There is a little bit of a cult around the notion of "pushing yourself." It comes from sports coaches, who justify their positions by pushing their athletes' limits further. Perhaps "cult" is too harsh of a word, because your muscles do only grow when stretched beyond their limits. But is constantly pushing yourself, especially if you're not trying to become a world-class athlete, really necessary?

In snowboarding, if you visit the terrain parks, the ones with jumps and rails, you will notice a gang of snowboarders clustered at the top of the hill, waiting. All of them are psyching themselves up, visualizing their next jumps. They will sit there for ten or more minutes at a time, mustering up the courage to try a trick they haven't done before. They are pushing themselves constantly, and as a result, are liable to injure themselves, thus potentially taking them out of the season for anywhere from a week to months at a time.

But there is another way to get better, which is to take the opposite approach, and not push yourself. Stay within your comfort zone, enjoy the ride, and inevitably the mountain will challenge you on its own. If you go to the terrain park, don't sit there, psyching yourself up, but instead just go on ahead with whatever you feel comfortable doing. Eventually, the run will seem so easy that you'll naturally throw in an extra feature here and there that will challenge you. You'll ride longer that day and you'll come back more often because you're having fun, and in the long-run you will gain skill faster than those around you because you don't have to take time-outs to recover from injury.

The idea of pushing yourself or of "no pain, no gain," appeals to our inner-ascetic, who believes that self-punishment is the only path to salvation. Which is a shame, and especially ironic in the case of snowboarding, because everybody is supposed to be there for fun.

There is a movement in productivity literature that emphasizes intrinsic motivation over extrinsic motivation. This movement started in academia with Mihaly Csikszentmihalyi's book Flow: The Psychology of Optimal Experience. His idea is that we are at our best performance when our tasks are in that sweet spot between anxiety and boredom, i.e. we have enough of a challenge to lean into, but not so much that we are frustrated. Daniel H. Pink then ran with this idea and made a more mainstream book called Drive that packages these concepts into a pop business book about motivation.

But technically, all intrinsic motivation is about extrinsic motivation. Evolution made us enjoy flow because that's when we are developing our skills the fastest. It's enjoyable so that we can do more of it, and therefore derive more benefit to ourselves. The popularity of these books in business proves as much. By following their guidelines and designing workplaces to be more intrinsically motivating, we are likely doing so to maximize either our output or the output of employees. If we just wanted to enjoy our work for its own sake, we would already be there.

What's interesting about aspirations (i.e. long-standing goals or dreams) is that there is a contradiction built into them. Aspirations are things you've wanted for a long time, but are also things you haven't pursued or achieved for a long time.

The first part is important because it means that pursuing those dreams won't be a waste of time. You won't change your mind at the first sign of weakness. You won't stop wanting the goal when the next distraction comes along. But the second part—that you've retained your interest in these goals, despite having spent so much time not achieving them—shows that there's a reason you haven't your achieved your dreams.

One explanation for this contradiction is that aspirations are clues to achieving your maximum potential. For example, if your dream is to play professional basketball, it must be born out of some physical prowess you already have. If you had no prowess, you would have abandoned the dream at the first sign of discouragement on the court. On the other hand, if you don't have enough physical prowess to automatically be in the NBA, the dream is telling you that you have good initial conditions, but also a long ramp-up that could lead to self-actualization.

Another explanation is that you may already be close to achieving something, but just need an extra nudge or kick to get over some hump. For example, if it's always been your dream to work in a particular industry, the reason you're not there yet may be due to the initial headaches in organizing applications or finances. The dream is like the light at the end of the tunnel, you just need one more good sprint to finish.

Thirdly, aspirations are ultimately about unraveling personal mysteries. We don't dream about things we already are, but rather about things that we are not (yet). For if the components for achieving our dreams were already apparent to us, we would already have grabbed the trophy and turned in the towel. But because we haven't, that means there's something beyond our understanding of ourselves that will be borne out by the quest.

Imagine a world of zero managers. Such a company could exist if it followed the philosophy of motivation espoused in Flow and Drive. Daniel H. Pink (author of Drive) suggests that workers are happiest when they have control over three "Ws": What, When, and Who. Happy, autonomous employees, are happiest when they can control what they work on, when they work on it, and who they work with.

