Finding And Fixing Bad Systems (AKA What’s in my Backpack)

I get a loving, but heaping, amount of crap for my backpack setup from friends and family.

Looking at it objectively, I can’t be too mad about this fact - it’s well-earned, as I’ve always been a bit of a “gear guy,” which means that for me my backpack is an amazing canvas for the artform. Making sure that my bag is ready for a wide variety of common scenarios is important to me, and being able to pull out a bandage, secret serving of coffee, or provide laptop power in a plug desert is one of my love languages. So the razzing naturally follows, as it feels like I can sometimes pull anything from my slightly oversized black backpack.

This post, however, isn’t about what’s actually in my backpack (I’ll be detailing that next week), but instead it’s about how I failed in the past to have a backpack that worked for my needs, and how I eventually was able to identify its failings and build a better version which has allowed me to do more with just a little applied intentionality.

This post is about identifying the small, overlooked systems that we quietly let shape our lives, as well as how we work and move through the world.

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Recognizing the Problem

For the past ten years I’ve been running a startup called BugSplat. We don’t have an office, and our team members live remotely. I love this because it’s allowed me great freedom to turn a lot of different types of places into my “office.” Over the years I’ve worked on BugSplat out of coffee shops, coworking spaces, camp spots with spotty power, on airplanes, sitting on friends’ couches, in the desert, while sipping coffee in ski lodges, and, one memorable time, while on a small boat in Maine.

The constant in this journey was my trusty backpack.

But here’s the thing: up until a few years ago, my bag was constructed without any real intentionality. Nothing scientific about the collection - it was simply filled through gradual accumulation of items that added up to a sum without really considering the equation.

That meant it nearly fit its purpose, but not quite: too heavy, too messy, and often missing critical pieces for the moment. Which meant that I was dependent on a system I had let shape itself, instead of one I had built with intention to fit its purpose.

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What’s Wrong With That?

I’ve noticed that this happens in my life, and the lives of my friends and loved ones, a lot. Here’s how this problem occurs for me: I have a small issue I need fixed in a moment, so I reach for the quickest fix to my immediate problem. Then, over time, I stack those fixes on top of each other until I end up with a system that kind of works - but one that was never really designed for the job.

Admittedly, my backpack is actually a relatively low-stakes (but fun) example of this problem.

But this patch-on-patch approach creates small headaches even as it fixes big ones. They don’t always derail your day, but they act like speed bumps of my own making. In software development we call that tech debt, and it’s kind of what the role of Product Managers was created to avoid.

Not having a PM for your own life, it’s important to learn to recognize that the process of respond, react, move on creates a collective momentum and a feeling of “ahh it’s good enough,” which can make it hard to step back and see that you’re perpetuating systems that kind of suck and hold you back.

What we want is the ability to identify things that, in hindsight, can feel blindingly obvious. Think of it like the old trope of being blind to the location of the ketchup in the fridge, only for your frustrated parent, sibling, partner, or roommate to be called over and pull it out of the ether right in front of your eyes.

I want to be able to “materialize the ketchup” for myself — to be alert to, and self-reflective enough to examine, the things in my life that have been built up through momentum and small choices which, when combined together, create a system that works alright, but where putting in 5% more effort upfront could remove barriers of your own making, eliminate frustrations you often deal with, or allow you to do more with the same amount of time, energy, and opportunities presented.

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The Equation

Absolutely it is - I’m using a stretched-out analogy about my backpack to encourage a shift in perspective. It’s doing a lot of hard work, this backpack analogy, but the goal is to notice where and when you’re tacitly accepting self-created resistance - the little weights you’ve accidentally shackled yourself to.

Nobody can look 100% objectively at themselves and see all of these at once - or ever. But what I’m searching for are more of those moments when I suddenly see something, tilt my head, blink a couple of times, and think: “Do I actually want to be doing it this way, or is this just kinda happening?”

From there, I run it through a simple framework:

If the output looks positive - higher benefit than effort - then it’s probably worth acting on.

Once you start spotting these little inefficiencies, you realize they’re everywhere - in your inbox, your kitchen drawer, your bike setup, your project workflow. The trick is turning insight into action.

The truth is, we all have those moments already — this isn’t rocket science. But what I’ve found is that the truly difficult part is turning these insights into consistent action (more on that later), and doing so makes this all the more powerful.

So in the end, do I recommend everyone go out there and trick out their on-the-go backpack setup?

Yes!

Well… erm… no, I guess I got carried away there because I think it’s fun.

What I do suggest is that you identify the biggest “backpacks” in your life and put in that extra 5% of effort and intentionality to remove the common roadblocks and frustrations that present themselves every day in your own life, and see what that frees up and allows you to accomplish.