Stop Solving Problems. Start Anticipating Them.

A practical guide to looking around corners, at work, in your career, and with your life.

Years ago, my team was responsible for a critical service at Amazon that handled millions of requests per minute. The service was getting intermittent errors from a downstream API it called. The fix seemed obvious. I added a simple retry mechanism in the code. If a request failed, the service would immediately try again, up to three times in rapid succession.

And it worked. The intermittent errors on our dashboards vanished. Problem solved. Everyone was happy.

Until a few months later, when the downstream API had an extended outage. When their service finally started to recover, it was immediately overwhelmed and fell over again. The culprit was us. Our service, along with others, unleashed a "retry storm"—a massive, concentrated flood of requests that hammered their recovering systems back into oblivion. My "quick fix" for the small problem had created a catastrophic failure condition for a much bigger one.

We had solved the first-order problem, but we had failed to see the second-order effects. If you’re curious, the solution involved exponential backoff with jitter and some other tricks, but the lesson was simpler: you have to look around corners.

Most knowledge workers are paid to be problem-solvers. But the best are paid to be problem-anticipators. The difference is a mental model called second-order thinking. It’s the skill of looking past the immediate solution and seeing the cascade of effects that will follow.

At Amazon, looking around corners was a highly-valued skill, but something they never gave training or guidance on. I had to learn it myself. In this article we’ll dive deeper into the concept and I’ll give you some practical ways you can start incorporating it in your work and life.

1. First-Order Thinking: The Lure of the Short-Term Fix

First-order thinking is the process of looking for a simple, direct solution to an immediate problem. It's fast, reactive, and it feels productive because it makes the current pain go away. We are all incentivized to think this way. Our performance is often judged on short-term results, and quick action make us look decisive and effective.

But in any complex system, a project, a company, a career, we have to be diligent that short-term fixes won’t lead to long-term consequences.

Consider a team tasked with creating an important report for leadership. To get it done quickly, they pull data from the most convenient source, even though they know it's flawed, the data is not complete in some critical cases. The first-order effect is positive: they deliver the report ahead of schedule and are praised for their speed. The second-order effect is that a month later, another department makes a critical business decision based on the flawed data in that report.

Or think about a leader who avoids giving a team member critical feedback to spare their feelings in the short term. The first-order effect is that the conversation is comfortable. The second-order effect is that the team member continues to underperform, their habits bring down the rest of the team, and the leader eventually has to have a much more difficult conversation down the road.

This happens at the company level, too. A corporation might decide to switch to cheaper, lower-quality materials for its products to boost quarterly profits. The first-order effect is a success. Profit margins increase, and the stock price gets a bump. The second-order effect is that customers notice the drop in quality, the brand's reputation for excellence erodes, and long-term customer loyalty evaporates, leading to a weaker company in the long run.

Actionable Advice: Practice asking the "Future Self" question. The next time you're about to implement any solution, pause and ask: "If I do this now, what problem am I creating for my future self in six months?" This question forces you to consider the long-term costs of your solution. It makes you think about the person who will have to deal with the consequences of your decision, and it encourages you to choose a path that makes their life easier, not harder.

I always ask myself whether “Future Steve” will be pleased with me, or whether he’s going to be annoyed and angry.

I used to be terrible at submitting my expense reports. I’d finish a business trip with a folder full of receipts and tell myself I’d do it tomorrow. I avoided the 45 minutes of annoying administrative work. But as I made that choice, I could almost hear my future self groaning. I knew that "tomorrow" would turn into next week, and the task would hang over my head, creating a low-grade anxiety that was far more draining than the task itself. I would put it off for so long that I’d take another business trip, making the receipts from the first trip that much more annoying to find. Future Steve was not happy.

To please him, all I did was create a new system that didn’t take more time at all. When I went on a trip I would preemptively start the expense report while at the airport. Whenever there was a receipt, I just took a picture of it on my phone. On the flight home I would upload all of my receipts. The last step was simply to add the receipt for the ride back from the airport and submit.

2. Second-Order Thinking: Finding the High-Leverage Tweak

Thinking about long-term consequences doesn't mean you always have to choose the hard way that explodes your workload to "do it right." You don’t have to choose between the quick fix and the perfect solution. More often than not, the perfect solution doesn’t even exist, so trying to find it is its own trap. If you can avoid binary thinking, you can usually find a high-leverage tweak that dramatically reduces the long-term cost with minimal short-term effort.

My "retry storm" is a perfect example. The right answer wasn't to avoid retries altogether, or to rebuild the system “the right way”. The right answer was a smarter retry. Adding exponential backoff and jitter was a small tweak to the code, but it had a massive impact on the long-term stability of the system.

