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.

A "bucket list" is meant to be a list of things to do before you "kick the bucket" or die. Typical examples are to travel around the world or try skydiving. However, a real bucket list should be about discovering passions or further defining your spirit, rather than being a tourist.

The difference between the two comes down to the difference between curiosity and interest. Consider this metaphor: While as curiosity is what gets you to notice an intriguing book cover, open the book, and see what's inside, interest is what gets you to buy the book and read every page. We often confuse the two. We're all curious as to what skydiving is like, but not necessarily interested in skydiving itself.

Our bucket lists, therefore should not express curiosities, but rather long-standing interests, ones that have been dormant or that we've made excuses for not pursuing. Otherwise, then the cliche bucket list (with checkboxes like "travel the world") is just the kick start for the longer bucket list, the one with items that can't be merely checked off.

The modern journey to death, with its lengthy battles against incurable diseases like cancer, has an ascetic, Judeo-Christian feel to it. For most, the end of life is a drawn-out gauntlet, a tunnel where technology and nature whip us on both sides. Meanwhile, we peer forward at the faint light at the end of it, a glimmer of a chance for extending our golden years.

Being stingy or frugal when one can afford to spend more is, in a way, like slumming. Slumming is the act of living or participating in a lifestyle that is below what one can afford. The term is pejorative because it's inauthentic. To dip into living poorly is to show a false sense of struggle, and therefore elicit a false sense of endearment. Or to dip into living poorly is to temporarily taste alternative lifestyles, without any of the challenge associated with them, making for an incomplete or inauthentic experience.

Being frugal is usually considered a good thing, but the presentation is still inauthentic in the same way that slumming is. If a millionaire eats cheap burgers at fast food restaurants, they are presenting a false image to the rest of the diners. How you consume is the most telling indicator of class, and both the slummers and the frugal are guilty of consuming beneath their station.

Nietzsche weighed in on the debate over free will by nullifying it: There is no free will just as there is no unfree will. Unity of agency is what matters most.

The way to understand this is to consider the difference between effective wants and actual wants. An effective want is what you are apparently driven towards. If an alien were to study you from the outside, without asking you what you thought, they would look at how you spend your time to understand what drives you. These would be your effective wants. Your actual wants would be the self-description of your wants. So if you keep saying you want to break up with your lover, but are still spending every waking moment with that person, there is a chasm between your effective and actual wants.

The more overlap that a person has between these two wants, the less likely there is to be discord in their heart.

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.

Scarcity will always exist because those who take more will crowd out those who take less. Even as technology makes it so that one farmer can feed hundreds, we are ever clever in making new things scarce. The scarcity of diamonds, for example, shows that scarcity transcends caloric needs. We are also finding scarcity in areas that aren't limited in quantity per se, but more so limited in available quality, such as the scarcity of good opera seats or good homes in good cities.

And we are designed for this scarcity. We have a sliding scale of happiness that doesn't depend on our absolute quality of circumstance, but rather vaguely shoots for fifty-percent happiness since that's the optimal level required to keep us striving.

None of which is to say that utopia can't exist, but rather that it will exist in variables unrelated to abundance. So, for example, utopia might mean a decline in violence and the elimination of poverty, but just because technology leads to abundance, there will still be widespread discontentment. Abundance has existed many times in human history, and each time, we prevailed.

Maturity is about respecting consequence. When teenagers learn that words hurt people, or that driving drunk is dangerous, they've learned something about cause and effect. But maturity is also about disregarding consequence. Adults face mind-boggling decisions about committing to marriage, having children, and buying a house, and so it takes maturity to ignore all the fears of the potentially traumatizing consequences of those decisions, and proceed regardless.

I always forget to put my phone on silent until after I've laid down to bed and appreciated the onset of cushiony, pillowy bliss. The reason this doesn't get fixed is that the best time for me to learn a lesson or reinforce a mnemonic is in the first few minutes after I realize I've forgotten to silence my phone. However because the error isn't dire enough, I fall asleep before I get a chance to internalize a flag to prevent the mistake in the future.

When you make a mistake, you not only need to raise a flag in your consciousness, but you also have to raise ceiling space for the flag-raising ceremony. In the above case, I'd have to realize my recurring meta-mistake, of falling asleep too quickly, before I can learn from my actual mistake. I'd have to exhort myself, "Don't fall asleep," so that I can exhort myself, "Next time put your phone on silent."

Likewise, when you have a close call while driving, you have to not only mind the direct causes of it (i.e. texting or daydreaming), but also the causes of those causes.

Now that we're living beyond our ancestor's average life expectancy, it might make more sense to have a multiple lives perspective, with each "life" spanning between 15 and 20 years.

The stages are longer. If one spends ages 5 through 22 in school, that is like a lifetime as a student. Waking up for attendance, getting grades, and socializing with colleagues drives every student's daily existence, and then after 22, that rhythm stops. For most students, that final commencement ceremony is like a funeral.

