Life as a Grand Strategy

March 24, 2009

I used to carry a lot of fear. What if I lose this? Or, ‘I have to monitor that in case something bad happens.’ Worse, I would be unsure of how to act in certain situations, whether to advance or maintain or do whatever else somebody asked me to do right away. I was petrified of anything that could be considered a step backwards. I think I once wrote that I promised myself I’d never work on a wage-basis ever again.

Now I’m starting to understand that this was foolish. It’s an attitude prevalent in what Robert calls “tactical hell.” After I formulated, at least ephemerally, what I was after, the feelings melted away. In fact, in laying out and looking at the chessboard I saw instances where there was not only nothing shameful in taking a job like that but doing so would be the best possible move.

This is what is known as Grand Strategy. It means knowing in a very deep way what it is you’re trying to accomplish. It’s important because once you understand where you intend to finish in that distant, far off sense, you can take in, in perspective, how insignificant many individual decisions are. Left or right, what does it matter? Take this, leave that – knowing how you can turn either to a productive, contributive step means you’re less dependent on circumstance and less anxiety for you to carry.

Let’s say you wanted to become something like Tyler Cowen. Tactical hell would be thinking of ways to acquire what he possesses – getting a huge audience, bothering an editor at the New York Times Book Review, setting up a blog and trying to get linked by other important writers. It would be hell because you’d probably fail at each of these things. Grand strategy would be to think of what and why you want to be like Tyler. Perhaps, it’s that he’s paid to be curious or that you think you’d find fulfillment in the intellectually productive life he appears to lead. The separation of the person and the position leads to an understanding that latter flows from the former. The grand strategy is clear.

Whether you choose this class or that one, work or travel, books or people, these are small, tactical decisions. You know that the standing order is to turn each into an interesting, engaging process; everything is a challenge to examine and a chance for insight.

Think about Fight Club. The whole, it’s only after you’ve lost everything that you’re free to do anything. Well what does he really mean? I think what he’s saying has little to do with possessions. He means that after you’ve cleared out dependency and distractions, you acquire, in a way, a kind of grand strategy: a sense of self. When that becomes your only guiding principle, what is happening on the outside is irrelevant. You’re free because grand strategy gives way to formlessness. And formlessness to peace and calm and self-assurance.

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

16 responses to Life as a Grand Strategy

  1. Ryan, I think the underlying message is not to sweat the small stuff. The wind will blow you off course a little here and there, but if you keep glancing up at the horizon from time to time while taking those steps you will get there.

  2. It’s interesting that you use grand strategy as your chosen term for this sort of conceptual discussion. In my line of study we often debate the nature of states’ grand strategy. There’s a rift in the political science discipline as to whether grand strategy is the simple maximization of rational self-interest, or if indeed a state can have a psychological overlay to its foreign policy.

    I’m inclined to the latter. I’ve studied Japan for quite some time. Their 19th century Meiji Restoration shows how a unitary concept – a desire to catch up and surpass the West in all modern endeavors – drove an at times contradictory foreign policy. It works well as an explandum for behavior that defies rational choice.

    One of my favorite posts thus far. Well done.

    P.S.: BTW, cool first name 🙂

  3. What do you do if you don’t know what you want to accomplish?

    • I suspect you either a) do know what you want to accomplish, yet are too lazy/nervous about going after it OR b) you really don’t know. In which case I recommend going out and experiencing new things. Have interesting conversations with interesting people. Who do you admire? Take this advice of a grand strategy to heart.

      PS. I just started reading your blog Ryan, and bought all 3 books immediately. Good fucking shit man.

  4. I made the break from being a paid employee back in 2001, and never looked back. For a long time I believed that I was unemployable, in that I could never go back to having a boss.

    Interestingly people tend to overvalue the things they have, be that a job, material things, or a significant other. These are the exact things they take for granted until they are in danger of losing them. Rocky said it best, “It is not how hard you hit, it is how hard you can get hit.”

    ps ever read the Halo Effect? That is a real eye opener.

  5. Am going through a similar phase you just described.Where everything small seems to matter,is this in coherence with my values? where i want to be? what I want? Then am like fuck it, ill figure it out later. Which then brings about a contradiction of belief, attitude and results, which isn’t healthy, it brings about confusion. This post helps keeps stuff in perspective. Good stuff.

  6. It’s really interesting which of your posts get solid comments and which don’t.

    Anyway, the epiphany for me was making everything effortless. Just doing, or being. Task lists/goals became reminders of who I was rather than big declarative statements.

    Good stuff, man.

  7. Still one of the most important articles you’ve ever written. This one goes so deep, especially for the current generations of youth, in it’s relevancy and necessary application. With everything being so results-driven, lot of people are learning the hard way the cost of not having deliberate rituals and processes built into your life and decision-making frameworks. Grand Strategy and process go hand in hand. They drive each other in life, which will ultimately decide where we end up.

  8. This brings to mind the idea of commander’s intent. If you know what the objective is to find a way to achieve it. I read about in a Malcolm Gladwell book and another by the Heath Brothers. I think the concept is similar.

Trackbacks and Pingbacks:

  1. Advice to a Young Man Hoping to Go Somewhere (Or Get Something From Someone Successful) « - September 7, 2011

    […] an exit strategy. Know how this all fits into your grand strategy, this is the Start-Up of You. But also have the easily explainable, non-threatening goal that you […]

  2. How not to screw up your career – Lone Gunman - September 8, 2011

    […] an exit strat­egy. Know how this all fits into your grand strat­egy, this is the Start-Up of You. But also have the eas­ily explain­able, non-threatening goal that […]

  3. Only L<3Ve @ - April 16, 2013

    […] an exit strategy. Know how this all fits into your grand strategy, this is the Start-Up of You. But also have the easily explainable, non-threatening goal that you […]

  4. How To Find Mentors | Thought Catalog - August 5, 2013

    […] do you want to get out of this? What’s your grand strategy? If you don’t have the answer to that question, it’s going to be hard to really get the most of […]

  5. A Letter To The Graduating Class Of 2014 | Thought Catalog - June 3, 2014

    […] thinking of your big plans. Not to say you have to actually know exactly what you want and need to do, but if you don’t even […]

  6. Grey Oak » Advice to a Young Man Hoping to Go Somewhere (Or Get Something From Someone Successful) - June 3, 2015

    […] an exit strategy. Know how this all fits into your grand strategy, this is the Start-Up of You. But also have the easily explainable, non-threatening goal that you […]