Andrew Sean Ryan

Long ago, I was a struggling college baseball player. I had shown up to practice every day for two and a half years, but progress in my game was coming at a snail’s pace. My confidence, especially around hitting, was below zero, and every time I touched the field, I felt as though I didn’t belong. 

Then, one day, I chanced upon a conversation with a former baseball player that changed my swing, but more importantly, it also changed my life. I asked him how he had done it. What did he do to get drafted by the Dodgers? How did he manage to start in front of MLB legend Joe Carter in college? His answer seemed too simple: he said he took 300 swings every day, no matter what. 

I dug deeper, and he provided some valuable details. He took these 300 swings on a baseball tee, and 150 swings were on outside pitches—the hardest pitch to hit for most hitters. The following 100 swings were for balls that were right down the middle, and he set the last 50 swings for inside pitches. That was it. He went on to explain the magic behind his method of hitting. He focused 50% of his swings on the outside pitch because all other pitches become easier to hit when you learn to hit the outside pitch. [I could dive into the fundamentals of hitting to explain why hitting the outside pitch makes all other pitches easier to hit, but it would be a distraction from the broader purpose of this post. So you will have to take my word for it.]

I’ll be honest that I initially thought his daily routine of hitting off of a tee sounded mind-numbing, and I also knew it would be more challenging than it sounds. When thinking about his strategy, visions of children playing tee-ball may come into your head, but in reality, hitting a line drive off a tee is relatively tricky. But even with my apprehension, I decided to try it. 

The first week was humbling. I often hit more of the tee than the ball, and I’d watch the ball dribble away from me. That familiar feeling of humiliation crept in, but no matter what, I kept swinging till I reached 300.  

After about a week, I began to see a consistent change. More and more balls were coming off the tee as hard line drives. I also noticed that, just as the old player had said, the middle and inside pitches became easier to hit as I got better at hitting the outside pitch. It was happening. I was turning into a hitter. I felt like a different player, and I was hitting the ball with authority for the first time. In just one month, I had successfully overhauled my swing. I was on cloud nine.

Now, I wish this story ended like a Hollywood movie, where I went back to school as a transformed player and went on to play in the MLB, but that wasn’t my destiny. The truth is that one month after beginning my routine of  300 swings per day, I tore a tendon in my leg that required surgery. Unfortunately, that injury cascaded into many more injuries, and before I knew it, my baseball career was over. It was humbling and slightly troubling that I never got to show my teammates the progress I made, but what I gained was far more important than baseball. 

I began to experiment with designing new strategies based on what I had learned from “300 swings per day” in different areas of my life. I changed how I studied in college, and immediately I began getting straight A’s for the first time since fifth grade. I designed a strategy to improve my math skills before taking the graduate school entrance exam (known as the GRE). I developed protocols to learn to ski, surf, and speak new languages. Each time I implemented the process, I refined it a bit and learned more about the individual ingredients in the recipe.

Progress Vs. Efficient Progress

Through all my experimentation, I learned that there is progress, and then there is efficient progress. We should accept progress in whatever form it comes, but we should choose the efficient path when possible. Why? Because efficiency means less energy used, fewer resources invested, and less time wasted. 

In the diagram above, you see a looping solid red line that signifies progress, and you also see a straight, dotted yellow line that represents Efficient Progress. The solid red line and the dotted yellow line both start at the beginning and end at the goal. The lines share the same outcome, but the red line is roughly four times longer. That means that compared to the yellow line, the red line used four times as much energy, time and resources to get to the goal. Both are good, but we should strive to get as close to the dotted yellow line as possible. 

So how can we tell the difference between progress and efficient progress? Well, progress can be had by any haphazard means of practice. For example, if you are looking to progress as a basketball player, just play pickup basketball games once or twice a week. With this method, you will see progress over time, but you will be taking the red, looping, long path to your goal.  

If you want to make efficient progress, you might need to step back from playing pickup games for a little while. Instead, you would be better off scheduling a few days per week where you do focused drills around the micro-skills that make up the macro-skill of basketball: dribbling, shooting, defense, and other skills. 

Let’s look at the essential ingredients to Efficient Progress:

Efficient Progress = Consistency + Humble Approach + Deliberate Practice 

(EP = c + h + dp)

Let’s break it down a bit:

Consistency: 

For any type of progress, this is the essential step. Even a terrible plan that’s executed consistently will show results, and even the best practice plan will lead to subpar results if you don’t show up damn near every day. So make a schedule for your practice and stick with it no matter what. If you want to improve quickly, I suggest setting aside at least 30 minutes per day, 3-6 times per week, for deliberate practice (more on this below). 

