Welcome to the fifth 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.

Marissa's Dilemma:

Today's question comes from Marissa, who has been offered a life changing-opportunity that may come with some significant tradeoffs.

What we'll cover:

  1. The Ideal End-State: You'll learn how to visualise the future and make decisions that future versions of yourself will thank you for.
  2. Optimisation and Optionality: We'll look at how to optimise our choices based on our current needs and values while keeping future options open and avoiding the trap of being limited by our past decisions.
  3. The Variance of Outcomes: We'll delve into the concept of considering both average and extreme potential outcomes for any decision, using the Dinner Table and Pub Tests.
  4. Hunting your Alts: Every decision creates multiple possible futures. Hunt down alternate versions of yourself to avoid falling victim to unforeseen consequences.
  5. The Power of Course Correction: You'll learn to identify key signals that will show if you've made the right or wrong decision and plan how you can adapt to these signals, transforming your decisions from a one-time action into a continuous learning process.

Marissa's Move

Here's Marissa's question:

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“I've been offered a scholarship for an arts program in another country. It's a great opportunity, but it means leaving my friends, family, and current life behind. Should I take up the scholarship and move or stay where I am?”

Marissa finds herself at a crossroads, a point of tension between an exciting opportunity and the comfort of familiarity. There's a thrill in stepping into the unknown, yet a deep-rooted desire to hold onto what's familiar.

Let's dive in.

Quick note

Have a problem you'd like us to tackle? Send it here, and you could be featured in an upcoming issue of wayfinder.

Step 1: Defining the Decision

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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 the problem. Marissa needs to identify and evaluate the underlying factors that define her dilemma. What are the core elements of her decision? Is it career progression, passion for arts, personal growth, or fear of missing out?

➡️ Inversion: This mental model involves looking at problems in reverse, to find solutions. It's about thinking what not to do, rather than what to do. Marissa should think about what would happen if she didn't take this scholarship, and compare this scenario with her life if she decides to move. Would she regret not taking the opportunity, or would she be content to stay in her current situation?

First of all, congratulations on the offer! Sounds like it can be an incredible opportunity. But it's still worth weighing up.

Not long ago someone reached out with a similar problem.

She'd received two job offers for her next role and was wondering which would align best with her desired trajectory. One role was in the same city she lived in, and the other would involve moving abroad.

After we spoke, she decided not to move. She updated me recently and seems very happy with that decision.

Meanwhile, when I was in a similar position a decade ago, I took the opportunity to go halfway across the world and work at a mid-size law firm in Shanghai. It was a great decision for me.

I share these two anecdotes just to set the baseline that there isn't one option that is better by default.

Here's the first question to ask:

What is the ideal end-state I am ultimately trying to achieve?

Right now you're only making a decision that pertains to the next 2-4 years of your life - this isn't a decision to move forever, or move for work, so that does take a little pressure off when considering the long-term consequences.

But don't just answer this question now - ask three different versions of yourself. Today's you, you in three years, and your 80-year-old self.

What am I optimising for right now?

Your values change as you age. You may not even recognise the future version of yourself. Sometimes that's a good thing. But sometimes we forget the wisdom of our past selves.

What do you care about most right now? Is it nurturing your skills as an artist, is it the opportunity to build friendships, do you care about enjoying novel experiences, or are you simply just trying to put yourself in the best position for employability later?

What's the best gift I could give to my future self?

Now step three years ahead. It's not so much time that you're an entirely different person, but it's enough to be a little older and wiser.

What actions could you take today that your future self would thank you for?

This doesn't just apply to the decision in front of you now. There's a spectrum of decisions that compound over the course of your life.

What you read, how you eat, who you talk to, and what you do with your money. These decisions are investments that pay continual dividends.

Luck can strike at any time, but you can certainly be the architect of your own serendipity. Choosing where to live, where to work, and where to spend time online can be a crucial part of that.

I'd check out my conversation with Stu Patience for more on that.

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Every decision you make sends ripples into the future, opening some doors and closing others.

