Planning for Disruption

Planning is impossible and essential. We can’t predict the future in a complex, uncertain world, yet we do it all the time. We plan our days, weeks, projects, meetings, vacations, births, marriages, careers, and retirements. Often, as we hate uncertainty, we ignore it, then learn the hard way even the best laid plans are subject to disruption. Some try not to plan, but that’s like trying not to think. Iterative, incremental planning makes sense when we must act to understand, but even an agile process is a plan.

Planning is a skill. This means we can get better. Infants barely plan. As our minds and bodies develop, so does our capacity to plan. Some kids have more interest and aptitude than others. Some have better teachers. Our skills are shaped by interaction with our parents, peers, culture, and environment. As we mature, the way we plan becomes a habit. We plan without thinking about how we plan. We get things done efficiently but miss opportunities that go unseen. Fortunately, since planning is a skill, people of any age or ability can grow their literacy by learning and practicing.

Planning creates possibility. We spend most of our lives on autopilot. Our ways of acting and seeing are deeply ingrained. Planning opens the door to change. If we try new ways of planning that are social, tangible, agile, and reflective, we may discover better paths and goals. Planning is an invisible lever that can move the world.

Tell me, what is it you plan to do with your one wild and precious life? Mary Oliver

Plans are built on beliefs. To understand and navigate an infinitely complex world, we digest experiences, attention, theories, and judgments into models and beliefs.1 Plans, which include goals and strategies, are built on top. But the map is not the territory, so our predictions go awry. In search of truth, we must use information, experiments, and metrics wisely. To observe reality better, it helps to go meta. By being mindful, we can see the gaps, adjust our maps, and build more viable plans.

Strategies are built on options. There is no strategy without choice. There are no options without awareness. Before defining a path to a goal, how might we grow our understanding of possible steps and sequences? What if we reimagine the project as a process? What if we focus less on probabilities, more on consequences, and make optionality a priority?2 A strategy is a plan that’s shaped by options, values, and risks.

There is no one right way. We might plan by framing, imagining, narrowing, deciding, executing, and reflecting. But that’s not the only way. We can act to understand. Prescription may lead to diagnosis. Our methods must fit the context, use our skills, and realize our goals and values. To this end, we can learn from all sorts of people such as project managers, architects, designers, executives, teachers, and the military.

In preparing for battle, I have always found that plans are useless, but planning is indispensable. Dwight D. Eisenhower

We must use experts wisely. There is value in education, experience, and contextual expertise. On the other hand, experts are subject to bias and perverse incentives. Try to ensure your expert has skin in the game. It’s easier to trust pilots than doctors. Ask them to map the plan. Seek understanding, demand agency, and never follow blindly.

We can plan a better future. These are the days of miracle and wonder. Disruption holds promise and peril. People and technology are imperfect. Artificial intelligence is no substitute for intelligence augmentation. In an era of autonomous drones and demagogues, we can’t get by on autopilot. So let’s disrupt ourselves by changing how we plan. Imagining a light at the end of the tunnel is the first step out of the dark.

Planning can be fun. If you hate planning, you’re doing it wrong. Plan with a friend, make a map, embrace uncertainty, and go for a walk. Our ability to imagine, organize, and shape the future is a gift. So stop procrastinating and start playing with planning.

I’m planning to write a book on planning. These nine theses are a start. I’d love feedback!

You might also enjoy listening to these interviews, attending my talk at O’Reilly Design, or participating in our workshops at XD Silicon Valley and the Information Architecture Summit.