Humble Approach:

The humble approach is all about staying in the beginner’s mindset and letting go of the worries of how others perceive you. We tend to avoid the things we need to work on most, especially when others might see us flailing in our attempts. Instead, embrace your current skill level and welcome a little healthy embarrassment. If you can’t keep a humble approach, you are likely to miss fundamental steps in whatever skill you hope to acquire, and in some cases, this could lead to severe consequences, such as injury. 

I have personally struggled with this step a lot in my life. I tend to get overly embarrassed and try to progress past the beginning stages of any given skill too quickly. I find it helpful to remind myself that everyone was a beginner at one point, and anyone who judges you for being a beginner is forgetting their own path to skill acquisition. They once floundered just like you, but they aren’t self-aware enough to remember it.

Deliberate Practice: 

Deliberate practice breaks down a macro-skill (i.e., basketball) into micro-skills (e.g., dribbling, free throw shooting, defense) and designs drills to improve at these specific micro-skills. So, first, you need to break the skill down into micro-skills. It might be helpful to research or ask a coach/expert what the most pertinent micro-skills in your macro-skill are. For example, there are five types of hits in tennis: forehand, backhand, volley, smash and serve. There are also five “tools” in baseball: hitting, hitting for power, running, fielding, and throwing. In surfing, there are numerous skills that a beginner needs to learn: paddling, balancing on the board, body position, wave selection, catching a wave, popping up, and riding a wave. 

Once you’ve broken your macro-skill down into micro-skills, you can design drills to work on each one. For example, you might create exercises that focus on practicing guitar scales. Or you could use flashcard software (I recommend Anki) to study the 500 most commonly used words in the language you are learning. Or maybe you could hit 50 backhands swings in a row in tennis. If paired with consistency and a humble approach, deliberate practice leads to mastery of any given skill.

Some Examples Of Using The Equation for Efficient Progress In Real Life

Here are a few examples of how I’ve utilized this in my current life/recent past to design drills and programs to acquire new skills:

Learning Turkish:

• Consistency: I practice for 30 minutes every day in addition to regular interactions around Istanbul (where I currently live), where I am forced to stretch my language skills. 
• Humble Approach: this one is easy. I currently live in Turkey, and it is impossible not to be humble when you have the vocabulary of a two-year-old in a foreign country.
• Deliberate Practice: I use two software programs to learn grammar and vocabulary. First, I do fifteen minutes of Duolingo Plus on the computer (not the phone) to learn basic grammar and some vocab. Duolingo is a much more powerful learning tool on the computer since you can turn off the word bank on the desktop version, which forces you to recall and type the words with no prompts (there are no word banks to rely on in real-world interactions). Then, for the next fifteen minutes, I use Anki (a powerful and free flashcard software that uses algorithms to decide what words you need to review) to learn vocabulary. I am currently focusing on a flashcard deck of the 500 most commonly used words in the Turkish language (hat tip to Tim Ferriss). Why try to learn the whole dictionary instead of focusing on the most frequently used words in written and spoken language?

Learning to ski:

• Consistency: unless you live on the mountain, you can’t go skiing every day. But I went as much as possible. In my first two years of skiing, I went nearly 20 times (this was my go-to activity during two COVID-19 winters). 
• Humble approach: No matter how many times people told me I could go faster or go down a more difficult slope, I didn’t listen. My goal was to keep my knees intact and not severely injure myself while still having a good time. I stayed on the bunny slopes with the toddlers for my first few days on the mountain, and I never touched an intermediate hill until I had spent five full days on my skis. When I first went on an intermediate slope, I did my research and found the easiest “blue” hill on the mountain, which began to build my confidence. 
• Deliberate Practice: I didn’t try to carve or do anything fancy when learning to ski. I focused on going down the mountain as slowly as I could. I exaggerated every turn and practiced a mini-hockey stop on each turn down the hill until I had confidence that I could always stop if I needed to. Remember, going fast is easy when you have gravity on your side; going slow is what is hard when going down a mountain. 