The rules of such a hypothetical company would be the following:

• Employees can show up whenever they want
• Employees can fix problems however they want
• Employees can choose their teams

What, then, would be left of management? Instead, managers would be replaced by people who simply give feedback. Feedback is the critical component of flow, in that people need to see measurable results of their efforts to learn and feel a purpose to their striving. These feedback-givers wouldn't be called "managers" anymore, but rather the more aptly-named "critics."

Do people become experts in their area of deficiency? There are a few examples from the sciences: George Vaillant's area of expertise is relationships, yet he has intimacy issues himself. V.S. Ramachandran has done fascinating research in areas related to strange brain behaviors, and yet he has a pathologically incapable memory (he can never remember his wife's birthday—or even birth month). And there are some famous examples from the arts: Beethoven was deaf, and Monet had vision problems when he painted some of his greatest works.

Other classic examples come from the world of oratory: Dr. Laura (the stern advice queen of talk radio) has had a love life that would be considered a failure according to her own message. Also, politicians seem very genuine when they expound about virtue, but perhaps they get passionate about what they say because they're talking to themselves on the stump.

These examples could just be exceptions since there are plenty of people who enter fields that suit their natural talents. But if you apply the principles of flow to careers, it makes sense that the ideal career is one that requires a long ramp-up. Flow suffuses work when the practitioner is constantly in that sweet spot between boredom and anxiety, between proficiency and non-frustrating challenge.

Flow-like conditions would then match situations where you recognize that you're deficient in one area but have a skill in another to compensate. Dr. Laura has had struggles with relationships, yet has always been a good orator (always good enough for broadcast) and so her radio program gives her a chance to slowly learn about relationships by leveraging her primary skill. Likewise, those scientists above compensated by capitalizing on their aptitude for research.

Perhaps the strive to excellence in a niche is evolution's way of helping us achieve balance as a whole.

One of the fundamental points of self-improvement is to get people to set goals. The Purpose-Driven Life, for example, is pretty much just about convincing the reader to set that highest of goals, a sense of purpose. But oftentimes, goals cause more harm than good. For example, when you attach a monetary reward to certain activities that require creativity, workers become less creative and less motivated. (Read Drive by Daniel H. Pink).

The best way to figure out when goals are good and when they're not is to break down the various benefits of goals and turn them into faults.

Goals are good for organizing - By setting a goal, you then have regular high-level side-bars where you break down the journey to the goal as a series of stages that build upon each other. But there are many cases where you don't want this kind of reductionism. For example, if the reason you haven't obtained your goal yet is because you don't know how to get there, then forcing yourself to create false intermediary stages may lead you down the wrong path, when really you need to be exploring or engaging in spontaneous activities.

Another problem with organizing is if the reasons you wanted the goal are defeated when it gets reduced to stages. For example, if your goal is to "find work that you love," you could break it down into stages, with the first stage being, "Obtain $50,000 in savings so I can afford to go back to school." To earn that $50,000, you might take on tedious work that you hate, and it might take you years longer than you expected to earn that money. Taking this route would go against the spirit of your goal, which is to not do work that you hate.

Goals are good for tie-breaking - Let's say you write down "My goal is X," but then you find yourself equally driven towards two activities: one that helps you achieve X and another that helps you achieve Y, the fact that you wrote down that your goal is X would tip the balance in its favor.

This can be counter-productive, though, if you're not just seeking X, but also personal growth in general, the kind of growth that could make X seem silly or moot. If you're seeking growth, a garden-path is actually better, as it leads to more serendipitous activities. There may be subconscious or hidden reasons why you're more compelled to seek Y instead of X, and setting a goal made you ignore those reasons.

Goals are good for justifying deliberate side-bars - For example, if your goal is to squat 200% of your body weight, you could take a side-bar and spend months just working on your arm strength or your back strength. Or you could take cooking classes so that you learn to create tasty, healthy, and protein-rich meals for yourself. These sub-components would then help you build up towards the greater goal.

