Lessons from Great Strategic Minds

Ryan Holiday, the author of The Obstacle is the Way and Ego is the Enemy posted an article at Thought Catalog with 29 brief lessons learned from great strategic thinkers. An excerpt is below. The full article may be read here. You could do worse than to adopt these lessons.

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 malorum—for 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.