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How Will You Measure Your Life? Chapter 3 - The Balance Of Calculation and Serendipity

Carlsbad, New Mexico

January 6, 2020

Options for your strategy spring from two different sources. The first source is anticipated opportunities—the opportunities that you can see and choose to pursue. When you put in place a plan focused on these anticipated opportunities, you are pursuing a deliberate strategy.

The second source of options is unanticipated—usually a cocktail of problems and opportunities that emerges while you are trying to implement the deliberate plan or strategy that you have decided upon.

A company has to decide whether to stick with the original plan, modify it, or even replace it altogether with one of the alternatives that arises. The decision sometimes is an explicit decision; often, however, a modified strategy coalesces from myriad day-to-day decisions to pursue unanticipated opportunities and resolve unanticipated problems.

When strategy forms in this way, it is known as emergent strategy. When the company’s leaders made a clear decision to pursue the new direction, the emergent strategy became the new deliberate strategy. But it doesn’t stop there. The process of strategy then reiterates through these steps over and over again, constantly evolving.

In other words, strategy is a continuous, diverse, and unruly process.

Balancing Emergent and Deliberate

I’m always struck by how many of my students think they’re supposed to have their careers planned out, step by step, for the next five years. High-achievers, and aspiring high-achievers, too often put pressure on themselves to do exactly this. Starting as early as high school, they think that to be successful they need to have a concrete vision of exactly what it is they want to do with their lives.

Underlying this belief is the implicit assumption that they should risk deviating from their vision only if things go horribly wrong.

Having such a focused plan really only makes sense in certain circumstances. In our lives and in our careers, whether we are aware of it or not, we are constantly navigating a path by deciding between our deliberate strategies and the unanticipated alternatives that emerge. Each approach is vying for our minds and our hearts, making its best case to become our actual strategy. Neither is inherently better or worse; rather, which you should choose depends on where you are on your journey.

Understanding this—that strategy is made up of these two disparate elements, and that your circumstances dictate which approach is betree—will better enable you to sort through the choices that your career will constantly present.

If you have found an outlet in your career that provides both the requisite hygiene factors and motivators, then a deliberate approach makes sense. Your aspirations should be clear, and you know from your present experience that they are worth striving for. Rather than worrying about adjusting to unexpected opportunities, your frame of mind should be focused on how best to achieve the goals you have deliberately set.

If you haven’t reached the point of finding a career that does this for you, you need to be emergent. This is another way of saying that if you are in these circumstances, experiment in life. As you learn from each experience, adjust. Then iterate quickly. Keep going through this process until your strategy begins to click.

As you go through your career, you will begin to find the areas of work you love and in which you will shine; you will, hopefully, find a field where you can maximize the motivators and satisfy the hygiene factors.

It is rarely a case of sitting in an ivory tower and thinking through the problem until the answer pops into your head. Strategy almost always emerges from a combination of deliberate and unanticipated opportunities.

What’s important is to get out there and try stuff until you learn where your talents, interests, and priorities begin to pay off. When you find out what really works for you, then it’s time to flip from an emergent strategy to a deliberate one.

What Has to Prove True for This to Work?

It is easy to say be open to opportunities as they emerge. It’s much harder to know which strategy you should actually pursue. Is the current deliberate strategy the best course to continue on, or is it time to adopt a different strategy that is emerging? What happens if ten opportunities present at once? Or if one of them requires a substantial investment on your part just to find out whether it’s something that you’re going to enjoy?

Ideally, you don’t want to have to go through medical school to figure out you don’t want to be a doctor. So what can you do to figure out what has the best chance of working out for you?

There’s a tool that can help you test whether your deliberate strategy or a new emergent one will be a fruitful approach. It forces you to articulate what assumptions need to be proved true in order for the strategy to succeed. I call it, “What has to prove true for this to work?”

The way this works in business is the project teams compile a list of all the assumptions that have been made in their initial projections. Then ask them: “Which of these assumptions need to prove true in order for us to realistically expect that these numbers will materialize?” The assumptions on this list should be rank-ordered by importance and uncertainty. At the top of the list should be the assumptions that are most important and least certain, while the bottom of the list should be those that are least important and most certain. Only after you understand the relative importance of all the underlying assumptions should you green-light the team.

This approach of “What assumptions must prove true?” offers a simple way to keep strategy from going far off-course. It causes teams to focus on what truly matters to get the numbers to materialize. If we ask the right questions, the answers generally are easy to get.

Before You Take That Job

This type of planning can help you consider job opportunities, too. It’s too easy to get too far down a path before you’ve realized that choices aren’t working out as you hoped. This tool can help you avoid doing just that.

Before you take a job, carefully list what things others are going to need to do or to deliver in order for you to successfully achieve what you hope to do. Ask yourself: “What are the assumptions that have to prove true in order for me to be able to succeed in this assignment?” List them. Are they within your control? Equally important, ask yourself what assumptions have to prove true for you to be happy in the choice you are contemplating. Are you basing your position on extrinsic or intrinsic motivators? Why do you think this is going to be something you enjoy doing? What evidence do you have?

Every time you consider a career move, keep thinking about the most important assumptions that have to prove true, and how you can swiftly and inexpensively test if they are valid. Make sure you are being realistic about the path ahead of you.


Once you understand the concept of emergent and deliberate strategy, you’ll know that if you’ve yet to find something that really works in your career, expecting to have a clear vision of where your life will take you is just wasting time. Even worse, it may actually close your mind to unexpected opportunities.

While you are still figuring out your career, you should keep the aperture of your life wide open.

Depending on your particular circumstances, you should be prepared to experiment with different opportunities, ready to pivot, and continue to adjust your strategy until you find what it is that both satisfies the hygiene factors and gives you all the motivators. Only then does a deliberate strategy make sense.

When you get it right, you’ll know. As difficult as it may seem, you’ve got to be honest with yourself about this whole process. Change is difficult, and it will probably seem easier to just stick with what you are already doing. That thinking can be dangerous. You’re only kicking the can down the road, and you risk waking up one day, years later, looking into the mirror, asking yourself: “What am I doing with my life?””

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