Serendipitology: The Art of Good Luck

"Serendipity" is the unexpected discovery of something beneficial at the time you happen to need it. When you plan on one course of events but something better falls across your path, that's serendipity. We have all experienced it from time to time: Some unexpected opportunity walks in the door when we happen to be ready for it, so we grab it and run with it.

Serendipitology: The Art of Good Luck

The classic case of serendipity is the scientist working on a tough theoretical problem. He is stumped by it and is tempted to give up, but then he takes a long walk. Along the way he notices something random, like a child playing with a common toy, and it jogs his brain. The toy helps him see his technical problem in a simpler way, and suddenly everything falls in place. The serendipity was this seemingly random event which turned into the catalyst for solving the unrelated scientific problem.


You have probably experienced similar serendipity in your own life. You had a problem to solve, were trying to address it by your usual methods, then something unexpected came out of the blue to help you solve it in a more efficient way. Although it wasn't part of your original plan, when the better opportunity was offered to you, you were smart enough to see it and take advantage of it.


 Some would call it "luck", but serendipity is more than that. It also includes the wisdom to recognize your luck, the practical freedom to change and personal initiative to exploit the opportunity when it happens. These things are not random chance but acquired skills. You can't know how, when or where unexpected opportunities will strike, but you can be ready for them in a general way and act wisely when they occur.


With experience, you can even learn to see opportunities and good luck where no one else can. Losing your job, being rejected in love, failing in some project that was important to you... all of these things are usually seen as "bad luck" when they first occur. But within every apparent disaster is a kernel of opportunity. If you are skilled at such things, you can quickly locate the potential windfall, shift gears and change lanes to accommodate it. In the end, you may look back on the "bad luck" and see it as the best thing that ever happened to you!


The idea that you have some control over your own good luck is the basis for a new field of study called "Serendipitology". (Don't look for it in your Funk & Wagnalls, because I just invented the word.) Serendipitology is the field of study concerned with understanding and exploiting unexpected fortuitous events. If you are a student of Serendipitology or are particularly adept and turning random events to your favor, you can call yourself a "serendipitologist". So far, there are no accredited PhD programs in this field, but the rest of this article should get you started with the basics.


Each of us plans our life as best we can. Into that plan, there are bound to come disruptions. There will be both bad disruptions ("bad luck") and good disruptions ("good luck"). By definition, we don't know what these unexpected events will be, where they will strike or when they will occur. The only thing we can be sure of is disruptions will occur. The world is a complex place, and no one can predict everything. No matter how finely tuned your plans may be, reality is bound to come along and throw monkey wrenches into them. Part of being human is learning how to deal with these disturbances and turn them to your advantage.


Preparation and Response


The art of Serendipitology involves two sets of life skills: preparation and response. Preparation means you design and manage your life in such a way that you are expecting disruptions, are ready for them and aren't thrown into turmoil when one occurs. You are ready to surf the big waves when they happen, even if you don't know exactly when and where they will come. Response means you act appropriately after a disruption actually occurs, moving quickly to take advantage of it or minimize its damage.


The most important act of preparation is leaving yourself as much future freedom as possible. If you are already locked into a fixed path far into the future, you don't have the option of taking unexpected paths, no matter how fortuitous. Disasters are doubly disastrous if you can't change course to adapt to them, and fantastic opportunities are useless if you can't stop what you are doing to explore them. Almost any meaningful project involves some commitment of your future time and attention, but many open-ended commitments are foolish and unnecessary, locking you into a long-term path with little benefit. There are always social and emotional pressures to sell off your future freedom, and sometimes it is unavoidable. Preparation means you are carefully navigating this minefield, committing your future resources as necessary but still leaving yourself open to unexpected change.


People whose lives are set in concrete are not open to serendipity. Very little good luck happens to them because they are not even in a position to even see it. They can accept the existence of new opportunities only when they appear within the narrow scope their existing investments allow. They may buy lottery tickets and would probably accept that sort of simplistic good fortune, but other forms of opportunity are frightening to them. People who are committed to a fixed path tend to be fatalistic naysayers. They will give you countless contrived reasons why an apparent opportunity doesn't exist or won't pan out, because they are not in a position to even try.


