There's not one among us who hasn't been exposed to the image of the overworked, stressed out executive unappreciated by his bosses, given an endless amount of tasks for which he earns too little praise.  Perhaps you've been or are that very executive, eager to raise your middle finger in your superior's direction so as to advise the boss to stick it where the sun don't shine.

Gurus, work-at-home schemes (or scams), and multi-level marketing operations thrive on this imagery.  Why spend hours commuting and working for someone else when you can be the top dog working for yourself?  You will be endlessly urged to become your own boss and earn what you 'deserve.'  Seminar legends promise to instruct you, for a hefty fee, how to become an 'expert'  and position yourself so you can charge thousands of dollars per hour working when you want, with the implication that this will be as little as you want.  Not long ago a bestseller came out with the assurance to teach you the magic formula to have a single-digit work week and live a life of leisure.   

It's really critical in situations like these to separate the sizzle from the steak.  What the consultants and seminar stars and self-help coaches dangle before you is achievable . . . for some.  It's just not achievable for all and doesn't come with hours per week of effort. 

Take leadership for starters.  Not all of us can be leaders.   Not everyone has the personality, temperament, or skill to be a leader; but even if we accept fully that leadership in its entirety can be taught, if everyone were a leader, then who'd be the followers?  Military organizations work because of their top down design.    Soldiers need commanders to tell them what to do, just as the commanders need the soldiers to do what they're told.   Some soldiers will, over time, rise the ranks to become commanders and give their own orders.  Those that do will achieve the honor by the strength of their commitment and perseverance.   Most won't get there. 

And this is where I think the majority of seminar studs and self help gurus are being disingenuous.  At least in the military, when most start out with a hard to reach goal, such as being an air force pilot, each is warned up front about the tremendous challenges ahead and that most at the starting gate will never cross the finish line.  These odds are posed as a challenge -- do you want to be one of the select few?  The gurus, on the other hand, promise or allude that everyone can be an expert/millionaire/happiness junkie, provided they pay the workshop fee.

Don't misunderstand me.  I'm not suggesting that everyone hawking an excellence seminar or how-to-become-a-millionaire course is a charlatan.  The well known gurus really have achieved some degree of success in what they're peddling, though in most cases you can't be sure if most of their success came from the field they're instructing others in or from getting others to sign up for that instruction from them.  I can readily think of one financial literacy 'expert' who markets a very popular line of financial independence books.  He's very vague about how he personally climbed the financial ladder, and many of his tips have been ripped to shreds by other experts.  It would be readily believable that this guru achieved his big financial paydays from hawking his message rather than practicing it. 

Where the gurus are misleading, assuming they walk their talk, is in convincing anyone that they can successfully mirror the guru's progress.  If I am shown to possess sophisticated ballet talent, then perhaps I'll be in a position where I can mirror Mikhail Baryshnikov.  An average dance student would never get to that position, even with intense practice at young ages.  Tiger Woods was a golfing prodigy by the age of three.   He wasn't the first toddler to take up golf, but how many have achieved his progress?   The path to riches isn't as clear cut.   One needn't be the best, the smartest, or the first to get rich.  Nonetheless, one has to be clever, have good ideas, or be able to execute mundane ideas better -- and not everyone has this ability.  Simply put, not everyone possesses the ability to get rich.  Or to be a great writer, a great masseuse, or his own boss.  It's just a simple fact of life. 

Nor can everyone be a well-positioned expert.  The dictionary definition of expert is somebody with a great deal of knowledge about, or skill, training, or experience in, a particular field or activity.   The acceptable definition in today's internet age is more like somebody perceived to have a great deal of knowledge, skill, or training in a certain field.   True experts satisfying the dictionary definition are very hard to find.   The true expert understands his subject matter inside and out, so well that he can discern patterns and relationships across seemingly unrelated fields.  An expert chef, for example, might be well versed in food science, farming techniques, and nutrition, in addition to cooking -- or at the very least, he's studied cooking in a variety of venues to perfect his craft and had real diners do the judging.  The perceived expert is someone who seems to know what he's doing.  We see him on television or his book on the shelves, and we imply, like we're supposed to, that he's an expert.  How else could he have gotten the TV show or the book deal?  Perceived experts, more often than not, are experts at marketing, if nothing else.

A perceived expert usually makes more money -- a lot more -- than the real expert.  This is because the real expert is actually out there furthering his expertise while his perceived expert cousin leverages his perceived expertise to sell a highly marked up product or service.  Think of most infomercials you see on television in which an 'expert' offers to share with you his 'secrets' -- it could be for no-money down real estate, cash flow notes, or a making money package.   If each of these "experts" were truly making a mint doing what they're going to teach you, why then would they be offering courses for hefty fees so you could purportedly do the same?  You don't see Warren Buffet in an infomercial hawking investment courses or Brad Pitt soliciting students for a do-it-at-home movie star acting course.  Each man is too busy making money actually investing and acting.    'Expert' is so watered down a word nowadays, when I see it next to a name, I instantly think of the terms "award-winning filmmaker" and "gold medal beer winner"  -- fancy sounding phrases that have been used too often and too indiscriminately to mean much on their own.

