My uncle used to tell me “When you’re up to your ass in alligators, don’t forget the objective is to drain the swamp.”
He’d usually say that when I was facing a bug in code or fighting some tech challenge.
I could disappear into a problem for hours – sometimes even days, tracing dependencies, testing edge-cases, and digging through layers of logic until I finally found what was broken. There’s a particular satisfaction in solving problems nobody else can see. For a few minutes, the world makes again.
Then I’d lean back from the screen and realize the larger objective hadn’t moved. I had solved the problem in front of me, I hadn’t made progress.
You can solve the problem in front of you without changing the condition that created it.
My uncle was a Vietnam-era Army pilot. He had a way of compressing an entire way of thinking into some short, memorable phrase that would stick with me. At the time, I assumed his advice was about focus or productivity. It took me years to realize that it was about perspective.
A Flight West
That old saying returned to me on a flight from South Carolina to California. I was headed west to retrieve my Jeep, which I had left at a friend’s in San Diego from a summer trip. I typically spend a couple weeks in September off-roading in Utah and Colorado, this year my schedule shifted a bit. The plan was to pick up the Jeep and drive roughly 3,000 miles home over the course of a week or so.
I’d work remotely along the way, stop at one of my favorite hot springs in Utah, finally visit a wilderness in Colorado I’d been trying to reach for five years, and take enough back roads to keep the trip interesting.
That was the plan, anyway.
Professionally, I was in the middle of one of the most consequential stretches of work in my career. My team and I have spent months building a platform intended to change how a collection of applications would be delivered, managed and evolved. The first application was nearing launch. Years of technical debt, legacy constraints, and accumulated workarounds were beginning to give way to something new.
But the application isn’t the real point, neither is the platform.
We were trying to change how work moved. How an idea becomes a decision. How a decision becomes a requirement. How a requirement becomes something real without losing it’s original purpose along the way.
At the same time, I was preparing for an off-site presentation with many of the people who use these systems every day. I knew I didn’t want to spend an hour talking about technology. They don’t need another tour of features, architecture diagrams, and roadmaps.
I wanted to explain what all the work was meant make possible.
Honestly, I was still working that out for myself.
I boarded the plane carrying all of it my head. Somewhere during the flight, I opened Brené Brown’s book, Strong Ground.
Holding the Tension
One chapter stopped me: “Paradox and the Human Spirit.”
Some tensions aren’t problems to solve. They’re realities we have to learn to hold.
Strength and Vulnerability
Confidence and Humility
Planning and Uncertainty
Action and Reflection
We’re uncomfortable with that kind of tension. We want to choose a side. We want one idea to be right so we can discard the other and move on. But meaningful work often requires two apparently opposing things to remain true.
Transformation requires relentless attention to detail. It also requires enough distance to see what those details are creating. Organizations need people willing to solve the problem in front of them. They also need people willing to ask why the same kind of problem keeps appearing.
You have to deal with the alligator.
You also have to deal with the swamp.
The work requires us to be close enough to understand the alligator and far enough away to remember the swamp.
Somewhere over the Southwest, my uncles’ voice returned after years of silence. I looked out the window at the desert below, and the opening of my presentation began to take shape.
Plans, Repairs, and Side Quests
By noon I was standing beside my Jeep in Southern California, pointing it east.
The Jeep had no air conditioning.
Under normal circumstances, that would have been uncomfortable but manageable. That week, with temperatures hover between 95 and 100 degrees for much of the drive, it became a constraining fact of the journey. I’d find myself pulling off near rivers and streams, walking into the water, soak myself completely, climb back into the Jeep, and continue east until the heat dried me out again.
It turned out I had chosen the hottest recorded summer heat in the lower 48 for a 3,000 mile journey with no air conditioning. It sounds miserable when I say it that way, it wasn’t. It was hot. It was inconvenient. It required adjustment. But discomfort and misery are not always the same thing.
I made it to one of my favorite hot springs in Utah just after midnight, and set camp (nice way of saying I slept in the back of the hot Jeep). After a nice morning soak, with thunder and lighting rolling in, I made my way to Moab for an afternoon on trails before retreating to a hotel for the night to escape the weather. From there I continued toward Colorado, where the Jeep decided my thoughtfully imagined route needed revision.
I’d been trying for five years to reach the Flattops Wilderness. This was supposed to be the trip when I finally made it. Instead, I spent that part of the journey dealing with transmission repairs.
Another alligator.
I could have treated the repair as the moment the trip went wrong. In one sense, it did. I missed the place I been trying to reach for years. But the wilderness would still be there. The road home continued. So I adjusted.
A change in route is not always a change in direction.
The route bent through Kansas, Missouri, and Arkansas. I followed back roads, wandered into places I hadn’t planned to see, and stopped by any body of water I could find when the heat became too much. These were side quests in the truest sense. They didn’t advance the itinerary I had orignally imagined. Some existed only because something hadn’t worked out. Yet they became part of the journey rather than evidence the journey had failed.
What Road Trips Reveal
One reason I enjoy long drives is that they change my relationship with time.
