According to The CEO Genome project, a 10-year study exploring how people make it to the top job, the most successful careers are nonlinear. For instance, people who are appointed CEO faster than the average of 24 years often go off the expected track, sometimes taking sideways or what appear to be backwards steps along the way. Sure, you’ve heard plenty of stories of folks with the perfect pedigree that appear to have had a straight shot to the top. Maybe some of them even happened that way. But more often than not, when you dig below the bio-friendly version you’ll find that the full story isn’t so polished. Most success stories involve unexpected opportunities, uncertainty, discontinuity, and pivots but most are ultimately portrayed as linear because people tend to edit out the rough patches. The linear, “inevitable success” story is nearly always mythology.

For every kid that says they’ll grow up to be president of the United States, even more aspire to be an animal.

This situation is analogous to companies undergoing digital transformation—though few companies are thinking about it in this way. Many companies approach transformation by creating a PowerPoint presentation that presents an idealized end state, and then lays out a multiyear plan for how to achieve it. Make no mistake: there are clear steps that companies need to take in order to digitize their technology, operations, and workforce. But becoming a digital company—one that is capable of capitalizing on everything that digital technologies enable—requires something else entirely.

At the highest level, digitization adds connections. And when you increase the density of connections in a system, you also increase the complexity of that system, meaning that it becomes harder to predict how it will behave. What this means for companies is that not every aspect of succeeding in complex environments can be planned. It means that companies have to become more flexible, because sticking to the plan against a dynamic market is a recipe for failure. They have to plan for the unplannable. Instead of hiding behind the perceived security of fully-baked strategies and comfortable processes, companies have to engage in activities that help them to manufacture serendipity, such as pursuing partnerships and an open ecosystem strategy.

Markets have always been complex systems. What’s different today is that we no longer have the luxury of being able to ignore this fact, thanks to the dense connections and increased dynamism that digitization brings. Rigid plans will only lead companies astray in this environment. Instead, successful digital transformations are discovered at least as much as they are planned.

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