Response is the process of reacting to a disruption after it occurs. Smart people react promptly but thoughtfully, without  panic, assimilating the unexpected turn of events into their future behavior. Dumb people deny that the disruption occurred or overreact to it. They cling desperately to their old way of doing things until change is forced upon them. Opportunities pass and disasters get worse when you don't turn toward the disruption, acknowledge it and take control of your own response.


To accept a new opportunity, you almost always have to give up something from your past—some habit that doesn't really work but that you are accustomed to or invested in. Apart from your own fear of change, you have other people to worry about. To step out of straight line to explore a new opportunity, you may have to let some of them down. There can be all sorts of social pressures to not change, including substantial obligations to those who depend on you. No matter how you cut it, diverting from your current path into a new one takes courage and inner strength most people don't have. They would rather move straight ahead in a familiar path, even if it is a painful, self-destructive and unproductive one.


Courting Randomness


Apart from preparing for opportunities and responding to them when they happen, it may seem you have no control over the opportunities themselves. Who can change luck? By definition, if events are "unexpected", you can't plan on when and where they will occur, right? True, but you can still design your life to encourage more of these random events.


If you spend all day in your room, very few unexpected opportunities are going to come your way. If you get out and explore the world, deliberately pushing yourself into challenging areas, you give serendipity many more potential points of entry. True, the dangers also increase if you step out of your routine, but as long as you are reasonably prudent about your safety, the benefits usually far outweigh the risks.


You don't need a life of total chaos, just a healthy diet of new experiences outside your normal pattern of behavior. If nothing else, serendipity can introduce you to all sorts of new environments and lifestyle options. For example, you may sit next to someone on a plane, start talking to them and find yourself entering a whole new world you weren't previously aware of. A large portion of your serendipitous experience is meeting people at random who turn out to offer new keys to you own life. These chance encounters are only going to happen if you put yourself into situations where you can meet people and comfortably interact with them without preconditions.


By default, most people's lives are heavily preprogrammed, with little opportunity for any kind of randomness to intrude. Every day, they go to work at the same place, getting there by the same route, then they go home and do the same things. They think there life has depth because they watch different TV shows every night, but in reality it is a very restricted existence. Give people resources, and they seek out stability, building a bubble around them that is intended to protect them but also imprisons them. We may envy people in wealthy neighborhoods, but their imprisonment can be the worst. They are protected from every kind of threat but also most forms of serendipity, because security lies in eliminating all random occurrences.


It doesn't help serendipity to do the same sort of things repeatedly—like climbing one mountain after another—because the more you repeat something and know its angles, the more you close yourself off from random experience. You need to continually push yourself into new areas just beyond your comfort zone. You know you are probably expanding yourself if you feel a tinge of anxiety as you approach a new experience. You don't know exactly what will happen and are a little afraid, but this is good. You don't have to make huge and dangerous leaps into the unknown like Christopher Columbus. Small steps are usually better because they give you more time to adjust to the opportunities you encounter. (Poor Chris made a huge leap but never understood what he discovered.) Whatever you are already comfortable with, push it a little farther.


Serendipitous opportunities are more likely to come to people who deliberately seek new and unpredictable experiences, who continually push themselves beyond their own previous fears. Serendipity rarely presents itself to people who stay at home or repeat the same familiar activities over and over.




Letting go of your old ways is frightening, even if they don't work very well. We are all creatures of habit, and a promising opportunity can be as much an emotional disruption as an obvious disaster. Our fear of change is often expressed through the mechanism of paranoia. When our emotional system doesn't want change, it invents imaginary barriers and delusional dangers. If a good opportunity crosses our path and we interpret it as a threat, we don't have to deal with the emotional dilemmas it presents us with. This offer must be a trick, we figure—a wolf in sheep's clothing. There is no good thing that can't be seen as a bad thing under the influence of paranoia, and that's how we allow good opportunities to pass.


Paranoia can be obvious, like when someone believes the CIA is beaming mind control rays into their brain, or it can be very subtle, like a belief that an offer is "too good to be true" when in fact it is true. In one form or another, paranoia is seeing barriers where none exist, usually to reduce ones private emotional dilemmas. If you are already committed to one path and serendipity offers you a better one, your emotional system desperately wants to devalue the new path or construe it as a threat. Otherwise, you would be forced to make some hard emotional decisions. It's sort of like a romantic partner detecting a potential rival and wanting to rip the rival's heart out: The more talented the rival, the stronger the need to demonize that person and find flaws in them.


