Every day, I mount my black Surly Steamroller like a saddle-worn steed—saddlebag lashed tight, grommets aired, cinch straps taut—and every day I thank muscle memory, situational paranoia, and the predatory instincts honed during my courier days for keeping me alive.

This bike isn’t just a ride—it’s a companion, a tool, a totem. I’ve poured years into it: swapping hubs, rewrapping bars, tuning gears, patching tires. Seven years deep into our relationship and she still carries me like it’s our first sprint through morning traffic. This isn’t a shiny road toy—it’s a warhorse built for the urban jungle.

I don’t own a car. I gave up motorcycles. I get around with my legs, my bike, the 16 bus, Metro, and the occasional Uber Pool when it’s pouring rain or human frailty catches up with me. But most days? It’s me and the Surly. Always.

I’ve ridden through Clinton, Bush, Obama, Trump (once and again), and Biden in between. I’ve filtered through Beltway gridlock on a Honda XR650L, toured cross-country on a BMW K1100LT, and delivered time-sensitive filings to the Hill on a brakeless fixie in the ’90s. I’ve seen Berlin’s perfect cycling infrastructure and Portland’s hipster flow, and nothing—nothing—feels quite like surviving rush hour in D.C. on two wheels.

Let me be blunt: the streets now are worse than they’ve ever been.

More weed. More screens. More Uber drivers. More scooters. More Amazon vans doing illegal U-turns to shave seconds. More gig workers blasting through yellow lights with fries in one hand and a map in the other. Every intersection is a game of “what fresh hell.” If you’re on a bike in 2025, you are not a cyclist—you are a cockroach sprinting between kitchen tiles, praying the slipper doesn’t drop.

This is not Copenhagen. This is not Amsterdam. This is not a dream of urban harmony. This is a war zone dressed up in bike lanes and green paint. And your helmet? Your helmet is a foam wish. Don’t get me wrong—wear it. But ride like it won’t save you.

This updated guide—an evolution of my original 2016 post, “Tips to Survive City Riding on Bikeshare”—is for the clueless commuter on a rental bike. For the e-scooter tourist with AirPods in. For the fixie kid who thinks style equals invincibility. For the seasoned roadie who forgot that riding fast isn’t the same as riding safe.

If you think you’re safe out there, you’ve already lost. It’s time to recalibrate. Time to ride like a ghost through the cracks. Time to survive the city you think you own.

Chapter I: Know Thy Place — You're Prey

You are not a car. You are not a Tesla. You are not protected by armor, crumple zones, or airbags. You are flesh and bone and Lycra. Or in my case, canvas shorts, steel frame, and a stubborn refusal to die.

You’re not the main character. You’re a critter.

Traffic doesn't care that you’re in the bike lane. The driver in that Suburban doesn’t even see the bike lane. Most don’t see you. Some resent you. A few might even aim for you. That’s the spectrum.

Your mindset has to be this: every ride is a stealth mission. You are not asserting your rights. You are infiltrating. Flow like water. Evade. Escape. Do not demand space. Take it only when there's no cost.

Chapter II: My Messenger DNA

In the ’90s, I was a bike messenger for WEx in D.C.—when fax was king and email was a rumor. I hustled legal documents between K Street firms and the Hill. No helmet. No brakes worth a damn. Just guts, gears, and gall.

I had carte blanche in my D.C. I could flash into a Senate office, skulk through Capitol tunnels, and duck into the cafeteria for an iced tea before riding back out into the blast furnace of a D.C. summer.

Then: open buildings, light security, forgiving traffic. Now: lockdowns, bollards, surveillance, and traffic that doesn’t even know it’s traffic anymore.

I miss those days. But what they gave me—the sixth sense, the predator-prey radar—it still works. It still saves me.

Flashback: Pre-Internet in a Big Way When I was a courier in Washington, it was pre-Internet in a big way. Since lawyers are always doing things last-minute, I would end up shooting across the city on my bike with just minutes left (after flirting with the hot receptionist), only to reach the maw of a heavy dun-colored Official Time Stamping machine seconds before it was put to bed. I made it every time. There was nothing to impede me. The city was open. Now they call it “vulnerable.”

