In great movies, the protagonist – or even the villain – often executes detailed and thoughtful plans. Movies often have a twist where an unexpected setback turns out to be part of the plan, revealing a mind-blowing strategy that explains lots of previously unconnected points. Think of the bank heist in Ocean’s 11, or the killer’s extraordinary coup at the end of Se7en.

Now compare all that to an ordinary person’s real life.

Most people barely have a to-do list, let alone a well thought-out long-term strategy. At most, people just have a bunch of shit they hope to get done by the end of the day, or an itinerary for their trip that’s almost certainly not going to work out well.

People buy a house and just kinda hope they’ll end up with retirement money. People start using a dating app with some vague idea that they’ll end up in a good relationship. People take their carefully planned out workout regime to the gym, only to have it all fall apart when they see that the big dude is using the machine they need.

Very few people go out about their day with little more than a vague hope for success, a stressful sense of being “behind”, and a thoughtlessly written to-do list that always seems to get ruined by “bad luck” (i.e. real life variables).

People are bad statistical thinkers. Daniel Kahnemann demonstrated that with his Nobel prize-winning work in Thinking Fast and Slow. But it’s not that we’re incapable of calculating odds and making appropriate plans and preparing for eventualities. It’s just that for some reason we never seem to put this skill to use.

Imagine if you actually planned shit! Most people just feel their way through life, running on autopilot and using planning systems that they were conditioned to use and have never really challenged. Imagine if you actually took a moment to calculate, and have a detailed and thoughtful strategy for what you’re trying to achieve.

I’m going to share 9 thinking techniques that will seriously upgrade your decision-making capability. Rather than playing “hope chess” (making moves that you hope won’t be noticed by your opponent), you can learn to be strategic and prepared for most likely circumstances, as well as being able to quickly pivot when things go “wrong” so that you’re never badly affected by misfortune.

Work backwards from destination

I think the biggest problem is the goal: most people aren’t really aware of what they’re trying to achieve, so they are busy but aimless. They just have a vague sense of urgency and obligation and a need to finish things, without stopping to clearly ask, “What’s the point of what I’m doing?!”

Know your desired destination before you start moving. What is the most important thing for you to achieve at work today? And how does this serve your greater career plans? How does this reconcile with the other goals in the other areas of your life? What’s the best way to balance it all in a realistic fashion? Who do you want to be?

Planning is really just working backwards from the destination. The distance between you and the achievement of your goal is dotted with a series of cause-and-effect milestones. 

If the destination is to become a successful plumber, the step before that is to start your own plumbing business… and the step before that is work for someone else… and the step before that is do your apprenticeship… and the step before that (the one in front of you now) is complete a basic plumbing qualification.

You can think this way about everything. You can work backwards from what a successful grocery-shopping experience would look like, to make sure you can do all the steps in the right order without being dumbfounded by unexpected setbacks, like the supermarket being closed on Sundays (e.g. step #2: quickly check online to see which shops are currently open).

If/then

Rather than hoping your one ideal way of things happening will be what eventuates, take a moment to think about other likely ways this could play out. What if the weather suddenly turns against you? What if there’s an accident and traffic? What if your friend is unexpectedly running late?

The “What if?” question is often associated with worry. That’s only because people don’t bother to actually answer the question! Rather than just ruminating about the potentially disastrous consequences, think about how you will respond.

If the weather turns bad, you can take the party inside. If there’s an accident, you can listen to a podcast while waiting for traffic to thin out. If your friend is late, you can call your mother and catch up to use that time wisely.

Even if you can’t think of every possible if, just putting yourself in the mindset of preparing for different possibilities makes you less rigid and hopeful, and more thoughtful and ready to adjust.

Always be prepared

The boy scouts were onto something. 

I have a satchel I take everywhere. It has my keys, wallet, phone and sunglasses. It also has a micro-bag in case I need to do last-minute shopping. It has a mini-sunscreen bottle. It has wet wipes. It has a Swiss Army pocket knife. That bag can solve almost any normal unexpected problem I might encounter when I’m out and about. It has often saved the day!

Both my phone and my smartwatch are capable of making debit card payments. My phone doubles as portable wifi with the hotspot function. I have pictures of my ID, and each member of my family’s passports on a secure folder in my phone. I have a secret protected file with all my passwords and logins, which I can access from any smart device.

How long could you survive if your house lost power for a sustained period of time? How would you handle your partner suddenly requiring long-term hospital treatment? Do you have an emergency account with 3 month’s worth of salary saved and ready to access? How’s your first aid kit and home-pharmacy looking?