If you talk to an alcoholic living in the street—or indeed any kind of addict anywhere—and you offer them new options for resolving their problems, he is probably going to give you reasons why each of those options can't work. If you say, "The factory down the street is hiring," he will tell you there's no point in even applying. No matter how easy it is to get the job, his paranoia will always come up with reasons why it can't be done. As miserable as his current existence may be, he have made an emotional investment in it. He needs to believe he is powerless. If serendipity steps in to offer him a better opportunity, he will concoct some sort of barrier to get in the way. Then he can say, "You see, I have no choice. My problems are not my fault."


Serendipitology involves recognizing and neutralizing your own natural paranoia about new opportunities. We all say we want them, but when they actually come to us, part of us wants to shoot them down. Some of our fears are rational while others are merely attempts by our emotional system to neutralize perceived threats to our existing investments. Your job as a serendipitologist is to stand back and evaluate your options objectively. Just because you have invested huge resources in your existing path doesn't make it the best. You have to set aside the past and evaluate each road based on what it offers going forward.


Serendipity and Personality


Some people have all the luck—or at least seem to.  We are amazed by the good fortune and remarkable experiences that seems to befall them wherever they go. "They're just charmed," we say, asserting that the same things could never happen to us because of the bad hand life has dealt us. It is hard to comprehend that good fortune follows them for a reason. Maybe their gift is not luck but vision, the ability to detect the luck that other people don't notice and draw it out for their own benefit.


Other people seem to have consistent bad luck. Nothing they do goes right. One disaster after another befalls them, and no good news seems to come their way. While we shouldn't discount the fact that bad things like cancer and auto accidents can happen to anyone, the people who are walking disaster areas must have traits within them that encourage this to happen. Take two people and put them into identical situations; one will find great opportunities and take advantage of them, and the other will find only disaster and dead-ends.


The people with all the luck may have a set of personality traits that help them detect and exploit opportunities more effectively. This includes both positive skills of vision and initiative but also a lack of bad habits that get in the way. They are not stuck patterns of the past. They believe in their own ability, which encourages them to use it, which gives them more skills and experience, which leads to better success and makes their belief real.



Personality is an addiction, as powerful as cocaine. Once adults settle into a pattern of behavior and a set of philosophical attitudes, they prefer to repeat them indefinitely even if they don't work and cause them great pain. Whether you believe you have control or believe you have none, that believe is self-fulfilling  and guides your actions for the rest of your life.


One destructive attitude is fatalism, the idea that everything in life is predetermined and that any control you seem to have is an illusion. If you believe in fatalism, you can't be an active agent in your own life; you will only follow the pattern established by others. The fatalist can follow orders and respond to disasters after they happen, but he won't take preemptive action to improve his life. You will insist that no opportunities exist, but that’s because he refuses to see them when the happen.


Fatalism is probably the most important axis of personality. The majority of people, in every culture, are highly fatalistic. They respond to their environment and follow the patterns their society has set up for them, but they exert little force of their own. A special minority are low in fatalism—meaning they have high internal confidence in their ability to change their own habits. While humans can exhibit countless other personality traits, fatalism is the one that matters most to serendipitology.


Fatalism is an invitation to disaster. If you think this way, then you are not likely to take discretionary actions to improve your own life because you believe all such actions are ineffective. A fatalist is more likely to pick up addictions and less likely to quit because he believes he has no power to; therefore his risks are elevated. If he duplicates this powerless attitude for all the risks of life, the fatalist becomes highly disaster prone. At some point, one disaster after another is probably going to pummel him because he didn't take early steps to mitigate the risks.


The fatalist will tell you he has no choice and that no good opportunities ever befall him. He will tell you that every new thing he has tried in the past has failed, so he has just given up. Offer him an opportunity, and he'll probably turn it away, giving you a million reasons why it can't work. He can't change this attitude because he is invested in it. If he ever did acknowledge that he had control over his life, then he would also have to accept that his past failures are his own fault, not the work of fate. This regret would be too much to bear, so his fatalism continues.