If they then spend ages 22 through 40 being single and dating, then that is also a lifetime within those rhythms. Then raising children for 18-22 years is another lifetime. Having an empty nest, another, and so on. Life-extension means more and more lives stacked back-to-back like a bookshelf.

If such a mindset were prevalent, we might revive coming-of-age rituals, but rename them "coming-of-life" ones. In these parties, people shed their past, maybe even their names. Or extending even further, a lifetime prison sentence could be between 15 and 25 years, because that's equal to "life" imprisonment; The difference between being imprisoned for 20 years versus 40 years is not much. That man or woman will not see their children have a lifetime's worth of aging. And when the criminal returns to the free world, they will be so different that they won't re-enter society with any of the same friends or assumptions. In other words, they won't be the same person.

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.

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.

Is there, or isn't there, value in pat advice? A common one is, "be natural," but is this something you should do all the time? Does being natural lead you to the desired life outcomes? One way is to compare the piece of advice to a metaphor from computer science: the greedy algorithm.

A greedy algorithm is a method of searching for a larger solution by finding smaller solutions and adding them up. So, for example, if the overall goal is to be happy, then a "be natural" algorithm would seek happiness at this moment, and the next moment, and so on, with the idea that it would build happiness in the long-run.

In computer science, greedy algorithms are known for being reasonably efficient at getting good solutions, but they have one glaring weakness: it's possible to get stuck. For example, "be natural" could dictate that you act on your anger at this bar at this moment, and so you punch a patron in the face, which lands you in jail. Jail then makes you less happy than if you had just made some long-term assessment of consequences, acted unnaturally polite, and walked away.

So clearly "be in the moment" or "be yourself" aren't rules we should follow at every minute of every day. But how often then? Is this advice applicable 99.99% of the time, 95% of the time, or just something we should say to ourselves every once in awhile when our acting unnatural is getting overboard, and doing us more harm than good?

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.

There are two kinds of acting: method and standard. In standard acting, you put on a smile even if you're unhappy or bored on the inside; the inner doesn't have to match the outer. In method acting, you first synchronize the inner with the outer. In order to smile, you think happy thoughts. Then when it's time to produce a smile, it all comes out naturally.

The problem with method acting in everyday life, though, is that it compromises your inner-authenticity. You have to bend your understanding of the truth to accomplish a social outcome. Self-deception isn't inherently wrong, though. Much of our social cognition steers us to ideal social outcomes. For example, flirting is often unconscious to give ourselves plausible deniability. Or, we often believe the best in others for game theoretic reasons, to encourage games of reciprocity.

But method acting adds a layer of self-deception on top of our unconscious one. At least with standard self-deception, your deceptions are consistent. If you unconsciously believe yourself to be more powerful than you are, for example, when the world proves otherwise, you'll still maintain that self-image. But if you consciously prop yourself up with positive thinking, when you encounter resistance, that inner muscle responsible for keeping your self-image may become satiated, losing its force, and leading you to a reckoning.

Happiness may require self-deception, but if you consciously convince yourself to be happy, then you'll have to consistently apply pressure against your inner truth to make the outer truth work. If you apply enough of that intentional thinking, your cognitive load will distract you so much, that your mannerisms will lack the vitality and life of someone behaving spontaneously. By that point, you would have been better off with only relying on the occasional fake smile rather than becoming a robot.

The radio program This American Life has an episode titled "Wrong Side of History" about a father who steered his daughter away from Bernie Madoff's multi-billion dollar Ponzi scheme. All of the father's hectoring, though, strained their relationship, when the daughter's millionaire in-laws enjoyed Madoff's riches for 15 years.

The father-in-law died early, before Madoff was caught, whereas the other father lived long enough to be vindicated. Had the vindicated father died earlier, would he had enough solace on his deathbed knowing that he championed sound investment principles? Would 15 years of strained family ties have been worth it? What if it was 150 years? How long does an investment have to seem to be doing well for it not to matter that it is fundamentally bad?

Happiness is everything. You wouldn't ever do something that you didn't think would make you happy, right? You might object saying that making other people happy is more important, but then, it could be argued that that virtuous feeling of making others happy ultimately makes you happy. Some people believe that all motives or thought processes can be unified by single personal imperatives like happiness or pleasure. The objectivists believe everything can be ultimately reduced to self-interest. And some psychologists believe everything can be reduced to symptoms in the head.

But to focus solely on one's personal experience is to live life with a mirror constantly in one's face. It's akin to measuring the world only by the feelings it generates in you, and not on the actual content of the world. The philosopher Robert Nozick asked, "Would you rather be a brain in a jar that was stimulated all the time to feel happy?" Most people would answer no, which Nozick ascribes to the reality principle. Being connected to reality is important in of itself. We do things often because of their intrinsic value, not because of their felt qualities. People help others not just because it feels good, but because they believe it to be good. And while it could be argued that following one's righteousness feels good, the helper is not chasing the prospect of the good feeling of righteousness. If the payload of good feeling is removed from the equation, as it is often reduced to a split-second of satisfaction, then pretty soon it starts to look like the virtuous are chasing virtue for its own sake.

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.