Welcome to the second issue of Wayfinder.

Wayfinder is about learning to navigate life’s toughest decisions. The choices that keep you awake at night. The decisions that have you second-guessing yourself. The moments when the stakes are high and the path isn’t clear.

Wayfinder is designed to guide you through the fog of indecision, and make choices that align with your values, ambitions, and lifestyle. And we’ll do this using a powerful tool — decision algorithms.

Ancient Polynesian wayfinders traversed the Pacific, discovering island after island by learning to read patterns in sea swells, bird movements, and star constellations. Likewise, I propose we throw away rules, maps, and abstractions. Instead we'll build mental models to help navigate life's challenges.

Diego's Dilemma:

In today's issue, we're diving into another dilemma from one of our own - Diego.

Diego is a seasoned headhunter with a steady income but a growing concern. He's seen the effects of AI on various industries and wonders if it's time to make a career move before AI revolutionizes his field.

Here's his question:

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How do I decide if it's time to leave my job in headhunting, given the potential impact of AI on the profession? How do I navigate the uncertainty and evaluate my options?

Before every section, I'll flag the mental models and principles we'll be using to get a firm handle on the problem.

Alright, let's break this down.

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P.S. If you'd like to be featured in an upcoming issue of wayfinder, click here. In the future I'd love to jump on a call with some of you to discuss your problem live. Fill the form if you're up for it 👆🏾

Step 1: Visualizing the Extremes

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➡️ First Principles Thinking: This involves breaking down complex problems into basic elements and then reassembling them from the ground up. It’s about ditching preconceived notions and going back to the fundamentals of a problem.

➡️ Heuristics: These are cognitive shortcuts or rules of thumb that simplify decisions, used when time is limited or when there's too much information to process.

Diego, the first step is to get clear on your desired professional destination, your North Star, as well as your professional hell, the scenario you want to avoid at all costs.

Your North Star isn't a specific job title—especially in a potentially AI-driven world where new roles are constantly emerging. Instead, it's a blend of characteristics that define your ideal professional life. Reflect on the intersection of what you love, what you're good at, and what you could be paid well for (a concept beautifully captured in Cal Newport's 'So Good They Can't Ignore You').

Are you drawn to work that challenges you intellectually? Do you value flexibility and control over your time? Do you want to make a societal impact through your work?

Get concrete about your ideals and non-negotiables.

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It's easy to forget that you're not just charting a career path, you're designing a life. Don't accept the default - build with intention.

Conversely, your professional hell might be more than ending up in a dying field. It could be working in a role that doesn't align with your values, drains your energy, or doesn't provide the financial security you need. The clearer you are about these extremes, the better you can navigate your career transition.

Step 2: Assessing the Costs

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➡️ Cognitive Biases: These are systematic errors in thinking that can affect decisions and judgments. When assessing the costs, be aware of biases that might overemphasise certain costs and underemphasise others.

➡️ Divergent Thinking: This involves thinking outside the box, generating many different ideas about a topic in a short period of time. It's free-flowing thought where many creative ideas are generated and explored.

Next, it's time to weigh the costs of staying versus leaving. This includes immediate financial costs, i.e. loss of income if you take a step back professionally, but also second-order consequences and opportunity costs that might not be immediately obvious.

It may seem tedious to go through all these questions rather than jumping to the assumption that you have to jump ship and find a new industry, but taking a methodological approach will ensure you've covered all bases.

Staying in your current role might mean missing opportunities to diversify your skills or enter burgeoning fields. But leaving prematurely could lead to uncertainty and financial instability. You could be taking chips off the table instead of letting your skills and experience compound.

Consider these costs across different dimensions of your life: financial, emotional, relational, and even societal. For example, staying might offer financial stability but cause stress or regret if your field begins to wane. Leaving might be risky but could open doors to roles that are more aligned with your values and long-term goals.

You can't tell the future but you can prepare for it and hedge against it. I wrote here not long ago about how to balance planning for finite vs infinite time. Be aggressive and decisive about what you can see while hedging against the unseen.

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Every career decision is an investment. Look beyond the obvious—consider second-order consequences and hidden opportunity costs.

Step 3: Aim for Optionality

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➡️ Asymmetry: This involves making decisions based on the gap between potential gain and loss, or between the output and your input. Typically, you want to make decisions that create leverage over time.

➡️ Optionality: This involves maintaining flexibility by keeping future options open. The idea is to avoid becoming trapped in a single path and to have the ability to change later if necessary.

Here's the key question to ask yourself Diego - what choice could you make that would preserve the widest range of future choices? And which option could you pursue that creates the greatest potential outcome relative to the amount of work you put in?

For example - you could back to school for a year of extra education and come out with a degree that gives you more job options and higher pay - but considering the amount of effort that would go into it, that's hardly an asymmetric outcome.

On the other hand, you could take a one-day online course or just devote a few hours each weekend and develop a skill that produces the same result.

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Use this question for a regular check-in: What choice could I make today that my future self would thank me for?

Instead of switching paths now, you could build runways to a range of future paths that you'll be able to pivot to as needed. This prevents you from ending up trapped in either your current path or your next one.

Step 4: Establish Your Waypoints

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➡️ Levers and Variables: These are factors that can be manipulated to cause a change. In the context of waypoints, these can be skills to learn, connections to make, or roles to take on that can change your career trajectory.

➡️ Probabilistic Thinking: This is about thinking in probabilities — the chances of different outcomes happening, instead of thinking in certainties.

As you contemplate this transition, think about what signposts would indicate you're moving closer to your North Star or drifting further away from it. These are your waypoints—concrete indicators that it's time to reassess your path.

For instance, if demand for headhunters begins to drop sharply or if AI starts replacing key aspects of your job, these could be signs that you're on a sinking ship. Conversely, if you find opportunities to leverage AI in your work, or if you identify a new field where your skills could be valuable, these could be signs that you're moving closer to your North Star.

Think also about how you can prepare for these waypoints. This might involve upskilling, networking in potential new fields, or even starting a side project to test the waters.

By identifying these signposts in advance and planning your actions, you can navigate your career transition with greater confidence and clarity.

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AI in the workplace is not about replacement, but enhancement. It's about leveraging technology to focus more on the distinctly human aspects of work.

What next?

That's it for this edition of Wayfinder.

I hope our exploration of Diego's dilemma has sparked some insights for your own decision-making journey.

Have a decision you're wrestling with? Send it my way and it might just feature in a future edition of Wayfinder.

Stay decisive.

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