- Chief Rabbit
- Posts
- The Upstream Solution: Why We Keep Solving the Wrong Problems
The Upstream Solution: Why We Keep Solving the Wrong Problems
Why fixing problems never ends. And what to do instead

In high school, I had a health teacher named Mrs. Burkhardt. She was a little strange. Her socks never matched, she called everyone by their full name, and she answered questions while looking slightly to the left of whoever was speaking.
Most kids didn't like her class—myself included. But she was fascinating.
But one day, she had our full attention. She started class with a story::
A man was hiking in the mountains when he came across a river. As he walked along the riverbank, he spotted someone struggling in the current. Without hesitation, he jumped in, pulling them to shore. But as soon as he caught his breath, another body came floating downstream.
Then another. And another.
Again and again, he waded into the frigid water, pulling people to safety. Soon, a few of the people he had saved recovered enough to help. Together, they formed a chain, dragging body after body from the rushing water.
Finally, exhausted and overwhelmed, the man made a decision. While the others continued their rescue efforts, he ran upstream to find out what was happening.
A little further on, he found the source: someone was throwing people into the river. He tackled them, stopping the assault before more victims could be swept downstream.
Mrs. Burkhardt let the silence hang in the room. We sat there. Processing. Wondering if this would be on the final exam.
I don't remember much else from her class, but that story never left me. It comes back to me over and over whenever I find myself stuck in cycles of fixing problems without solving them.
Years later, I learned there was a name for what Mrs. Burkhardt was teaching us. Management theorists call it Double Loop Learning. It’s the practice of looking past immediate problems to fix the system that creates them.
So this week, let’s talk about Double Loop Learning, the difference between fixing problems and actually solving them, why we resist questioning our own assumptions and, most importantly, how to start breaking bad cycles in your own life.
The Critical Difference: Are You Fixing or Actually Solving?
Fixing problems and solving them aren't just different approaches. They're entirely different mindsets.
Fixing is what we do when we pull people from the river: it's immediate, necessary, often urgent. Patch the hole, put out the fire, keep the wheels turning. And sometimes, it feels heroic—because, in the moment, it is.
But solving problems is a different beast entirely. It requires us to step back, even if every instinct screams at us to stay and help. It means asking harder questions: Why are people falling in? Where's the guardrail? Who's pushing them?
Fixing is answering every email in your inbox. Solving is figuring out why you're getting so many emails in the first place—and then doing something about it. Maybe your team needs better documentation, clearer processes, or just fewer meetings. It's like playing whack-a-mole: you can spend all day hammering down problems as they pop up, getting more exhausted with each swing, or you can unplug the machine. Fixing keeps you busy. Solving sets you free.
Look, I get it: fixing feels productive. It's full of quick wins, clear metrics, instant feedback.. It's full of quick wins, clear metrics, instant feedback. It triggers that dopamine rush. Solving is slower, messier, often frustrating. It forces us to sit with uncertainty, rethink processes, and sometimes admit we've been doing things wrong for a long time.
But if we never move beyond fixing, if we never go upstream, we lock ourselves into an endless cycle of crisis management. We get really good at pulling people from the river but never stop to ask why they're falling in.
We all like to believe we're rational thinkers, guided by logic and facts. But in reality, we largely operate on assumptions: mental shortcuts that help us navigate the world. Most of the time, these serve us well. They speed up decision-making, prevent analysis paralysis, and provide a sense of stability.
But what happens when those assumptions are wrong? Or worse, what if they were never right to begin with?
Challenging our own assumptions feels threatening. It forces us to confront potential mistakes and that’s some scary stuff. It can feel like an attack on our competence or experience. After all, if we've operated this way for years, surely it can't be fundamentally flawed? Can it? And even when we suspect there might be a better way, change feels risky. What if doing things differently blows up in our face?
Take hiring for example: For years, I felt like our company should require four-year degrees for most full-time roles. I assumed this guaranteed competence and the ability to commit. I operated this way because that's what we did at Adobe and hey, if it worked for them, right? But what if that assumption was blocking some really great talent who took nontraditional paths? How many amazing candidates did I miss out on because I was too stuck in my ways to question the status quo?