Learning to surf:

• Consistency: Whenever I am near the ocean, I plan to surf every single day, no matter what. Since I can’t control the size of the waves or the conditions, I make significant adjustments to my deliberate practice routine depending on the conditions (more on this below). 
• Humble approach: My first foray into surfing was admittedly not humble, and I paid the price. As a beginner, I went into the water when the waves were far too big for me, and I got a very nasty concussion. After that experience, I didn’t surf for years and had to overcome some mental trauma when I reentered the water. I restarted at square one as a humble newbie, and I doubled down on embracing my beginner status. 
• Deliberate Practice: I always have something to work on when I go in the water. When the conditions are good for me (clean small/medium-sized waves), I focus on wave selection, turning on the wave and riding them for as long as possible. Some days the waves are too big for me, so I stay in the shallows, practicing my turtle rolls, paddling, and popups while being battered by the white water. I’m sure I look crazy to people on the shore when I do this, but I am gaining confidence, skills and strength that I can use when the conditions are better. 

I hope these examples are helpful for you as you begin to implement the equation for efficient progress in your life. If you combine consistency, a humble approach, and deliberate practice, you will certainly see improvement in just about any area of your life. So pick the thing you want to work on, design a practice schedule, decide what staying humble means to you, and work out a plan for deliberate practice.  Remember, you can constantly adjust all of the variables as you learn more about the skill you are trying to acquire. 

Good luck, and feel free to reach out to me if I can help you as you roll out the equation for deliberate practice in your life.

— Andrew

P.S. — I can’t begin to explain how grateful I am for every person who reads this. I would really love to hear if this triggered any thoughts for you, whether good or bad. Did I swing and miss on this post? Let me know. Did this post make you think about some aspect of life differently? I’d love to hear it. I am on a journey of self-improvement, so your feedback is priceless. Also, if you know anyone who may enjoy this, please feel free to send it along to them. Lastly, you can subscribe to get notified whenever I publish something new by clicking here. Many thanks for your time and attention, and best wishes on your life’s journey.

If you dig deep enough, there’s always a story. Think of a truly remarkable person—the rare type with uncompromising character, compassion, conviction, novel insights, and courage. If you look hard enough at their life, there are sure to be unthinkable struggles in their past. To be clear, I’m not saying that all who suffer are transformed to greatness, but all who are great are transformed by suffering. 

This transformation is the alchemy of life, reshaping our greatest pains into the foundation on which a hero can be built. As Joseph Campbell showed in The Hero with a Thousand Faces, all heroes—whether in fiction or real-life—are tested and pushed beyond their limits. The future hero must face their greatest fears and “slay the dragon” in what Campbell called “the abyss.” Only after this does the hero rise like the phoenix. 

We can look at some real-world heroes as examples. Would Nelson Mandela have succeeded at his life’s mission to end Apartheid if he hadn’t first been imprisoned for 27 years? Would Viktor Frankl have created a new school of psychology and written a book that changed countless lives if he hadn’t endured unthinkable suffering in the Auschwitz death camp? Would Harriet Tubman have risked life and limb to free as many enslaved people as possible if she hadn’t first lived the horrors of slavery for thirty years? I think the answer is an unequivocal “no.” Each of them had to pass through the abyss before rising as a hero.

The suffering of Tubman, Frankl and Mandela was more than I would wish on my enemies, but the power they derived from it leaves history in awe. They took their suffering and used it to become exceptional, just as the alchemist turns lead into gold.  

“The world breaks everyone and afterward many are strong at the broken places.” 

– Ernest Hemingway

In comparison, any suffering we go through is likely to be minute, but it still has the power to transform us into elevated versions of ourselves. And there is nothing more honorable or respectable than to have endured, to have been transfigured and improved through hardship. 

The problem is that many of us want to be a hero, but we don’t want to go through the hero’s journey, and we certainly don’t want to pass through the abyss. So we run from suffering, and we hide from our fears. We push our worst pains deep inside, suffocating their innate power to transform us into what we yearn to become.

Instead of running from struggle, we should rather face our pains and heartaches with courage, viewing them as an asset. What can we learn from this pain? How will this heartache make us better people moving forward? Is there any wisdom to be gleaned from this experience?

There are many names for this kind of thinking. You can call it resilience or stoicism, but I call it alchemy. And I know each of us can become an alchemist in our own life, with the ability to take the lead that life gives us in the form of hardship and turn it into the gold of wisdom.

