Welcome to the fourth 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.

Falak's Dilemma:

In today's issue, we're breaking down another dilemma from a fellow Wayfinder, Falak.

Falak asked a question so juicy, my response accidentally turned into a detailed productivity essay featuring some of my best ideas and frameworks.

What we'll cover:

  1. The Optimisation Problem: Are you focusing on immediate gratification or long-term benefits?
  2. Preparing for a Mental Prime: Embrace the idea of preparing now for a mental prime later in life.
  3. Avoiding the Productivity Trap: Focus on long-term trends over short-term streaks.
  4. Options and Implications: Use the Pareto Principle to focus on the 20% of actions that yield 80% of results in both skill acquisition and nurturing relationships.
  5. The Importance of Your Circle: The people you spend time with will influence your habits and decisions.
  6. Planning and Execution: Identify the skills you want to develop and apply the Montage Razor mental model to find the quickest path to basic competence and plot the critical milestones to mastery.
  7. Embrace Failure: The path to mastery isn't a straight line. Expect and embrace failure as a part of the learning process.

Falak's Fork in the Road

Like many of us, Falak finds themselves caught between the comfort of routines and the ideal image of a self-actualised future.

Here's Falak's question:

I want to learn a lot of things in life lots of skills but when I'm free or with people, I don't know what to do and waste that time. And I feel guilty for the time I didn't use to learn something, and I can't improve myself just by staying the same for years.
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At its core, Falak's question is about how to manage our time effectively to acquire new skills and develop ourselves, while also navigating social interactions. Here are the three core ideas:

  1. How to make the most of your time.
  2. How to balance your desire for self-improvement with social engagement.
  3. How to choose the right skills to develop
  4. How to manage feelings of guilt when time isn't used productively.

I think at its core this is a sorting problem - you're trying to decide how to align your values with the range of possible actions you could take.

Let's dive in.

Step 1: Defining the Decision

➡️ 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.

➡️ 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.

Let's start with some First Principles Thinking. Here's a guiding question:

What is my ultimate goal in sorting these options?

What are we optimising for when we talk about 'wasting' or 'utilising' time? Is our focus on something in the present, such as immediate fulfillment, or is it aimed towards future benefits like increased optionality or skill compounding?

That's something only you can answer, but it's important to realise those two goes can often be incompatible. It's easy to get sucked into a whirlpool of actions which are immediately satisfying but provide no lasting benefit.

So let's reframe this definitively:

How can we spend our time today on things (skills, relationships, knowledge, status) with lasting or even compounding benefits?

Preparing for a knife fight

A framework that comes to mind is physician Peter Attia's 'Centenarian Decathlon'. Attia suggests that if we want to maintain our physical abilities into old age, we should consider the body's natural rate of atrophy and devise a workout plan that prepares our body in advance for what we'll need as we age.

The analogue I developed for myself years ago was preparing for my 'mental prime'.

We typically hit our mental prime in our late 40s or 50s. By age 50 you're roughly at your peak earning potential and can make decisions with the highest level of impact, using all the knowledge you've gained up until then.

To preserve the optionality of my future self, I've been gearing up for a knife fight.

I've been actively saving and investing since I was 18, visited at least 50 countries before turning 30, and read as many books as possible every year (fiction and non-fiction).

I don't want to sound like a psychotic productivity nut, but I strongly believe in gathering as many data points as possible.

For me, that has meant going to new places, having interesting conversations, trying new things, quitting misaligned jobs, and leaning hard into the 'explore' side of the explore/exploit tradeoff, so I can make better-informed decisions later on, with more lessons learned.

Decision quality depends on goal clarity

I'm absolutely not saying you should do what I've done, because you may be optimising for something different. But I think it's a useful example of how you can use first principles thinking to harness the power of compounding and optionality.

Travelling as much as I have could be a waste of both time and money if my goals were different. Scrimping and investing throughout my 20s could have been a terrible waste if my goals were different.

Quitting my dream job in corporate law after just 5 years could have been a terrible decision. Sitting indoors writing nearly every Saturday for the last 3 years could have been a waste... etc. It all depends on what you're optimising for.

The productivity trap

You also need to steer clear of the 'productivity trap' and the feelings of shame and unfulfillment that come with it.

It's not always worth 'optimising' to the nth degree.

Just because you want to be healthy and fit, that doesn't mean you have to gather a million data points on your body, count every calorie you consume, and spend your days drinking all your protein through a straw.

You don't want to fall into the trap of thinking you must be perfectly productive all the time.

One of my favourite personal maxims is 'trends > streaks' (I'll write a proper essay on this soon) meaning it's more important to be the kind of person who will do the right thing 9/10 times on average, than someone who just happens to have done the right thing on the last 9/10 occasions.

More often than not

I think basing your identity on what you do 'more often than not' is more powerful (and healthy) than trapping yourself with 'what I did yesterday'.

Streaks only work in retrospect. Every time you miss, you're back to zero. There's a lot of self-loathing in that hole.

When you focus on trends instead, every swing gives you the opportunity to improve your batting average.

Don't worry about streaks. Focus on trends.

​A streak is your behaviour. A trend is your identity.

Another interesting quirk of the 'trends > streaks' mindset appears when you make the distinction between input metrics vs output metrics. It's easier to focus on the trend of your inputs than the streak of your output.

More often than not, I write every day. I break the input streak all the time. Some days I'm busy, tired, lazy or distracted. But the general trend remains, and suddenly a streak of output emerges: there hasn't been a single day in over three years that someone, somewhere wasn't reading my work.

Step 2: Options and Implications

➡️ Asymmetry: This involves making decisions based on the asymmetry between potential gain and loss, or between the input and the output.

