhood street on a sunny evening after a fresh spring rain and thought, Hmm. That looks kind of nice.
For the past five years, I’ve lived in a city where bike commuting is both common and well-supported by infrastructure and driver behavior. I’ve also worked for a bicycling-forward company. We have access to showers, secure bike storage, and even an orange office bike that anyone can borrow for local trips. With all these factors, you’d think bike commuting would be a no brainer. There was just one problem. Until very recently, I hated biking.
In 2006, Roger Geller, Bicycle Coordinator for the Portland Bureau of Transportation, spearheaded an effort to understand how people in his city felt about biking. The team found that attitudes could be split into four categories:
- Type 1: Strong and Fearless
- Type 2: Enthused and Confident
- Type 3: Interested but Concerned
- Type 4: No Way No How
I like to think of them as 1—my college professor who’d bike on any rural highway. He loved cycling so much he’d show up to lecture in his lycra bibs and cleats; 2—my coworkers Cameron and Amy, who zip zap all over Portland. Cameron repairs bikes in his free time, and Amy bike shepherds me home regularly. (You’ll hear from both of them in a little bit.); 3—Me, a girl absolutely green with envy watching other people bike around the city but who found the realities of biking unbearable; and 4—My friend who despises biking because her biking dredges up every feeling of being excluded from sports as a kid. Bikes aren’t for her. They will never be for her. We love her anyway.
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Like everyone else, I purchased a bike during the pandemic with big dreams of riding it around the Iowa town where I was living at the time for graduate school. I thought I’d breeze down city streets, lock it up outside the building, and proceed smoothly into the library to pick up my socially distanced books. Here I was, about to be the coolest girl in town, saving money, getting exercise, and reducing my carbon footprint.
Cut to me arriving sweaty (from traffic stress, exertion, and the corn-fueled summer humidity) and having to white-knuckle it back home with a far too heavy backpack. On this formative afternoon, I learned that bike commuting was not for me.
Fast forward six years, and now I live in Portland, Oregon, a city that consistently ranks among the best cities in the country for bicycle infrastructure. To embrace my new city, I tried riding to work and taking a leisure bike ride along the waterfront. I hated how sweaty I got and how the immense weight of my backpack pitched from side to side as I pedaled. I thought riding for leisure was boring.
But much as I hated biking, my envy of people who did bike only grew. What pushed me over the edge was not Portland’s beautiful summer weather, its great walking and biking network, or the fact that I lived just two miles from our downtown office. It was my budget. I added up what I was spending on bus fare ($2.80 each way) and time (sometimes as much as 15 minutes waiting for the bus and then another 15 minutes on the bus).
And let me be clear here. Transit is beautiful and amazing, and I love the bus. Portland works hard to make the bus affordable for people who need financial assistance. I’m just a millennial who can’t be out here paying $2.80 in bus fare twice a day, five days a week.
On days I walked home (an activity I adore), I saved the $2.80 but then had a 50 minute door-to-door trip back. If only there was a mode that was quick, free exercise, and cost less than $112 a month! That’s right, dear listeners. It was at this moment that I realized I had to get serious about my bike.
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Remember those colleagues I mentioned, Cameron and Amy? They got serious about their bikes for other reasons.
[Amy: Sure, cost savings, time savings, environmental benefits, and convenience of bike commuting are all factors that keep me bike commuting through the middle of winter when I’m tired and I don’t want to be cold and wet. However, what got me to start bike commuting was my joint love of being active and being outside. I started bike commuting when I moved to Portland in 2018 for an internship with Kittelson. I was living in a cute neighborhood right off a major bike corridor. I had an easy-paced, 45-minute bike ride in the cool summer morning air, mostly along a waterfront trail. Imagine having the sun lightly kissing your face and saying hello to your fellow bike commuters as you travel to work every morning. There’s no better way to start (and end) the day!]
[Cameron: I started riding a bike as a freshman in college, when I figured out it was the fastest way to get to my 8 a.m. class across campus when I rolled out of bed at 7:50. Like Amy, I got more serious about riding for transportation during a 2018 internship with Kittelson in Boise. I did the math on parking, gas, and upkeep costs for the drive to the office that summer and splurged on an upgraded bike with the same budget. I was committed to breaking even on that purchase and rode to work every day that summer. Turns out, that purchase was the best investment of my life! My perspective on daily riding totally changed when I realized how fit I had gotten over three months with relatively little effort.]
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I identify as a risk adverse and generally anxious person, and when I set out to transform myself from worried-girl-who-doesn’t-bike to worried-girl-who-does-bike, my brain flooded with fear: What if I get hit by a car and get hurt? Even worse, what if I tip over at a stop light in front of strangers?!
