Tools, Dependence, and My War with the Road

It was dark when I stood up. There was a flash and a lot of movement, and then it was dark. Except for one streetlight, and then another. The road was a black canyon, kept awake by the steady blinking of my back taillight.

Instinctively, I moved every limb and concentrated on the pain. Where was it coming from? I was scraped up. I already felt stiff. My head was okay. My leg … it hurt. My wrist felt shock. My shoulder. My foot. A slow inventory, done in a fraction of a second.

This post originally appeared September 5th, 2015, as part of The Pastry Box Project.

I had hit something. I didn’t know what it was. It was dark when I stood up, but there were streetlights, now. I was on a residential street, by a school under construction for the incoming school year, a few blocks from my friend’s house, no more than two or three miles from home.

I did the inventory again. I shook it off. I got back on my bike to ride.


I do a lot of thinking at my job, but I don’t do anything without consulting with my tools. I have programs that I trust – programs that keep me honest, and programs that help me with the mundane tasks, and programs that lead me toward answers.

My job is based in thought and creativity – free of tangibles, stripped of weight, from project management to front end development to strategy and sales. But that creativity depends on tools. It is freed by those tools. I try to master those tools and I give in to those tools.

But, like, what happens when those tools fail us?


This had happened once before. When I was 17. I had stopped to adjust the tire on my bike, and I forgot to tighten the quick release, and then I headed down a hill about a half a block from my house. The speedometer on my bike said 21.5, though that could be an exaggeration from years of telling the story.

What happened at the bottom of the hill was no exaggeration. I lifted my front wheel to miss a bump. Ha! Look! It’s like a mini-wheelie! My wheel had other plans; it kept on its path, independent of the front fork. I planted, and I flew.

These were the days before my feet were clipped into the pedals. These were the days before I wore a helmet. I was 17 and invincible and I was going to rule the world someday and then my fork hit the concrete.

And then I hit the concrete.

And then I slid.

Rumor is that my handlebars had twisted a full 90 degrees, and that there was a chunk of cement missing from where my fork planted. All I knew is that the one tool I had managed to master – this bicycle, my main form of transportation – had failed me, and I stood up and ran to my house, my hand against my face, blood dripping onto my favorite Sunny Day Real Estate shirt, hearing my friend laugh at me in the background because he had no idea what had happened.

The world had betrayed me. My tools had betrayed me. It would be years before I’d trust them again.


We learn our crafts through careful mimicry, pouring over the guides and handbooks and stealing bits and pieces from others. We look to others for confirmation as we try to find our own place. We grasp desperately for anything that can help us gain ground.

Through this process, though, we sometimes forget that those guides and handbooks are just that – they are guides. They show us one way to go, but it’s up to us to read between the lines to better understand the theory, the practice, the nuance.

They are tools, and they are important. Because tools help us do our work more efficiently. We all have personal – and in some cases, organizational – methodologies, and those methodologies are important tools. They help us keep things on track, and they help vet our processes, and they make education and consistency possible.

They are also fallible. The programs and processes we build up are single points on a wide spectrum of work. From a pencil and pad to a bloated Omnigraffle template; from a discovery workshop to a wiki-based style guide – each tool helps complete one portion of an overall project. Which tools we use depends on the client, the task, the user.

I used to play a game called 24, where through basic mathematics functions you were tasked with taking four random numbers to a total of 24. Four numbers, different functions, but the answer was always 24.

That’s what we do. We borrow and combine our tools in search of the right decision – mixing and matching on our way to 24. If we depend too much on a single process, we lose the ability to think on the fly. We don’t know what to do when we have to go off script. We’re not sure what’s going to happen when our lights are too dim. When our life throws us on our ass. When we’re looking up into the dark wondering what to do next.


I rode my bike for about 50 feet before my derailer snagged my chain and my bike ground to a stop.

“What the ..?” Like it was a surprise. Like I hadn’t just torn myself apart and torn my bike apart, speeding down the road faster than I should have, in the dark. Like the chunk of concrete I had caught – a friendly reminder of the construction next door – wasn’t real and that standing up was all I needed to do.

That’s when I realized that things weren’t going so well. My bike was in worse shape than I had thought. A shifter was off center, and back where I had landed lay half of my bike light, a scatter of its batteries, a button from my backpack, and a pen that had fallen out of a pocket.

Walking back to the scene – the scene I had simply tried to escape; fight or flight or just ride your bike away super fast, I guess – I could see that things weren’t going well. I felt the blood on my elbow, could see the road rash on my leg. I took off my helmet, finally, and saw the inch deep crack down the side – a crack that continued several inches on the inside. The pain in my wrist came to the forefront, and my rib suddenly sprung to life.

I stared at my bike. The tool I trust more than anything, as an extension of my body, as a companion that’s taken me across Iowa, and around the city, and across over 4,000 miles of road and trail, and I couldn’t believe what it had done to me.

Betrayed again.

But as the night went on, and as the ibuprofen slowly took hold, and as I finally began falling asleep, I thought about all of the things I had done. Riding too fast. Depending on a light designed to be noticed and not detect obstacles. Foolishly staying out as late as I had. Thinking about anything but the road and my ride.

And I thought about the things my tools did.

My derailer broke away as designed, allowing the chain to go free and saving me from hundreds in structural damage. My backpack, which had weighed heavy on the way down, filled with a change of clothes, padded my fall and took the brunt of the road. My lights had worked perfectly until I had pushed them too far. My helmet did nothing except exist, saving my skull. Saving a lot more.

Inanimate and lifeless, my tools still tried to do their part, but they couldn’t overcome my role. I depended on them for everything, and took a spill as a result.


I remember the first time I discovered that Pages for Mac didn’t autosave documents. I lost a few hours of work. It wasn’t great, probably, so maybe Pages did me a favor. But I didn’t think it was so cool at the time.

I blamed Pages. But, really, I blamed myself for depending on Pages. For not confirming assumed functionality.

After being thrown from my bike, I blamed that chunk of concrete. I blamed my light for missing it. I blamed my clipped in shoes for not allowing me to be faster on my feet.

But it was all me. I depended on my tools, and they didn’t live up to the task.

When a project doesn’t go well, it’s easy to blame the client, or our team, or the tools we used, or our lack of research or silos or subject matter experts or anything really. But with every strategic web project, there is a single point of failure: the person in charge.

No matter what, someday our tools will fail us. And that’s okay. They’re just tools. It’s up to us to make them work.