Helping you Make Better Decisions

Category: Thinking

Thinking is critical behaviour in decision-making. In our attempts to gain the perfect outcome, how we think matters the most.

The young lady is saying stop and ask these 3 simple questions to help you with making big decisions

3 Simple Questions to Ask Yourself When Making Big Decisions

“So, what do you want to do?”

Here I was, fourteen, acne-ridden, and faced with a big decision. At the time, I didn’t see it as a big decision, with the game of football I was missing occupying my mind. My mum and the deputy-head thought otherwise.

“I’ll stay where I am” I stammered. “Are you sure” challenged the deputy-head.

Assurances tumbled from my mouth that the lower maths set was right for me, convincing them with my words.

Two years later as I sat on the steps of the fire escape, smoking, and hiding from the office manager, I knew I had made the wrong decision. The lower maths set trapped me. It put a cap on me, rooting me in the below-average performance of my fellow students. No one cared. We didn’t study, we didn’t do homework, and we didn’t pay attention in class. As a result, I entered the set as a high average student and left with an exam qualification of a low average student.

The fire escape belonged to a building surveyor company. One, who up until my poor exam results, had a job offer for me. Now, a future of work combined with a college placement swiftly disappeared.

Why did I get my big decision wrong?

Thirty years on from that decision and I still live with regret.

‘What if’ is an easy question to dwell on when you know you’ve mucked up. Don’t get me wrong, I’m happy with the life I now have, with the wife I have, and the children we have in our lives. And I know I wouldn’t have those if I hadn’t lived the life I have.

What troubles me is my decision-making.

I was more worried about what my friends might think of me for choosing to move to the higher set. I certainly wasn’t thinking of my career, or even of my exam results. My lack of maturity, which comes when you’re fourteen and gripped by adolescent sensations, was a factor in my choice. The stigma attached to moving to the ‘top’ set wasn’t one I wanted.

I will never know what exam results I would have gotten moving to the top set. Some might see it as an irrelevant thought, but it forces me to accept my decision was the wrong one. Now, I have a learning opportunity. I have a chance, should I find myself in a similar position, to at least not repeat the decision-making steps I took.

My big decision errors

As I look back, I can see the following errors.

  • I was blind to the cap I was putting on my grade by staying in the lower set. Probability factors would have shown the grade value coming from being in the top set were vastly increased. I ignored what I knew to be true.
  • The only thought in my mind was now. There was consideration of the long game, of my career and life ahead. Consequently, I had no perspective on the upsides of moving to the top set. There was no thought about how I might feel about this decision in the future.
  • I didn’t consider the negatives of not moving. I had little thought on the risk of doing nothing. All I could see were the upsides of staying in the lower set.

I assumed my grades would be okay in the lower set. I didn’t challenge my assumptions. My emotions locked me into a position of focusing on how my friends would react, and lastly, my inbuilt biases prevented me from assessing the risks of my decision.

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3 questions for big decisions

What I needed were three questions, which when we ask them, will question our assumptions, challenge our biases, and check our emotions.

In short, they are as follows.

  1. What do I know to be true?
  2. How will I feel about this decision in six months or six years?
  3. What is the risk if I do nothing?

My approach is to give your decision-making three points of information to consider; they are facts, an alternative perspective, and a view into the window of entropy.


Every decision comes with a myriad of information surrounding it. Facts are the principles of truth on which you can build your decision. Assumptions are not facts, therefore, they are assumed truths and left unchallenged, they will ruin your decision. Asking why and how questions will give you a first principles view of the fundamental truths in your situation.

At the same time, you will also become aware of incomplete information. Seeing this for what it is will improve how you decide.


Perspective is a superpower when making big decisions. It’s like superman’s ability to fly, it changes everything, separating him from the rest of us. Perspective enables you to see a different view of your options. When you’re faced with a big decision, losing perspective is the last thing you want, but often the first thing that happens.

Perspective, whether it be from changing your period or seeing it from someone else’s eyes helps you see the decision before you differently.


We think doing nothing risks nothing. This is not a fundamental truth. Seven billion people let alone countless organisms, and the forces of nature make this world what it is. We feel their impact through chance, through serendipity, and if we do nothing, entropy. The fact is, all these elements are beyond our control, and although you’ll never irradicate them when you do something, you’re potentially distancing yourself from their influence.

The risk of doing nothing is an invitation to the forces of chance and luck, and then entropy to rule over your decision.

Concluding thoughts on making big decisions 

At the age of fourteen, the concepts of fact, perspective, and entropy weren’t in my mind. But they should have been. Making better decisions should be a life goal. Making our dreams or ambitions a reality comes down to the quality of our choices.

Even as adults, I know we don’t focus on making better decisions. Most of us don’t anyway – and that’s the point of this article. It doesn’t matter whether your fourteen or fifty-four, the big decisions are the ones we should ensure we get right.

Of course, you can’t predicate the outcome.

But, by finding fact from fiction, from shifting your view from now – to the future, and by being aware that doing nothing risks far more than first appears – you stand a chance of getting your big decision right.

The purpose of these three questions is to lead you towards those crucial concepts of fact, perspective, and entropy. Making the process of thinking easier, is a path to better decision making. So, the next time you’re faced with a big decision, ask yourself:

  1. What do I know to be true?
  2. How will I feel about this decision in six months or six years?
  3. What is the risk if I do nothing?

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As this man reaches for the sun, so he grasps the ability to reason from first principles

To Reason from First Principles, You First Need to Understand

Every year, at the same time, the same thing happened, and the company I worked for responded to it in the same way. It was a crisis, a moment of panic as work threatened to overwhelm the business, damaging client relations along with it.