— Andrew

P.S. — I can’t begin to explain how grateful I am for every person who reads this. I would really love to hear if this triggered any thoughts for you, whether good or bad. Did I swing and miss on this post? Let me know. Did this post make you think about some aspect of life differently? I’d love to hear it. I am on a journey of self-improvement, so your feedback is priceless. Also, if you know anyone who may enjoy this, please feel free to send it along to them. Lastly, you can subscribe to get notified whenever I publish something new by clicking here. Many thanks for your time and attention, and best wishes on your life’s journey.

As I move the mouse pointer across the screen, I feel apprehension seep from my core and out into my extremities. I take a deep breath, press my finger down, hear the dull “click,” and see the words “post published” appear at the bottom left of the screen. I close the computer’s lid, hiding from the results, or more likely, the lack of results, and think to myself, “one percent…one percent.” I exhale as a bit of cortisol exits my bloodstream.

Many people don’t know this, but I’ve always been wildly self-conscious, very easily embarrassed, and tend to shrink under the spotlight. I’m proud of how far I’ve progressed on this issue, but I still have a lot of work to do. 

Even now, I can easily open up to individuals or small groups, but every now and then, when I get in front of larger groups, something changes. I feel their judgment—real or imagined—like a black veil that slowly envelopes me and constricts me from being my whole, genuine self. Then, the “benign” tremor that I was diagnosed with as a teenager suddenly isn’t so benign, as it quadruples in intensity until I’m visibly shaking. It’s humbling.    

It’s irrational, but for me, the feeling I get when I hit the publish button on these blog posts is no different than when I’m standing on stage.

In many ways, my life is a contradiction. I feel the need to create and share ideas, but I’m terrified to do it. I know my words will be imperfect, and even if they were perfect, many people would still dislike or disapprove of them. 

Of course, I would prefer to have a message that is wholly acceptable to humanity, but I know it isn’t possible. The idiosyncrasies of human taste, preferences and beliefs are too broad and varying for one message to reach all people. And even if one message could reach all of humanity, it would be diluted, having to kowtow to the extremes of ignorance while also providing something of value to those at the pinnacle of wisdom. Impossible.

Knowing this, I have to accept that everything I write is guaranteed to have a sizable group of people who dislike, disapprove, or possibly even hate it. Obviously, this is troubling for someone like me, with a propensity to be embarrassed and shrink under the judgments of others. 

So, is there any hope for those like me? Or are we doomed to keep our creations hidden away like a hoarder, our minds overflowing with ideas that will never be useful to others? 

Luckily, I believe there’s a way forward. One helpful trick is to reframe the whole situation. I like to ask myself the question, “What would happen if 99% of people hated what I wrote and 1% loved it?”. Well, if somehow I reached the entire globe, that would mean that 79 million people loved my work. That’s a hell of a lot of people, and I think 1 out of 100 people liking my work is an achievable target.

With this framing, the shy artist can change the rules of the game. Instead of focusing on the 99%, we emphasize reaching more and more of the 1% that will be positively affected by our creations. And if we could wave a magic wand and actually connect with 1% of the entire globe, can you imagine what that like-minded group could achieve together? I think it’s fair to say that they could change the world.

 When you think about things this way, 99% disapproval sounds pretty good.

So, are you one of the 99%? I appreciate your time; I know it’s scarce. Or maybe you are part of the 1%? If so, and you think you may know another person in the 1% who would benefit from this post, please pass it along to them.  

As always, thank you so much.

– Andrew

P.S. — I can’t begin to explain how grateful I am for every person who reads this. I would really love to hear if this triggered any thoughts for you, whether good or bad. Did I swing and miss on this post? Let me know. Did this post make you think about some aspect of life differently? I’d love to hear it. I am on a journey of self-improvement, so your feedback is priceless. Also, if you know anyone who may enjoy this, please feel free to send it along to them. Lastly, you can subscribe to get notified whenever I publish something new by clicking here. Many thanks for your time and attention, and best wishes on your life’s journey.

I once read a theory that humans are nothing more than a conglomeration of countless habits. This is likely an oversimplification, but the power of habit is undeniable. Each tiny little habit steers us to a destination, our good habits bringing us closer to the person we want to be in life, and our bad habits veering us off course. 

The tricky thing is that comparing one habit to another can sometimes be like comparing apples and oranges. For me, breaking bad habits can be incredibly challenging, but good habits disintegrate with the slightest amount of neglect. These two classes of habits seem to be fundamentally different in some way.

