29 Lessons From The Greatest Strategic Minds Who Ever Lived, Fought, Or Led

Orest Ukrainsky
Orest Ukrainsky

Whether you’re starting a business, writing a book, playing a sport, or negotiating a salary increase with your boss, a strategy is essential. Without one, what exactly are you doing?

Most people are not strategic. They are reactive. A critic of the inventor John DeLorean described the leadership style which sunk that company as “chasing colored balloons.” Meaning that he’d chase one thing from the next—there was no plan, no vision, no sense of how one thing fed into the next. That’s not to say he wasn’t working hard—he was, but his passion and energy (and ego) weren’t productive and ultimately, he failed catastrophically.

The same will happen to us without a strategic mindset and strategic plan in matters big and small. This strategic wisdom is not something you’re born with. It is developed, both with experience and with education. I’m not saying you have to study the battles of Napoleon to get it, but there are plenty of small and actionable lessons from warfare, the corporate jungle and the wise minds of history that will improve your strategy—both in business and in life. Below are a collection of insights from some of the greatest strategic minds who ever lived, fought or lead.

Let them guide you on whatever you do next.

1. Avoid Tactical Hell — Robert Greene, the strategist and bestselling author of 48 Laws of Power and 33 Strategies of War explains that “most of us exist in a realm that [he] call[s] tactical hell.” As he defines it, tactical hell is a place where we are perpetually reactive to other people’s demands and needs, driven by emotional instead of logical impulses, fighting battle after battle after battle. You need to escape it, and as he put it, choose “strategic heaven.” Because as Robert says, “strategy is a mental process in which your mind elevates itself above the battlefield.” Instead of being in the fray you are seeing things from a distance—with objectivity and detachment, gaining the skill of seeing the bigger picture.

2. Plan All the Way To the End — There is another lesson I learned from Robert which is best expressed by the French poet Jean de La Fontaine: “In everything, one must consider the end.” Before you jump into anything—say, writing a book—you need to fully envision the end result and have a clear objective before you throw yourself into action.

3. Think Long Term — Jeff Bezos, the Amazon founder and CEO explained the importance of long term thinking nearly two decades ago in his 1997 letter to shareholders. As he said, “We believe that a fundamental measure of our success will be the shareholder value we create over the long term.” For companies—as is the case for individuals—there are always pressures to be myopic and narrow in our focus and vision. Bezos, unlike most business leaders, refused to play that game. As he explained, Amazon will always focus on the long term, “rather than short-term profitability considerations or short-term Wall Street reactions.” He understood that the real value lies in thinking decades ahead. His maxim for business opportunities is also relevant here: “Focus on the things that don’t change.”

4. Practice the Art of Negative Visualization — This lesson in strategy comes from the great Stoics philosophers like Seneca and Marcus Aurelius. They had a term—premeditatio malorumfor visualizing failure in advance. Why would they do that? Because if you imagine failure you start seeing all the ways that have led to that result. And you can start actively working on addressing and mitigating them in advance.

5. Don’t Get Caught Off Guard — General Matthew Ridgway had the following motto behind his desk: “The only inexcusable offense in a commanding officer is to be surprised.” As a strategist, your job is to see the bigger picture and the potential perturbations in what you set out to do. Things never go according to plan—be ready and on guard for whatever comes your way.

6. Utilize the ‘Draw-Down Period’ — John Boyd was one of the most brilliant strategic minds of the 20th century. He was responsible for the F-15 and F-16 fighter jets as well as key concepts like the OODA loop (used everywhere from the military to business). Before he would jump into an idea and go full steam, he had a pre-production phase, a time he called his ‘draw-down period.’ It’s the reflective period after you’ve had the idea, after you’ve put the first round of thinking into your plan and then step back and ask: “Ok, what do I really have here?” “Do I actually have something?” “What is this really going to be?” “What am I hoping to accomplish?”

7. Take the Indirect Way — The historian and author of Strategy, B.H. Liddell Hart, condensed William Tecumseh Sherman’s strategic genius in the following maxim: Attack along the line of least expectation, and tactically along the line of least resistance. In other words, catch them by surprise, right where they are weakest.

8. Stuff Adds Up — A strategist cannot compromise on the essentials and they cannot allow distractions and tangents to slow them down. One of George Washington’s favorite sayings was the Scottish adage “Many mickles make a muckle.” Cutting a corner here and there adds up. Making this exception or that exception adds up. Waste is contagious. Related to this is a strategic concept called “mission creep.” You start out with a clear goal of what you plan to achieve—but you make this addition and that addition and let so-and-so add their pet projects too. Soon enough, it becomes something else entirely.