Capitol Hill Was Open Door You could move freely between buildings. From the Capitol to Senate and House offices, even the GPO. I could drop off a package, grab lunch in the cafeteria, and head back out. Now it would take 45 minutes and a cavity search.

Security Eats Time Even office buildings have TSA-lite setups now. Security adds time, friction, hassle. The only thing that moves fast today are the rideshare drivers on their sixth delivery of the hour.

The Insidious Model Security has been internalized. Everyone is watching everyone. The whole city feels like it’s holding its breath.

Chapter III: The 2025 Shitshow Rundown

1. Smart Cars, Dumb People – Autopilot has made people worse drivers. They trust sensors more than their own eyes. Lane-assist is their god now.

2. Weed Fog Everywhere – Legalization made things mellow—and sloppy. Stoned drivers are slow to react, drift between lanes, and kill you with soft indifference.

3. Screen Zombies – Every driver is holding a phone. Whether it’s FaceTiming, TikTok, or texting—it’s all eyes on screen, not on street.

4. Gig Economy Chaos – Uber drivers. Amazon vans. DoorDashers. They will U-turn across five lanes in traffic to make a drop. You are a rounding error.

5. E-bike Tourists & Scooter LARPers – Rentals have flooded cities with clueless new riders who don’t know street rules and assume safety is baked into the experience. It’s not.

Chapter IV: Golden Rules (Now More Golden Than Ever)

Every parked car has a door about to open.

Every pedestrian is a TikTok sleepwalker.

Every taxi is a chaos demon.

Every bus will absorb your lane without warning.

Every pothole is a death trap.

Every driver is high, distracted, or half-dead inside.

Your helmet? It’s a polite fiction. A foam wish. It matters—but only after you’ve already failed. Your real protection is avoidance.

Chapter V: Street Wisdom from a Motohead

Cover Your Brakes – Always ride with fingers resting on your brake levers. Always. Shaves milliseconds when milliseconds matter. It’s your hand hovering over the trigger.

Eyes Steer the Bike – Don’t look at the car. Look at the gap. Your bike goes where your eyes go. Target fixation kills. Escape vision saves.

Exit Plan Always – Whether it's a swerve, bunny hop, or a hard veer to the sidewalk—never ride without knowing where the hell you’re bailing if it goes sideways.

Head on a Swivel – No mirror replaces situational awareness. You need to see the body language of traffic before it acts. This is body-reading, not just observation.

Chapter VI: Ride Philosophy for the 2025 Cockroach

Do Not LARP Safety – This is not Denmark. That green bike lane is a suggestion, not a shield. Paint does not protect.

Don’t Play Indignant Chicken – Yes, you have the right of way. Yes, they’re in the wrong. Yes, you're still the one who dies. Don’t be righteous. Be alive.

Say Thank You – Wave to the car that yields. Thank the pedestrian who waits. Reinforce good behavior. It’s rare. Treasure it.

Stack the Odds – Lights. Tires. Routes. Clothing. Every decision you make should reduce risk. Stack your survival probability every time you mount up.

Chapter VII: Tech & Gear in 2025

Tires: I run 38c Schwalbe Marathon Plus. Bombproof. They’ve taken more hits than my ego.

Brakes: Rim brakes still, because I like the punishment—but disc brakes are the play in modern traffic.

Lights: Day and night. Rear blinking. Front solid. Assume you’re invisible and still act like it.

Helmet: Yes, wear it. But ride like it’s not there.

Mirror: If you use one, great—but don’t rely on it. Trust your ears, your instincts, your paranoia.

Glossary

Cager – Driver in a car. Steel shell, soft brain.

Dooring – Sudden car door opens in your lane. Instant wreck.

Indignant Chicken – Holding your line just to prove you're right. Dead-right is still dead.

Bike LARPing – Pretending you live in Copenhagen. Acting like painted lines protect you.

Escape Line – Your planned swerve path if shit goes sideways.

Prey Vision – Eyes always moving. Watching everything. Staying hunted to stay alive.

Covering Brakes – Riding with fingers hovering on brakes. Instant response time.

FAQ

Q: Are bike lanes safer now in 2025?
A: Only if you believe in unicorns and shared civic responsibility. Assume nothing.

