Why Your Dream Job Doesn’t Exist

Why Your Dream Job Doesn’t Exist

How do you become an entrepreneur? The answer may seem anticlimactic, but it’s surprisingly simple.

Just decide to be one.

Entrepreneurship requires no sign-up form, no application process, and nothing outside of your own head. You don’t need to be certified, and you certainly don’t need to have a business up and running.

All it really requires is a way of thinking less bound by normative cultural conventions… and perhaps a logical evaluation of the alternatives.

The Dream Job

I’m going to challenge a big idea here:

I don’t think you should spend your entire life looking for your dream job.

In fact, I think that for most people, the whole notion of a ‘dream job’ — a job that you look forward to each and every day because it’s intrinsically fulfilling and enjoyable — doesn’t exist. There are three reasons I make this claim:

First, very few people enjoy their jobs at all. According to a 2017 Gallup poll, 85% of people working full-time jobs do not find them engaging. Not only do they lack emotional commitment to the stated goals of whichever organization they work for, but over half of them would literally leave if given the chance. Statistically speaking, it does not appear that most of the world ever finds themselves in the dream occupation they spend their entire lives looking for. ‘Dream jobs’ appear to be the minority, not the majority — they are exceptions rather than the rule.

Second, most people, when asked to picture their ‘dream job’, picture not a job at all but instead a hobby or something with similar nonfinancial motivations. Merriam-Webster defines a job as ‘the work that a person does regularly in order to earn money’. Most people, however, presuppose that their employment at their dream job is contingent on them having enough money not to worry about working in the first place. But this is a logical paradox: if they are working for reasons other than to earn money, then by definition they are not really working. It might be better to call it a ‘dream hobby’, or, more generally, ‘what someone would do if they were free from financial constraints’ (an important point for later).

Third, the time most people spend agonizing over not working at their dream job could simply be better spent making more money. Because the more money you have, the less you need to feel obligated to work at a job you don’t like in the first place.

‘The grass is greener on the other side’ is a common saying for good reason. People always want what they don’t have. Idealizing about the so-called dream job is simply another way people take their minds off the mundanities of their current occupation.

I may be wrong, of course. Perhaps everybody does have the perfect job out there, just waiting for them. But that doesn’t seem likely considering what the nine-to-five job actually represents: a social convention. In fact, all jobs are. Every job on the planet, including those you may create yourself, is the product of a socially agreed-upon pattern of behavior that trades time for money, not an intrinsic part of what defines our humanity.

Sure, there are probably some jobs that are more dreamlike than others, jobs you would enjoy more due to similarities between your learned disposition and the job requirements. But all jobs fall privy to the same fault — that they are jobs, and that, due to the dissonance between what we evolved for and what we are actually doing, eventually our minds will find some fault with the activity so as to render it no longer a ‘dream’.

If you think about it, people don’t really need to work at all. There’s no string of base pairs in our genome that codes explicitly for cubicle skills. Work is certainly a fundamental component of the society we find ourselves living in, but there is nothing endogenous to the human mind that says it must be so. Humans don’t need to clock in to their jobs any more than a cat needs to poop in a litter box. These are learned behaviors — products of a specific cultural upbringing.

Freedom Proxies

What people really want is not so much a specific type or piece of work, but freedom. Freedom to decide what they want to work on, not their employer. When they want to work on it, not when the bureaucratic system handling corporate hours dictates they have to.

And what’s the best way to get that freedom?


Money is a proxy for power.

And power is a proxy for freedom.

Therefore, the amount of money you possess (including assets) is directly correlated to the amount of freedom you have in any given situation. If you possess money, then you also possess a means by which to exert your influence on the world (power); if you possess power, then you also possess the means to choose what you want to do, and what you don’t.

Want to go parasailing in Cancun? You need money. Because money gives you power, which gives you the freedom to make that choice.

Want to quit your job and lay on the couch to watch Friends all day? You need money. Again, because money gives you power, and power gives you the freedom to make that choice.

Money can’t buy you happiness.. but it can definitely buy you freedom (which, according to this study, has a significant positive correlation with happiness).

I would venture to say that, paradoxical to what society may have you believe, most people would actually be happier if they spent their days lusting over money as opposed to pursuing an ill-fabricated dream career that may or may not even exist. But hey, that’s just me.

At this point, it likely appears that my goal is to convince you that only determining factor of a job should be the money associated with it. And you’d almost be right, but not entirely. In reality, there are other important factors; among them, the health risks associated with the job, your own domain-specific expertise, and the degree to which you truly do or do not enjoy your work. But these still pale in comparison to the freedom attainable with sheer money, and so for the sake of argument we will assume:

1. To be an entrepreneur carries with it no excess health risk

2. Entrepreneurship requires an average, certainly achievable, level of domain-specific expertise

3. Entrepreneurship doesn’t require that you love your job. Ambivalence is fine.

Now the hypothetical ‘you’ is in all cases, average.