Which path leaves you with the largest number of high-quality future paths? And which path might be dark and fraught with danger but offers a reward/experience you wouldn't trade for anything?

You don't want to become a slave to chasing optionality, but you also don't want to find yourself constrained by the shadow of your past self.

I talked more about one-way vs two-way doors (reversible decisions) and the concept of ergodicity (irreversible losses that absorb future gains) in a previous issue of Wayfinder.

How would I answer the rocking chair test?

Imagine you're 80 years old, having lived a long life. When you take the long-term view of how this decision might align with your values, what would you regret more?

Do you think you'll regret opportunities you may have missed by staying close to home, spending more time with loved ones and nurturing close relationships?

Or will you feel more pain when you consider the road not taken, and the adventures you may otherwise have had?

Here's a different way to ask it:

Imagine you're 80 years old and you look back on this decision. You've made the choice. You already know how this pans out. In retrospect, you are absolutely certain that you made the right decision. What happened? What would have happened in either scenario that would absolutely convince you that you made the right choice? Which story resonates more?

For me, it's knowing I came back with a much greater understanding of the world. I had some crazy adventures and didn't die. I improved my Mandarin and made some memorable new friends. I also did something that's hard to replicate, which made me harder to compare to peers when I was applying for jobs later.

But like I mentioned to Falak last time, it could also have been a terrible decision if I was optimising for something different.

Step 2: Options and Implications

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➡️ Optionality: This involves maintaining flexibility by keeping various options open. The idea is to avoid becoming trapped in a single path and to have the ability to switch paths if necessary. Marissa should consider how this decision might open up (or close) other options for her in the future, such as career advancement, networking opportunities, or personal growth experiences.

➡️ Second-Order Thinking: This principle is about thinking beyond the immediate consequences of an action and considering the subsequent effects of that action. Marissa should reflect on the potential second and third-order consequences of her decision to either accept the scholarship or remain at home. How might her decision affect her career, personal growth, and relationships in the long term?

Once you're clear on your ideal end-state, the next question to consider is:

What are the immediate consequences of getting this decision right/wrong, and what are the potential consequences of those consequences?

Every choice we make has knock-on effects, some predictable, others not so much. By visualising the immediate and long-term consequences, Marissa can better anticipate potential outcomes and better prepare for them.

If Marissa chooses to move, what will be the immediate effects?

Adjusting to a new culture, building a new network, and facing the challenges of living independently are likely among the immediate consequences.

In the long term, she might gain global exposure, improve her skills substantially, and have a vastly different lifestyle.

Choosing to stay would mean maintaining her current relationships and lifestyle.

But what about the long-term consequences? Would she always wonder what might have been? Would she feel content or regretful? Considering these potential consequences can give Marissa a clearer picture of what lies ahead on each path.

The hidden future

I just painted a simple vision of the future on either side of Marissa's decision. But if we stopped there we'd be falling for a common trap - I'd liken it to optimism bias.

When we think of what may happen in the future, it's easy to base our assumptions on the best-case or average scenario without considering the full range of possible outcomes.

You think about moving abroad and primarily think about all the magical experiences you'll have and the great people you'll meet. You pre-emptively discount the haunting isolation you might feel while still finding your feet and potentially navigating language barriers.

Earlier, I told you that I went to work in Shanghai and had a wonderful time.

I didn't mention the part where my visa expired and I had to go to Hong Kong, faced the worst plane turbulence I've ever experienced, got robbed, and then spent a week crying in a box room with no windows, in a towering slum packed with criminals and brothels.

But that's a rare experience. It's in the 'long tail' on the bell curve of possible experiences. I've taken hundreds of flights and that set of events has only happened once. However, it's important to think about.

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When making any decision, try to consider the distance between the average potential outcome and the extreme outcome on both ends. Good vs best. Bad vs worst.

Here are two tests to consider this easily:

The dinner table test

You're in a nice restaurant. At the table next to you, you overhear someone casually recounting the story of a time they made the decision you're facing. They either had the average positive outcome or the average negative one.