No-one could see the repeating pattern and after five years – and five new department managers, my manager decided he wasn’t going to be number six. He – we – looked at the historical data, and realised the same thing happened every year.

A fixer: a firefighter would step in and manage the crisis. She was great at putting temporary systems in place to deal with the chaos, which had everyone running around like headless chickens.

The irony – the firefighter didn’t know what the cause of the problem was.

She couldn’t explain it. No one could. Everyone could explain the effects, but no-one could explain why. Earlier managers had gone to great lengths to manage the effects, but none had dealt with the why.

We didn’t want to manage the effects, we wanted to understand the problem – and so, we started asking why.

First Principles - the building blocks of life

Why we reason from first principles

Clever people reason from first principles. Reasoning from first principles is a process of critical thinking. It is a way of understanding how the world works, from any level we want. What’s more, it offers a way to solve problems and to find alternative solutions when we become stuck.

It is a means of considered thinking broken into two parts.

  • Understanding the fundamental truths which sit at the heart of a problem or question.
  • Use this understanding to find an alternative solution.

Finding a solution when you’re faced with a problem requires a new way of doing the same thing. This is how people like Elon Musk solve problems. Having grasped the fundamental principles of flying in space, or working with batteries, Elon can reason from these points to reinvent what’s gone before.

Understanding why launching rockets cost so much, enabled Elon and Space X to create reusable rockets – thus dramatically reducing flight costs.

We all want to be clever – hell – we all think we’re clever.

Seizing on the language of first principles is easy.

But here is the thing, when you try and find examples of people who successfully use first principles thinking, it’s hard. Yes, we know about Elon of course. A Google search reveals a lengthy list of articles, of which, I’m sure this will become one.

But where else are there examples?

I found several involving Nick Kokonas, the CEO of Tock, and the co-owner of Alinea, Next, The Aviary and others including:

  • Tuesday is not Saturday.
  • Food costs money
  • How to self-publish your book

I’m going to reference the first two below, but this link to Nick’s article explains the book deal he crafted for himself.

Tuesday is not Saturday.

When Grant Achatz, Nick’s partner and head chef fell ill with Cancer, it led to Nick becoming more involved in operations at the restaurant. Observant as he was, he quickly noticed empty tables on a Tuesday evening, but overbooking on a Saturday night. [1]

“Why?” he asked.

As he searched for answers, so began to learn what was happening. Demand for tables on a Friday and Saturday was massive, with tables booked ahead for weeks. But some wouldn’t turn up, leaving empty tables and lost revenue. Customers made a verbal reservation, meaning if something came up, it was easy not to go.

The customer stood to lose nothing.

Some would turn up having booked a table for six when they wanted a table for two – and only two would attend – losing the restaurant more revenue. To factor against this and the no shows, the restaurant would overbook, allowing customers to wait as they juggle tables on busy nights.

It was a poor experience for the customer – and the restaurant.

The beginning of Tock

Nick now understood the fundamental truths of selling seats in a restaurant. He understood the first principles and could now reason from them. He could see this was a supply and demand problem.

Reasoning from first principles enabled Nick to mimic other supply and demand businesses. Nick could see his restaurant was no different from a theatre selling tickets. In a theatre, the better the view, the more the seats cost. Applying the same logic in a restaurant, the busier the night, the more a table should cost. Conversely, the less demand, the cheaper the table could be.

The other issue Nick could see was prepayment. When you go to the theatre, you pay upfront for your seat, not after, or not even at all if you don’t show up.

So, Nick opted to build an online booking system which would enable customers to book online – and pay a deposit – to secure their table. Tuesdays were cheaper than Saturday’s, and so on. It became a system of dynamic pricing for restaurant reservations.

The skin in the game – the payment to secure the booking – changed everything. Empty tables became a thing of the past. As quickly as they released new dates for reservations, they would sell out, the demand beyond expectation.

It not only led Nick to increase seating occupancy at The Aviary, but it also turned the cashflow model on its head. Oh, and it also led Nick to create Tock, a software system he could licence to other restaurants to use. [2]

Food costs money

As previously noted, taking payments upfront from customers changed the cash flow model for the restaurant. Instead, of collecting payment at the end of the meal, The Aviary had a huge chunk of it paid in advance.

Nick began thinking about how they could use this to their advantage. Typically, like most restaurants, suppliers got their money several months after they had supplied their products. Credit terms were sometimes as high as 120 days – 4 months after supply. [3]

With the cash in the bank, Nick contacted a meat supplier and asked him a question.

“What the price be if paid you in advance for the next four months meat orders?”

“I’ll get back to you.” came the reply. The reply blew Nick away. The price was now $18 a kilo, down from $34 kilo, which was nearly half.

 “I’ll pay you $20, if you tell me why”, Nick wanted to know.

The answer lied in the hidden cost of selling meat. Once beef went past a certain age, price reductions occurred to help sell it or dispose of it. With the security of the payment and the amount the supplier needed to deliver, disposal costs were irrelevant.

Of course, Nick was quick to try this with other suppliers, and the restaurant’s food costs tumbled, increasing margins significantly.

Nick’s method is the same as Elon’s. First, they understand.

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First, you need to understand.

We think we understand things, but we don’t – not like Nick and Elon.

More importantly, we don’t take the right steps to understand. We miss opportunities to learn; we don’t ask questions like a child.