The breakthrough comes when we realize that questioning assumptions isn't admitting defeat—it's actually embracing growth. The best leaders, teams, and organizations regularly challenge their own thinking, not from insecurity, but because they understand that staying locked in a broken cycle is far more dangerous than acknowledging the need for change. Sometimes the scariest part isn't being wrong—it's realizing how long we've been wrong without knowing it.
Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.
Breaking Free: A Practical Path Forward
It’s one thing to know you are stuck. It can be quite another getting unstuck. When you're trapped in the middle of a pattern, change might feel impossible. But there is hope: you may not need a massive overhaul. One small change leads to another. Then to another. Before you know it, you're working in a completely different way.
Here's a simple way to start: regularly ask yourself two powerful questions:
What are we dumb for STILL doing?
What are we dumb for NOT doing?
What are we dumb for still doing? These are the zombies. The habits, routines, or processes that hang around long after they’ve stopped being useful. It might be that weekly report nobody reads, the three-level sign-off process that bottlenecks everything, or your own habit of checking email before your feet hit the floor. If something feels like a relic of the past, it probably is.
What are we dumb for not doing? These are the obvious improvements we keep putting off. Maybe it's automating those mind-numbing repetitive tasks, finally setting boundaries around your time, or making that decision you've been dancing around for months. If you keep saying "We really should...", it's time to actually do it.
Put this into practice with these three steps:
Find patterns, not problems. When the same problems keep showing up (missed deadlines, constant rework, endless meetings), stop treating each instance as a one-off.. Ask yourself: What's the thread connecting these? Instead of reaching for another quick fix, dig for the root cause.
Get to first principles. Surface answers are usually symptoms, not causes. If your team is overwhelmed, your first instinct might be "they need better time management." But dig deeper: Why are they struggling to manage time? Maybe it's unrealistic workloads. Why are the workloads unrealistic? Maybe priorities aren't clear. Why aren't they clear? Keep going until you hit the fundamental issue—the one that, if solved, makes the other problems disappear.
(Quick note: First principles thinking is amazing, I’ll dedicate an entire newsletter to it soon.)There are no sacred cows. Make it a habit to question something you take for granted—whether it's a work process, a personal routine, or a belief about yourself. Do you really need that standing meeting? Is your morning routine actually serving you? Pick an unquestioned habit and ask: Is this actually serving us, or is it just comfortable?
In Conclusion
What Mrs. Burkhardt taught us with that river story wasn't just some random lesson in health class…ok maybe it was. But she was showing us that without looking upstream, we could spend our entire lives just pulling people from the water. She was an odd duck but she understood something fundamental about changing your way of thinking. Over the years, I've watched it play out in all sorts of places: in companies, in teams, in my own habits. We can get really good at fixing, but never quite get to solving.
So here's your challenge this week: Pick one frustrating problem that keeps showing up in your life or work. Instead of jumping in to fix it like you always do, force yourself to pause and ask: Why does this keep happening? What are we dumb for still doing? What are we dumb for not doing? Then take one step—however small—toward an actual solution.
Because here's the truth: The longer we keep doing things the same way, the harder they become to question. But the moment we start looking upstream, we open the door to something better. And sometimes, that makes all the difference.
As always, thanks for reading,
Derek
p.s. Have something interesting you think I should write about? You can reply to this email (or any previous Chief Rabbit email) to suggest it.
Quick favor! I'm adding weekly anonymous polls to help make this newsletter even better. Your input helps me choose both content and partners that'll be most valuable to you. It takes 30 seconds:
What's your highest level of education? |
Chief Rabbit thrives when the community grows. If you found value in this newsletter, it’d be great if you shared this with a friend.
Also, if you like newsletters, check out some on this list, I get a little referral when you sign up. They're all free!
JOIN THE WARREN
Chief Rabbit reaches over 25,000 readers each week with actionable strategies for productivity, mindset shifts, and leadership to help you turn small changes into remarkable outcomes.