The guy with all the luck usually believes otherwise. He thinks he does have control over his life, and this prophesy, too, is self-fulfilling. He frequently tries new approaches to solving his problems. Most of them fail, but some of them work. His own faith that something will succeed keeps him going beyond the low threshold of pain where the fatalist quits. Believing he can improve his life through his own actions, he is constantly watching for new opportunities. When "luck" happens, he jumps on it. When it happens to a fatalist, he dithers and lets it pass.


Serendipitology is a deliberate attempt to cultivate luck, to distill it and draw it out. You can't force luck or make it happen on demand, but you can learn to become more open to it, see it in more places and use more of it to your advantage.


The Profit of Failure


A common attitude of the fatalist is, “Everything I have tried has failed, so what’s the point in even trying?” The answer is: Because trying itself is valuable, regardless of whether you win or lose. Just by making an attempt, you are learning about the world and the field you are engaged in. You learn nothing by staying in your room and not trying.


The value of any journey is not just the destination but the things you learn along the way. You study a place or a process on the internet, read books about it, think deep thoughts about it, but you only way you can know how the pieces fit together is to actually go there and do it. If you at least make a stab at this activity you have theorized about, you can begin to gain real-world feedback about it, regardless of whether this attempt leads to success or failure.


Failure, in fact, can have its advantages. Success tends to lock you into a certain activity and a certain pattern of activity, whereas failure is more likely to leave you free to completely rethink the problem and try again from another angle. Not all failure is benign. Some of it can leave you crippled for life. But if you manage your failures wisely and prepare for they just like you would for success, they can be powerful resources. Success is often build upon a series of failures, each of which may be embarrassing but contributes to our understanding of the processes involved.


Early success is often more volatile, less satisfying and even dangerous. If you decide to become an actor, audition once and get a starring role on your first audition, it may not turn into the right kind of success because you never had a chance to understand, through a series of failures, what you really want. In any field, early successes are frequently mismanaged and often flame out because the seeker wasn't emotionally ready. You may have to "pay your dues" through a series of failures before success is even possible. It is not the pain that makes success more likely, but the direct hands-on experience you can only get by trying.


When opportunity knocks, the fatalist sees only the probability of final success, which indeed may be very low, while the non-fatalist may see a whole spectrum of potential benefits apart from the end result. The non-fatalist calculates the chance of winning but also the benefits gained by trying, so he's going to jump into more opportunities with a marginal end reward. Just taking the journey provides an opportunity for exploration and experimentation and a greater likelihood that some form of serendipity will step in.


Goals and Meta-Goals


It is reasonable to have goals, things you hope to do with your life, but serendipitology dictates that those goals not be too rigid or specific. If you expect to get to a certain place at a fixed time, serendipity probably won't help you. However, if you want only the move only in a general direction, you have much greater chance of finding random winds to carry you there.


The cliched advice for young people is "Never let go of your dreams." They usually take this to mean they should fixate on a goal—like football hero or movie star—and overpower every barrier that stands in their way. The trouble is, by focusing solely on that one goal they may miss more realistic and profitable opportunities that fall across their path.


When people set goals, they are usually envisioning some stereotypical accomplishment others have achieved in the past. If Steven Spielberg made it big following a certain path, they think they can achieve the same success by following the same route. What they don't realize is the world has changed in the interim and the path no longer exists as it once did. What successful people have usually done is taken advantage of the unique opportunities available to them at the time. If you are determine to reach a fixed goal regardless of your opportunities, then you will probably miss the unique opportunities you have right in front of you.


If you are focused on a specific goal and a different kind of opportunity presents itself, you are probably going to reject it because it doesn't match your fixated plan. If you can accept broader goals without specifics, you can acknowledge a wider range of opportunities. If your fixed goal is to become a world famous actor by the age of 30, there is only a narrow range of opportunities you can accept. If your goal is a general one of seeking greater creative expression, a lot more opportunities can get you there.


Broad, non-specific wishes could be called "meta-goals". Simply put, you want to be able to do more of the things that make you happy and fewer of the things that are a painful burden. You want to move in the direction of greater creativity, more freedom and more control over your own life. With those simple aims, there bound to be plenty of fortuitous events to help you out.


