The Wisdom of Decision-Making Comes from the Accumulation of Experience and Knowledge | 5Y View
How to Develop Strategic Thinking?
Strategic acumen and the wisdom to make decisions aren't innate — they're built through accumulated experience and knowledge. For most people, decisions are knee-jerk reactions. But we can draw practical lessons from history's sharpest minds to help train our strategic thinking.
This article is about how to cultivate strategic thinking and develop wisdom in decision-making. It distills small, actionable principles from strategists, entrepreneurs, and others — hoping it sparks something for you :)
Reposted from 36Kr's Shenyi Bureau
Original: https://36kr.com/p/2442744871180421
Avoid Tactical Hell
Strategist and bestselling author of The 48 Laws of Power and The 33 Strategies of War, Robert Greene, explains: "Most of us live in what he calls tactical hell." As he defines it, tactical hell is where we're constantly reacting to others' demands and requests — and those reactions are driven by emotional impulse rather than logic. You need to escape it. As he puts it, choose "strategic heaven." Strategy, Robert says, "is a mental process by which your mind is forced to fight itself." Be objective and rational, not blindly impulsive.
Think It Through, Plan to the End
Jean de La Fontaine once said: "In all things, one must consider the end." Thinking through the full picture, planning with a clear beginning and end — this is another lesson I learned from Robert. Before committing to anything, like writing a book, you need to fully envision the final outcome, set a clear goal, and only then begin.
Think Long Term
As the old saying goes, "He who does not think about the far future will have worries near at hand." Nearly two decades ago, Amazon founder and CEO Jeff Bezos articulated the importance of long-term thinking in his 1997 letter to shareholders. He wrote: "We believe that a fundamental measure of our success will be the shareholder value we create over the long term." For companies, as for individuals, we constantly face pressure toward short-termism and narrow horizons. Unlike most business leaders, Bezos didn't fixate on immediate gains. He prioritized planning ahead and thinking long term. As he explained, Amazon would always focus on the long term rather than short-term profitability. As his famous line goes: "Success is about focusing on what won't change in ten years."
Practice the Art of Negative Visualization
This strategic lesson comes from the great Stoic philosophers like Seneca and Marcus Aurelius. They had a term: premeditatio malorum — the premeditation of evils. Negative visualization is a common Stoic training technique and daily practice: imagining your life without something vitally important to you. Why do this? Because if you imagine failure and loss, you begin to see all the ways it could happen. Then you can start working actively to address and mitigate those risks in advance.
Prepare in Advance
General Matthew Ridgway had a motto behind his desk: "The only unforgivable sin of a commander is to be unprepared." As a strategist, you must plan far ahead, anticipating potential disruptions before they arise. Things never go according to plan — so be ready, vigilant for anything that might come your way.
Use a "Reduction Period"
John Boyd, one of the 20th century's most brilliant strategic thinkers and the originator of concepts like the F-15 and F-16 fighter jets and the OODA loop (used from military to business), had a "pre-production" phase before throwing himself fully into an idea. He called this the "reduction period." It's a reflective period after you've had an idea, after your first round of thinking about a plan — step back and ask yourself: "Okay, what am I actually trying to achieve?" "What is this really?" "What do I want to accomplish?" "Can I actually do this?"
Take the Indirect Approach
Historian and author of Strategy B.H. Liddell Hart distilled William Tecumseh Sherman's strategic genius into this maxim: Attack along the line of least expectation, tactically along the line of least resistance. In other words, surprise them, hit them where they're weakest.
More Is Better
Strategists don't compromise on what matters most, and they certainly don't let distractions and trivialities slow them down. One of George Washington's favorite sayings was the Scottish proverb "Many mickles make a muckle." Cutting corners, skimping, making exceptions — these all add waste. Related to this is the strategic concept of "mission creep": start with a clear goal, know what you plan to achieve. Don't overcomplicate, don't bring others in unnecessarily, and don't change the goal midstream.
Make Haste Slowly
According to the historian Augustus, he believed that being a trained leader was nothing more than avoiding haste and recklessness. This explains why festina lente — make haste slowly — was among his favorite mottoes. As Arthur Schlesinger Jr. said of Franklin Delano Roosevelt, "His caution was always based on the assumption of constant advance." When we're young, we're often "busy for busy's sake," lacking deliberation and care. If you're always rushing around, remember this: be busy, but not chaotic.
Avoid Competition
In one of the best books on strategy, Blue Ocean Strategy, the authors explain the difference between "blue oceans" and "red oceans." One is a space with no competitors; the other is everywhere filled with brutal competition where you'll be devoured. Which do you want? This is why billionaire investor Peter Thiel says: "Competition is for losers."
Actively Seek Criticism
Dwight D. Eisenhower, one of the finest commanders of the last century, had this to say about the necessity of criticism: "I have no sympathy with any man, whatever his station, who will not tolerate criticism. We are here to get better, to improve ourselves to get the best results." As a strategist, you understand that you're accountable only for results; your job is to plan how to achieve them. You actively listen to others' feedback and criticism — this is how strategic plans get better.
Adopt Systems and Processes
According to Ron Chernow's biography of George Washington, another of Washington's favorite sayings was: "System in all things should be aimed at, for in execution it is the soul of business." When you're clear on what you're pursuing, you need to ensure you're taking the right necessary steps to achieve it. Part of this comes from systems, routines, and rituals that keep you from going off track. Build a system, and you'll be better able to do the strategist's most fundamental work: thinking long term.
See Things as They Are
The samurai Miyamoto Musashi emphasized the difference between perceiving and observing. He wrote that the perceiving eye is weak; the observing eye is strong. Why? Because winning in business or in sword combat requires seeing things objectively as they are. It demands that we avoid letting fear or overconfidence cloud our thinking, and instead view reality rationally.