Q: Are drivers really that bad?
A: Worse. Between screen addiction, legalized weed, and tech overconfidence, they barely know they’re driving.

Q: Should I ride with a helmet?
A: Yes. And ride like it won’t help.

Q: What if I get hit anyway?
A: You probably will, eventually. Focus on minimizing damage, not pretending you’re invincible.

Q: Do I have to act like a cockroach?
A: Yes. That’s how you stay alive.

Final Word: Keep the Rubber Side Down

Every time I swing a leg over my Steamroller, I ride like I'm invisible. Like I'm already a ghost navigating the living. I don’t ride for glory. I ride because the city is mine if I know how to survive it.

You want to live on two wheels in 2025?

Drop your ego. Drop your entitlement. Ride like a cockroach with a mission.

Good luck. I hope I don’t see you in the trauma ward.

—Chris Abraham, ex-messenger, moto veteran, still rolling

"Survival isn’t macho. It’s humble. It’s grimy. It’s slipping through the cracks and riding off like a shadow. That’s urban cycling in 2025."

From Bikeshare Tips to Cockroach Survival: Evolution of Chris Abraham’s Urban Cycling Philosophy (2016–2025)

Introduction

Chris Abraham’s two nonfiction essays on urban cycling – the 2016 blog post “Tips to Survive City Riding on Bikeshare” and its 2025 update “Surviving the Streets: Urban Cycling in 2025 – A Bike Messenger’s Updated Guide to Not Dying on Two Wheels” – together paint a vivid picture of how much the urban cycling landscape (and Abraham’s own outlook) transformed over nearly a decade. The original 2016 piece is a practical list of tips born from Abraham’s decades of biking in Washington, D.C., offering newcomers advice on how to stay safe amid city traffic. By contrast, the 2025 essay is a far more urgent, expansive “survival guide,” delivered in a gritty, metaphor-rich tone that reflects both the harsher realities of 2020s city streets and Abraham’s evolved perspective as a veteran cyclist.

This essay compares the two works, examining changes in tone, content, and perspective, and situating them in their historical and cultural contexts. It analyzes national trends in transportation, cycling infrastructure, urban safety, and road culture from 2016 to 2025, explores Abraham’s personal development as a cyclist and observer of urban life, and discusses the broader implications of his writing – from critiques of civic design to the ethos of urban survivalism embodied in his metaphor of the cyclist as a “cockroach.” In doing so, we gain insight into not only how cycling in cities has changed in this period, but also how one cyclist-writer’s philosophy can shift from optimistic encouragement to hard-edged realism without losing sight of the goal of staying alive on two wheels.

Shifting Tone: From Optimistic Mentor to Hard-Boiled Survivor

One of the most striking differences between Abraham’s 2016 and 2025 essays is the shift in tone and attitude. The 2016 blog post adopts a pragmatic yet encouraging voice. Abraham writes as an experienced friend offering down-to-earth advice to less-seasoned cyclists, especially those using bikeshare for urban commuting. The tone, while frank about dangers, remains optimistic and even warm. He starts by expressing pride and happiness at seeing more cyclists in D.C., noting that “every day, my D.C. is feeling more and more like my Berlin did.” This enthusiastic observation sets a hopeful tone: in 2016, he sees D.C.’s cycling scene blossoming and welcomes new riders. Throughout the piece, he balances warnings with encouragement – for example, ending with the cheerful send-off, “Good luck and please keep the rubber down — I am proud and happy to have so many of you all around me on the city streets.” This mentorship tone positions him as a guide who genuinely wants others to enjoy city biking safely.

By 2025, however, Abraham’s tone has hardened considerably. The updated guide is darker, more urgent, and laced with sardonic humor born of frustration. Abraham now portrays the urban cyclist’s situation as outright war. In the very opening lines, he establishes a gritty metaphor: “No matter how confident, cool, or kitted-out you are, remember this: to the urban traffic ecosystem, you’re a cockroach. Agile, adaptable, impossible to kill—until you’re not.” This jarring image of the cyclist as a cockroach immediately signals a shift in tone – it’s a far cry from the helpful, somewhat paternal voice of 2016. The 2025 essay brims with visceral language and metaphors of violence. He describes the modern city streets as “a war zone dressed up in bike lanes and green paint” and pointedly calls a helmet “a foam wish” – useful but ultimately just a “polite fiction” against the magnitude of danger. The prevailing attitude is deeply cynical about the environment cyclists face: “If you’re on a bike in 2025, you are not a cyclist—you are a cockroach sprinting between kitchen tiles, praying the slipper doesn’t drop.”