Specific goals are usually a little suspect anyway. Why exactly do you need to become a famous actor by the age of 30? Do you really love acting all that much, or are you seeking the unlimited glory you think fame will bring? When we seek a specific goal, we aren't really seeking accomplishment as much as the socially accepted symbols of accomplishment. We want to receive an Academy Award but don't have a clue what we should be doing to deserve it. Real accomplishment means doing something different than has ever done before, and impossible to tell in advance exactly what it will be. You can only head in a certain direction until you find it.


Rather than focusing on end goals, it is much more satisfying to look at the real world around you and see what needs to be done and can be done. Then you do what you can with the resources you have, looking for clever way to leverage those resources into something bigger. It is much better to be an Einstein—an original thinker in a whole new field—than an actor playing Einstein, which is essentially what you are doing when you see a specific goal.


It is not uncommon for someone to set a rigid goal, work hard, achieve it by some miracle, then realize, "Why am I here?" A rigid goal, once achieved, rarely brings us the happiness we think it will. That's usually because the goal was delusional, made for dubious philosophical reasons. We wanted to be loved and were seeking the symbols we thought would buy it.


Rigid goals mean fewer opportunities for good luck to help you out and a lowered probability of those goals actually being realized. A more promising approach is to know the general direction you want to go, move in that direction with the tools available and look for fortuitous opportunities along the way that might help you make better time. When an unplanned opportunity comes along, it doesn't matter exactly where it leads so long as it moves you in the general direction you intend.


Serendipitology is like sailing ship in unpredictable winds. Getting to a specific port on a fixed schedule could be very difficult, but going in a general direction, like East or West, should be a lot easier. If you don't care what port you land in as long as it is east of here, there are bound to be fortuitous winds to help you out. If you are flexible on your destination, then a lot more options are open to you, probably including one you weren't expecting that turns out to fulfill most of your personal needs.


What Really Makes You Happy?


If your goals are broad, you have a better chance of hitting them, and more serendipitous opportunities will probably come along to help. One tenet of Serendipitology is to widen your specific goals into broader meta-goals, but what should they be?


The broadest meta-goal is simply to be happy! Happiness consists of two things: reducing your frustrations and doing more of the creative things that seem to give you satisfaction. You don't have to have perfect vision of your destination to pursue greater happiness. You just need grab hold of passing opportunities that carry you in that general direction.


Happiness, in fact, is a moving target. There is no one thing that can permanently make you happy. Every joy is bound to become a prison if you lock yourself into it. Happiness is more a process than a destination. If you look back on your own periods of happiness, it was probably times when you were working toward meaningful goals with few frustrations standing in your way. The goals were important, but the happiness was in the mission. When the goal is finally reached, you don't usually experience any great euphoria. You just use that success as the basis for your next mission.


Whatever happiness may be, you are probably not feeling it when you are dealing with difficult people, cleaning house or struggling to make ends meet. There are always plenty of things causing you discomfort, and if no other goal appears to you, at least you can work to reduce them. Knowing what your frustrations are, you can look for serendipitous solutions. There are always more efficient ways to perform the routine functions of life; you just have to be open to them.


Greater experience in life—in the actual doing of things—is likely to give you greater knowledge of what truly makes you happy. In our early years, we tend to see the symbols of happiness, like awards, prestigious positions and material wealth. These are ways of telling others, "You see how happy I am!" but in terms of your current neurological happiness, they may not actually work. Awards make you happy only for a moment. Your happiness lasts longer when you are working toward something, and you probably feel the most serene when that something is both meaningful in itself and using the best of your skills.


The secret of happiness is active experimentation to find out what makes you happy. You can't depend on what people tell you. You have to work it out for yourself. Make unbiased observations of when you are happy and when you are not, and a course of action will probably form on its own.


Limits of Modeling


Serendipity is an important personal tool because the world is a big place and you can't hold all of it in your head. You make for yourself, but these plans can't possibly consider everything that might happen in the real world. Serendipity is usually the intrusion of some unexpected aspect of reality into your well laid plans, presenting an angle you hadn't considered before or had previously discounted.