But mercifully, in addition to an anxiety disorder, I posses an unshakeable belief that I can learn to do just about anything. So I queried colleagues who commuted by bike, including Amy and Cameron, and did more than a healthy amount of late-night stress Redditing to figure out how to make this work for me. I learned:
- The best bike for bike commuting is the bike you already have. To comfortably bike commute, you just need a solid, reliable machine. You don’t need to go out and drop a couple Gs on a new bike. In my case, I was able to use the bike I bought back in 2020. I’d ridden it so infrequently, my bike shop said it was practically new. [Cameron: That old bike in your basement might be an awesome commuter after a quick tune up. There’s also a thriving used bike market thanks to all the people who purchased a bike during the pandemic, like Jenn. Bike co-ops and collectives are another great resource. These organizations provide low-cost or sliding-scale bikes, parts, and services to anyone that walks through their doors. They can even help you get comfortable with a wrench in your hand.]
- It’s also all about the accessories. Accessories are what turn any old bike into a commuter bike. Fenders keep water from the road off your pants, racks and panniers hold all your stuff, a bell alerts people that you’re near, and a mirror helps you see traffic behind you. [Cameron: If you’re not sure what accessories you might need, you can visit your local bike shops or co-op. They might help you figure out what you need and even get it installed on your bike for you. It might just be the Portland effect, but I recommend you make your bike weird. Get stickers, pizza-shaped bags, colored cables, a hot pink safety triangle, maybe even handlebar streamers. A lot of people believe that the more personalized your bike is, the less enticing it is to steal.]
- Bike commuters are like onions: they have layers. The right clothing can make almost any weather comfortable. I’ll be honest with you, the first five minutes of biking in the rain is unpleasant, but with a breathable waterproof layer, you’ll quickly warm up and it will feel delightfully bracing. Glasses help a lot too. I recommend you get sunnies for when it’s bright and clear glasses for when it’s raining or cold. (Without them, winter will make your eyes water.) My colleagues recommend starting bike commuting in the mildest season (spring or fall for most places). But I recommend the opposite: by starting in the worst season, you’ll ensure that every other season feels just fine. [Amy: It’s also okay to be a fair-weather cyclist. Maybe you have a long commute that doesn’t feel safe or feasible in the winter or heavy rain? That’s okay. The bus is a great option for particularly hot or windy or rainy or snowy days—for me it’s the perfect backup on the unfortunate occasions where I’ve gotten a flat tire. (Remember, we love transit!)]
- Be sure to sort out your cargo plan. Cargo was my biggest bike commuting hangup. Between my behemoth of a laptop, a change of clothes, and eco-conscious glass lunch containers, my backpack was hefty. It was extremely uncomfortable on my back and made my bike too tippy when it was stored in a basket. I now use two panniers, each clips to one side of my rear rack. One is a convertible backpack/pannier that I can carry into the office. It holds my laptop, notebook, and other office-related items. The other is a traditional pannier that stays on my bike all the time. I stash my change of clothes, toiletries for freshening up upon arrival, and my lunch in this bag. Keeping the weight low and near my rear axle—and more evenly distributing the weight across both bags—made my bike much easier to manage.
- Don’t assume the most direct route will be the most comfortable. When I started bike commuting, I relied on your standard turn-by-turn online maps that took me through bicycle infrastructure that was good quality but not especially comfortable for me. A short stretch of narrow bike lane between 40 mph car traffic and parked cars was enough to make me dread each trip. [Cameron: To help find nice routes, I recommend looking for local bike maps. For example, the City of Portland has a digital map of all its neighborhood greenways and protected bike lanes, and even calls out difficult crossings. “Heatmaps” are another great resource to identify bike-friendly routes; platforms like Strava and RideWithGPS collect data from lots of cyclists and give you map layers showing where lots of people are already riding. The best option for finding routes, though, is to ask folks who regularly bike what routes they like and recommend.] When I told Amy I hated that section of my ride, she told me about a slightly longer but far more scenic and relaxed option through a neighborhood. That section is now my favorite part of my commute.
- Use the buddy system. Take a note from the Portland Bike Bus (and other bike buses around the world) biking is more fun when you go together. I made my first tentative trips around the city with friends who could show me the right way to lock up my bike, how to use things like bike boxes, and the safest way to cross streetcar tracks. Even now, when I bike somewhere new or in new conditions, I will often ask someone to go with me. [Amy: The social aspect of biking is such a treat. Over the years I’ve gotten to bike commute with many people who live along a similar route to me. I look forward to riding bikes together, catching up, and sometimes encouraging each other to take the long way home along the waterfront to see the cherry blossoms or to get a bite to eat at a food cart pod right off of our route. Being a bike buddy to me is just finding more people to share the fun with!]