What caused this tonal evolution? In part, it reflects changes in urban conditions (discussed later), but it also reflects Abraham’s personal development and perhaps a loss of patience. By 2025, he is writing not just as a friendly mentor but as a self-described survivor who has “ridden through Clinton, Bush, Obama, Trump (once and again), and Biden” and seen it all. The years seem to have made him both wiser and more jaded. Where the 2016 article gently chides cyclists to control their temper or adjust their saddle height, the 2025 guide bluntly admonishes riders to “drop your ego. Drop your entitlement” and “ride like a cockroach with a mission.” The tone is often sarcastic and brutally frank. For example, whereas in 2016 he cautioned that even if a driver hits you and is at fault “you’ll be dead so you won’t be able to gloat,” in 2025 he doubles down on this fatalistic pragmatism: “Yes, you have the right of way… Yes, you’re still the one who dies. Don’t be righteous. Be alive.” The voice has shifted from optimistic mentor to something more akin to a drill sergeant or “urban survival coach,” impatient with naivety. This change in tone underscores the essay’s broader message: the street environment has become more hostile, and only a hardened mindset – seeing oneself as a beleaguered but resilient “critter” – will suffice.

Content and Structure: Practical Tips vs. Comprehensive Survival Guide

The content and format of Abraham’s two essays also differ significantly, mirroring the shift in tone. The 2016 piece is essentially a list of tips or rules, presented in a conversational but straightforward manner. It reads like a checklist of survival strategies gleaned from experience, each introduced with a pithy principle. This structure is simple and practical; a novice cyclist could almost print it out as bullet points to remember. The content focuses on basic defensive cycling wisdom: avoid crashes at all costs, don’t assume others see you or follow rules, watch out for common hazards like car doors, and keep your emotions in check to ride defensively rather than aggressively. Abraham emphasizes anticipating the worst from others. The content is pragmatic advice distilled into memorable maxims. The structure is essentially a list of do’s and don’ts with explanatory commentary, reflecting the blog-post style of the time.

In 2025, the essay’s structure is much more elaborate and resembles a guidebook or even a manifesto. Abraham has organized the content into chapters and sections with dramatic titles, walking the reader through a comprehensive mindset and strategy for urban cycling. He explicitly frames the 2025 essay as an evolution of the original, meant for a wide range of riders: from clueless bike-share tourists to cocky fixie riders and even seasoned cyclists who need a reality check.

The content itself in 2025 is far more extensive. Abraham includes sections like “Know Thy Place – You’re Prey,” which establishes the fundamental mindset of vulnerability. He follows with “My Messenger DNA,” a reflective section in which he reminisces about being a bike messenger in 1990s D.C. and contrasts it with today’s environment. This personal history serves to bolster his credibility and also to highlight how much the city and security climate have changed.

Perhaps the most telling part of the 2025 essay is “The 2025 Shitshow Rundown,” where Abraham itemizes the modern perils that make urban cycling in 2025 particularly chaotic. He details phenomena barely on the radar in 2016: overreliance on semi-autonomous driving tech, widespread marijuana use among drivers, smartphone distraction, Uber and Amazon delivery chaos, and an influx of inexperienced riders on e-scooters and rental e-bikes.

Subsequent sections of the 2025 essay delve into specific techniques and philosophies. He re-emphasizes tactical riding skills, articulates mental rules, and promotes positive behavior reinforcement through actions like waving to courteous drivers. The 2025 guide further includes sections on gear and technology, a glossary of slang, and a brief FAQ – adding a pedagogical, almost textbook quality to the piece.