Assumptions dress up our knowledge, fooling ourselves and others we understand. When I think of the way Elon looks to learn, I can see how we fool ourselves. Elon takes a subject, and like a tree, he is only interested in the trunk and main branches. These reveal the fundamental truths, which he focuses on, as these are the first principles. The detail, the assumptions – all lie within the smaller branches and leaves.

A child needs to learn.

Children’s reasoning from first principles – understanding.

As any parent will know, when a child reaches the age of 3-4, they suddenly become inquisitive of the world around them. They seek understanding – not knowledge –they want the tree trunk.

The word ‘why’ is a word parents begin to fear from their pre-school children. The reason is simple. Children want the trunk; they want to understand, and they can’t accept assumptions – they must understand. And so, they ask why.

In my piece, First Principles Thinking: Why We Need to Ask Questions Like a Child, I explain how children ask questions not to learn, but to understand.

My nephew is five. Like every five-year-old, he questions everything. “Why is it bedtime?” “Because it’s dark and time for you to get some sleep.” Replies dad. “Why does it get dark?” and often this is swiftly followed by “Why do I need to sleep?” My brother-in-law tolerates the questioning to a point, but as with most parents’ his patience soon disappears. 

Like every five-year-old, my nephews’ brain is like a sponge, and he wants to fill it. But, even at such an early age, his mind wants to utterly understand what is in front of him. If the first answer he gets doesn’t make sense to him, he keeps asking why until the explanation is something he understands.

First-principles thinking is the way children learn until they reach school age, at which point memorization becomes the dominate way they learn.

Young children have an innate urge to want to understand. It drives their questioning and their thinking beyond just knowing something. They want to fully understand what they see and hear.

Richard Feynman said it best when he said, “If you can’t explain it to a six-year-old, you don’t understand it yourself.” The simple reason being a child will keep questioning. It is the first principles thinking in action.

First Principles thinking: why we need to ask questions like a child

Understanding is the quest for young children with hollow brains. They aren’t interested in the second part I highlighted earlier. All they need is to develop an understanding of the world around them.

Nick Kokonas is no different. He always asks why – he is looking for the same tree trunk of knowledge so he can understand.

Of course, this takes effort. Which is why as adults we don’t ask questions. Instead, we accept assumptions, we accept the insights from the leaves and small branches of knowledge, rather than look for the fundamental truths of something.

Reasoning from first principles

As my boss and I began to ask why, so the trunk of the knowledge tree in this situation revealed itself. One fundamental truth was the algorithm the company used to distribute work – and unsurprisingly – no-one understood it.

As we unpacked this pathway, so the historical data made sense. Surges in work, combined with a limited ability created bottlenecks the software couldn’t process. The effects were clear and highly visible to clients and customers.

The first principles of this business were now within our hands – and now – we could reason from them to overcome the problem. We understood. The trunk from the tree of knowledge was where we focused, and thus, we developed the understanding so we could reason from first principles.

We were able to make tweaks to the algorithm, but also increase our ability to handle surges in work. The crisis became a thing of the past, meaning no more firefighting.

Maybe the earlier managers weren’t aware of first principles. The firefighter wasn’t. But whether they were or weren’t, without understanding the fundamental truths of the problem, they had no hope of fixing it.

Concluding Thoughts

It sounds utterly simple, doesn’t it? To reason from first principles, you first need to understand. But understand what exactly?

The answer: The fundamental truths of what you’re trying to reason from.

We all marvel at first principles thinking. We lap up the wisdom which flows from Elon Musk and his use of this powerful way of thinking.

But then, we ignore the hard part.

We assume we understand. We don’t question our assumptions or what others are telling us. Instead, we try and solve problems without understanding the underlying principles of what stands before us.

To reason from first principles, you first must understand what those first principles are. This means – as Elon puts it – boiling things down to their fundamental truths.

The challenge we all face is we think we know those truths already. So, when we reason from them, we’re reasoning by analogy, not first principles. We end up with saying like “We’ve always done it this way.”

We accept what’s gone before as fact.

And that’s the crux of this. If you want to reason from first principles, first, you must understand.


[1] Tim Ferriss Podcast with Nick Kokonas – 18th October 2018 – Nick Kokonas — How to Apply World-Class Creativity to Business, Art, and Life (#341) – The Blog of Author Tim Ferriss

[2] Medium – Nick Kokonas –

[3] Nick Kokonas – Know What You Are Selling – Podcast with Patrick O’Shaughnessy Know What You Are Selling – Colossus (

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think differently like this man is by standing on his head

To Think Differently, First, You Need to Think Deliberately

Think differently.

I bet you tell yourself you think differently, don’t you? You’re the crazy one, the round peg in the square hole, the rule breaker. The one who can change the world.

I bet you gorge yourself on the iconic apple advert. You know, the one with Richard Branson, Muhammad Ali, Jim Henderson, and John Lennon and others. Yes, you could be a crazy one.

Okay, you’re not going to change the world. But you can change things at work and in your life. You tell yourself you see the world differently, with your energy and enthusiasm for life. Somehow, though, you can’t break free. The monotony of living every day – of doing the same things – takes over. No matter your thoughts, the ideal of thinking differently isn’t changing your life.

 You say you think differently – that you can be the crazy one – but you can’t. You want to think differently, but just end up the same as everyone else.

How hard can it be to think different?

Think Different

Steve Jobs and Apple’s second most famous marketing campaign (after the 1984 advert) derived from a response to IBM’s one-word pitch; ‘Think’. Between Chiat Day and Steve, they produced the sharp two-word mantra.

Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently — they’re not fond of rules… You can quote them, disagree with them, glorify, or vilify them, but the only thing you can’t do is ignore them because they change things… they push the human race forward, and while some may see them as the crazy ones, we see genius, because the ones who are crazy enough to think that they can change the world, are the ones who do.