- Accept that biking is embarrassing. If you’re anything like me, you will fall over on your bike from a complete stop, thirty feet from your front door. It will take eons to lock your bike up the first couple of times. And it is my professional opinion that it is impossible to look cool and be safe while riding a bike. So yes, you do look silly in that clunky helmet, with your neon yellow vest and rain paints with one pantleg wrapped in a fluorescent band so as to not get caught in the gears. And you’re right, all those lights are a bit much. But these are small prices to pay to protect your brain and your body. [Amy: Once, as I was biking between bollards that blocked cars from entering a path, I misjudged the width and caught my handlebar on a bollard. I fell right over. I was going at a slow speed so the only thing that was harmed was my biker-girl ego. And now I know to be a little more careful when squeezing between posts!]
- And be gentle with yourself. If it’s pouring rain and you don’t want to bike to work. Take that bus. If something goes wrong—you get a flat, you miss your turn, you tip over at a light—remind yourself you are learning and this is all practice. You are a student, and students get to make mistakes.
- Finally, when your nerves start creeping in, remind yourself what appeals to you about bike commuting. Is it the environmental benefits of non-motorized transportation? Is it, as my partner likes to say, the “free cheese” of cardio to and from work? Perhaps it’s the sound of the birds in the morning or watching the sunrise as you pedal across the bridge. Maybe it’s having some quiet time to decompress between the office and home or the sense of community you get from riding among strangers all pedaling toward your anonymous workplaces. For me, it’s all those things—and how European I feel when I bike a loaf of bread home from my favorite local bakery. [Cameron: Most days, my commute home is the best part of my day. How many people are lucky enough to say that? I’ll often find myself taking the long way home to run errands I’d rather do by bike, ride along with friends, get in a quick workout, or explore a new part of town!]
Using these tips—and a lot of help from Amy and Cameron—I’ve made myself into a perfectly functional bike commuter. I think I might even like it.
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I know that a big reason I get to like bike commuting is because I live in a place that values bike infrastructure. When bike infrastructure isn’t there, people like me really don’t want to bike. But luckily, a lot can be done by cities, business owners, and neighbors to make commuting by bike a lot more feasible and pleasant. Here are some factors they should keep in mind:
- Folks won’t ride if they don’t have a secure way to store their bike. Our office has a great secure bike room where we can store our bicycles away from the elements and bike burglars. It even has a stand and tools for quick repairs. [Amy: It’s also important to have secure bike parking options throughout the city because bike commuters want to be able to ride our bikes after work (and on weekends) to restaurants, grocery stores, and parks, so we need a safe space to lock our bikes in all of those locations.]
- Folks also need a way to transition from cyclist mode to person-who-works mode. Having a way to freshen up after a ride is HUGE for encouraging more biking to work. Our office has a bike room with lockers, changing rooms, and showers, which means that we can arrive fresh to work even on a hot summer day.
- Communities also need facilities that are comfortable, easy to navigate, and well-maintained. Different types of cyclists feel comfortable on different facilities. [Amy: For example, Jennifer Dill with Portland State University’s research shows that bike boulevards especially increased women’s odds of cycling, reducing or eliminating the gender gap between men and women cycling.] To make routes easy to navigate, cities can invest in bike network maps (like the interactive bike map the City of Portland hosts online that Cameron told us about), wayfinding signs, and pavement markings that clearly direct bicyclists to the best facilities for their needs. [Cameron: Don’t forget about maintenance. Taking care of the bike network is ultra important. Even the best separated bike lane becomes unfriendly if clogged with mud, wet leaves, or broken glass.]
But one of the biggest and best things a community can do is to support biking joy.
[Cameron: You’ve never seen a party like a bike party, unless you’ve been lucky enough to have one roll by! Every year, Portland hosts a “Bike Summer” festival, with themed rides every day. You’ll see rides for fans of the music artist Prince, rides to follow a flock of crows around the city, rides to swimming holes, and the popular classics like Bike Prom and Loud and Lit (a massive ride with DJs and lights).] [Amy: One of my favorite rides is one where they act out a play between stops. Last year it was Monty Python and the Holy Gear.]
[Cameron: The feeling of riding your bike with a huge group—or a “critical mass”—is unlike anything else. Drivers stop and gawk, rather than rush by, and your safety is all-but assured by “corkers” who are other cyclists that block traffic at intersections. The group crawls at a leisurely pace. You’ll be amazed at what people can strap to their bikes—kids, adults; snacks and coolers; speakers, lights displays. It’s pretty amazing.]
[Cameron: To find bike joy in your community, keep an eye out for bike-themed meet-ups, custom bike shows, bicycle-themed movie festivals, and of course, all the different rides. Events like these are amazing ways to find community with like-minded people from all walks of life.] [Amy: Plus, the confidence you’ll build and the new routes you’ll discover will only make biking throughout the community even more fun!]
Together, all these ingredients—fenders, stickers, bike racks, bike buses, protected bike lanes, and big group rides—can make even the most skeptical bike commuter excited about saddling up every morning.
To continue this conversation about how much we love (or are learning to love) bike commuting—or to get expert help making bike commuting more feasible in your community—please contact us! Until then, happy biking!
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