In summary, the 2016 essay’s content is concise and focused on the cyclist’s behavior, delivered as a series of practical rules, whereas the 2025 essay’s content is comprehensive and contextual, covering not just what a cyclist should do, but why they must do it given the broader state of the streets. The structure evolved from a simple blog list to a full-fledged guide with chapters, stories, rules, and reference sections – reflecting Abraham’s growth as a writer and the increased complexity of the topic by 2025.

Urban Cycling Contexts: 2016 vs. 2025

The 2016 essay was written in an era of optimism for cycling infrastructure. D.C.’s bikeshare program had grown massively, and bike lanes were increasingly being integrated into city planning. Cycling was on the rise, and though road dangers were real, the cultural moment suggested momentum. Legal reforms were beginning to acknowledge cyclist vulnerability, and there was a broader national discussion around Vision Zero and city livability.

By 2025, however, despite infrastructure progress, the streets had grown more dangerous. Cyclist fatalities had increased significantly across the country. The causes were many: distracted driving (especially from smartphone addiction), overreliance on semi-autonomous vehicle tech, the rise of gig economy drivers making unpredictable maneuvers, and the influx of inexperienced users on e-scooters and e-bikes. Weed legalization, while culturally significant, also introduced the new challenge of stoned drivers.

While there were infrastructural gains – more protected bike lanes, wider cultural acceptance of cycling – Abraham’s essay reflects that these gains have not translated into perceived safety. His take is clear: the street ecosystem has become more hostile, not less, despite progress in design. It’s not about infrastructure alone; it’s about culture, attention, and respect – or the lack thereof.

Chris Abraham’s Personal Evolution as a Cyclist and Observer

In 2016, Abraham presents himself as a seasoned yet lighthearted urban cyclist – an elder messenger offering street-smart wisdom to the rising tide of bikeshare commuters. He jokes about never wearing a helmet, and though he preaches vigilance, he clearly enjoys the growing bike culture. His tips are sharp but laced with warmth and advocacy.

By 2025, he has hardened. The helmet-less bravado is gone; he now wears one, but insists you “ride like it’s not there.” His tone is darker, his metaphors sharper, his cynicism deeper. He reminisces about the open Capitol Hill buildings of the '90s, compares the current streets to war zones, and calls the entire urban cyclist experience “infiltration.” Abraham now identifies more as a survivalist than a guide – a survivor of D.C.'s asphalt jungle who has given up motorcycles and motor vehicles, relying instead on his legs, his street instincts, and his decades-long partnership with his Surly Steamroller.

His journey from prideful participant to grim realist parallels many longtime urban cyclists’ experiences. He’s still generous with his knowledge, but less optimistic that the system will ever change. His evolution is one from witness to war correspondent, reporting back from the frontline.

Civic Design, Urban Survivalism, and the “Cockroach” Metaphor

Abraham’s essays are not just personal reflections; they are damning critiques of civic design and American car culture. His metaphor of the cyclist as a cockroach is grotesque and profound: despised, ignored, underestimated, but surviving nonetheless. It speaks volumes about how cities – especially in the U.S. – have failed to integrate cycling safely into the urban fabric.

Painted bike lanes, he implies, are performative. City governments may claim progress, but if the cyclist still must behave like prey, then nothing substantive has changed. His insistence on humility, paranoia, and non-entitlement is less about fear and more about realism. It is an urban survivalism born of broken promises and inadequate protections.

Abraham doesn’t offer a blueprint for reform. Instead, he gives cyclists the tools to survive in a system that has not yet evolved to protect them. His work is as much a guide for civic resilience as it is a cycling manual.

Conclusion

Chris Abraham’s two urban cycling essays – one from 2016 and one from 2025 – are more than just how-to guides. They are urban ethnographies, personal chronicles, and cultural critiques. Together, they document the evolution of a city, a transportation culture, and a man. In 2016, he offered tough love to a growing cycling community. By 2025, he’s offering survival tactics to fellow cockroaches dodging slippers.

In a time when cities brand themselves as smart, sustainable, and livable, Abraham’s writings serve as a sobering reminder: if cyclists still have to ride like prey, then progress is an illusion. Until the streets reflect true safety, the cockroach must keep riding, hidden in the margins, fast, paranoid, and alive.