Steve Jobs, 1997

The video, the imagery, the script, the mantra; they each embody a culture which captured colleagues and customers alike. Two words – that’s all it took. But it was more than words; it was a spirit, an understanding of who and why the world could be changed.

Yes, two words defined it, but the culture it showed was to challenge the status quo.

It is, and was exciting, uplifting, and inspiring. But there was a small detail missing. How do you think differently?

Think deliberately.

If you want to think differently, first, you need to think deliberately.

How often do you think deliberately? I mean to think with purpose; with vigour as you ponder with intent, thinking in patterns to make a major decision, or solve a hard problem. Do you think deliberately by using mental models to gain perspective on the challenges you face?

If I posed the question to a group, most would argue that they do think deliberately. Of course, they would. I’m sure, as you’re reading this you are telling yourself you think deliberately too.

What does it mean to think deliberately then?

Before I jump into the answer, I want you to appreciate the complex world we live in. As humans, we barely understand ourselves and how our bodies work. We can’t explain how we think, or how our emotions work. Then there is the complex environment around us. Most of which is beyond our understanding.

Over time, humanity has worked out some of the answers. There are laws; facts which when repeated we see repeatedly. We have defined these laws and, in many cases, simplified them. It makes them easier to learn, understand, and remember.

We define them as mental models, but another, easier way to think of them is as patterns.

think differently - Pinterest tile

Thinking deliberately means thinking in patterns.

The sweet spot of computer science is pattern matching. We teach computers to look for sequences in data and when they’re seen, implement a response.

Our brains are no different.

Most of the patterns in our minds are subconscious ones. Think of how and why we hydrate. We react to feelings of thirst; a dry throat and mouth represent a pattern. We then respond by drinking to quench the thirst, but more importantly, to keep our body hydrated.

Now, ask yourself what patterns you look for consciously when thinking?

The chances are you’re not.

To think differently means thinking deliberately. It is this one skill which separates most of us from the crazy ones. The round pegs in the square holes; the ones who change the world.

If Apple re-shot the iconic crazy one’s video today, Elon Musk would certainly be one of those crazy ones. He is changing the world, firstly with PayPal and now with Space X and Tesla.

His quest to make a difference to the world begins with a childlike mental model; first principles thinking. Using this mental model, he looks first to understand. He views knowledge as a semantic tree – making sure he understands the fundamental principles – the trunk and the big branches – before getting to the details.

Thus, his approach ensures he understands the first principles of anything he is working on. Elon is clearly thinking deliberately which is causing him to think differently. From this, he can think from first principles to improve whatever he is working on, whether it be electric cars or space rockets.

To Think Differently, First, You Need to Think Deliberately

The key to thinking differently is to think deliberately. It means using proven methods of critical thinking to maximise your thinking time. Use the power of patterns to look at the world around you.

Humanity has an inbuilt drive to want to improve the world around us. We want to be quicker, smoother, healthier, and more creative than the last person. Without it, we would still be living in caves, rubbing two sticks together to make fire.

To evolve is to think differently. But that urge must start with an action to think deliberately. Only then can you unlock the power of your mind to begin tackling the issues before you.

I wrote this article for two reasons. One, to clarify my thoughts on what it means to think differently. What steps can I take to transition to a crazy one? But, also to nudge you, the reader. Think about the Apple video, who would appear in it today, if it were reshot?

I can’t help but think there aren’t enough Elon Musk’s in the world right now.

We all have the capacity to think differently, but first we need to think deliberately. An attribute we can all display with effort. Thinking in patterns, learning mental models; the truths of life can enable you to think beyond your normal limitations. Then you’re thinking differently.

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thinking in patterns - just as these chairs are laid out.

How Thinking in Patterns Will Make You Think Better

Unbelievably, right now you’re thinking in patterns. Some you might be aware of, but most of them, you can’t see or even describe them.

Take the lost time of daydreaming. Only a few minutes ago my train of thought was gone from me. Vertical blinds decorate the window in my office; the type that twists to block the glare of the sun or hide the invasion of the night. I’m irked, although the blinds are all lined up, hanging against the cloud drifting behind them, their angle against the glass is wrong. The imperfection grates me, my awareness awakening as I stand and reach for the pole. A slight twist adjusts them as I correct the angle, settling the scene before me.

Just as my mind thinks in patterns, so it sees them too.

You see, I’m lost in a pattern of thought beyond comprehension. Subconsciously, my mind is processing a multitude of different patterns. From the itch in my beard to the thirst in my throat. A quick scratch and a slurp of coffee calm those thoughts – for now.

Each response is a step in the pattern of thinking and doing. Each part, the itch in my beard through to the scratch I administer is a pattern – a process of behaviour. One so subtle we’re not even aware of.

Thinking in Patterns – what does that mean?

We have little appreciation for the complex way our minds work. We wake up, often around the same time every day as our brain – energised from its night’s sleep – starts to engage its subconscious patterns.

Often, our first need is to use the toilet. If we’re not awake, the subconscious action turns into a conscious one as we rise and walk to the bathroom. Our minds are using patterns to make us move, use the loo, and get on with our day. It is a marvel lost on us; such is the complexity of what we do every day.

Our brain holds thousands of patterns and we use them all the time. Each of them helping us as we manage our safety and our survival. Mundane tasks, such as eating and drinking, or driving, or turning on the tv; all they are is patterns.

