68 - Second-order thinking: carefully count what you see and find out what you don’t



Second-order thinking makes us imagine the _unseen _problems and opportunities created by every action we take.

Say you’re early into your career and you want to build your skills and earn more, in that order. You’re debating between staying in your current job and finding a better position elsewhere. Here’s how to apply second-order thinking to make a better career decision.

1️⃣Look beyond the first available option, no matter how right it feels:

The first answer comes from your reflexive system. It is where your biases rule. So if your ‘heart’ tells you that staying with your current employer feels right, ask why. Is it because you’re comfortable in your team? You’ve built good friendships? Did you feel as comfortable when you were new?

2️⃣For each option, list down what may happen if it does and does not work out: What will happen if things go well? What will happen if they go poorly?

Instead of doing pros and cons for each option, map the results of each option faring well and poorly in the long term.

For example, the current job going well could mean you learn new skills, work on interesting projects, and get a hike and promotion in the next appraisal. If it went poorly: business priorities change, you play a support role, skill-building is harder.

3️⃣List down the information you need to decide on the best option:

Once you’ve a map for what may happen if things go well and if they don’t, you can now focus on gathering evidence that will tell you what decision has a better chance of bringing you closer to your core priorities.

In the continue-versus-leave question, your scenario list could point you to the evidence you need to gather. Are you someone with a unique skillset in your team? How fungible may that skillset be elsewhere? What positions or roles does your current skill set leave you out of? What additional skills could expand the employer pool for you?

Asking these second-order questions for a consequential decision is a good first step toward reducing uncertainty. Second-order thinking helps to understand not just the potential opportunities but also the problems that may emerge from your choice.

Say you’re debating between doing an MBA and getting a new job. Instead of doing pros and cons for each, map the results of each going well and poorly. For example, business school going well could mean you upskill, build the right network, and do all this on a scholarship. A negative outcome for the same choice would be a low demand for the skills you learn and run up a huge debt that could limit your job choices later.

In the MBA vs job question, your list should point out what you need to find out to make the decision. What are the chances of a scholarship for your profile? What’s the placement record of your school? What’s the variance in salaries? What’s the tuition workload like? Will it allow you to take a part-time position to reduce your debt? And so on.

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