➡️ 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.

As much as we believe in our own self-determination, our decisions don't exist in a vacuum.

Here's the next question to ask yourself, Falak:

Are there social factors or group dynamics that may influence the priority of these options?

Our social relationships play a crucial role in shaping our behaviour.

Friends can motivate us, challenge us, offer fresh perspectives, and provide a safety net when we falter.

It's imperative you find a balance between building an enriching social life, and focusing on your developmental goals.

Here, the Pareto Principle becomes your silver bullet.

The critical few

With a multitude of priorities vying for your attention, it's virtually impossible to do everything. The Pareto Principle suggests that we concentrate on the 20% of actions that could yield 80% of the results.

This principle holds true whether you're focusing on maximising productivity or nurturing relationships.

It's about identifying the 'critical few' and concentrating on actions that have an asymmetrical impact. We'll delve deeper into this concept in Part 3 where we introduce a mental model that supercharges this idea.

Focus on the critical 20% of actions that have an asymmetric impact on progress towards your goals, and you'll have more time to enjoy socially.

Focus on the 20% of social experiences you could engage in that have an asymmetric impact on the depth of your relationships and you'll have more time to devote towards your projects.

The quality of your time matters more than the quantity of it. This applies equally to work and relationships. 2 hours of deep, meaningful time outweighs 10 empty, distracted ones.

Birds of a feather

You may have heard this phrase before: 'You're the sum of the five people you spend the most time with'.

The fastest way to learn a language is the fastest way to build a skill/habit: immersion.

Surround yourself with Spanish speakers and your Spanish will improve. Surround yourself with productive people and your productivity will increase (study).

The people you spend the most time with influence the habits you develop, the ideas you sit with, and the products you buy.

This phenomenon even extends to the friends of your friends. One study found that not only do the habits of our friends affect us, but our friends' friends' habits do too. Even the health habits of individuals three degrees removed from us can impact our own health habits.

In the words of Dan Pena, "Show me your friends, and I'll show you your future."

Set the right baseline

Your friends and your environment set your sense of 'normal'.

They create the baseline against which you measure your actions and reactions.

If you're accustomed to the quiet and slow-paced driving in the suburbs, driving at 40mph might seem fast.

But drive at that same speed on a highway and people will think you're asleep at the wheel.

Most people have no idea what their top speed is. They stop trying once they overtake a few cars.

You could easily spend your whole life in first gear.

If you want to know how fast you can go, find people who make your current speed look pedestrian.

But, find a balance.

Most people find one gear and stay in it. They work like this. They play like that.

Gear 1 people burn out on the highway. Gear 5 people can't make it up a hill.

Different seasons of life require completely different strategies. You have to intentionally transition as you move.

It's crucial to diversify your experiences, switch lanes, and explore new contexts to avoid becoming trapped in a singular, limiting perspective.

Learning to oscillate between different speeds will help you become more resilient in the long run.

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.

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

Here's your next question, Falak:

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

I haven't forgotten - a crucial part of your question is figuring out exactly which skills to work on building, and how.

Here, we'll discuss a mental model I've been experimenting with, provisionally named the 'Montage Razor'.

The Montage Razor helps in navigating decisions that involve a time-versus-competence tradeoff, such as when learning a new skill.

It revolves around two central questions.

1. How quickly can I become 'dangerously competent'?

You're not looking to be masterful yet, just sufficiently skilled to be functionally effective.

Think of this in terms of learning to play Go versus Chess. Chess is slower to learn but technically easier to master, while Go is much easier to learn but challenging to master.

When applying the Pareto principle, which options allow you to hit that crucial 20% competence the fastest?

The second question focuses on the learning journey.

2. What are the pivotal moments on the path to mastery?

This is where you envision your montage moment.

The second part of the Montage Razor involves visualizing your learning curve as a movie montage – the inspirational sequence where the protagonist rapidly evolves from amateur to expert in a few minutes for the viewer but days, weeks or months for the character.

Think Rocky Balboa's intense training before his big fight, or Elle Woods hitting the books in "Legally Blonde."

Think Mulan. Think Karate Kid. You have to find your 'wax on, wax off' moment.

Identifying and planning for 'montage moments' can ensure you're on the most efficient route to your destination.

Your montage moments are waypoints.

If you're learning to code, your montage moments could look something like this:

  • The first time you crack open a resource on coding (a book, course, or web page)
  • Your first time trying to piece together commands
  • Printing 'Hello World'
  • Your first two-hour coding session
  • Your first active prototype
  • Launching your first app

For someone learning to play the piano, their "montage moments" might include their first recital or the moment they master a challenging piece. Someone taking up running might focus on their first 1K to the first time they achieve a sub-8-minute mile.

By identifying these moments in advance, you can tailor your learning pathway towards them, ensuring you're always working towards a clear, tangible milestone.

Clear waypoints not only break up the journey but also provide motivation and a sense of achievement.

Dr. Albert Bandura has done extensive research that supports this idea. His studies demonstrate that individuals who set specific goals and monitor their progress (akin to our montage moments) are more likely to improve their skills and behaviour than those who don't.

But the magic doesn't end there.

Think back to the Mulan example - all the first moments of the "I'll make a man out of you" montage were people stumbling over themselves, dropping things and falling down.

The path to mastery isn't always a straight line. The bright dawn of a breakthrough is often preceded by a long night of failure and frustration. Stay up. Keep at it.

A study by Pham and Taylor (1999) in the Journal of Personality and Social Psychology showed that participants who envisioned both the process and the obstacles of a task performed better than those who only visualised the end goal.

Remember failure is part of the process.

What next?

That's it for this edition of Wayfinder.

I hope our exploration of Falak'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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