Melissa Pepers Futurist Fortune Teller Bonbo

What Fortune Telling Can Teach Us About Strategy

In uncertain times, what I want to know are possibilities for the future and what pathways will lead me there.

The problem with creating new futures is that the status quo is to use the same processes which ineffectively lead us to more of the same results. This is where learning the ancient arts of divination taught me how to be a better strategist. 

I do not believe anyone can tell me my future and nothing ignites my inner rebel like being told ‘x is who you are and y and z is what will happen to you.’ 

When the future is unclear, I rarely want to hear a prewritten narrative that says it is. It makes me suspicious of the narrator, skeptical of the story, and inclined to seek out an opposing perspective. Meanwhile the most undesirable aspects of this future create a need to reassure my inner belief in free will.

Tarot Reader draws Death – the card of transformation

 “You will marry your soulmate and forever be torn about which of you is Bert and which, Ernie.”


A strategist is hired when results are needed – people only hire me because they want to manifest desired outcomes. I do so by understanding what possibilities exist, creating processes that lead to those possibilities, and anticipating problems so they can be solved before they occur.

Most people have strategy and problem-solving listed somewhere in there resumes. However there are two key blindspots in the way that strategy is approached when it isn’t priority one, like it is for me.

Jeff Survivor "Outwit, Outplay, Outlast"

Imagine a fortune teller with cards laid out in front of them in various arrangements. Each card when revealed, contains archetypal imagery that represents different ideas. In a Tarot reading, a good reader will not tell you a deterministic future.

The first lesson the fortune teller has for us is systems thinking. Typically, when strategy is not priority one, it goes a little something like this. 

  • Articulate the result that is needed

  • Think of different ways that result could be produced

  • Select the optimal way(s).

The result is that people chase the same outcomes and follow the same methods – the way it’s always been done. Minimal, if any, tailoring is done to ensure the strategy makes best use of available resources and unique capabilities. A better, truly innovative way is rarely discovered.

A great reading uses a very different approach. The reader knows that the querent has an ideal solution in their mind already. They are also aware that their client already knows whether or not that outcome is truly feasible. Therefore it is not their job to tell their customer what they want to hear, but to ensure that no stone goes unturned when analysing their situation. Each card represents not a different outcome, but a different lens through which to view the situation. A reading will involve many lenses and also different arrangements of the cards. These arrangements are an opportunity to try new ideas on for size and see how they might fit together. This approach is so powerful for its recipient precisely because it does not look at problem solving as getting from A to B in the shortest, straightest line possible. It looks at the entire system as a whole comprised of many moving parts, allowing new patterns and harmonious relationships to emerge. It also ensures that thinking styles and considerations that are not usually that person’s flavour to be given equal weight – a way of surpassing the limitations of our own thinking and bias.

The second lesson the fortune teller has for us concerns how we use our time. They intuitively know how to overcome Parkinson’s Law of Triviality. This law is simple, yet pervasive in its detrimental impact on strategy – that it’s easy to come up with lots ideas on what to do for the simple parts of a challenge, and difficult to come up with lots of ideas for the complex parts. Thus we spend most of our strategising time ‘problem-solving’ the bits that aren’t problems, because it feels good. Oops. Ever wondered why meetings never end early? That’s why, and it’s a result of natural human bias. What that means for time spent strategising is that it tends to lead to a fairly obvious answer, with incredibly alluring decorations.

Emoji Fortune Teller

There are no shortcuts in divination. Typically, a querent comes to a fortune teller because they want to stop ruminating and start processing. Alone, they were moving in circles instead of toward a solution. Throughout the reading, the reader will continually compare and contrast each card with the original question. Their skill is not in knowing what the cards mean, but in keeping the real challenge front and centre throughout the process. It’s quality time and this ensures each insight is an aha-moment where it counts. Additionally, there are different types of card layouts (called spreads) best suited to different types of challenges. A strategy for the strategy, if you will. Like the best fortune tellers, the best full-time strategists learn to think meta-strategy. It ensures that each moment of time is spent effectively.

In some situations, the obvious strategies aren’t bad at all. They’re a proven model, often well supported, understood by many, low risk, and may be easy to implement. They’re safe. In situations where we know all of the variables these strategies are great strategies. If it ain’t broke, right? In reality, the most important and the most ambitious outcomes occur in increasingly uncertain environments. The obvious strategies might make us feel safe in uncertainty, but easy answers – just like being told your exact future – are answers worth being skeptical of. Effectiveness and results come from dynamic processes that create new paths for a new future. After all, we cannot create something new by continuing to think in the same ways.

If you've been waiting for the type of business magic that only comes from unique thinking, watch my free masterclass how to reimagine your niche.
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