Detailed Plans (And Other Fairy Tales People Believe In)

Why Learning To Navigate Life Is A Better Strategy Than Making Complicated Plans

I sometimes get the damndest responses from people. Eyeballs dart around in their sockets, foreheads crinkle and confused half-smiles appear on faces as people look at me like I am some combination of stupid and crazy. When you tell people that you don’t believe in planning, it sometimes seems like your words smacked them on the side of the head.

Still, I have empathy for the people who are confused by my lifestyle. When they make elaborate plans, they are seeking feelings of stability, security, and responsibility. And when they hear about my lack of planning, it is easy to attribute it to laziness, a chaotic lifestyle, or carelessness. Perhaps there is some truth to these labels, but in my approach, there is more than what meets the eye. Deep down, buried beneath a slovenly veneer, there is a strategy at work that provides great opportunity for success, meaning, and unforgettable experiences. And there are people far more successful than myself who pioneered these strategies long before I was born.

But first, let’s clear up one distinction. While I don’t believe in detailed planning, I do believe in goals and preparation. Goals provide an intended destination, allowing us to aim our efforts in a specific direction and are an essential ingredient for success. Preparation is equally important. Suppose you go on a long journey into the wilderness without water, food or a map. In that case, you are unprepared and setting yourself up for big problems (I should know since I recently went on a solo overnight backpacking trip without packing enough food & water. The icing on the cake was when I came down with COVID-19 while thirsty, hungry and alone on top of the mountain, but I’ll save that story for another day).

Why Planning Isn’t Always the Best Plan

Before jumping into strategies, tactics and examples from some of the world’s most successful non-planners, let me first provide a general overview of why relying on detailed plans often leads to suboptimal outcomes.

First off, elaborate plans allow no room for spontaneity or serendipity. Some of the most beautiful things in life are surprises, and some of the great innovations in history were unintended discoveries. For example, if Dr. Alexander Fleming had stuck to the plan, he would have never discovered Penicillin—an antibiotic that has saved hundreds of millions of lives since his discovery. The growth of Penicillin in his petri dish was not supposed to happen and was an unintended detour on the path to his goal—studying bacteria. But instead of sticking to the plan, he followed his curiosity and made a world-changing discovery. Maybe your next detour won’t change the world, but it can definitely change your life. I have noticed that whenever I travel to a new place, it is invariably the unplanned moments—the detours—that are unforgettable. But if you have reservations and plans for every moment of your trip, you won’t have the flexibility to take the detours that lead to the most meaningful moments.

Second, many people never move out of the planning phase because the plan isn’t “100% perfect” yet—a form of paralysis by analysis. The grueling work of creating plans that cover every detail can create the illusion of progress, but usually, we are spinning our wheels in the mud. As the famous military maxim goes, “no battle plan survives first contact with the enemy.” So, stop spending all your energy making plans that will never be used and instead jump into the battle—which is where the real learning happens.

Most importantly: Many plans are created with the desire to rid ourselves of anxiety and discomfort but the mass majority of detailed plans are works of pure fiction. Sometimes the stories we come up with are well-thought-out, but they are fabrications nonetheless. So, while making plans may reduce anxiety in the near-term, your discomfort is likely to increase drastically when the wheels of your plan start falling off down the road. We have all met the recent high school graduate who has their whole life mapped out: what career they will have; how many kids they will have by the age of 30; and when they will retire. Yet, these plans never seem to take into account stock market crashes, wars, pandemics, personal tragedies, heartbreak, or numerous other setbacks that are bound to come our way. It is an uncomfortable truth, but life is impossible to predict, and black swan events—both on the world stage and in our personal lives—are guaranteed to occur, but they are rarely captured in our fictional plans.

If you choose to live your life through complicated plans, with all of the drawbacks listed above, be my guest. But there is an alternative. You can choose to live an entirely different kind of life that offers much better prospects for success: a life of maneuvering, seizing opportunity, and constantly improving. In short, you can learn to navigate.

What Do Seasoned Sailors, Top Generals, and Successful Entrepreneurs Have In Common?

Navigate[ nav-i-geyt ]
1. to successfully find a way from one place to another.