These, and many more besides are examples of thinking in patterns. A computer scientist would declare them as algorithms. Others, such as Daniel Kahneman would explain them as stemming from one part of our brain. System one thinking, a process Daniel explains in detail in his book, Thinking Fast and Slow.

Our brains have two systems of judgement and thought. The first, system one, runs within our subconscious and manages most of the choices we make. System two is the one we are conscious of, and is often underused, as system one wants to do everything for us. This means we end up applying thinking patterns in the wrong way.

Thinking deliberately – in patterns

We all think; it is the one thing we’re doing all the time. But, as I alluded to at the beginning, thinking can take us off on some strange, unproductive tangents. My brain was procrastinating at the start of this article. Daydreaming is easier, as another pattern distracted me from the task in hand.

“We rarely often create deliberate patterns of thought to help us think or make decisions.”

Matt Mullenweg

Subsequently, when we need to think critically, we default to our learned behaviours – meaning system one takes control.

Instead, we should be thinking deliberately.

We should be thinking of patterns to help us be more effective. Applying an application of thought which will help us in our moment of ponderance. Whether it is understanding something, solving a problem, or considering a choice.

As Matt Mullenweg said recently, we rarely often create deliberate patterns of thought to help us think or make decisions. Instead, we allow our subconscious patterns to take control. Sadly, they’re not good enough for the big decisions we must take. 

Matt also makes the point that once we have a pattern, we should practice it. Practice improves performance, ask any athlete – and our goal should be to make the pattern stick. The reason: when you’re under pressure the deliberate pattern becomes a default – just like your subconscious patterns are.  

But what patterns should we be thinking in?

This isn’t an exercise in re-inventing the wheel. Although talk of patterns and thinking might lead you to believe it is. We are fortunate. We have our forefathers who have lived through the same experiences. As nature intended, their experiences – and learnings – have transcended generations.

Today, we know these experiences as mental models. Mental models provide us with frameworks which the describes on their page on mental models.

What Are Mental Models?

Mental models are how we understand the world. Not only do they shape what we think and how we understand but they shape the connections and opportunities that we see. Mental models are how we simplify complexity, why we consider some things more relevant than others, and how we reason.

A mental model is simply a representation of how something works. We cannot keep all the details of the world in our brains, so we use models to simplify the complex into understandable and organizable chunks.

Of course, there are many different models – for we live in a complex and diverse world. And of course, you don’t need to remember them all, but some you do. Some are vital to enable to understand how the world works, just as some will help solve problems, all helping you to make better decisions.

Practical Thinking in Patterns

You will know some mental models already. You may not be able to name them or you might not even think of them as thinking patterns, but they very much are.

Think of leverage, the notion of using a leaver to move another object. The longer the lever, the easier the move will be.

Another model is second-order thinking. Grandmasters in Chess show how to use this thinking pattern by considering the impact of what will happen before moving a piece. By thinking ahead and considering the knock-on effects, they can choose a move which helps them and damages their opponent.

 There are many others, but for now, here are two models I’ve found to be highly effective.

I have a personal love for first principles thinking. It is a mental model found in young children, as they look to understand everything in front of them. Like a sponge in a bath, a child’s brain looks to suck up great quantities of knowledge. 

School eradicates first principles thinking. Instead, we drown children in a sea of information. Not to give them understanding, but to cram their memories full. After fifteen years of education, the mental model of first principles thinking is a forgotten power. But, once remembered and reused, it unlocks an array of learning opportunities.

Check out my article on First Principles thinking; why you need to ask questions like a child.


Despite our urge for simplicity, we live in a complex world and as a result, problems often occur which need solving. Using inversion as a mental approach is a powerful way to gain a new perspective on a problem. We often seek excellence without realising it is easier to do the opposite, which is to don’t be stupid.

Inversion shifts the focus from the normal view to one where you consider the alternative.

Concluding thoughts

Thinking is a task we commit hours to, with little thought about how to think better. This approach limits our ability to think critically, to solve problems, and to make effective decisions.

Overcoming this means understanding how our subconscious works. The much talked about system one is a foundation of established patterns, all of which work and help us navigate life. We fall when we use a pattern in a different situation. The outcome is one we don’t want.

As Matt Mullenweg explains, we rarely stop to think in patterns deliberately. When we do, we open our minds to the opportunity to think better. We can significantly improve our thinking by using mental models; thinking patterns which qualify predetermined facts.

It makes the complex simple.

We move to new perspectives, ones which enable us to think more rationally, solve complex problems and make better decisions. Thinking in patterns won’t just make you think better, it will improve your outcomes.

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Annual Review time

The 1 Lesson We Should Take from This Year’s Annual Review

Dam…it’s nearly Christmas and amongst the many traditions of the year, I’ll be doing my own annual review. Yep, for the last three years, I’ve dismissed new year’s resolutions in favour of a more reflective assessment of the year gone by. I try to objectively reflect on the past year, compare where I am to where I wanted to be, and seize upon any lessons I can take to make me a better person in the year ahead.

The annual review builds upon my goal to become a better person. So, I look to answer the following questions…

  • What were my goals?
  • Did I achieve them?
  • If not, why not?
  • What could I have done better?
  • What would have helped?
  • If I did, why?

As I’ve begun to reflect on what has happened, I realise my 2020 review is going to be unique. Not only will my annual review hold the drama of COVID-19, so will everyone else’s. We have faced a global pandemic, one which has taken the lives of many people but also turned the way we live on its head. I – and probably you – have had to cope with lockdowns, face masks, social distancing, possibly even illness and loss – all of which have disrupted my life and others.  