Be Generous in Success
The famous Persian leader and conqueror Cyrus the Great understood the dangers of greed in success: "Success always demands a greater generosity, though most people, lost in the oblivion that success induces, mistake it for an occasion for greater greed. The accumulation of wealth was not an end in itself but only a means to empire. Now, except as a means to winning new friends, wealth is of no use to us."
Don't Straddle, Don't Be Greedy
Author Greg McKeown, in his book Essentialism, says that "straddling is simply the failure to make a trade-off between your existing strategy and a competitor's strategy." The problem is that many strategies are mutually exclusive — what matters is knowing clearly what your goal is. Leadership is the art of making trade-offs and hard decisions. If you're too greedy, trying to have it all, you'll end up with nothing.
Accept the Loss
Former trader and philosopher Nassim Taleb has an extremely unorthodox trading strategy that makes massive money during severe market turmoil — his bets before the turmoil may lose money for weeks or even years, but once the market crashes, he reaps substantial returns. He knows certain crashes are inevitable, but because of how these financial instruments work, he has to wait. On April 9, 1865, Confederate General Robert E. Lee surrendered to Union General Ulysses S. Grant, marking the South's defeat. When Grant faced Lee, he'd done the math. The Union had more troops and resources than the South. Though both armies were taking casualties, Lee could afford them least. Some called Grant a butcher, but he won the war because he was willing to fight battle after battle to a draw — all for ultimate victory. Strategy often requires accepting short-term losses for greater future returns. Don't let short-term deficits distract you.
Focus on "What," Not "How"
Sam "the Banana Man" Zemurray wasn't always one of the industry's most powerful figures, but he always grasped the strategic knack. When his young upstart company was contesting United Fruit's legal claim to a valuable disputed tract in South America, United Fruit took the conventional approach: find the legal owners and offer to pay them. Zemurray, on the other hand, didn't look for legal owners — he paid anyone with any claim to the land, even if he had to pay multiple times for the same piece of land. Forget how you're supposed to achieve your goal, and constantly remind yourself what you're trying to accomplish.
Bring in Outsiders
General Stanley McChrystal has said that once you've developed a strategic plan, the key is to bring in outsiders who have no stake in it. In military terms, they're a red team, and their job is simple: help you find holes and problems in the plan. Again, as a strategist, you remove yourself from the equation — you should be grateful when people expose flaws and problems in your approach. This is why companies need to appoint a chief dissent officer, an internal gatekeeper who can ruthlessly kill bad ideas.
Address Problems Early
There's an old saying: the best time was yesterday, the second best is now. Don't procrastinate on dealing with problems — they'll only multiply. The philosopher Publius Syrus, himself once a slave, had a maxim: "Rivers are easiest to cross at their source." Great strategists don't wait. They don't put off until tomorrow what can be solved today.
Use Your Opponent's Own Energy
A fundamental principle of martial arts is using your opponent's strength and energy against them. Alexander Hamilton explained this to George Washington in a letter: "The best way is never to try to stop the current, but to divert it." Think of Gandhi — he didn't use military resistance against the British Empire; that would have been foolish. Instead, he employed passive resistance, turning the tables in the court of public opinion, demonstrating his own strength and force.
Learn to Prioritize
Another key lesson from Eisenhower is his decision matrix. It asks you to divide tasks into a 2×2 grid based on whether they're important and whether they're urgent. Most of us spend our time on work that is neither important nor urgent, easily distracted. But as we know, real value comes from doing important, difficult work — which requires avoiding distraction and choosing the hard work over the easy tasks that give us illusory accomplishment.
Know Your Terrain
One of the most outstanding Union commanders of the Civil War was William Tecumseh Sherman. But before his achievements, he was a young officer who spent his first years of service riding across nearly the entire United States, never taking the same route twice. These experiences proved extraordinarily useful later. His famous "March to the Sea," destroying railroad stations and tracks, sweeping through plantations and farms — this was an extraordinarily bold strategic plan, and its success depended on the precise terrain he had surveyed and studied in his youth. You need to study and understand your environment, whatever form it takes.
Beware of Specialization
If you're too shortsighted, confined only to your own work, you may lose sight of the big picture. Because of this, Viktor Frankl, author of Man's Search for Meaning, said this: "I would define an expert as a person who no longer sees the forest of truth for the trees of facts."
Regroup, Stay Focused
Napoleon once said: "Two armies are two bodies which meet and try to frighten each other. We must turn fear to advantage." We all take hits from time to time, but so do our opponents. What matters is how quickly we adjust and optimize, turning defeat into victory. As Marcus Aurelius said: "When jarred unavoidably by circumstances, revert at once to yourself, and don't lose the rhythm more than you can help. You'll have a better grasp of the rhythm if you keep on going."
Learn to Wait
One of the most counterintuitive strategic lessons comes from Quintus Fabius Maximus Verrucosus, the Roman tasked with defeating Hannibal, who had not only crossed the Alps but won major victories on Italian soil. Fabius's genius lay in understanding that refusing to engage Hannibal was the path to success. He knew Hannibal lacked sufficient forces to assault a walled city like Rome, and being far from home, he couldn't sustain his campaign indefinitely. Some argue the South should have used a similar strategy in the American Civil War — but it requires discipline and patience. Attacking is exciting and easy; waiting is hard.
Boost Morale
Napoleon had a famous line: "The moral is to the physical as three is to one." Or in more modern terms, as Colin Powell put it: "Perpetual optimism is a force multiplier." Optimism and high morale multiply the effectiveness of everything else — which is why they're critical factors to consider in any endeavor.
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