However, not all goals benefit from side-bars. Sometimes goal-setting is a distraction to actually stepping up to the plate and swinging. If your goal is to be a successful businessman, it might justify the side-bar of getting an M.B.A., but you may already know what you need to get started, and it's just a matter of taking the initiative to start a business today.

The negative spaces of successful educational techniques often beg the question, Why are we designed to learn this way? For example, consider the hit memorization technique "spaced repetition." It's based on the notion that there is a critical time period after first learning something when it's best to re-learn it. When your recall dips down to 90%, a refresher will shorten the time it takes for you to get back down to 90%, and so on and so forth until the curve of forgettery disappears and you've created permanent knowledge. The graph of this process initially looks inefficient and brings up the question, Why aren't we designed to retain everything the first time we learn it?

However, this learning curve closely matches our omnivorous nature for task-selection. Whereas the woodpecker has only a few tasks to learn in life, we pick and choose tools and methods as our environment and culture demands. When you first encounter a tool, like a knife or pick, you may or may not use that tool again. So at that moment, it's not necessary to retain that knowledge. It may be a while before you return a second time—if you return at all—and so forgettery happens quickly early on. If you come back a second time and have sustained interest, you are liable to come back a third time sooner, and a fourth and so-on. Your learning therefore ramps up according to the understanding that you're actually interested in becoming familiar or developing a mastery of the tool in question.

When you are intrinsically interested in a task, your learning will naturally follow spaced repetition, but when you are not, such as when you're studying for an exam, then software and an application of the principle will be necessary to trick your brain into following its optimal and natural pattern.

A common strategy for achieving success is off-goal targeting. This is usually represented in templated expressions of the form, "Just focus on 'x,' and then 'y' will happen naturally." In other words, focus on a tangential objective that indirectly contributes to the other, "real" goal. A common example, as often expressed on the blog Daring Fireball is to focus on delivering truly high-quality user-experiences. If you make product interfaces an absolute joy to use, then those products will sell themselves.

The point of this exercise is two-fold. First, it gets your mind away from short-term expectations of success. If you step into product development with the idea that you want to make as much money as possible, you will likely cut corners and sacrifice quality in order to more efficiently maximize income. This mindset is likely to be self-defeating or only lead to short-term gains.

The second aspect of this goal is to focus on something you can control. It's much easier to control quality because you can measure it yourself, every day. Since there are many uncontrollable factors that play into how successful a product is (e.g. luck, timing, and competitors), by focusing on quality, you can quiet distractions. Your anxiety will be reduced because you've narrowed your attention to a locus of control (as described in 7 Habits of Highly Effective People). If your product doesn't do as well as you had hoped for, at least you can rule out quality. This would encourage you to possibly retry marketing, or to wait and see if market conditions improve. Whereas if you had made a shoddy product to begin with, and the returns don't come in, all your effort will have been for naught.

Off-goal targeting is ultimately a hedge against failure. If your off-goal target is to "learn programming" or "build things of quality" then even if those products don't succeed commercially, you'll have improved your overall experiences and built up your portfolio, all of which will outlast the initial gains from a quick success.

If you're an over-achiever and take on a new sport, your instinct is to focus on improving the aspects you're not good at. For example, a beginner snowboarder, who notices that one side is easier to ride on than the other (either toe-side or heel-side), is likely to concentrate riding on their weaker side. The idea being that developing balance is necessary for progressing to the next skill levels.

While this makes sense, from a productivity standpoint, it isn't much fun. True, you would eventually become a better rider and move on more quickly to more challenging aspects, like jumping. However, if you extended this pattern to your whole progression in a sport, you run the risk of turning this fun hobby into something that resembles work.

This is like living according to the Peter principle for corporate hierarchies. The Peter principle states that since workers get promoted whenever they reach a level of mastery at their current position, then all employees will tend to rise to their level of incompetence. Likewise, if you're always challenging yourself to do things you can't do in a sport, then you're always operating at a level of incompetence, rather than of confidence.