The good news is that with the loose definition of expert practiced today, it's a lot easier to get yourself classified as one.  The bad news is that most people still don't possess the marketing chops demanded to position themselves as a pseudo-expert able to call his own employment shots. 

It doesn't really matter if real or imagined expertise can be taught either, because there's still an even more compelling reason why everyone can't be his own boss: time and goal management.  To be your own boss, you have to be able to set your own objectives and find ways to fulfill them.  If you truly are an expert, you have to find ways for people to know about you and employ you.  (Ultimately, you're never your own boss.  Your customers are your boss, and without them, you have no job).   You may have to develop your own product, and once that part is finished, find out how to reach the people who'd benefit from it.  It's not easy, and most of the be-your-own-boss crowd would give up before they started.  For those that forge ahead anyway, they have to know how to break tasks down and then allot the time it takes to complete the tasks, never knowing for sure if the effort will pay off. 

The majority of people go to work for a boss.  Their superiors tell them what to do and by when to have it done.  They don't have to hunt for clients or assignments unless that's their job description.  Quite possibly, they hate their jobs, but all they have to do is show up and do the work to some satisfactory standard and get along with fellow employees to some degree to be assured of collecting a predictable salary.    

As tempting as it could be to shout four letter expletives at the bosses, it's these bosses that tell you how you're going to utilize your day to earn that predictable income.  You might have better ideas how you want to spend your day, like playing pool or watching sports games on cable, but those ideas don't generate an income.   At a regular job, in which superiors monitor your work, you couldn't take 4 hour naps and read Comopolitan out in the open.  You have to document some kind of productivity.  When you're your own boss, there is no one above you to tell you what you can't do.   You must monitor your own progress.   

The conventionally employed show up in an office during conventional hours.  The Be-Your-Own-Bossers work when they want.   An advantage of being able to set your own hours is that you can fit in activities the conventional worker can't, like go kiteboarding for three hours mid-afternoon or do laps in the pool.  The disadvantage is lack of productivity.  With no one but you to oversee your progress, it's too easy to be unproductive.

For the undisciplined, unstructured time becomes a license to waste it.  Watch the typical conventionally employed during their time off.  They lounge in front of the television set or sleep half the day.  It's not an issue for them.  They can waste this time.  There is a clear delineation between their time on and their time off.  Not so for the be-your-own-bossers.   A be-your-own-bosser has to be more vigilant with his hours.    

Are you the type of person who can manage your own time well when there's no one else around to set your agendas?  Or are you the sort of person who turns all unstructured time into your own personal free time?  How you answer will determine whether you are even qualified to attempt to be your own boss. 

And then there's the last important consideration.  Can you motivate yourself to work regardless of the project and discipline?   To many, a job is a job, and if that's how you see your current conventional employment, stick with it.    All a job fundamentally is to you is a way to earn money to pay the bills and elevate your lifestyle.  A be-your-own-bosser sees the work as an extension of himself.  He's putting in so much of his own time into a project he personally chose to be involved with that what he does should matter to him, so much that he can summon the energy to work long hours without a surefire payoff.  The upside is certainly there if his ideas and efforts pan out.  The downside is all that effort could be in vain.  But the be-your-own-bosser doesn't see it that way.  He feels his full potential would have gone untapped had he remained a conventional employee doing what The Man dictates.

I always possessed the be-your-own-bosser mentality. I zoned out when asked to work on tasks that had no interest to me.  On the other hand, I could self initiate projects and see them to completion without supervision or guaranteed promise of reward.  When I'm out on the waves kiteboarding for several hours, I have a gnawing of guilt that I should be working.  It's this feeling that pushes me to advance some project to some degree every single day -- unless I'm away from home on vacation, ill, or have some other pressing reason why.   I don't always know how to get from step A to step B -- in fact, most of the time I have no clue -- but I know there's a step B, then a step C, and then a step D I have to reach.    I wish I could stand to work conventional hours at a conventional job, a pipe dream about as concrete as wishing that most conventional jobs offered work for me that was fascinating and amazing.  Sadly to say, most of those jobs aren't so thrilling.  When I worked as a software engineer for a Swedish startup, even I fell asleep describing to others what I did.

As if it hasn't been made abundantly clear by now, I don't believe you can teach the be-your-own-boss mentality; and for those that would argue that you can, certainly not as easily or as quickly as the seminar and infomercial jocks promising you quick riches would have you believe.  Being your own boss is more a life mission than a vindictive act against all the prior superiors who've wronged you.  Like durians, caviar, and disco, being your own boss is not for everyone.