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.1

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.2 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.

  1. 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. []
  2. As intriguing as this may sound to an idler. []


  1. “In order to succeed in a transition, embrace strategic planning” – I like this part a lot, since I am a Planner Par Excellence. But aren’t we always in transition, really?
    And I’m interested in how you came to read Don Miller’s work. I only heard about him from WDS2013- you, too? I wouldn’t have picked up a “Christian book,’ otherwise, so it was good to hear what he had to say without that framing.
    And since I am doing plenty of strategizing these days, I am happy to hear that will give me stories later… maybe all my trips, my experiments, my observations, are feeding into something I can’t even know about yet! But I bet it’ll be good! :-)

    1. Margaret, I definitely think your strategizing will bring some good pay-offs storywise. You’re also right that there are lots of “transitions” we are experiencing, even though in this case I’m aiming at a bigger change in life, like starting a new business. I should probably somewhere define my use of the term. ;)

      As for Miller, I probably wasn’t part of his target group for the book, but I’m interested in story. Read it back in 2012. The book is great and I’d recommend it to anybody who wants to get inspired about “living a story”. He’s not evangelizing in any (traditional) way, I’d say, so the Christian aspect wasn’t relevant for me.

  2. Fabian, very thought-provoking. When you said, ” Thinking about the story you want to live can be a great trick to get you into developing a strategy,” I got the image of a character in a post-modernist work, contemplating her place in shaping the story.

    The phrase “high-level planning” also stuck in my mind as I tend to get stuck in minutiae when I’m working on a task. I tend to stay at that level even after completing a particular task. Your post reminded me of the importance of getting more altitude to survey the landscape of my choices and to reconfirm the direction that I want to go. As a wannabe idler, it reminds me of the importance of choosing those things that you invest your time and energy on.

    1. Thanks for bringing up the idleness context, Greg. I definitely think that our “pace of life” is part of a decision that’s either strategic or imposed on us by society. So if we don’t want to operate in external velocity, some planning is required.

      Also, interesting connection to post-modernism that, if we follow down the rabbit hole, poses some weird questions about reality itself.

      1. This post and the “Tricks” post has gotten me thinking about the nature of story and strategy. It reminded me of the work of George Lakoff with the embodied mind and the nature of metaphors. Can “common sense” or “this is the way the world works” be seen as different stories that have some social capital behind it that is promoted by large and powerful systems within culture and society? Just thinking aloud.

        1. Greg, happy to have you as another public thinker in the comments! As for your idea, it has been a while since I read Lakoff, but I’d say we’re surely living in some kind of socially negotiated “narrative” with all its heroes, villains, threats, quests, and so on.

          This is what makes it so hard to take a step back and think about whether this specific story serves us a) as individuals, b) as a group of people (tribe, polis, village, and so on), and c) as humanity as a whole: We’re part of it and it’s tough to get into the strategic “view from 50.000 feet”.

  3. Firstly, I adore the quote by Matke.

    Secondly, I believe that making yourself a story is a terrible mindset. Think: the Narrative Fallacy. In this age, it’s easier than ever to proclaim your story to the world before you make any real progress with it. This is, however, different than thinking out loud. Thinking out loud is about humility, discussion, and openness, while telling your story is only about ego (unless asked).

    Sure, you could keep your story to yourself maybe, but how often will doing gritty work and adhering to reality (eg. innovations don’t come from Eureka! moments) seem like a hindrance to your fantastic tale? It’s more impressive to get through the work and let the world make a story for you. (Niall Doherty accomplishes this fluidly.)

    But I heavily agree with the need for strategy. A good idea I’ve been following is to fake it till you make it. Find a mentor (dead, out of personal reach, or younger than you, these things aren’t of much importance), and make sure you have access to their flaws and weaknesses as well as their accomplishments and successes. Emulate the good, learn from the bad. You can even take snippets of all kinds mentors. (eg. I don’t want to be a marketer like Ryan Holiday, but I admire his reading habits.)

    Looking forward to more.

    1. Radhika, the thing with the narrative fallacy is that you fall for it in retrospect, making up connections where there are none. This is not what I’m talking about. Nor am I suggesting to market yourself with a story (though that certainly works). Rather, I believe that for people who eschew strategy (but love good stories), it could be helpful to look at it from a different point of view: If you plan and operate strategically starting today, you’ll have a better story to look back at later. This might even be something that drives people like Niall, but of course it’s not something necessary for everybody.

      As for mentors, I’m totally with you. The same idea is in Beyond Rules, chapter 2: Learn from everybody, but draw your own conclusions. :)

      1. Thanks for that background, Fabian. I tend to be one of those who over-plans. Obstacles frustrate me and I end up wishing the obstacle away rather than using an arsenal of strategy. Maybe it’s because I lack enough of an arsenal?

        Also, from personal experience, I participated in the narrative fallacy from a present/future state. Although, maybe it isn’t called the narrative fallacy since it’s in a present state. Maybe it was the hormones (I was 13), but the decisions I made were enough to never correspond myself and stories again.

        Still, looking forward to way more on this topic.

        1. Radhika, I’d say it’s not too late to build your strategic arsenal. As with everything, small steps you take now can add up to substantial power in only a few years.

          I’d be interested to learn more about your own “narrative fallacy” if you don’t mind sharing it. No details needed, of course, but to get a better idea of whaat you refer to.

          1. Basically, I was balancing two different pursuits, similar to the day-job artists. I ended up dropping the day-job component, but didn’t know how to work as an artist. (The drive for the artistry was because the day-job was too boring and unfantastic.) I continually let out work I didn’t actually work on, because I believed (from hearing stories about artists) that that’s how artistry works.

            I’m not into artistry anymore, but if I look at “stories,” I will probably gravitate towards overnight successes, the genius inside, etc. Now, I’m trying to focus on the process and small goals. It doesn’t turn into a story that way, and if I get distracted by daydreaming, it won’t be my fantastic life as a troubled artist.

            It was really just way too much vanity, looking back.

          2. Thanks for your explanation, Radhika, that’s a great insight learned the hard way. It reminds me of this old Overcoming Bias post about seeking your anti-story.

            Thinking about it, this is very relevant for the tactical part of this series. Concerning strategy, it just means tht day-dreaming probably doesn’t cut it. But tactics-wise, this is exactly what it’s ll about: “Process and small goals”, tiny but tangible steps.

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