Modern work trains us to measure our days through immediacy. The next notification. The next meeting. The next escalation. The next thing somebody needs from us.
Road trips measure progress differently.
A cross-country drive doesn’t always care how closely you followed your original itinerary. It asks whether you are still headed toward your destination. Every turn matters, but only in relation to the route. Every mile matters, but only in relation to the destination. Miss a turn and you can correct it. Find a road closed and you can find another. Spend a day in the repair shop and the journey doesn’t cease to be a journey.
You’re delayed. You’re re-directed. You may be disappointed. But you’re not necessarily lost.
That distinction is easy to forget at work.
We create plans and begin treating the plan as the purpose. We define requirements and begin treating the requirements as the outcome. We establish dates, milestones, and measures because they help us move.
Then something changes.
A dependency fails. A constraint surfaces. A decision takes longer than expected. Someone discovers that the problem we planned to solve isn’t quite the problem people actually have.
That’s the moment when purpose matters most. If the plan is the mission, every deviation looks like failure. If the plan serves the mission, we can adjust without losing the way.
We See Alligators Better Than Swamps
Somewhere between the planned route and the accumulating detours, I began to see the same pattern in my work. People naturally notice events. Systems operate through structures.
We see the outage. We don’t see all the dependencies behind it.
We see the delayed decision. We don’t see the missing information, competing incentives, and accumulated uncertainty that made the delay predictable.
We see the frustrated person. We don’t see the process that has trained frustration into the,
We see the alligator because it has teeth. The swamp is harder to see. It surrounds us. After enough time, it begins to feel like the natural state of things. We become skilled at navigating it. We create workarounds. We build spreadsheets. We add meetings. We memorize who to call when the official process fails.
Eventually survival begins to look like competence. Sometimes it is competence. But repeated heroics can also be evidence that the underlying condition hasn’t changed.
The people who solve emergencies earn trust. The people who understand the hidden workaround become indispensable. The people who keep the old machinery running receive praise for saving the day.
Nobody means to preserve the swamp. Still, every successful rescue makes it easier to postpone draining it.
The Question Beneath the Work
As the miles passed, the presentation I was preparing became less about the platform and more about the purpose behind it.
I kept returning to one question:
What swamp are we actually trying to drain?
Not what project are we delivering.
Not what application we are replacing.
Not what requirement we are implementing.
What condition are we trying to change?
What should become easier when we succeed?
What should no longer require heroics?
What becomes possible that isn’t possible today?
Those questions changed how I understood the work.
A project tells you what you’re building. Purpose tells you what should be different when you’re done.
The platform was no longer just a collection of technology and the process was no longer just a collection of tasks. This was a chance to remove friction teams had learned to accept. We could preserve intent across handoffs rather than requiring each person to reconstruct it. We could make the system serve the work instead of continually asking people to bend themselves around the system.
The technology matters, its just not the mission.
You Still Have to Deal With the Alligator
I’m tempted to turn all this into easy advice:
Rise above the noise.
Ignore the details.
Focus on the big picture.
I don’t believe that.
If an alligator is coming at you, that’s probably not a time to deliver a lecture about systems thinking. The Jeep still needed to be repaired. The failing code still needed to be fixed.
Some immediate problems are genuinely immediate. People depend on us to handle them. Almost every worthwhile responsibility requires us to enter the mess and deal with what’s directly in front of us.
Perspective without action is just observation.
But action without perspective becomes reaction.
The discipline is learning to move between the two.
Get close enough to understand the details. Step back far enough to understand what they mean. Handle the immediate problem, then ask what made it likely. Return to the work, then find enough distance to decide whether the work is taking you anywhere worth going.
Competence can become its own trap. If you’re good at solving emergencies, people will keep bringing you emergencies. If you’re good at surviving broken systems, other may mistake your survival for evidence the system works.
At some point, you have to ask whether you’re solving the problem or helping the conditions that created it survive another day.
Perspective doesn’t remove us from the work. It changes how we return to it.
The Road home
When I look back at that week, I don’t think first about the route I planned.
I think about the hot springs and trails in Utah, a repair shop in Colorado, back roads through the Midwest, and the relief of stepping into cool water before climbing back into a sunbaked Jeep.
I think about the wilderness I didn’t reach. I’ll try again.
Most of all, I think about how easy it is to confuse an obstacle with the whole journey.
Some alligators have to be handled. Some roads close. Some plans don’t survive contact with the terrain. None of that releases us from the responsibility to remember where we were headed in the first place.
My uncle’s lesson was never that the alligators didn’t matter. It was that they could command so much attention that I might forget why I entered the swamp at all. That’s the danger in our work and in our lives. We can become so capable at responding, adapting, and enduring that we never stop to ask whether all that effort is carrying us toward the future we meant to create.
Deal with the alligator in front of you. Change the route when you need to. Stop at the river and cool off.
But don’t surrender the horizon.
The real measure of progress isn’t how many alligators you’ve fought. It’s whether, when the immediate danger has passed, you’re still changing the conditions that keep producing them.