The goal of second-order thinking isn't just to see the future problem. It's to find the smallest possible change you can make now to avoid it. Let's revisit the examples from before:

The Flawed Report: The "hard way" is to delay the report by weeks to fix the data pipeline. The "quick fix" is to send the flawed report and hope no one notices. The high-leverage tweak is to ship the report on time, but add a prominent note at the top that explicitly states the data's limitations and caveats. This takes 30 seconds but preserves speed and credibility, and prevents the long-term consequence of a bad business decision.

The Avoided Feedback: The "hard way" is to schedule a formal, direct feedback session that feels confrontational. The "quick fix" is to say nothing. The high-leverage tweak is to frame the feedback collaboratively and focus on a specific, forward-looking observation. For example: "I noticed in the last project didn't land as strongly as it could have, with issues X, Y, and Z. What's your take on how we could approach that differently next time?" This invites a conversation about performance without feeling like an accusation.

The Cheaper Materials: The "hard way" is to refuse to cut costs at all. The "quick fix" is to switch to cheap materials across the board. The high-leverage tweak is to identify one or two non-critical components where a cheaper material won't impact the core user experience or durability, and run a small A/B test with a subset of customers to measure the impact on returns and satisfaction. This allows for a data-driven cost reduction without damaging the brand.

Actionable Advice Practice identifying the driver of the negative outcome. When you anticipate a future problem, don't just focus on the problem itself. Ask: "What is the one thing that is driving this potential negative outcome?" In the report example, the driver isn't the deadline, but the risk of misinterpretation. In the feedback example, the driver is the fear of conflict. By focusing on the driver, you can look for a small, targeted solution that addresses the root cause, rather than trying to solve the entire future problem at once.

Sometimes finding the high-leverage tweak takes work. I remember being on the cusp of a massive feature launch that involved many teams. The launch date was a huge deal, with a lot of pressure from leadership to hit it. A week before the launch, our Quality Assurance team came back with bad news: they had found a list of showstopper bugs. The feature wasn't ready, so we had a choice. The first-order, easy choice was to launch anyway. We could make leadership happy, hit the date, and deal with the bugs later. The second-order consequences, however, would have been disastrous: a buggy product, angry customers, and a burned-out team forced into months of fire-fighting.

I pulled the teams together to really scrutinize what was a showstopper and what could be a fast-follow or easily mitigated. It turns out that most of the issues came from a small sub-feature that wasn’t considered a show-stopper. The high-leverage tweak was to put that functionality behind a feature flag so we didn’t have to delay the launch because of it.

3. The Art of Intentional Foresight

It’s one thing to think about long-term consequences when a crisis hits, like in the launch story above. But even then, there is a choice. You can react with surprise and panic, or you can shift into proactive damage control. The latter is a sign of intentionality, acknowledging the reality of the situation and immediately thinking two steps ahead about how to mitigate the fallout.

The real skill is to practice this thinking proactively, when there is no immediate crisis. The goal is to confront future problems, not to stick your head in the sand. We avoid thinking about the future because it’s difficult and uncomfortable, but the problems we ignore don’t go away. They just get bigger.

Consider a common project planning. The first-order choice is to create an optimistic timeline that assumes everything will go perfectly, with everything in scope, instead of a realistic plan that has a more reasonable scope. It makes everyone happy in the short term. A proactive, second-order choice is to schedule an early check-in milestone, that if the project is slipping, triggers an escalation. You can come to that meeting prepared with solutions and approaches that probably should have been considered at the start.

Actionable Advice The tools for second-order thinking are most powerful when used proactively. You can think of building this skill at three levels: as an individual, as a team member, and as a leader.

• As an Individual: Use the 10/10/10 Rule for Your Career. Once a quarter, apply this rule to your career path. Ask, "Based on my current trajectory, what will my career look like in 10 weeks? In 10 months? In 10 years?" This forces you to lift your head up from the immediate tasks and think strategically about the long term.

• As a Team Member: Schedule a "Premortem" for a Calm Project. Don't wait for a high-pressure deadline. Pick a project that seems to be going smoothly and run a premortem. Ask, "It's six months from now and this 'easy' project has somehow become a disaster. What happened?" This builds the habit of looking for risks when there's no immediate fire to fight.

• As a Leader: Appoint a "Chief Skeptic." On your next project, assign someone the official role of "Chief Skeptic." Their job is not to be negative, but to actively question assumptions and ask "And then what?" about every major decision. This institutionalizes the practice of second-order thinking.

Conclusion

Of course, some second-order effects are impossible to anticipate. When the automobile was invented, no one could have predicted the snarling traffic jams that would define modern cities a century later.

The goal isn't to be a perfect fortune-teller. It's to be intentional in making the conscious effort to look beyond the immediate. The practice of looking around corners is what matters.

That is the shift from being a simple problem-solver to an engineer of future success.

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