Your Strategy Becomes Your Story

Disclaimer: This post is thinking in public. Feel free to discuss it, append it, rip it apart, or just enjoy it as it is.

Last week, I suggested to trick yourself better in order to succeed in a transition. Whether your transition is about building a business, converting from Star Trek to Star Wars, or moving to a new country, it’s always related to a longer time perspective. This is where story and strategy become relevant.

Story is strategy in retrospect. A well-crafted strategy results in a great story, just as a flawed strategy easily turns into a bad story. “The moment you aim for results, you are in the realm of strategy,” as Robert Greene puts it. This makes strategy uniquely relevant for anybody in a phase of transition. If there’s no strategy at all – the default mode for most people – all you’ll get is mediocrity, ending up somewhere around the top of the bell curve.


First things first: What is a story? Here’s Donald Miller’s take, from his (wonderful) A Million Miles in a Thousand Years:

A story is a character who wants something and overcomes conflict to get it.

According to Miller, a story can help you live a better life. On a personal level, the character from his definition is… you! The thing you want is some kind of goal, and the conflict describes the obstacles you have to overcome to get it. This is relevant on any level from getting simple tasks done to realizing a larger transition. But it’s especially relevant for the latter. After all, you could spend your whole life on smaller tasks and errands, without ever getting to the juicy parts that matter. This is why you should care about strategy.

So, what’s strategy? Here’s Wikipedia’s definition:

Strategy is a high level plan to achieve one or more goals under conditions of uncertainty. Strategy is important because the resources available to achieve these goals are usually limited. ((This definition of strategy isn’t without controversy. Lock a dozen of self-proclaimed strategists up in a room to agree on a collective definition of the term outside of warfare and they’ll rather starve to death than to come out with a result. While that strikes me as both tragic and surprisingly unstrategic, the Wikipedia definition seems to reflect at least some kind of consensus, and it suffices for my look at strategy from a transition perspective.))

For the scanners, what have we got so far in terms of strategy?

  • Make a high-level plan.
  • In order to achieve a goal.
  • Using available resources.
  • Under conditions of uncertainty.

Isn’t that strikingly similar to Miller’s definition of story?

If you want to “achieve a goal” you’re basically Miller’s character who wants to get something. As you operate “under uncertainty” – the future isn’t written yet! – you’ll most likely encounter conflict on your way. In order to overcome that conflict you must “use your available resources”.

Interestingly, there’s one thing missing from a strategic point of view: The plan! And this is exactly what I’d like you to do if you follow this blog series with more than just academic interest: In order to succeed in a transition, embrace strategic planning.

Stories and Strategies

The problem is that people like me (and maybe – just maybe! – people like you) tend to eschew strategy. I strongly dislike planning everything, and I hate getting caught up in worries about a future that hasn’t arrived yet. Unfortunately, eschewing strategy comes with a price. The price is that you end up marking time for weeks, months or even years. During this time, a lot of things will “happen” – but they will rather happen to you instead of you making them happen.

At the same time, people like me (and maybe – just maybe! – people like you) tend to be into stories. I certainly am. Stories are intriguing. Stories are captivating. Stories are motivating.

So here’s my reasoning: If you use strategy as a tool to live a better story, thinking about strategy could actually become interesting. From this point of view, strategy is about adventure and exploration instead of warfare and domination. Thinking about the story you want to live can be a great trick to get you into developing a strategy.


To be sure, you’re aiming for a high-level plan here. Strategy isn’t about the minutiae. It’s not about foreseeing how every single detail of your life is going to unfold. Rather, it’s about preparation and positioning. To quote Wikipedia once more:

Strategy is […] about attaining and maintaining a position of advantage over adversaries through the successive exploitation of known or emergent possibilities rather than committing to any specific fixed plan designed at the outset.

Strategy is a constant effort to position yourself in order to mitigate the negative events in your life and to take advantage of the positive ones. The term “positioning” itself connotes the continual character of strategy: You make a plan to pursue a goal, but you never achieve it irrevocably. ((As intriguing as this may sound to an idler.)) As long as you’re alive, any greater goal requires you to keep moving – either to maintain it, or because reaching it opens up new goals to pursue.

Robert Greene quotes Helmuth von Moltke:

[Strategy] is more than a science: it is the application of knowledge to practical life, the development of thought capable of modifying the original guiding idea in the light of ever-changing situations; it is the art of acting under the pressure of the most difficult conditions.

According to Moltke, “no plan survives the first enemy contact”. For you and me, I hope that your life won’t be full of enemy contacts. What you can take away, though, is that strategy requires constant reassessment and adjustment. In the transition, this means that your actions should be directed by an overarching principle, but they shouldn’t be inflexible.

Embracing strategy means getting out of reactive mode, choosing what to focus on, and also “choosing what not to do” (Michael Porter). It means adopting a higher perspective, a “vantage point outside and slightly elevated” from “the day’s swirling events”, as Sam Carpenter describes it in Work the System.

These are just pointers, but they should be enough to get you started.


To recap my public thinking on story, strategy and making a transition so far:

  • A great story is a great strategy in retrospect.
  • Consequently, use strategy to live a better story.
  • Prepare and position yourself: What’s your goal in the transition, what’s your overarching principle, what are the likely obstacles you’ll encounter?
  • To succeed, embrace high level planning – but be flexible to adjust on the way.
  • Use all available resources.
  • Also choose what not to do.

More on this (and the respective tactics) over the course of this series. For now, I’d be delighted to hear your take on story and strategy in the comments.

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