Take a moment and envision a sailor from the 1500s. The potential problems a crew of sailors would face were numerous and varying: weather events, mutiny, pirates, disease, and the doldrums, to name a few. The captain knew they could run into any of these issues, but it was impossible to come up with detailed plans for each, as they all present in unique ways. Instead, they had to rely on their training and preparation to respond to challenges as they arose. They stocked their boat with plenty of food, water and supplies to get them to their next port, and once out to sea, the captain relied on a process of constantly checking their compass and surroundings to ensure they remained on course and avoided threats. If they followed the process throughout the entire journey, they were likely to reach their destination. Their hope of survival lay in excellent preparation and trusting their ability to navigate, maneuver and persevere through any adversities they might face.

The sailors of hundreds of years ago had compasses, but in your pocket, you have astronomically more information than they could have dreamt of. You can use this data to inform your journey, much like sailors used their compass, but you still have to navigate.

There is a lot to learn from the sailors of yesteryear, but they aren’t the only people who knew the benefits of navigating a situation instead of making detailed plans. In my view, the patron saint of never-having-a-plan should be General William Tecumseh Sherman. Historians agree that his brilliant strategy and tactics helped bring the Civil War to an end. Entire books have been written on this topic, but I will try to cover the basics in a handful of sentences (wish me luck).

General Sherman rarely had concrete plans, which made his movements impossible to predict. He would regularly set course for an area between two targets of interest and wait to see which city the Confederates moved to defend. He would then attack the city they had left unreinforced. He did this over and over again until his enemy was left completely demoralized.

In order for this strategy to work, Sherman had to go against the norms of warfare in the era. First off, he focused on speed. He avoided slow and brutal trench warfare at all costs and trained his troops to be the fastest army in the country. While other armies marched in rigid formation, Sherman’s men were ordered to move as fast as they could, no matter how it looked. This speed allowed Sherman to outmaneuver his slower enemies and provided him the benefit of being able to choose when and where battles occurred.

He also refused to be tied to supply lines, so Sherman taught his troops to live off the land. They didn’t need to repair train tracks or wait on shipments of food like other armies because they didn’t rely on them to survive. Instead, they ate from the fields and storehouses they passed on their journey. This flexibility allowed his troops to move freely around the country instead of sticking to areas with operating railroad lines.

Lastly, Sherman always knew where the enemy was. In addition to intelligence gathered from reconnaissance missions and scouts, many stories note how Sherman would sleep during the day so he could be awake in the middle of the night when his camp was silent. This silence allowed him to hear enemy troop movements—even at a great distance—and alerted him to their maneuvers. This knowledge of his enemy’s movements kept him one step ahead.

The southern generals always assumed Sherman had a master plan that they couldn’t figure out. But the plan was to have no plan and take what the confederates left available to him. He navigated away from danger and aimed to inflict as much damage on the south as possible while incurring the least amount of casualties for himself. He was never going to willingly fight the Confederates head-on. Instead, he would use his speed, flexibility, and unpredictability to his ultimate advantage.

Much like sailors navigating the sea, this was General Sherman’s strategy for navigating warfare. He used the tools and processes at his disposal to avoid danger and seize opportunities as they arose.

Now, I am no General, in fact, I barely know my way around a rifle, but I believe there is a lot to learn from Sherman. If flexibility, speed, and lack of concrete plans works on the battlefield—arguably the most extreme and high-stakes environment in the human experience—why wouldn’t it work in everyday life?

While not at the same level of risk as war, the high-stakes game of business also has a lot to teach us, and many successful tech entrepreneurs have also embraced the idea of nixing detailed plans. Successful tech startups the world over have coined numerous terms to embrace the business practice of navigation: scrum, pivot, lean and agile, to name a few. These startups have proven that elaborate plans seldom lead to innovation or products that delight customers and change the world. Instead, successful products and companies are brought about by a never-ending cycle of launching imperfect products and features, getting fast feedback and iterating.

Many promising businesses have been dashed to the rocks because they stuck too close to their original ideas. These days, so many companies switch business models after launch that they invented the term “pivot” to describe the phenomenon. Many companies have become billion-dollar companies after making massive pivots on the fly. For example, Slack—the communication platform that recently sold for nearly $28 billion—morphed from a video game startup to a communication tool for teams; YouTube became the home for online video entertainment after starting as a dating app; and Nintendo began as a maker of playing cards back in 1880.

