Welcome to the third issue of the Wayfinder series.

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.

Wayfinder is about forging paths, not following them. It’s about leveraging powerful decision-making tools and algorithms to turn daunting dilemmas into clear, confident choices.

Nathan's Dilemma:

In today's issue, we're diving into another dilemma from one of our finest, Nathan.

Nathan is an established consultant contemplating a shift towards work that is more purposeful and better aligned with his personal values. However, he's finding that such work clashes with his preferred lifestyle and the realities of raising a family in a major world city.

Here's his question:

“I’ve chosen to leave my comfortable position in consulting to seek more meaningful, purposeful work that is aligned with my personal values and lifestyle choices. The problem is, such work seems few and far between, and in tension with my preferred lifestyle and various costs (monetary and otherwise) associated with raising a family in one of the major world cities.

Should I seek my preferred lifestyle, even if it means giving up the creature comforts to which we have grown accustomed?

How might we find meaningful work? How might we find others with shared values with whom to collaborate in purposeful work — no matter where in the world they choose to reside?”
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 👆🏾

First of all, let me just say this is a wonderful set of questions Nathan. And I've struggled with many of them at various points in my career. Some of your questions have other questions/assumptions nested within them - here's how I see them breaking down:

  1. How can we find work we love?
  2. How do we balance prioritising our values against our financial, familial and social needs?
  3. How can we adjust our needs to align with our values (e.g. avoiding lifestyle creep or golden handcuffs)
  4. How can we find like minds, and friends for the road?

I think your main question is number two so we'll start there.

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.

Step 1: Defining the Decision

➡️ 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. Nathan needs to identify and evaluate the underlying factors that define his dilemma.

➡️ 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. Nathan can use heuristics to quickly identify and prioritize his values and lifestyle choices.

I think this is our guiding question:

What criteria are most important for prioritising these options?

When you go to the doctor complaining of leg pain, the first thing they'll ask is 'Show me exactly where it hurts'.

Very often we can suffer from some nebulous pain in our careers - it could be a dull throb or a vicious sting, but you can't apply the right treatment until you're crystal clear on the causal factor.

My question for you Nathan, might be 'Where does it hurt the most?'

List all your various life factors, even the ones that don't seem competitive (e.g. job security, sense of purpose, personal values, financial security, family time, lifestyle, location, friends, etc.). Then run through the list and ask which ones are worth sacrificing for all the others. Which 1-3 would cause you the most pain if left unfulfilled?

Not everything in your life has an equal place. Ringfence your non-negotiables in advance and you can safely set fire to the rest.

And a quick flag for anyone reading this - don't delude yourself with virtuous answers. Be honest about what matters most to you right now. Your values and priorities are personal, and they will evolve over time.

Step 2: Options and Implications

➡️ Asymmetry: This involves making decisions based on the asymmetry between potential gain and loss. Typically, the decisions we choose have a higher potential gain compared to the potential loss. Nathan needs to consider the potential gains and losses of his decision in order to make an informed choice.

➡️ One-Way vs Two-Way Doors: This principle suggests that some decisions are reversible (two-way doors) and others are not (one-way doors). Knowing which type of decision he's making is crucial for Nathan to understand the implications of his choice.

Your values

and priorities may change over time. So how do you prioritise them sustainably?

How might my choices now affect the future ordering of these options?

I had a great conversation with Luca Dellanna about the concept of Ergodicity, and it applies perfectly here.

The way you prioritise today could irreversibly affect your ability to prioritise tomorrow.

Here's an example. Accelerating right before the traffic lights change isn't a great idea - but you've probably done it before. Many people have. That's because the average impact of accelerating before the traffic lights change is that nothing happens, and you save about 60 seconds of your journey.

But here's the problem. The average odds aren't the same as the individual odds. 100 people could speed past the traffic lights and 99 would be fine. But one person may not survive speeding past the lights 100 times.

It's like playing a game of Russian roulette. Yes, five of the gun chambers are empty. But there's no guarantee you get to pull the trigger five times. You pull it once and the game could be over.

What does this have to do with how you prioritise your life factors?

Each year you prioritise career progression over spending time with your family could irreversibly alter your ability to spend time with them in the future. The principle of ergodicity is that any irreversible losses will absorb the possible future gains.

Some areas of your life can be re-prioritised at any point with minimum impact.

But with some things, getting them wrong early on could irreversibly affect your ability to get them right later.

Which areas of your life diminish when de-prioritised, and which are resilient to time and chance?

It's important for Nathan to consider how his decisions now will affect his future ability to order and re-order these factors. For example, if he chooses to sacrifice his earnings and lifestyle now for more fulfilling work, how might this decision impact his family's well-being or his ability to seek comfort later on?

Step 3: Planning and Execution

➡️ Divergent Thinking: This involves generating many different ideas about a topic in a short period of time. It usually occurs in a spontaneous, free-flowing manner, where many creative ideas are generated and explored. Nathan can use divergent thinking to explore all the possible ways he could balance his work, lifestyle, and family responsibilities.

➡️ Third Ways: This involves not settling for two options but instead looking for an alternative or compromise that may offer a better solution. Nathan might find that there's a third way that allows him to fulfill his personal values while also maintaining his preferred lifestyle.

Nathan must figure out how to effectively implement his decisions. Does he need to make drastic changes all at once, or can he gradually introduce changes to his lifestyle and work while carefully observing and adjusting based on the results?

What is the most efficient way to execute this sorting decision, and are there any drawbacks to taking the most efficient path?

The most efficient path for you right now could be to make some immediate and drastic prioritisation decisions - but is that the optimal outcome?

Is there a third way here? What exactly does it mean to do meaningful, purposeful work? And is that a binary choice or a gradient where you could perhaps find work with slightly more meaning, which could limit the sacrifices you make in other life areas?

Could you find the same level of fulfilment entirely outside of work hours? Or should you flip the script and find a side gig that meets your financial needs, leaving your work hours free to focus on what matters?

Approaching this from another angle, would your efforts be better spent making small iterative lifestyle changes so there's no hard shift for your family when you finally decide to make the leap?

Consider the various drawbacks of different approaches, in light of your priorities and non-negotiables.

The most efficient path isn't always the best one. It's easy to follow the default path, but what's optimal for you depends entirely on your values, priorities and circumstances.

What next?

That's it for this edition of Wayfinder.

I hope our exploration of Nathan's situation 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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