A better way is to actually keep doing the things you're great at or that feel the most fun (which are often the same), and let the lagging skills get better on their own through passive effort. So in the case of snowboarding, the suggestion would be to keep riding on the side you're comfortable on, even if it means limiting your options while turning. Eventually, though, the weaker side will pick up on its own. Mastery on one side will leak over to the other side, and eventually both will achieve relative parity.

Aspirations are goals, but they're the best kind of goals because they give extra emphasis to two important features: time and personal attachment.

Time - Aspirations are wants that have festered in your heart for a long-time. Because of this time component, aspirations have survived the ebb and flow of your moods and the cycle of seasons. This is important because those same ebbs and flows will greet you on the path to achieving your goal, and one of the most common reasons goals fail is because of a lack of true, sustained interest.

Personal Attachment - You can set a goal to anything. You could say, "My goal is to make a 100 sales this month." In this case, goal-setting is a form of remote-control, whereby you dangle a carrot in front of you to give you an extra boost of motivation or to work a few extra hours. Aspirations, on the other hand, come from deep-seated longings. They're not arbitrary or invented. Rather, they emerge from accumulated life experiences. They are fantasies that have gained increased resolution over time.

What's great about aspirations is that you will always want them. Even if you fail in an attempt, you're likely to still want the goal, and this will summon the perseverance necessary to try again.

Reading a book about intrinsic motivation is potentially self-defeating because we often read these books to maximize our output. Therefore, we are extrinsically motivated to seek intrinsic motivation. Doing so corrupts the process because we don't need to create intrinsically motivating tasks; They should already draw you in.

Perhaps the technique, then, is simply to give more permission and space to intrinsically motivating tasks. But if you tell yourself, "Do more of that thing you love, it'll be better for you," again you've partially corrupted the thing that you love.

Nebulous goals like "fulfilling your potential" and self-actualization have a way of becoming an obsession for the mid-life seeker. Such goals presume that there is this fixed thing called your "potential" that just needs some extra sauce to turn it into a reality. Perhaps you have a budding music talent. In which case, your potential then is to produce pop hits, if you could only put in something extra, whether it's practice or getting into the right school.

But your meta-potential is also part of your potential. You may have that music talent, but you don't have the discipline to do all the practice. Or you lack free time because you have to work extra jobs to pay your bills. Or you have trouble working with authority, and therefore always have had bad relationships with music coaches. So while, on some level, you do have the potential to be a superstar musician, you don't necessarily have the potential to turn that potential into a reality.

In other words, the word "potential" is a really a synonym for "lack," and obsessing over it is just another way of pushing the goal post further back and adding more conditions on your happiness.

Does Mihaly Csikszentmihalyi's Flow propose yet another stretch goal to vex the minds of pop psychology students? Is it meant to be for everybody? A similar stretch goal is the 10,000 hours of "deliberate practice" suggested in Malcolm Gladwell's Outliers or the state of self-actualization as proposed by Maslow's ladder. These pop psych ideas have a way of just creating more conditions for achieving wholeness.

Because these concepts are relatively new and hard to measure, scientists haven't thoroughly examined them. The question with Csikszentmihalyi's book is, Just how often is flow a part of people's lives today? How often do people lose themselves in their work like a passionate master, minding all the little details with tender love and care? Various studies show somewhere between 45 and 65% of Americans are happy with the jobs, so it would be interesting to know how many of them have flow as a major component of their work lives. Is it on the order of 5% or is it more like 50%?

Finding this out would help determine whether flow is a worthy goal or not. If flow isn't something that regularly occurs in a significant number of people, then perhaps it's not natural. Perhaps flow is not for everyone. Since Gladwell and Csikszentmihalyi make their case by studying those at the top of their fields, perhaps flow and 10,000 hours are just meant for masters and master candidates.

At some point, our society has to outgrow its obsession with low unemployment numbers. If perpetually increasing GDP is the goal of all modern economies, and if such increases are sustainable—which they have been, when taking the long-view, and including all nations—then the logical conclusion is full unemployment. At some point, the time it takes to create enough GDP for every single human being on earth to have the basics of food, clothing, and shelter should be trivial.