Take a moment before you leave the house and just remember some of the repeated setbacks you’ve faced throughout your life. Are you ready for them to happen today? Do you have everything you need to deal with most normal eventualities, like weather changes and unreliable people?

Quick-pivot optimism

Things will go wrong. Plans always get punched in the face by life. There are just too many variables to be prepared for, so you need the ability to quickly adapt to the unexpected, without needing to know what it’s going to be.

Oddly enough, I’ve discovered that this is mostly about an optimistic point of view. Everything that happens contains possible opportunities and escape routes and new ways of achieving the goal. Nothing is really a total disaster unless you see it that way.

If you prime yourself to see all obstacles as a possibility for growth, or new adventures, or additional creative ideas, then that’s how you’ll respond when they arise. Arriving too early becomes an opportunity to get in some extra steps with a walk around the block. Being stood up on a date becomes an exercise in courage to eat alone at a restaurant. Getting fired becomes the catalyst for a new career path.

Skipping chapters

Few things bother me more than watching someone pointlessly delay the inevitable action they must take. All too often, I can see that someone only has one reasonable option in front of them, and yet they waste hours and sometimes even days either complaining that it’s not fair, or searching for better opportunities that clearly just don’t exist.

“Skipping chapters” is the term I use for getting past pointless information and cutting straight to the conclusion of the story. Sure, sometimes we need to look for better options, but often there’s a quick choice to be made to just move on, especially when it’s compulsory or this isn’t an area of life worth spending a lot of time deliberating over.

If you get a surprise tax bill, just pay it. You’re going to pay it eventually anyway. Delaying only increases your stress and the possibility of getting in trouble. 

If your gym is closed during normal opening hours, don’t just stand there staring at the door. Don’t phone them up to ask why. Just get back in your car and drive home, giving yourself time to do some push ups in the lounge.

If your computer breaks down, just take it to the guy who fixes computers. Raging at the customer support person just adds time to the duration of how long you don’t have a working computer.

I once missed a flight in Kuala Lumpur. After raging for a while, I checked online and saw they only do one flight per day to my destination. It was clear I’d need to purchase a ticket for that flight. It was clear I had to wait 24 hours. There was no need to talk to helpdesk staff, or complain to my partner, or worry about the extra money. I had to buy that ticket regardless, so why bother reading the other chapters of the story if I know how it ends?

Grandmaster contingencies

Having one plan is great. Having a dozen plans is even better. Contingency planning is where you have separate parallel plans for all the most likely variations of what could happen. Like a chess grandmaster, you don’t just think of one pathway, you create different pathways for each possible response you might get. This is already discussed in the if/then paragraph above.

When we talk about contingencies, we don’t just mean back-up plans, but simultaneous plans. Trying to achieve your goals in 3 different ways at the same time rather than trial and error one at a time.

Let’s say I’m trying to sell something. I can simultaneously run ads, promote with social media posting, ask my friends for referrals, and cold-call people directly. This way, either one tactic will emerge as a clear winner, or they’ll all contribute in some way to create a sum greater than their parts.

Let’s say I want to make sure someone gets an important message. I can email them, and text them, and leave them a voice message on their phone, and ask one of their friends to check if they got it. Why do it just one way when with almost the same effort I can eliminate all doubt?

When my wife buys clothes online, she chooses stores with a free return policy, then orders a range of styles and sizes. She chooses the one she likes, and sends the rest back. It’s a bit more work than ordering one at a time, but in the long-run it’s much less effort than hoping to get the right fit or travelling to the store.

Every method and tactic has flaws and weaknesses. But when you combine multiple approaches you can seal up the gaps with complementary differences. Make it certain rather than leaving it to chance.

Carefully pick options rather than rush to the finish line

Taking a moment to consider various pathways available before you start moving can make a huge difference. Like a climber choosing a “line” up a mountain, which pathway offers the least resistance? Don’t just grab the nearest rock, take a moment to see the whole path to the top.

Oftentimes, the rush to get it over with leads people to choose an option that appears to be easier but hurts more and takes longer in practice. Like someone buying a car with financing rather than saving up. Or someone buying a cheap car that’s going to cost more in total repair and maintenance rather than waiting to afford a more reliable model.

Rushing is rarely the smart move. Very few things in life require an urgent response, yet we often feel like everything is urgent. This is an illusion. We are made to feel this way by other people and cultural conditioning and advertising. Truth is, you can carefully do your due diligence and forecast into the future before making your move on most things.