9. Make Haste Slowly — According to one historian, Augustus “thought nothing less becoming in a well-trained leader than haste and rashness,” which explains why festina lente (or make haste slowly) was one of his favorite sayings. As Arthur Schlesinger Jr. commented on Franklin Delano Roosevelt, “his caution was always within an assumption of constant advance.” When we are young, deliberation and caution often gets sacrificed at the expense of rushing unthinkingly into things. If you tend to sway that way, remember the lesson: festina lente.

10. Avoid the Competition — In one of the best strategy books out there, Blue Ocean Strategy, the authors explain the difference between a ‘blue ocean’ and a ‘red ocean.’ One is the virgin space without any competitors, the other is where you get eaten alive. Where would you rather go? It’s why billionaire investor Peter Thiel says that “competition is for losers.”

11. Actively Seek Criticism — Dwight D. Eisenhower, one of the best commanders of the last century has put his views on the necessity of criticism in this way: “I have no sympathy with anyone, whatever his station, who will not brook criticism. We are here to get the best possible results.” As a strategist you understand that in any endeavour there is no room for ego—you answer only to results. And your job is to plan how to achieve those. You actively submit your strategic plans to feedback and criticism—that’s how they get better.

12. Adopt Systems & Processes — According to Ron Chernow’s biography of George Washington, another one of Washington’s favorite sayings was “System in all things is the soul of business.” As you see what you are after in the distance, you need to ensure that you are taking the right steps necessary to get you there. Part of that comes from systems, routines and rituals—structures that prevent you from sliding off track. With a system in place, you can better do the most essential job of a strategist: think long term.

13. See Things As They Are — The Samurai swordsman Miyamoto Musashi has stressed the difference between perceiving and observing. The perceiving eye is weak, he wrote, the observing eye is strong. Why? Because strategy—whether in business or winning sword fights— requires objectivity and seeing things as they are. It requires us to put aside how our emotions cloud our thinking with fear or brimming overconfidence and see how the situation truly is.

14. Be Generous in Success — Cyrus the Great, the renowned Persian leader and conqueror, understood the perils of greed during times of success: “Success always calls for greater generosity — though most people, lost in the darkness of their own egos, treat it as an occasion for greater greed. Collecting boot is not an end itself, but only a means for building an empire. Riches would be of little use to us now — except as a means of winning new friends.”

15. Don’t Straddle — Author Greg McKeown in his book Essentialism says that “straddling simply means keeping your existing strategy intact while simultaneously also trying to adopt the strategy of a competitor.” The problem is many strategies are mutually exclusive. You need to know clearly what you are after. Leadership is the art of making trade-offs and difficult decisions. If you are greedy and try to have it all—you will get none of it.

16. Be Willing to Lose — The former trader and philosopher Nassim Taleb had an extremely unorthodox trading strategy to win big during serious market turmoils—he would be losing money for weeks, even years, on the bets that he has placed prior to those events but once the market crashed he would reap in substantial monetary rewards. He knew that certain collapses were inevitable but had to wait it out and lose money every single day because how those financial instruments work. When Grant was put against Lee, he did the math. The Union had more men and resources than the South. Both armies were losing men, but Lee could afford to lose them least. Some have called Grant a butcher, but he won the war because he was willing to fight to a draw in battle after battle, knowing that it was adding up towards a victory. Strategy often requires your willingness to bleed in the short term because you know the bigger payoff is further down the line. You can’t let the short term distract you.

17. Focus On The “What,” Not The “How” — The “banana king” Sam Zemurray wasn’t always one of the most powerful men in his industry. But he always had a knack for strategy. When his small upstart company was fighting the behemoth United Fruit over the rightful ownership of an important piece of contested land in South America, United Fruit approached it in the traditional way: looking for the legal owner and willing to pay them. Zemurray, on the other hand, dropped the rulebook of looking for the rightful owner of the land and just paid anyone who had claims over it—even if he had to pay multiple times for the same property! Forget how you should get to your goal and always remind yourself what you are trying to accomplish.

18. Form a Red Team — Gen. Stanley McChrystal has said that it is key once you develop a strategic plan to bring in people who are not wedded to it, the outsiders who have no interest in it. They are, as the military term goes, a red team whose job is simple: to find holes and problems in your plan. Again, as a strategist, you can’t have your ego involved—you should be grateful when people expose flaws in your approach. It is why companies need to appoint a Chief Dissent Officer—someone who can ruthlessly kill bad ideas in the making.

19. Deal With Problems Early — There is a cliche: The best time to do it was yesterday, the next best is right now. Don’t put off dealing with your problems. They will only grow (many are contagious). The slave-turned-philosopher Publius Syrus had a maxim: “Rivers are easiest to cross at their source.” A great strategist doesn’t wait. They don’t put off until tomorrow what can be solved today.