Entrepreneurs versus Employees

My main gripe with the notion of a dream job in the first place is that it pushes the idea of working for somebody else. The truth is, in the majority of cases, working for somebody else is ineffective. It holds people back, and keeps them shackled within a carefully constructed pattern of employment encouraged by both the government and modern educational institutions. If you complete their cultural checklist — if you go to school, get a degree, begin a job in a cubicle somewhere, and live out your days pushing pencils and gossiping around the water cooler — because you’ve been told, as opposed to performing the calculations for yourself and determining that working for somebody else is the most effective thing for you to do, then free is the last word anyone will ever use to describe you.

To clarify: I don’t think that working for somebody else, in and of itself, is bad. I merely think that for most people it is a less-than-optimal solution. Consider the average Canadian salary, ~$50,000. Most young adults today will start working in their mid-20’s, due to the time constraints of formal education. If we assume that retirement age stays locked at 65 (it won’t, but it needs to be fixed in order for us to perform meaningful calculations), that means that most young Canadians have around 40 years of working life ahead of them. Multiply the number of years by the average salary and you come to a frightening proposition: the average Canadian will make just over $2,000,000 over the course of their entire working life.

Now, $2,000,000 may seem like a large sum to many of you. But when placed in the context of an entire human being’s life, you start to realize the futility of listening to culturally mandated standards of what people shouldbe doing with their short time on Earth. I mean, seriously? $2,000,000? Is that the price you value your life at? The sum total of all your relationships, experiences, thoughts and desires? Obviously not. But in an economic sense, taking into account the government and the wider corporate stratosphere, Canadian human beings seem to consider themselves worth less than a new Bugatti Chiron (~$900,000 less, for those of you wondering).

Most young entrepreneurs and businesspeople do not consciously perform this calculation, but they perform a variant of it nonetheless. At some point in their life, the utility function that says “entrepreneur” begins beating out the utility function that says “employee”, and very few people ever consciously go back to wanting to work for somebody else.

I am of that camp as well. Personally, I’m of the honest opinion it is mathematically improbable that, if given a fair chance, a person could notgenerate more than $2,000,000 in 40 years on their own. Or, accounting for the vacation time afforded by an average job and re-framing in terms of the total number of hours worked (2087 hours per year multiplied by 40), 83,480 hours. That is a mind-boggling amount of time.

Even if one were to logically suppose that you only generated one $2,000,000-worthy business idea per year (and keep in mind, you likely have several per week) they would only need to succeed 2.5% of the time for them to beat out the average salaried employee after 40 years.

Of course, many salaried positions (indeed, half by definition) pay out more than $50K, so we should at least consider those as valuable alternatives to entrepreneurship. PhD positions, for example, pay out over 2x the Canadian average, and are in many ways likely preferable to the cognitive tedium that face low level white-collar workers. Or if you’re into something more exciting, the average trade worker in Canada earns ~20% more than the average cubicle worker, and some trades (particularly the more dangerous ones) can be compensated very well indeed.

But both of these alternatives require potentially lengthy bouts of schooling, which we need to take into account if we’re to perform an appropriate calculation. If we suppose the average PhD requires an additional 8 years on top of a Bachelor’s degree (a fair estimate, given this), that leaves you only 32 years to carve out an income, or ~$3.4M total. Compared to the average Canadian salary, you’d be doing well — but not that well. Certainly not as well as one might expect, given the fact that your job description literally involves the advancement of human knowledge.

Even the wage of a fully certified medical doctor isn’t immune to this sort of reasoning. Using similar calculations for other professions, the average Canadian doctor will make over $8.5M by the time they’re 65. This is a lotof money, especially in comparison to the jobs mentioned earlier. But is it still more money than you think you can make on your own, given 40 years worth of time?

Intelligent work

The bottom line is, working is not the norm. People may attempt to convince you of it, society may attempt to convince you of it, but it is not the norm. Human beings did not evolve for the specific use case of sitting in front of a monitor 7.5 hours a day and filling out forms. We did not conquer the African savannahs because of some intrinsic capability to send e-mails.

Yet it can’t be argued that some kind of work is an unavoidable consequence of living in our current economic system. Therefore, if you have to do it, you might as well do it intelligently, and at the least you should work out as many income-generating alternatives as possible before committing to a decision. If the rest of the West is going to play capitalist economics on you, you might as well play capitalist economics back.

Don’t follow the current just because the current exists — ask yourself if the current is being beneficial to you, and if not, find a way to bypass the river entirely. Don’t let the world succeed in convincing you that entrepreneurship is only reserved for the special, because according to the calculations performed above, it appears exceedingly more likely that it’s reserved for those special few who can perform fourth-grade multiplication.

Instead of sticking your head in the sand and wishing you were working at your ‘dream job’, why not take actual steps today — and by today I mean right this moment — to put yourself in a financial position where you have the freedom to choose to not work at all?

Perhaps your dream does exist. But in order to truly find it, you first need to unshackle yourself of the constraints of financial necessity and become free.