What they're describing is very similar to what most people who had a positive/negative experience would say.

e.g. they went to the beach and the weather was great vs it rained.

What do you expect them to say in either case about your decision?

The pub test

You're at a loud pub (or bar, for my US friends). Over your shoulder, you hear someone telling a crazy story of a time they made the exact same decision and something extreme but reasonably imaginable happened.

They're describing something that doesn't happen to everyone, but it happens to a decent number of people.

e.g. they went to the beach and bumped into a famous actor vs narrowly escaping an encounter with a sea creature.

What do you expect them to say in either case about your decision?

How big is the distance between the rare positive/negative situation and the regular one? Should this knowledge change the way you're approaching this decision? Are there any steps you can take to avoid or attract this set of circumstances?

Hunting your alts

It's hard to explain the current plot of the wacky show Rick and Morty, but at some point, Rick ends up locked in a battle with an alternate version of himself from a parallel reality that had been introducing unplanned chaos to his timeline.

You may not be a mad scientist but every decision you face creates multiple possible futures. When you only focus on a single possible outcome, you can easily fall victim to a series of events you never planned for.

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Carefully considering the range and variance of potential outcomes allows us to hunt down alternate versions of ourselves that could be roaming wild and causing chaos in a future beyond our contemplation.

You want to consider how you'll adapt if you encounter any of these possible future versions of yourself. We'll unpack this in the next step.

Step 3: Planning and Execution

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➡️ Third Ways: This involves not settling for two options but instead looking for an alternative or compromise that may offer a better solution. Marissa shouldn't view her decision as binary - it's not just "stay" or "go". Could there be a third option that allows her to pursue her passion for arts while keeping her connections with family and friends?

➡️ Probabilistic Thinking: This is about thinking in probabilities — the chances of different outcomes happening, instead of thinking in certainties. As part of her planning and execution, Marissa needs to assess the likelihood of various outcomes. What are the odds that she will be happier, more fulfilled, or more successful if she stays or if she goes?

In this final stage, Marissa you'll need to ask herself:

What are the key signals that will show I’ve made the right/wrong decision and how quickly can I adapt to these signals?

We're not adding anything new here, but simply pulling together our previous reflections.

We started by thinking deeply about what we were optimising for. And then we considered all the immediate and second-order consequences.

Now let's plan for adaptability.

Decisions often aren't as final as they seem. Life is a dynamic, ongoing process and our decisions can be adjusted as new information comes to light. However, for that to happen, we must remain vigilant and open to receiving feedback from our choices.

Marissa will need to think about what signs or outcomes might indicate whether she's made the right choice.

If she decides to go abroad, some positive signals could be novel experiences, new friends, and growth in her artistic skills. Negative signals might be feelings of loneliness, overwhelming culture shock, or a decline in her mental health.

If she decides to stay, positive signals could include continued happiness, deeper relationships, and growth as an artist despite turning down the program. Conversely, negative signals could be creative stagnation, fractured relationships, or a general feeling of being trapped in stasis.

Being aware of these signals will help Marissa not only make her initial decision but also make course corrections as she moves forward. It's crucial for her to realise that a decision isn't a one-time action, but a continual process of making choices, learning, and adapting.

Rejecting the scholarship may be irreversible, but it doesn't mean there's no other way to achieve the same outcomes.

How big is the distance between the rare positive/negative situation and the regular one? Should this knowledge change the way you're approaching this decision? Are there any steps you can take to avoid or attract this set of circumstances?

If you accept the scholarship, how else could you optimise for the goals you had in staying?

Once you start getting signals that the decision you made is trending up or down, you should have a plan for how you can course correct or double-down.

Remember, it's important to make the best decision you can with the information you have at hand, but also to stay flexible and open to new information and opportunities as they arise.

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Life isn't a straight path but a winding road, and our ability to adapt and change direction when needed is just as important as the decisions we make.

What next?

That's it for this edition of Wayfinder.

I hope our exploration of Marissa's question 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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