Startups have also largely done away with the business plan. These gargantuan documents average between 30-50 pages long and plan out every detail of what will happen in a business over the next 3-5 years[1]. Most people will tell you that a thorough business plan is the first step in starting a business, but economist Carl Schramm says, “If you look at all our older major corporations—U.S. Steel, General Electric, IBM, American Airlines—and then you look at our newer companies like Amazon, Apple, Facebook, Microsoft, none of these companies ever had a business plan before they got started. Empirically, it appears as if you don’t need a business plan.[2]” The founders of these companies knew what most people don’t: you are better off putting all of your energy into creating a thriving business than expending massive energy on a document that is primarily based on assumptions. They haven’t given up on planning altogether in the tech space, but instead of spending weeks or months writing business plans, many companies start with something called a Business Model Canvas[3]. This canvas is a one-page, visual document that breaks down the most important aspects of a business. This new way of doing things allows entrepreneurs to quickly map out a company, highlight red flags, and focus their energy on execution.

The tech world has even invented an entirely new form of project management that has moved away from long-term, detailed plans. The original form of project management is known as the waterfall method. Project managers would painstakingly plan out software solutions from head-to-toe and design features based on what they assumed users wanted. This created massive problems, as most of these assumptions about what the customer wanted were wrong and led to catastrophic failures. Enter Scrum and Agile. Using Scrum and Agile for project management can sound chaotic, but it works. Engineers pick what they want to work on, the team collaboratively estimates how hard each task will be to complete so they can “keep score,” and new tasks are added to the list every week as the company learns more about the problem they aim to solve. Imperfect products are shipped to customers quickly to get real-world feedback that informs continual iteration and improvements on the product, leading to an ever-improving and compelling solution.

Like sailors in the 1500s, and General Sherman on the battlefield, these companies are using the tools and processes at their disposal to navigate a fast-paced and ever-changing environment.

How to Navigate

So, as you can see, sailors, generals, and tech startups all shun complicated and detailed planning in favor of navigation—using processes and technologies to keep themselves aimed at their goals. For sailors, navigation was the literal process of checking their compasses and changing the boat’s direction based on the reading. General Sherman relied on speed, flexibility and intelligence gathering to navigate and constantly keep him one step ahead of the enemy. Likewise, tech startups navigate by gathering user feedback and analytics in real-time to drive iteration and improvements to their products.

This strategy of navigation is not rocket science. You simply need a process that continually points you in the direction of your goals. With that in mind, we first need to set a goal, an intended destination that our activities will lead to. Don’t worry about how you will get there yet; just set the destination.

Second, decide what behaviors or metrics will act as your “compass.” Your compass should consist of daily behaviors and processes that continually provide feedback that point you in the right direction. Make the behaviors or metrics concrete. If you want to improve your physique, you could decide on a strict daily caloric limit and check your body fat percentages regularly to see if you need to adjust your diet or workout. If your goal is skill acquisition, you could decide to dedicate 30 minutes daily to the focused practice of your new skill and come up with a way to test your skill level every week to measure progress. The important thing is that you track these behaviors and processes. The method you use for tracking, whether it be pen and paper, an app, an excel spreadsheet, or putting beads in a jar, is less important than using it on a daily basis

Third, we constantly optimize, tweak and adjust our behaviors based on feedback from our “compass.” When making adjustments, it is common to over-correct, but this is part of the process. We are very rarely pointed directly at our goals, but even when we are off course, we are moving closer to our destination. And as we fine-tune our corrections, our bearing gets closer and closer to being pointed straight at our target. So perhaps you will decide that in order to take your guitar playing to the next level, you will need to take a few weeks and learn the basics of music theory. Or maybe you will focus on marketing your product over the next month instead of putting your efforts into product improvements. The path has a way of teaching you things that you could have never known before you began, so put this newfound expertise to use by continually improving your processes.

Even with the best processes, success sometimes comes slowly, and the path to your goals won’t be a straight line, but if you stick with it, you will reach your destination. Soon, we will be like that sailor who has nothing but a compass and a direction to sail in. We will be like tech entrepreneurs who have thrown detailed plans in the trash and replaced them with terms like pivot, scrum and agile to better meet the problems of the day. And we will be like General Sherman standing still and alert in the middle of the night, listening for enemy troop movements.




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