Our Annual Review

An annual review isn’t only about your goals and whether you achieved them or not. It should also offer us a platform for some introspection. To look and assess our decisions – our choices – and how they worked for us. Vital to this is to reflect not only on the outcome but also the process of decision-making we followed.

2020 offers some insights to some different lessons for us though. Most of us live ‘normal’ lives, rarely are we tested by something so powerful as a pandemic. We get a view of how we deal with ‘life and death’ pressure. Now, how we see, how we orientate ourselves on the information we have, and then – the decisions we make – and the action we take matters far more than it ever has.

For me, this is one of the most interesting aspects of my annual review. Never have I had the circumstance of a pandemic to gauge my decision-making process.  Through my annual review, one lesson stands out. I suspect it will be many other reviews too.

We still don’t know what we don’t know

Our ability to assess risk has never come under greater scrutiny than it has in 2020. COVID-19 has shown how masterful confirmation bias is in us all - and that’s bad. It isn’t only confirmation bias which has affected our thinking.

We don’t understand the law of large numbers, we do not see loss aversion at work, and we accept the words of laypeople over experts.

In practical terms, our phones and TV’s are full of graphs and words we think understand, but we don’t.

Exponential is one of those words we don’t seem to get. Just as we can’t grasp probabilities, so we cannot get our heads around the much-referenced R-number. We marvel at the power of compounding without fully understanding how devastating it is in the hands of a contagious disease.

We don’t know what we don’t know.

Our biases are killing us

Blind to our biases, we do not see or challenge assumptions. We all have agenda’s - some more than others - and when the narrative doesn’t fit, we seek evidence to ensure our stories fit. Politicians have worried more about their future election successes, than the lives of the people they are there to lead and protect.

When it came to lockdowns, wearing masks, and social distancing, we did what suited us. In the beginning, the threat felt real, so we followed the rules. As time went by, and the more distant the threat felt, the less we followed the rules. Even though the virus was still with us.

The sad fact is, we don’t know what we don’t know. We make biased judgements all the time - often based on confirmation of information which suits our needs. If the facts don’t fit - we ignore them.

2020 has seen a year littered with evidence of our biases working against us. The people who we thought knew what they were talking about became compromised by incentives, more interested in their self-worth than the health of humanity.

Politicians started to put wealth before health. Pressured by those more concerned for their dividend payments, politicians buckled. “We’re following the science.” Well only until it didn’t suit them.

Our annual review lessons

Of course, 2020 has also shown had adaptable we are. Somehow, I have made it through the year without doing a Zoom call. Yes, I have used other video applications, but Zoom has escaped me - others haven’t been so lucky. We’ve also learnt to work from home, turning our dining rooms into makeshift offices at the same time.

Lockdowns have rewarded the introverts in us with peace - and cast extroverts into a world of gloom and suffering. The cost of solitude for those in need of company will no doubt become clear as we move on from this pandemic.

But we can’t escape what we don’t know.

It lurks, poised to defeat our ability to be rational when making decisions. It rails our assumptions into false positives, and it is, as I see it anyway, the biggest potential lesson from this year’s annual review.

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Overthinking as a man sits and a smokes

The All-Consuming Agony of Overthinking

If there was a competition for overthinking, I’m the winner. The crescendo of noise builds as I walk through the crowd, shaking hands with fans as I get closer to the presentation stage. Other competitors look on with envy, unhappy at their wasted time spent pondering the imponderable. As I stand before the trophy, I become lost in thought.

Yep, I’m overthinking again.

As I lift the trophy above my head, soaking up the vibrations and the buzz from the audience, I notice a beeping sound. It grows louder as I turn to the crowd and they raise an even bigger cheer when I hoist the trophy up high, punching the air to show my delight. Then, the beeping takes over; the crowd, the clapping, the trophy, they’ve gone. All I have is darkness and high-pitched beep which I can hear, but also feel…

Another blow lands as I become aware of the bedroom, my wife hitting me again as I awaken to silence the alarm, beeping for what my wife feels is eternity. I’m disappointed not to see my trophy, with an etching of Rodin’s The Thinker on the front, his chin resting on his hand as he ponders and overthinks.

Overthinking – Quantity not Quality

My dream was a sarcastic prod at something I do too much of. I think – a lot.

You won’t find me dealing with a three-pipe problem, unlike Sherlock Holmes as he sits in his armchair pondering the mystery in hand.

It is quite a three-pipe problem, and I beg that you won’t speak to me for fifty minutes.

Sir Arthur Conan Doyle

It is an iconic scene, as a haze of smoke drifts through the rays of sunlight as they pierce the window. Holmes is oblivious to it all, his only thought the problem in hand. His imagination is an engine room of creative ideas, as he considers a variety of solutions to the problem in hand.

For Holmes, it’s one problem pondered, imagined, and conceptualised, as he puffs through three pipes. His focus brings the quality of thinking required to solve the mysteries we know him for.

The Paradox of Overthinking

I marvel at my imagination. I marvel at how I’m able to think; to overthink instead of working slavishly on my work. Unlike Sherlock Holmes who concentrates deeply on one topic, I don’t.

My mind is like my nephew this summer; running along the sandy beach teasing the seawater as he waits to see how close it will get to the bottom of his shorts. For hours, he is dancing with the tide, running backwards and forwards, roaring with laughter as the crest of each wave tickles his legs.

Like my nephew, I never go deep when it comes to thinking. The waves take the shape of innovative ideas, old ideas, memories, regrets and a thousand other thoughts. Each one splashing at me for my attention as I try to think. As I start to think about one thought, another one comes along. Wave after wave pounds at my legs as I overthink on everything, rather than one thing.

