Second-order thinking

Best-case ⚖️ worst-case and taking a second opinion from your future self.

I’ve been wanting to write about second-order thinking for a long time. I hesitated, wondering what new insights I could offer beyond what experts have already shared, like here and here. And to be honest, I always thought it was beyond my simple “either/or” mindset. I tend to see things in black and white whereas this mental tool is multi-layered. The good news is that it’s not reserved for experts. We can all use it to make better decisions. Special shoutout to my 12-year-old, who inspired me to tackle this topic. He assured me my grasp of it was share-worthy. So here’s my simplest take on this powerful way of thinking. Enjoy the read! ❤️

It’s early evening, and the perfect time for both of us—my 12-year-old and me—to get outside. 🌳 🛝 He’s been cooped up with the flu, so he’s eager to hit the playground and see his friends. I’ve been sitting at my desk all day, itching for a run along the breezy East Coast. We lace up our shoes, ready to go, but just as we’re about to step out, it starts to drizzle. 🌧️

Now, do we keep going or not?

First-order thinking is simple: go with your gut. It's drizzling, no biggie. Let’s stick to the plan.

But second-order thinking asks us to dig a little deeper and consider what happens next. I’ll walk you through two simple ways to practice this.

Best-case ⚖️ Worst-case

It’s easy to let first-order thinking take over, but what happens if we consider both the best and worst outcomes?

Best case? The drizzle stops, and we carry on. Worst case? The drizzle turns into a full-on thunderstorm, and we get drenched. ⛈️⚡️

Now, the key question is this—Is the best case worth the risk of the worst case?

For my son, the best case is simple: no rain, a great time with his friends. The worst case? He gets soaked, catches a cold again, and misses even more playtime!

For me, the best case is an enjoyable, dry run. The worst case? I get stuck in a downpour and have to cut my run short.

The beauty of second-order thinking is that it's personal. My worst case isn’t the same as his, and neither is my best case. No one else can tell you what to do because your decisions are unique to you, shaped by your priorities, circumstances, and what matters most in the moment. In the same situation, two people might make entirely different decisions—and both would be right for them.

Another way to practice second-order thinking is as follows.

Take a second opinion from your future self

Who better to give you advice than your future self? Not the “5-min from now” version of you—the one that's still debating that chocolate cake for dessert. 🍰🤤

I’m talking about your 10-month future self, the one who will look back and say, “Was that cake really worth it?”

Second-order thinking asks us to think beyond the present moment. What would your 10-year future self say? That’s where true wisdom lies—the nth level of thinking.

• 10-min future self → First-order thinking

• 10-month future self → Second-order thinking

• 10-year future self → nth-order thinking

First-order thinking is reactive.

Second-order thinking is reflective.

nth-order thinking is long-term wisdom.

Applying it in real life

Let me give you a real-life example. My 12-year-old had a track-and-field class, but he was feeling lazy and wanted to skip it. Here’s how he used second-order thinking to make his decision.

His 10-minute future self:

“If I skip, I’ll feel relieved. If I go, I’ll be annoyed.”

But then he thought further ahead. ⬇️

His 10-month future self:

“If I skip today, I’ll be tempted to skip every week in the future. Less training means I’ll be slower in the long run. But if I go today, I’ll be in the habit of not skipping—and that will eventually make me faster.”

By considering the long-term effects of his decision, he was able to push through the temptation to skip, knowing it would benefit him in the future.

Now, let’s apply second-order thinking to a startup scenario. Imagine you’re considering quitting your job to start your own business.

Best-case ⚖️ Worst-case:

Best case: You launch your dream business, and it’s a huge success. Worst case: It doesn’t work out, and you struggle financially.

But, that’s not all. Let’s think deeper. What’s more to the matter than just these extremes? How about a third option like starting the business on the side while you’re still employed?

This allows you to build momentum and test the waters without the immediate financial risk. The idea is to find a more nuanced path between the extremes, helping you avoid the black-and-white trap.

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Second-order thinking isn’t as complex as it sounds. It’s all about looking beyond the immediate, obvious outcomes and considering the ripple effects of your decisions.

It’s personal, too—what works for me might not work for you, and that’s okay. The key is to bring your future self into the conversation and think about the long-term consequences.

By practicing second-order thinking, we can make wiser decisions that don’t just serve us today but set us up for success tomorrow. So next time you face a choice, ask yourself: What would my future self say? Is this decision about instant gratification or long-term growth?

In the end, second-order thinking isn’t about being right or wrong. It’s about being thoughtful, intentional, and wise in how we navigate the decisions that shape our lives.

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Until next time 🙌