All of our plans are based on models. We take all of the complexities of the world, reduce them to a few simple principles, then use these principles to guide our actions. We are making a model in our head, like a miniature model of a village, and using this model to work through what we plan to do in the real village. That's great! It is essential to model things in your head to make wise choices, but those models are always going to lack detail and access to information external to the model. Because a model is always a gross simplification, it is bound to miss other aspects of reality that you hadn't considered when creating it.


Take the law of gravity. If you are standing on the Earth, gravity seems pretty firm. What goes up must come down. Jump off a high ledge and you hurt'll yourself. After a lifetime of experience with gravity, it is easy to formulate some general principles, like "I cannot fly." These principles, then, guide our actions so we don't just off ledges. But our simple model of gravity doesn't explain everything. Birds and balloons seem to defy gravity, and some satellites go around the Earth without ever falling. Serendipitous events can clue us in to these seeming exceptions to our neat models. It is not that our theory of gravity is "wrong"; it just isn't telling us everything.


The history of manned flight is a story of serendipitous discoveries coupled with deliberate efforts to exploit them. Some elements of airplane technology were deliberately designed by engineers while others just happened. These were unexpected discoveries coming out of the blue that people then used engineering to explore. The gift of the inventors is to be able to use both forms of discovery.


In your own life, you have a personal plan for yourself based on your modeled notions of who you are and what reality is. By default, you plod along the path that the plan dictates, which is usually a straight line from "A" to "B". Your plan doesn't tell you about shortcuts, but serendipity might. Serendipity might deliver a clue that doesn't fit your model. If you are committed your path, then you're going to brush it aside. If you are open to change, then you will stop, follow this clue, and see where it leads.


Serendipity or Synchronicity?


Once you are open to serendipity, it can be spooky how things come together. Solutions come to us in ways we never dreamed, making us suspect a higher power is a work. When serendipity becomes almost cosmic, it is called "synchronicity"—the apparent synchronizing of events that have no known causal relationship. You are thinking about a friend you haven't seen in years, and ten seconds later the phone rings and it's them! Is it random, serendipitous chance or divine design?


The best answer is: It doesn't matter! Whether God or happenstance sent you this opportunity, you are still going to treat it the same. You can look at it with awe for few minutes, then you proceed to exploit it! God, if He exists, wouldn't expect anything less.


The one thing you shouldn't do, however, is expect divine intervention. If you have been blessed by a series of fortuitous events, don't make the mistake of planning on their continuation. It is when people thing they are charmed that they make their most dangerous blunders. These usually involve making commitments based on the assumption that the good fortune will continue. Once you do that, you become locked into a path and are unable to adapt when your fortunes shift.


Millions are suckered by such mistakes in every economic cycle. In boom times, serendipity delivers a steady stream of successes; the winners are lured into ever more grandiose investments then are brutally crushed when the bust finally comes. Every serendipitous success makes you feel more and more invulnerable, which leads to hubris and costly mistakes. Every great ride has to end sometime, and you have to be prepared for it just like you were prepared for opportunity.


Religious miracles and psychic phenomena may be real, but if so they are extremely fickle. Pray to God one day, and He seems to answer those prayers. Do it another day, and He seems indifferent, maybe even punishing. Instead of trying to read God's mind, which is a tricky and maybe even blastphemus, is best to proceed on your own concrete knowledge and wisdom. A just God wouldn't expect anything else.


If you succeed but don't fully understand the mechanism of that success, it is best to show restraint. If you invest in a stock and the stock price goes up, it may not be your prescience and skill but dumb chance, like a spin of the roulette wheel. This is exactly the mechanism that keeps gamblers gambling and assures they walk out of the casino penniless regardless of how much they won. Success leads to overconfidence leads to overcommitment leads to a bust.


The boom-and-bust cycle applies to every aspect of life, not just business and gambling. Experience a string of successes and you start making plans as though the trend will continue indefinitely. When the bust comes, you're trapped in those plans. Now, you're struggling to keep you're head above water, and among other disasters, you no longer have the freedom to pursue unexpected opportunities.


If you expect to enjoy the benefits of serendipity for the rest of your life, you have to treat it lightly, as a gift of chance that can be taken away at any time. As you get better at Serendipitology, more good fortune will probably come your way, but you must never take it for granted. If you marvel at the coincidences sometimes, never taken them as a trend.


The winds can shift at any time, and when they do you have to be ready to move with them.