Ten Years of Tips for the Striving (or Struggling) Strategist

I became a US Army Strategist about ten years ago, and first pulled on the uniform a little over twenty years ago. Reflecting on this time, I’ve come to two conclusions. First, I really have made a lot of mistakes, thankfully all of which were recoverable. Second, through that process of learning by sticking fingers in light sockets, I’ve gained a bit of knowledge, developed some preferences, that, when pulled together, looks like something that approaches a consistent way-of-life or operating system.

The list below is not in any particular order and meant as a set of small pieces of advice for military strategists in particular as well as those of the military profession in general. Whether you’re a striver or a struggler, I’m certain at least some of what follows will be helpful. Feel free to pluck what’s useful and discard what’s not.

  1. Know yourself first. Write your own mission statement, core competency, maybe even an oath for what you do. Know your contribution. You should be able to quickly articulate this to anyone at any time.
  2. Wear earplugs in the office to focus. They’re cheaper and work better than noise-cancelling headphones. Get colorful ones that scream “I’m busy.”
  3. You exist to increase insights and decrease errors wherever you serve.
  4. Know the VTC dial-ups yourself. Also know the techs that run the VTC in your organization. Bring them coffee (or at least shake their hands and smile kindly).
  5. Invest in tools, not toys.
  6. Ditch the smartphone. Buy a good pen and some paper instead.
  7. Embrace humility. The title “Strategist” does not mean “superior.” You will rely enormously on subject matter experts your entire career as you skip around to different and varied strategic problems.
  8. You can never learn how to “win wars.” You can only hope to learn to win the war you’re in.
  9. Write every day, whether directed to or not. Communication skills will make you or break you. Strategists are essentially writers in cammo.
  10. Have daily goals and objectives. Winston Churchill had “ACTION THIS DAY” stickers affixed to documents and projects to be completed in 24 hours. Adopt this practice.
  11. Get to know people. (Admittedly, this isn’t always my strong suit.)
  12. Be loyal, but never a lackey. Don’t continually search for “better” jobs.
  13. Don’t be a “bag handler” (AKA “aide” or “exec”). Sure, somebody’s got to do it, but that isn’t you. Even in the best circumstances, being an aide/exec is the very definition of a tactical job (which precludes strategic thought).
  14. Read what interests you, not what you think others expect of you. You can learn something from everything.
  15. Give Clausewitz a real chance, not the Cliff’s Notes version offered in professional military education settings with tight timelines.
  16. Be so entirely focused on self-improvement that it leaves you no time to criticize others personally. (Ideas are different. Ideas are fair game.)
  17. “Rowing well” will never be good enough.
  18. Constantly seek new opportunities to learn about modern war.
  19. Choose inputs wisely. We’re all the sum total of our chosen inputs.
  20. Be a storyteller. As Daniel Kahneman once wrote, “No one ever made a decision because of a number. They need a story.” So will you. Strategy-making is storytelling.
  21. Cultivate a life outside the military. It’ll make you a better strategist/officer, and a better ex-strategist/officer.
  22. Believe force can be used well and for good.
  23. No, the military’s purpose is not to kill people and break things (even if killing and breaking, as tactical tasks, may be a consistent core competency).
  24. Fiction and film can teach strategy (alongside history and theory).
  25. Maintain physical fitness. There can be no fully sound mind without a fully sound body.
  26. Take caffeine seriously; wield it wisely. (Ditto alcohol.) 
  27. Respect elders and superiors by continually coming up with ideas that challenge status quo and tradition.
  28. Believe in miracles, because as David Ben Gurion once pointed out, “Anyone who doesn’t believe in miracles is not a realist.”
  29. Never demonize enemies. As personally disgusting as you may find their behavior, your role demands you attempt to understand your adversary’s mind to anticipate their next move.
  30. Work smart. Know the natural rhythms of the day and ride those waves for productive flow.
  31. Take siestas. (And be so good that nobody bothers you if you do.)
  32. Learn to love the differences in the other military services and government departments. They may seem strange sometimes, but they’ll always make you better and stronger when woven together well. 
  33. Be polite. Be respectful. Talk profession and policy, never personal politics.
  34. Never care if your name goes on a document you’ve written. Everyone that matters will know anyways.
  35. Know in your bones that you serve every single American.
  36. Care about your work. Never seek perfection, but always find your momentary best.
  37. Bring food to work. It’ll save you $100,000 over the course of your working life.
  38. Education matters, but doesn’t make you better. Only more educated.
  39. Seek practice in strategy through the opportunities that arise in daily life. Devise personal strategies with roughly the same rigor you would plan for war.
  40. Know your flaws and biases. You have many.
  41. Strategy is always relative.
  42. Listen to one podcast every day.
  43. Speak up for the military profession as if no one else will. Because they won’t.
  44. Experience the environments you may be forced to fight in someday.
  45. See combat. Expose yourself to war’s consequences. Know them well.
  46. Maintenance matters: vehicle, technological, psychological, physical, personal…
  47. The pen is mightier than the gun. Really.
  48. Love it or hate it, make your peace with PowerPoint. (And for the record, I hate it.)
  49. Never a cynic, always a skeptic. Conduct premortems. Be the “tenth man.”
  50. Make your will and have a post-military work plan ready to execute. Only then will you have the backbone to take the risks required for success as a strategist and military officer.