How To Become A Master Strategist (Use These 16 Steps To WIN The GAME OF LIFE)

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How To Become A Master Strategist
Graphic © Background image – Pixabay (PD)

“Life for a warrior is an exercise in strategy.” — (Don Juan): from the book “A Separate Reality” by Carlos Castaneda.

“It is always your move” — Napoleon.


Most people understand what strategy means: Yet it is somewhat uncommon that you find people who have the ability to implement truly great strategy in their lives.

Strategy is the skill par excellence that makes the difference between a campaign and a haphazard series of actions. It is seen as one of the Skills Of The Masters – and if you have it, the chances are good that you will eventually be numbered among them.

Strategy is not an easy thing to master. As it is rare, it is not commonly taught well – if at all. And we are beset by challenges in life that make strategic action difficult.

Strategy is an “exotic” word. It is essentially a composite thing. That is to say, it is a single thing comprised of many aspects, many facets, many moves or actions. It’s hard to define precisely what a good strategy is, other than the statement that it is “one which works”. This is because good strategy is a union of many orchestrated components, bringing all together to create a force more powerful than the sum of the parts. Strategy often requires many abilities combined into a cohesive strength.

In a chess game, it is strategy that separates the winners from the losers. Faced with a high number of possible choices, the winners are the ones who are able read their opponent’s strategy, think further ahead, and create the most coherent masterplan.

As a strategist, everything you do should be for a reason, and every move should fit in with your overall plan.

To the outsider, the marvellous, mysterious thing about a strategy is that it is often unknown. Yet to the person who makes the strategy, the thing is planned, organized, and executed precisely. The master strategist makes moves which are either invisible or which confound and vex and keep opponents guessing. When they strike, it is with precise, controlled and devastating force. Everything is under control: They win the game.


There are numerous aspects which a strategy might contain and a great number of qualities the strategist might exemplify. Here are 16 of the most valuable:

1. The Choice To Act Strategically

The first step in strategy is of course to appreciate the immense value and power of strategy itself! Once this is grasped, strategy can be consciously implemented. Strategy is always based on conscious, decisive, proactive choices. Unconscious reactive choices are not strategic.

2. A Headquarters From Which To Plan

A successful strategist will invariably have an HQ, command center, retreat or sanctuary. Choose yours based on its ability to give you freedom from distraction, high security, access to information, a place to meet in private and the ability to execute / put plans into motion. A good headquarters will help with #3…

3. Clear Thinking

Ability to calculate, calm logic, lateral thought, objectivity, focus, ability to think “several moves ahead” and assess various possible outcomes.

4. Organization

If you are not organized, you cannot move decisively. You are bogged down in chaos, and little things that stem from your disorganization can cut giant holes in your ship. For example: Lose your car keys, and the whole evening can be ruined. However, if there is a place where your keys always live: In the same pocket while on the road, on the same hook in the hall when at home, you will seldom lose your keys: A simple yet effective strategy. In most scenarios it is prior organization and preparation that lead to fluid performance in the moment of action. It’s the things you do beforehand, that enable you to move like a tiger when the time comes!

A very wealthy person once said to me “Organization really is the key to the whole business of getting rich”.

Organization is fundamental to success. It is paramount. It really can be the difference between someone who appears to move effortlessly, gliding through life and getting pulled along like a waterskier, and someone who is in constant struggle – someone who never managed to get onto their feet yet is holding desperately on to the rope anyway and is getting dragged through the water.

Another pictorial concept that helps illustrate the idea is that of an engine. A really good engine runs smoothly, efficiently – with all the parts in harmony with each other, working together with synchronization, timing and reduced friction.

A poor engine is in chaos. All the individual parts may be good – but if they are not orchestrated and coordinated or put together in the right way – the thing will either not work, or it will make a lot of noise and smoke. It might look as though it’s trying really hard, but there’s no power when you step on the gas. It annoys people, costs too much to run, creates a load of drama and doesn’t actually achieve much despite the appearance of activity.

Does that sound familiar? It could be that you are missing some components of strategy. How is your life or your business? Does the machine run smoothly, quietly, with high energy output and a comfortable ride? Or is it all chaos, noise and smoke, struggle, start-stop. Organization takes a little “set up investment” to put together, but pays you back “with interest” over time. It’s strange that the most tedious of actions can lead to the greatest freedom, but there it is.

5. Systems

A system is a routine or workflow that may take a little “time investment” to set up, but will continue to pay you back. Not only this, but a smooth running system will provide clarity of mind and free up your time and creative inspiration for more important and valuable work. Those who resent “paying the price” of time invested in systems that free you, often end up the most bogged down. Focus in on all the areas of your life and examine your systems, routines and habits. Can they be improved?

6. A Clearly Defined Objective / Mission / Long Term Goal

Fail to plan, plan to fail! It’s advisable to have structured plans not only for your week or your year ahead, but for the entire arc of your life. Do you have a five year plan, a ten year plan, a twenty year plan and even a fifty year plan? Where would you like to be __ years from now and how will you get there? It’s time to think as far ahead as you can – because despite your immediate concerns, those days WILL come. A good plan contains not only goals and outcomes, but detailed steps illustrating in perfect detail how the goal will be achieved.

7. Flexibility

The ability to be mobile, to adapt and survive, so-called “brinksmanship”. A plan should be able to be modified as conditions change. Often, when making a strategy, you might be dealing with the unknown. If one move doesn’t work out – the master strategist is able not only to learn from this but is ready to adapt when necessary, and to chart an alternative route. You must have the mobility to be able to make changes.