It appears, at the moment, that such a fantasy utopia is simply a goal-post that keeps getting pushed further back. After all, with all the material abundance of America, unemployment is still in the single digit percentages and average vacation time per year is 2-3 weeks. Why is everybody still working? For one, there is the perennial hedonic treadmill. The more money people make, the more they spend, and so they have to keep working to make up the difference. Then there is the continuing economic inequality. Many of these GDP gains are being collected a few individuals, and the actual condition of the average American stays relatively constant.

However, both trends probably have their limits. The hedonic treadmill may only apply to middle-class incomes, but after a certain point, there's more money than an individual has time to spend in a lifetime. The existence of casinos and pseudo-casinos (like the stock market) are evidence of a population that has transcended the hedonic treadmill and instead is just recycling their excess income back into the system.

Economic inequality, despite its seeming infinite excesses in history, goes through corrections. The history of war is often the history of enriched lower-classes clamoring for new powers. The increased leisure time of the middle-class, buoyed by excess GDP, will embolden them to demand more power and a larger piece of the economic pie.

At some point, high unemployment numbers will become a point of national pride.

There are two ways of achieving success: naturally and artificially. To get into an Ivy League school, for example, you could set a goal, strive for it, hire college admissions coaches, and structure your activities towards impressing admissions officers.

To get there naturally could also include working hard, but doing so without much personal strain. You could do community service because you enjoy it, not because you want a line-item on your college applications. You could work hard for As but without sacrificing having fun and enjoying your teenage years.

Likewise, there are the successful who are the apparent result of their ambition. Think Hillary Clinton. Yes, they have some talents that are naturally suited to the positions they have attained, but the much greater source for their high station and accolades is their diligence and determination.

And then, there are the successful who are the apparent result of their natural talents. Think Joseph Campbell, who could've written more books, garnered millions in speaking gigs but was content to stay at Sarah Lawrence College for what seems like at eternity. His successes are a more authentic expression of his being, and more likely to have been garnered with joy.

You can read all the descriptions of a happy work life, but they may not really help you at finding one. If anything, it might make you more miserable with work for a couple reasons: a) You find more reasons to be dissatisfied or, b) You strive in vain to mold your work to be more fun or interesting, which further frustrates you.

You could read Drive for example, which talks about the importance of intrinsic motivation. The keys to fulfilling work are a sense of mastery, a sense of purpose, and a sense of autonomy. Autonomy can be broken down into control over three Ts: team, time, and technique.

However, perhaps these qualities should be read more like symptom report. If you are happy at your work, then intrinsic motivation and autonomy are the kinds of things you feel.

You could read up on Maslow's Ladder, about a hierarchy of basic human needs. Once you satisfy your basic needs for survival and your basic needs for self-esteem and pride in what you do, then you have to strive for self-actualization to be happy. But that may not actually help you in filtering for jobs that provide self-actualization.

You can't pull up craigslist, tap a drop-down, and choose self-actualization. You could take a Signature Strength test, but the results that come up--for example, that your signature talent is design--may not be a helpful filter on craigslist.

This matched my experience, whereby I knew all these the concepts from Flow, Pathfinder, What Color is my Parachute, and Maslow's Ladder. I tried to manually sculpt a career with the ideal attributes and that led to years of frustration with so-called dream jobs that weren't. A good example is my stint as a video game designer.

Part of the problem is that if you already knew how the ideal job was shaped, you would already likely be there. Because the only way you'd know that it has the ideal attributes is because you have had some familiarity and success working in that field already.

Since we don't know what we don't know, the emphasis has to be on a process that will surprise you on your way to what you really want to do. Even just a little bit more emphasis on process instead of outcome can go a long way to leading you to the ideal work-life. Take this very simple process: Quit your job if you're unhappy. Then if your boss objects and offers you a position in a new department, take it. If not, leave the company and just sign up for the next best alternative. Repeat until you stop being unhappy.

In computer science, this could be called a "hill-climbing" algorithm, whereby you simply keep jumping to the next alternative until you finally wiggle your way to a good place. It should actually be called "blind wanderer" algorithm, because the computer has no pre-set notion of what the top of the hill actually looks like. It just knows when its on an incline or decline, and then proceeds accordingly.