It is the all-consuming agony of overthinking. 

When we think about overthinking, we face a paradox; one where we convince ourselves overthinking is bad for us. We fret about daydreaming, of procrastinating and ending up with nothing.

The paradox is right. What must change is the focus.

The Three-Pipe lesson in Thinking

Sherlock’s superpower: his unique strength was his ability to focus on one problem and one problem alone.

We live in world of noise that no human has ever had to face before. A continuous stream of inputs all fights for our attention. Distracted by email alerts, message notifications, breaking news banners, the TV, interactive displays, and each other, so our thinking reflects our inputs. Our minds are a mirror. What goes in, comes out.

Multiple inputs mean a glut of outputs – that is thoughts and ideas spinning in our heads as we think. We call it overthinking.

Of course, Sherlock lived in quieter times. Free from the iPhone, the mac book, the iPad, and his iWatch, he didn’t have the inputs we do. His sources of information were books and a newspaper.

His inputs reflected his outputs.

For the time it took Sherlock to smoke three pipes, he would sit in silence. No distractions, no noise, no squeals for his attention. Nothing would distract him as he sat in his armchair and thought. His mind utterly focused on a complex case which the police were unable to solve. By the end of the third pipe, Sherlock had the case cracked.

All he did was sit and think about one thing.

The Power of Peace

“All of humanity’s problems stem from man’s inability to sit quietly in a room alone,”

Blaise Pascal

Pascal was clearly onto something with this infamous quote. The inverse of this quote also makes compelling reading.

All of humanity’s opportunities stem from our ability to sit quietly in a room alone.

Concentration, focus, attention; these are the superpowers of mankind. Often referred to as deep thinking, this concept is more alien to us now more than ever. Not because we can’t sit quietly, but because we can’t manage our minds in the same way.

When we do spend an hour free of distraction? When do we spend more than a few minutes contemplating a big decision?

The answer: we don’t.

Pinterest Banner of man overthinking as he smokes

My Overthinking Dream

I reflected on my dream about overthinking and I suspect my subconscious was mocking me. Let’s face it, nothing good comes from overthinking. I, like many others, become distracted with multiple inputs all trying to grab my attention. As I sit here, authoring this article my mobile is never far away. A flicker from the screen acts as a call for my mind, trying to pull me back in.

My urge to open my browser and check social media is equally unflinching.

Sitting for the time it would take me to smoke three pipes (approx. one hour) and only think about one thing, would be a sizable challenge. But I also know how good it could be. I know how much better my decision-making would be. I know I could solve problems which previously appeared unsolvable.

The trophy: well I consider it a prompt. A nudge to remind me where my, and humanity’s great superpower rests.

Superpower Thinking

To access this superpower means change. An easy answer might be to try and sit quietly for an hour, but drawing on the insights of Sherlock Holmes, it is clear this is entirely the wrong approach. Our minds are conduits; we feed in information and do our best to absorb it, using the lessons to inform our outputs.

It must be less in, less out.

Less in means an end to notifications; less time connected to the internet and less noise. I’m minded to the catchline of the Farnam Street blog, signal in a world full of noise. I must filter my inputs and improve my signal. Even without notifications, I’m still in an atrium of sound, listening, reading, and consuming vast swaths of information.

I recently committed to reading five books a year. The reason: to learn more, to understand more, and to build a better retention of the insights I’m learning. Previously, I read and read with little gain. I’m drawn to the image of my nephew in the sea again, my reading wasn’t deep, just flirtatious.

To become a deep thinker, I must become a deep learner. Only then can I expect not to get a trophy for overthinking.

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The Pleasure of Writing as the writer finishes and puts the pen down

The Pain and the Pleasure of Writing

Writing is both delightful and terrifying in equal measure. The journey can assault your senses, giving moments of joy as words flow quicker than water from an exposed fire hydrant. Smiles can quickly turn to frowns as ideas evaporate before your eyes.

Where can a writer find pleasure from writing?

It is unlikely to be a stinging assessment from a reader who didn’t appreciate your craft. The worst feedback is none, no words of praise or thanks. Only silence.

The Pain of Writing

The reader has little idea of the journey. No idea of the pain of forging one way with your prose, only to find a dead end. The delete button removing moments of thoughts as blocks of text become an empty white space. The white wall only serving to inspire the same emptiness of mind. Not ideal when imagination is the creator.

These moments of hollow thought are the worst. Your stomach churns with the realisation you’re alone, like an astronaut floating in space with no gravity to return you safely to the ground.

It is a feeling of true pain for the writer.

The Pleasure of Writing

We all crave pleasure; for writers, it’s the ultimate alternative to pain. Pleasure appears in many ways; it could be from the finished piece which is poised to entertain. Or the happiness from a positive comment, kind words spreading an internal warmth. The count of readers gives another shot of adrenaline to the pleasure-seeking writer.

Before the results appear, there is the internal monologue of joy when writing is at its best. When ideas spew forth and words tumble. Sentences knit themselves together like lines of a pattern, bringing the page to life.

It is the flow state of writing writers crave.

“Happiness is a way of travel. Not a destination.” Roy Goodman

It doesn’t matter whether one person reads the article or a hundred. The pleasure doesn’t come from the neatly adorned title, or the flow of words as they run down the page. No, the pleasure comes from the journey it took to get to the end. The thinking, the debate you have with yourself about whether to go this way or that way. The crafting of each sentence, of each word.

This is the way writers travel with their prose. It is their moment of happiness.

