Strategy is boring.

Yes, I know I have been a strategist for a long time. My success rates are relatively high as I think of strategies as infrastructure and direction; I create for uncertainty. They are designed to illuminate the field and provide action steps for navigating obstacles.

I have invested time, energy, and sometimes my heart and soul into being a better strategist; to enhance my natural capability for the work. But, as we shift into a future arriving faster than we anticipated, is improving this skill really the best investment?

What if my laser focus on strategic thinking and planning was misguided? We can’t see the future. Strategy requires some pretending – a belief that we can see what’s coming and plan for it proactively. With observation and attention, we can predict some of it, but how much is the illusion of control?

Humans want to feel secure. We want to be comfortable. We want to believe that we can know what’s coming to quell our fear and anxiety. It is actually my anxiety that I believe has made me good at the work of strategy. Catastrophic thinking actually has value here. The problem is that so often the lens of problem-solving focuses only on the whammies, the worries, and worst-case scenarios. The idea of grand plans that make us the master of the universe is usually built on ideating what could go wrong.

It begins to feel rote. We lose so much in the periphery. We create self-fulfilling prophecies. And so often omit the imagination, inspiration, and possibility of also considering what could happen if everything went right.

Exploration is exciting. Not knowing doesn’t have to be worrisome, it can also open the field of possibility. What if we broke apart the skills of strategy and re-arranged them to allow us to show up and move forward in an entirely new way.

Humans create. It is what separates us from the rest of the animal kingdom. If we’re being honest, business in and of itself is also something we imagined. It wouldn’t be real if we didn’t make it so.

But, the future requires something new of us. It requires us to create, to innovate, to drive change. Designing strategies to mitigate risk and obstacles doesn’t serve our better selves. We are soothing ourselves and since we can’t see the future, it is sometimes more work in the long run to allow ourselves to believe that we can create strategies to magic away potential problems.

It isn’t to say that awareness, analysis, acceptance, observation, and planning don’t have value. But, if you are preparing for an expedition- you think about what you might need, you imagine the landscape, and you take the information you do have to give yourself the best shot at success knowing that there WILL be things you didn’t anticipate. It frees you to be open to what comes and challenges your mind to adapt on the fly. That is exciting. It’s scary, too. Historically, explorers are often laughed at and thought to be crazy. It’s because explorers with imagination, curiosity, and belief that something we can’t imagine exists makes people uncomfortable. It feels risky. We know that risk is required for transcendence and innovation – it doesn’t mean that we like it.

But as my kids say… it’s okay to feel “scrited” (scared + excited) or “nervited” (nervous + excited). Risk gets the blood pumping, it activates our thinking, it can sharpen our focus if we train ourselves for it. Instead of believing that our strategies will save us, we can prepare for adventure. Sometimes, there isn’t a map. And sometimes, the maps we have are wrong or incomplete.

I’ve been thinking a lot about letting go, about finding the courage to move past all of the things I thought I knew. When I started thinking about re-wiring my mindset almost two years ago, my idea was to elevate experimentation over strategy. I don’t think I had the pursuit quite right. Today, I’m thinking about exploration over strategy. I’m thinking about the thrill of not knowing because, with the courage to move forward into a new world, it allows me to be open to new possibilities.

I don’t think I could stop thinking strategically if I tried, but I’m going to give it a go and see if I can have it take a backseat. Our landscape in business is often fraught with pockets of not knowing. We operate in ambiguity. We move forward with incomplete information. There is so much room for conjecture.

And the urgency (at least for me) is to use observation and intuition to fill in the gaps. We hypothesize. But, the problem with hypothesizing is that we pave the way for confirmation bias. We are seeking to confirm what we think will happen and because of the way the human mind works, we often find what we think is coming.

Good analysis means letting go of preconceived notions. It requires us to let go of our hypotheses and beliefs so we can see patterns for what they are. I’ve talked a lot about data-informed decision-making versus data-driven decision-making. We delude ourselves to believe that data speaks for itself. It doesn’t. It is open to interpretation. We translate it through our own perspective and lens of experience, through our known. Make no mistake- you can make data say whatever you want it to say. All the AI in the world won’t change that because at the root of it all is still a human… a human creating, a human designing. When humans are in play, bias exists, subjectivity exists.

So, maybe instead of imagining ourselves to be strategic masters of the universe, we allow ourselves to think like explorers, to imagine, to believe in the possibility of new and enlightening discoveries. What could change if we shifted our work away from trying to be masters of the universe to preparing for the unknown with an open mind and elevating the value of adapting in real-time to the changes in the environment? How might it change us?

If we are comparing the two, strategy is boring. It is imagined power to control what’s coming. And nothing is more dull and disheartening than investing time, energy, and dedication into designing something that doesn’t work, falls flat, or isn’t executable because the ground is shaking with new information.

But to move forward with a possibility mindset and excitement for the unknown unknown, to believe that being finished isn’t the goal and being right isn’t optimal… that it is instead a series of milestones on the adventure that opens the door to something we couldn’t have before imagined existed. That is thrilling. It requires us to be attuned, sharp, on our game, and fully present, to be what makes us uncomfortable on purpose.

This isn’t an easy shift in mindset. But, I believe, that the continuous reward will be well worth the effort and maybe it can open us to connecting with one another, curiosity, and work in an entirely novel way.

I know that I can be different and if I can do it, so can you. And if we can do it, so can anyone else. Courage is catching. And writing these words, my breath catches. It feels hard. So for this moment, I am going to breathe and believe and walk forward with a spirit of adventure. The only thing I have to lose is the idea of being right, of knowing, and even that is probably a good thing.

Ben Gates and Indiana Jones, lookout. Here I come.

annewinn.com blog | Originally posted on September 20, 2023 | Photo by Rachel Claire on Pexels

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