8. Experience

The more experienced you are, the more likely you are to be be able to anticipate what is going to happen next and to act accordingly. Sometimes there is nothing better than having access to someone who has “done it before”.

9. Resource Management

People think that firepower wins wars, but resource management is another vital key.

It’s one thing to have insight into what’s likely to happen next, but you also need some firepower (i.e. “financial muscle”) if you are going to be able to strike effectively. Imagine being a commander on a battlefield who has decoded the enemy’s tactics and senses what is going to happen next, but has no forces ready to maneuver. Resource management leads to the ability to have forces at your disposal at the critical moment. This can often mean the rationing and distribution of limited resources for maximum effectiveness. It is quite often a mistake to think that “If only I had the resources, I could do xyz.” Remember that almost everyone operates under limited resources – and making the best of what you have is an important strategic element.

10. Making Strong, Effective Choices

Every day of life is filled with choices. How will you spend your time? Often, others may attempt to pull you off your path or distract you. Will you be strong? Strategy is all about choices – and the ability to choose well, consistently, marks a master.

11. Time Management

Time, the most precious of all assets. You have 168 hours in a week, the same number available to you as Elon Musk and Leonardo Da Vinci!

12. Intelligence (In the military sense of the word)

This, broadly, means research and the obtaining of accurate information. Acquisition of the knowledge of the condition of variables that will affect things. It can be as simple as a weather report, or as complex as a full investigation. It can also include knowing what others are doing. These things all come under the general heading of “intelligence” and can often be the deciding factor in any victory. One of the great challenges we face is that many of our choices in life are speculative. There is often no way we can be sure what is the best path until we have taken it. Research, reconnaissance, study, testing, knowledge of the state of the game, “knowing the curve”, knowing external conditions, the moves of possible opponents, and any other forces which might affect play – these improve our chances of success.

13. Risk Assessment

A key trait of the master of strategy is in knowing what is worth the attempt, and what is to be avoided. All ventures that have the possibility of gain, have associated risks – and typically the amount of risk correlates to the amount of reward.

14. Realism

Why do many plans fail? Mostly because they are unrealistic. Being realistic is difficult. It is in fact one of the most difficult things for most people to achieve. This is for various reasons. One is that life is complex! There are many unknown factors – and always surprises in store. Be as realistic as you can.

15. Orchestration

All the skills we have described above are useful assets for the strategist. But, how can we roll them all together – unify them, if you will – into the formation of a complete strategy?

The difference between a strategic campaign and a sequence of disorganized actions is orchestration. This orchestration is the part they don’t teach you. They give you tidbits about how to use this skill or do that task, but most of the time in life, it is left up to you to fit it all together.

16. Choosing Your Battles

The master strategist is the one who is able to look at the campaign as a whole, rather than as a sequence of battles. Such a one will maintain a sense of what is important, and be able to prioritize. To win one battle is often a case of strength – but strength can never be infinite, it must be managed! How many are those who have risked too much to win one battle, only to lose the overall campaign? A victory in such a battle is known as a Pyrrhic Victory – after the ancient King Pyrrhus’ famous quote “If we win one more such battle, we will be ruined.”

The true strategist chooses their battles carefully and knows how to make the most effective use of what they have.


In one sense, we are all strategists. We need to be. Let’s take a really basic example: Going to the store to buy groceries! This action, which seems to us to be utterly simple (because we have completely mastered the strategy required to do it) is actually composed of many different strategic elements – each of which combine to form the overall plan. Driving, finding the keys, already having money, knowing what to buy, knowing how many days you need provisions for, having space in the trunk of the car for the shopping. What seems to us now a simple enterprise actually requires many individual aspects, disciplines and previous successes in order for it to work.

You can see that each successful action is in fact built on top of previous successful actions.

The more strategic you are, the more successful you are at the game of life. Strategy is ultimately about being effective.

Try to gain all of the elements of strategy and include all of them in your next endeavor as part of the masterplan. See what happens.

Have the self-discipline to stick to your strategy when this is required; the flexibility to change the strategy when it no longer serves the ultimate goal (or when a better way to serve the ultimate goal is revealed); and the wisdom to know the difference.

Further reading:

Here are a few famous and highly recommended classic works on strategy for your library (Amazon Links):

Machiavelli – The Prince
Baldassare Castiglione – The Book Of The Courtier (1528)
Baltasar Gracián – How To Use Your Enemies
Miyamoto Musashi – The Book Of Five Rings
Chanakya – Arthashastra: A treatise on the art of government (c.300B.C.)
The Thirty-Six Stratagems Of Ancient China
Carlos Castaneda: The Don Juan series of books (The Teachings of Don Juan, A Separate Reality, Journey to Ixtlan, Tales of Power, The Second Ring of Power, The Eagle’s Gift, The Fire from Within, The Power of Silence, The Art Of Dreaming).
Lao Tzu – Tao Te Ching
Carl von Clausewitz – On War
Robert Greene – The 48 Laws Of Power
Sayings of Confucius
Napoleon’s Maxims Of War
The Phoenician Letters by Wilfred Davies and G. Zur (rare but ESSENTIAL, get it if you can!!)
Dale Carnegie – How To Win Friends And Influence People
The Seven Military Classics of Ancient China
Sun Tzu: The Art of War (one of the Seven Military Classics)