Reading a book about intrinsic motivation (e.g. Drive by Daniel H. Pink) is at least partially self-defeating. You could sit down and design your workflow to maximize intrinsic motivation, but that design process might not be intrinsically motivating. Job-hunting for an intrinsically motivating job is also often not intrinsically motivating.

You could imagine what an intrinsically motivating work would be, and then take non-intrinsically motivating steps to land a job in that kind of specialty. You would then do the résumé grind on a jobs board, and when you get a call-back, you jump on the opportunity. You are then grilled for 1-5 hours about your qualifications, but you probably won't get a chance to return the favor and interview the interviewers. You could then end up with a boss you don't care for or a project you have no interest in, even though your blueprint said it was going to turn out fun.

To do a pure-play intrinsic motivation, both the meta-work and the actual work would have to be intrinsically motivating. You could stumble upon the work in a spontaneous, organic, pleasing way. For example, you could have a random conversation with someone at the cafeteria about a job opening in another department. Or you could be working on a hobby, not realizing that your side projects could eventually lead to something.

Success begets more success. That's a given. Early achievements come with a rush of euphoria, but later ones spike less and less, as you seek ever higher levels. The follow-on is not always a basic linear progression, though, where you win a high school championship, then a college one, then a national one, then you make the Olympics, and then you break a world record.

For most people, success progressions are more like fans, where the higher you go, not only are there increasingly difficult challenges, there is also increasing diversity. Linear definitions of success typically start with net worth, but it can also include an ever-increasing array of conditions, such as lifestyle enhancements (how hard do you have to work), number of side projects included (are you a semi-professional rock climber on the side, for example) or the nature of your work (are you running a cool collection of bars downtown). The epitome of this phenomena is the diversity of slash careers among ambitious Millennials such as the chef/entrepreneur (food trailer operator) or artist/programmer (creative director at a video game company).

The bigger challenge, then, is to figure out what kind of success to pursue. It's all too easy to get lost just figuring out which direction to lean into, especially if you've cultivated skills for a generalized success. This is evidenced by the paradox of meeting successful people (both moneyed and storied), who are not only bored but still somehow busy. What exactly are they working on?

It's almost like success needs to be re-defined, as the fan widens, to include a meta-success component: "How well are you conforming to your internal definition of success?"

Some people value career over family, and yet family is a much higher stakes game. Some people have no siblings, tons of siblings, bad siblings, good siblings, distant parents, or engaged parents. Some are in broken homes, in bad cities, with bad schools. And some are in the opposite.

Relatively speaking, a job is downright straightforward. For most of us, the workplace is where we will spend most of our waking hours. And yet it has the least amount of real risk. Every sex act can change your life. Every family meeting could make or break the plotline of the characters that matter most to you. By comparison, nearly every day at the job is roughly the same.

It's easy to deride someone who "wastes" all their time on social media doting on "boys" or "girls," or in discussing the comings and goings of their relationships. Perhaps we think it's a waste because we have much less control over the outcome of those games. But it's still the bigger game.

Life-hacking inevitably causes a reaction in many people. Tim Ferris is the leading proponent of life-hacking, selling millions of books with chapter titles like, "How I Learned to Swim Effortlessly in 10 Days" or "Disappearing Act: How to Escape the Office."

But even without in-your-face book titles, some implications from psychology about mastery and work are still troubling. Malcolm Gladwell, with the book Outliers, popularized the notion of 10,000 hours being a common ingredient in the masters of any field, whether it's piano or tennis.

What's troubling to many people about these gurus is the idea that "anything is possible." For example, if you put away the piano twenty years ago, you don't want to be told later that you could have, through certain techniques, have cultivated a very high-level of skill at it. We are attached to our weaknesses.

On the other hand, this resistance and skepticism are healthy in some regards. If you believe that anything is possible (as long as you can find the right secret technique), it could lead you on wild goose chases through sham self-improvement techniques. Ultimately, you could become a burned-out seeker, when you would've been fine if you had just accepted yourself, and stayed within your comfort zone.