Let go of the urge to grab the quick fix, and instead map out the consequences of that pathway. Look for the pathway that might appear slower at first but is quicker overall. It might take longer and require more courage to meet someone in real life, but dating apps are notoriously unsuccessful in helping people find healthy relationships. One year of meeting people out in the real world is probably more productive than 10,000 swipes on an app.

Quick decisions should only happen in your mastery element. If you’re a car trader for 10 years, you can quickly decide on a price to offer for buying a car. But if you’ve only ever bought two cars in your life, your “instincts” won’t be accurate. Trusting your gut/instincts should only happen in areas where you are an expert. In all other areas, ignore so-called instincts and try to think strategically instead.

Slow down to speed up

Imagine if time moved slower for you, perception-wise, the way it does for a fly. That’s why they’re hard to catch with our hands – to them, we move in slow-motion. Their perception of time is so slow that they can easily dodge raindrops.

The beautiful thing is that we can slow down our perception. Anyone who’s ever used an exercise machine knows how it distorts time – 90 seconds feels like 5 minutes! When we’re focused, not distracted, and deliberately taking our time to look around and assess our situation, we actually filter our perception.

In combat sports they often talk about “fight IQ”, a near-mystical ability some men have to just know where the next punch is coming from, when the opponent will drop his guard, and what weaknesses he can exploit. If you watch guys with high fight IQ, you’ll notice how they take their time to carefully observe and test their opponent. They don’t rush in with wild punches or show off with flashy moves. They watch, wait, pattern the opponent, and then tear him apart in a way he can’t comprehend or defend against.

Imagine you have all the time in the world to make your decisions. I don’t mean you should overthink them, but just consciously try to slow yourself down. Observe, allow your brain to gather data, and then notice what you notice.

When I’m coaching someone, I don’t rush to solutions. I just let them talk and start taking notes, recognising points of interest and key words that catch my attention. The longer they talk, the more clearly themes and patterns start to emerge. When I respond, they’re often amazed. They feel like I can read their mind, but they’ve actually told me everything themselves. I just took the time to listen.

Sustainability

The best problems to focus on solving are those with the most leverage. Most people are constantly “putting out fires” – staying busy solving small meaningless problems that have no leverage, like treating symptoms rather than curing the disease. Arguing with a crap boss is less effective than finding a better place to work. Spending hours cleaning your house costs more than hiring a cleaner.

Try to keep the long-term picture in mind. Rather than solving individual crises as they occur, get in front of it all by developing helpful and sustainable habits that prevent and reduce problems while developing towards your goals.

Rather than trying to quickly lose 10 pounds for beach season, find a style of exercise you can do every day for the rest of your life, and learn how to cook the Mediterranean diet until it’s second-nature and easy to do. You’ll lose weight slower at first, but be constantly getting healthier over time without massive relapses and resets.

Slowly increase and diversify your investments rather than gambling with high-risk trades for a quick return. Making money the smart way is boring. Learn to be bored, because most successful long-term strategies are repetitive, and the gains are slow and incremental.

Try it with small things

There’s a lot in this post. You couldn’t hope to apply it all at once. Rather, think about slowly integrating this type of thinking into your everyday life until it becomes an effortless default way of thinking.

You might spend one week simply focusing on slowing down. You might spend the next week only doing 2 or 3 important things in the morning rather than the whole to do list. You might spend the week after that trying to predict and prepare for variables with contingencies.

Apply this thinking to mundane tasks like washing the dishes, grocery shopping, and mowing the lawn. This will allow you to practice at a low-stakes level.

Then try it with bigger things

Once you’ve developed some experience and can “see” how this all works in real life, you can start integrating it into big-ticket decisions.

You could plan out a conversation with your boss around asking for a raise, imagining objections and coming up with responses for each.

You could write a business plan that starts with where you want to be in 10 years and works backwards in a series of milestones, and then include contingencies for potential setbacks. I recently got kicked off Facebook, but thankfully I’ve been re-posting all my material on multiple platforms for years, and I save and back-up all my information in separate folders just in case something like this happens.

And reflect. Look back over difficult days and those times in your life where things spiralled out of control, but be sceptical about your decision-making at the time. Was it really “bad luck”? Or did you fail to think strategically; rushing and panicking and trusting your “instincts” instead of calmly putting a plan together.

I think you’ll find most of the time your biggest crises would have been averted with some slightly more careful and intelligent decision-making. I know that’s true for me!

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