The assault on the senses when things flow is profound. The challenge for every writer is creating these conditions. It’s like trying to climb a mountain without a map, all paths lead to the top, but some offer an easier, less tiring ascent than others. Find the right path and you’ll make it to the top every time.

Writing is more complex than hill climbing.

A Journey of Discovery

You arrive at the foot of the peak blindfolded. No idea of your position or where the summit is. Your only goal; to reach the top as quickly and efficiently as you can. And you’re still sightless. It feels like an impossible mission. 

By some fluke you find a path, having spent hours circling the base looking for a way up. Not only does it have a handrail, but it’s also free of vegetation, and then you’re climbing. 

Creating the first draft, developing a structure, and formatting sentences is a similar experience. Writers have a multitude of pathways they can’t see. 

It makes it exciting; like Columbus on the Santa Maria, discovery is the end goal. For some, uncertainty is the starting point, for others, it offers a moment to freeze.

Slowly, but surely, you work it out.

Developing your ideas, creating a story, teasing the outcome, crafting the outline, all way markers to check off as your draft evolves. Yes, it’s tough, painful, and exciting — all at the same time. A rollercoaster of emotions throwing you in all directions.

It is the journey we love. 

It’s why we love the pain and the pleasure of writing.

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A young man ponders; clearing his mind as he works at his desk

Clearing my Mind in the Information Age

Every Sunday morning, I get a notification from Apple about my screen time for the last seven days. Last week, I spent fourteen hours looking at social media; this fries my brain.

Context is everything of course; I’m in bed for eight hours (asleep for seven) and yet, twelve per cent of my time awake is gone, scrolling through an endless stream of tweets and posts. I spend another hour a day reading articles, webpages, and the news. This excludes the thirty minutes a day I spend with my Kindle, reading to try and learn even more.

Putting all that together is quite frankly frightening. I am, like so many others in the world, the epitome of the first part of the quote from E.O.Wilson. 

“We are drowning in information while starving for wisdom. The world henceforth will be run by synthesizers, people able to put together the right information at the right time, think critically about it, and make important choices wisely.”


I am drowning in information, and at the same time, starved of wisdom.

I’m my quest to improve my decision-making I’ve come to see that my mind is cluttered. Cluttered from the endless streams of noise, all because I become consumed by the endless scrolling on social media. I don’t save the information I’m exposed to; I read it, but I don’t record it. I just hope I might remember it.

I need a Second Brain 

Note-taking is something most people do. There is an unlimited choice of apps and tools to help capture your notes. I’m also a prolific bookmarker, saving endless articles on Pocket. I read, rarely pausing to make notes.

When I do make notes, I’ve become stuck, jumping from tool to tool. I used Evernote in its early days and then moved onto OneNote. From OneNote, I moved to Notion. I wanted more flexibility than I was getting from OneNote, but with Notion, I still felt restricted. I love the way the databases interlink and come together, but it was still too hierarchical and rigid for me.

Through Twitter, I’ve found Roam Research, and it has changed everything for me.

Changing how I Process Information

Nat Eliason introduced me to the power of roam and the concepts behind his use of it, written by Tiago Forte. A personal knowledge system is a phrase I’ve only just discovered.

I’ve understood the principles but never had heard it framed in such a way, let alone consider a tool that might do the job for me. Every day is a learning day, and I’m certainly learning – and doing it quickly. The hierarchal frameworks of PARA (Projects, Areas, Resources, Archives) are calling me. Awareness of projects and the cascading effects of goals and tasks are well known to me. But using them to manage information is new to me – and exciting.

Now, I’m wondering how I should manage the information I interact with. As time continues to decline on the time I have left on this planet, I’m also contemplating the criteria I use for reading – both books and articles.

Brandon Zhang shared with me his thoughts in Reading with Intention, which offers ideas around the process of choosing what to read.  Not only am I looking to apply this to my book reading efforts, but also to the articles I consume.

There is another consideration for me. What principles should form the foundations of my note taking?

  • Should I copy the article?
  • Make highlights?
  • Add my own context to draw out the relevance?

There are lots of thoughts to me consider here. Thankfully, I’m guided by those who already know better. The insights from Brandon Zhang, Tiago Forte and Nat Eliason have proved helpful. Progressive Summarization is one example of a new way for me to capture information and keep it within my second brain.

Decision Tree’s

Like most people, temporary feelings influence my decisions and I feel the need to apply a more disciplined approach. One that removes impulse and emotion from the process.

Decision Tree’s offer that capability.

It means I can map out a ‘if this, then that’ method which will help safeguard against some of the inferior decisions I’ve made in the past.

For some, this will appear cold and clinical. But that is how it must be. Simple decisions like what to keep for my second brain, and how to keep it, start to open the way for me to begin clearing my mind. I find it quite frightening how I have allowed the consumption of information to dominate my time – and my mind.

As Nassim Taleb says: 

Nassim Taleb Quote

Clearing my Mind

Decisions are battles of thought we must overcome. Some of us hesitate; dithering on the outcome of what might or might not happen. What would help is clearing my mind. A brain free of information and keeping only wisdom, which would certainly help.

This is the point that Nassim Taleb is making. Our minds are so cluttered, so clouded with information that the opinions we form become blighted. Stepping free of the blinkers shifts the mind to a different space. A space where it can think deeply. Where it can draw on the insights and knowledge held in our second brains.

It is this space I want to get too. To be able to make decisions free of emotion. To control the urges of my system one thinking and use the more logical – and thoughtful – system two. The two decision systems as described by Daniel Kahneman in his book, Thinking Fast, and Slow.

With this process in place, one day I might get to that utopia of a clear mind.

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