For me, bad habits are often effortless to form. They come about mindlessly, simply popping up out of nowhere. If I lose focus for even a few weeks, I automatically start eating poorly, increase my screen time, or begin staying up too late at night. And once a bad habit is formed, watch out. My bad habits are made of steel, and I have to put all my energy into melting and pounding them down. I feel like a workman who labors away at dismantling my negative habits. Then, when I finish the job, I immediately find another piece of steel that I need to meltdown. It seems as though it never ends.

On the other hand, forming good habits requires my focused energy, effort and mindfulness. And once I’ve put all that energy into creating a good habit, they’re still exceptionally fragile. Unlike my bad habits, my positive habits are made of glass. I have to handle them with care and nurture them, or they’ll end up as a pile of shards on the floor. I can’t count how many times my positive habits have disintegrated under the weight of an unexpected life event or even something as small as a week’s vacation. 

If you are anything like me, this presents some big challenges. So what can we do about it? 

We can accept that anything worth having takes hard work and dedication. There is no easy path to fulfillment and purpose. And we can realize that the ultimate measure of a person is who we become in this indescribable journey called life. 

So we grab our proverbial hammer and blow torch and get to work with the never ending task of dealing with our bad habits. And we put on our cotton gloves to delicately handle and nurture our good habits, slowly acquiring more and more beautiful pieces of glassware. And if we do the hard work every day of building a better version of ourselves, we will constantly move just a tiny bit closer to the person we want to be. It isn’t easy, but there is nothing more important or rewarding. 

Now let’s get to work…

– Andrew

P.S. — I can’t begin to explain how grateful I am for every person who reads this. I would really love to hear if this triggered any thoughts for you, whether good or bad. Did I swing and miss on this post? Let me know. Did this post make you think about some aspect of life differently? I’d love to hear it. I am on a journey of self-improvement, so your feedback is priceless. Also, if you know anyone who may enjoy this, please feel free to send it along to them. Lastly, you can subscribe to get notified whenever I publish something new by clicking here. Many thanks for your time and attention, and best wishes on your life’s journey.

I stepped out of the hotel’s door and into the parking lot, the wind and snow whipping around me like a miniature frozen tornado. I thought back to the previous day when I had stood in the same exact location on a crisp, sunny morning. I had watched the gondolas go up and down the mountain and seen the skiers as they traversed the powdery snow to the mountains’ base. The ski hill was no more than a thousand yards away from where I was standing, but today there was no mountain to be seen. 

We were in full-on whiteout conditions, with a snowy fog that made it impossible to see even the length of a football field. If I hadn’t seen the view of the mountain 24 hours earlier, I would have never known that there was anything special about this location. I certainly wouldn’t have known that one of my greatest pleasures, an activity that often makes me feel like I’m in heaven—skiing—was only a short walk away. In the midst of this storm, the parking lot where I stood was just a tiny, lifeless world of white and grey with no defining features, curtained off from the rest of the world.

As I pondered this strange weather pattern, I realized that sometimes our emotions have a similar effect on our ability to see things clearly. But instead of limiting our visual sight, it alters our ability to see reality as it truly is, temporarily robbing our inner world of wonder, joy and awe. I began to wonder how many times an emotional fog had blinded me from seeing something beautiful, remarkable or exciting. How many opportunities, insights or experiences had I missed out on? How many times had I been brooding or sulking right next to my proverbial heaven? Probably more times than I care to know about.

But negative emotions are a fact of life that we will all have to contend with for the rest of our lives. So what can we do about it?

Probably the most helpful thing is to simply identify that we are in a fog and that things are probably not as they seem. And after this identification, we likely need to do something. 

Sometimes it may be best to wait out the emotional storm before taking drastic action or passing judgment. Other times (in my opinion, most of the time), it is appropriate to actively work to clear the fog through physical exercise, meditation, breathing exercises, reading a good book (not reading something on your phone) or another activity that calms or resets the mind. But other times, it may be appropriate to take courageous action. In these situations, we have to strike out into the fog, ask for directions from others who might have a better vantage point, and we have to explore beyond our current field of vision. Who knows, we might just find our personal little heaven sitting just beyond the fog. 

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 ]
Verb
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.

---

[1] https://www.sba.gov/offices/district/az/phoenix/resources/sba-recommended-business-plans-length

[2] https://knowledge.wharton.upenn.edu/article/burn-the-business-plan/

[3]https://canvanizer.com/new/business-model-canvas