20. Use Their Own Energy Against Them — A fundamental principle of martial arts is to use the opponent’s strength and energy against them. “The best way is ever not to attempt to stem a torrent but to divert it,” is how Alexander Hamilton explained in a letter to George Washington. Think of Gandhi—he didn’t meet the British Empire with military resistance, that would have been foolish. Instead, he used passive resistance, which turns shows of strength and force against itself in the court of public opinion.

21. Learn to Prioritize — Another great lesson from Eisenhower is his decision matrix. It asks you to group your tasks into a 2×2 grid deciding whether a task is either important or not and whether it is urgent. Most of us operate in the non-important quadrants and we let ourselves be easily distracted. But as we know, the real value comes from doing the important and difficult work that requires shunning distractions and choosing hard work over the easily accomplishable bits that give us a sense of illusory accomplishment.

22. Learn to Manage & Delegate — When Eisenhower entered the White House for the first time as president and walked into the Executive Mansion, his chief usher handed him two letters marked “Confidential and Secret” that had been sent to him earlier in the day. Eisenhower’s reaction was swift: “Never bring me a sealed envelope,” he said firmly. “That’s what I have a staff for.” As his chief of staff later put it, “The president does the most important things. I do the next most important things.”

23. Study the Terrain — One of the most outstanding Union commanders from the Civil War was William Tecumseh Sherman. But before any of his achievements, he was a young officer who in his first few years in service, traversed nearly the entire United States on horseback—never taking the same path twice—and slowly learning with each posting. These lessons came surprisingly useful later on. His famous march to the sea—a strategically bold and audacious plan—was rooted in his reliance on the exact topography he had scouted and studied as a young officer. You need to study and understand the terrain you are operating in—whatever form it takes.

24. Have a Clear Schwerpunkt — The German military uses the term schwerpunkt which roughly translates to ‘focus of main effort.’ In war, this means finding the enemy’s center of gravity and focusing all your strength on hitting it. In life, this means knowing exactly what and where you are trying to break through—find the opportunity or the hole that matters most—and don’t stop until you do.

25. Beware of Specialization — If you become too myopic and focused in your scope of work you might lose contact with the bigger picture. It is why Viktor Frankl, author of Man’s Search for Meaning, has put it this way: “I would define a specialist as a man who no longer sees the forest of truth for the trees of facts.”

26. Regroup and Stay Focused — Napoleon has observed that “two armies are two bodies which meet and try to frighten each other. A moment of panic occurs, and that moment must be turned to advantage.” We’re all going to get knocked on our ass from time to time. So will our opponents. What matters is how quickly we regroup and follow up. As Marcus Aurelius put it, “When jarred, unavoidably, by circumstance, revert at once to yourself, and don’t lose the rhythm more than you can help. You’ll have a better grasp of the harmony if you keep going back to it.”

27. Learn to Wait it Out — One of the most counterintuitive strategic lessons comes from Quintus Fabius Maximus Verrucosus, the Roman whose mission was to defeat Hannibal who not only had already crossed the Alps but had racked a number of important victories on Italian soil. Fabius’s genius came from understanding that not engaging with Hannibal is where success would come from. He knew that Hannibal didn’t have the army capable of attacking a walled city like Rome and that since he was far from home, Hannibal could only last for so long. There’s an argument that the South should have used a similar strategy in the US Civil War. But this requires discipline and patience. It’s exciting and easy to attack. It’s hard to wait it out.

28. Boost The Morale — There is a well-known remark from Napoleon: “The moral is to the physical as three to one.” Or in a more modern take, how Colin Powell put it: “Perpetual optimism is a force multiplier.” Optimism and high morale multiply the effectiveness of everything else—it is why they are key levers that need to be considered in any operation.

29. Crush Your Enemy Totally — One of the most prominent leaders of the Haitian Revolution, Toussaint L’Ouverture, once replied to an opponent: “If you have a hog that eats chickens, you may put out its one eye, you may put out its other eye, but it still will eat chickens whenever it can.” Asked what it means, he replies: “It means that the wicked are incorrigible.” It is a less intimidating summary of Robert Greene’s law: “Crush Your Enemy Totally.” You realize that sometimes in war total annihilation is what is required—you can’t afford making enemies for life. But the better lesson can be this: Avoid finding yourself in situations where you put yourself in a position to create lifelong enemies—reacting emotionally in situations is easy. Self-restraint? Not so much.

Of course, this is only scratching the surface of the strategic insights that will help widen your perspective and improve your efforts. If you want more, this list of 24 Books To Hone Your Strategic Mind can help. And here are 21 lessons from great coaches on how to think and win. Thought Catalog Logo Mark

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