Career Conspiracy Theories

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Part 1 – Why you might feel stuck

Why don’t more people like their jobs, or really like their jobs?

It is easy to feel like there is some conspiracy preventing us from career (or life) fulfilment. But only you can figure out what is helpful to you because only you really know your personal situation (if others knew, it wouldn’t be that personal). Plus, nobody is going to do the hard work for you.

It is more likely that advice doesn’t fit your present circumstances than the advice itself being wrong. Most advice comes without accounting for the variations across our unique experiences and desires. The map is not the territory; and we’re all in different territories. I can give generalizations based on what worked for me; but one’s specific circumstances (territory) and current understanding of them (map) won’t be the same as mine.

It is exceedingly rare to receive and difficult to give good advice. The diversity of human experience, how difficult it is to express ourselves to another person, the challenge of someone truly listening and empathizing with another, makes it so. In other words, if something doesn’t work, don’t get cynical. Get curious. Try to see the set of assumptions informing that piece of advice. Take the general principles and see how they apply to your particular situation.

Short-term vs. Long-term

We are wired to prioritize the short-term. And, fair enough: if you don’t survive the week, forget your plans for later this the year. The short-term focus of job security feels more urgent and worthwhile than the long term focus of a meaningful career. Yet prioritizing the short-term over the long-term leads to dissatisfaction in both the short- and long-term. This is how you end up feeling “stuck” in something.

Feeling stuck is an inflection point. It is the point when you realize that your short-term is under control but your long-term projections make you feel queasy. You’re going through the motions but have forgotten why. So the solution out of feeling stuck is to think — and act — with a long-term mentality. If you continue to focus on the short-term, expedient solutions, you will continue to feel stuck.

Career security, not job security

A job is not servitude. A job is not the same thing as a career. A job is an agreement you have negotiated with others to receive compensation for taking responsibility over something.

While job security is important, it is essentially a short-term deal. Even worse, job security depends on many factors outside of your control: company culture, economic climate, the success of the company, your boss’s abilities.

By contrast, career security is more important and it is largely within your control. Career security comes from having put in the work to develop skills or abilities of value in your domain. For example, take a lawyer who deeply understands the legal system, can strategize, and can carry cases toward favourable resolutions — this person has career security and, even if let go, a can almost definitely find another job because few can do these things well.

Part 2 – The MAP

The virtuous cycle

We feel a sense of fulfilment when there is alignment between short-term activities and long term goals. Job satisfaction plays by the same rules. As Daniel Pink mapped out, job satisfaction consists of having a sense of mastery, autonomy, and purpose in what you do. These three elements are largely within your control, so long as you’re willing to put in the hard work and patience. In a nutshell: mastering a skill makes you more in demand and gives you more options, which leads to more autonomy to choose your path, which enables you to pursue things that give you a sense of purpose.

If you’re letting excess competency idle while you sit there overqualified for your job, who benefits? If you shy away from pursuing a sense of purpose, you are shying away from contributing in a more unique and more needed way. Keep learning. Keep looking for new challenges that appeal to you.

Mastery: start here

Do you wash your hands before or after you pee? Sequence matters. Start with mastery. People need to trust you to be able to give you more trust. You can’t average your way up the ladder. You must do the work before people will give you more work. It’s human nature. Competence – the ability to do something successfully or efficiently – is the currency of trust. Mastery is working toward total competency in a specific domain. If you start exercising autonomy before you have much competence, you’ll just come off as entitled.

Mastery is long-term. You will go through dips and long slogs. A long slog may feel long, but that’s actually a shortcut, because it gets you where you want to go faster than any other path. It requires more patience and diligence than is at first apparent. It would be foolish to expect that a farmer could “cram” the growth of his crops and all the watering into three days, but we lose sight of this when we buy groceries. When it comes to mastery, you are the farmer. So don’t expect to master something overnight. It takes time, but with focus it is eminently achievable to attain more competence than you have now.

As you pursue mastery, you will begin to gather stories illustrating your competency. Keep track of these. Literally keep a list and update it regularly. A list helps you see how you’ve developed, which keeps up your momentum. It also serves as a quick reference to draw on for networking and job interviews. Lastly, a list will enable you to look back on what you’ve accomplished and see what actions where most helpful in your pursuit of mastery.

Autonomy: use it or lose it

For a moment, think of your career like a garden. You have the ability to create a beautiful garden based on your own definition. We all do. But gardens don’t happen by accident. Nature is indifferent. There is a lot of work to put in — clearing land, planting, etc. — before things start to feel like they are going your way.

A garden is an expression of autonomy. It only comes into being through exercising the freedom one has to create it. The longer you put off creating a garden, the harder it will be to carve out a plot. The less attentive you are to your plot, the more weeds will creep in.

The same goes for job satisfaction: if you want it, you have to carve it out of a largely indifferent world. Through patience and discipline you will eventually get moments where things go your way. You can build momentum, but you first need to overcome resistance. The only path is sustained, self-directed effort.

Putting something into the world gets you closer to the truth. The truth can be scary. What if the truth is that your assumptions were wrong? In the long run, it’s better to know. Always produce. Are you producing something, however bad? As long as you’re producing, you’ll know you’re not merely using the hazy vision of “someday” as an opiate.

Autonomy is your calling card. Your intentions aren’t visible from inside your head. Like a garden, people only see the by-products of our intentions. To the rest of the world, what you produce is what they know of you. Producing means giving an accurate signal to the world what you care about. This, too, can be scary; but it is the only way to get put in touch with those who share your values. And that, certainly, is worth a little bit of fear.

Purpose: there isn’t “one”

It is a real challenge to find compelling work. Build foundation of knowledge (mastery). Try out smaller projects (through exercising autonomy). And through this relentless experimenting, you’ll find something that really matters to yourself and others. Keep experimenting because, as Viktor Frankl explains, the meaning of life is not static:

The meaning of life differs from man to man, from day to day, from hour to hour. What matters, therefore, is not the meaning of life in general but rather the specific meaning of a porson’s life at a given moment. To put the question in general terms would be comparable to the question posed to a chess champion: “Tell me, Master, what is the best move in the world?” There simply is no such thing as the best or even a good move apart from a particular situation in a game and the particular personality of one’s opponent. The same holds for human existence. One should not search for an abstract meaning of life. Everyone has his own specific vocation or mission in life to carry out a concrete assignment which demands fulfilment. Therein he cannot be replaced, nor can his life be repeated. Thus, everyone’s task is as unique as is his specific opportunity to implement it.

As each situation in life represents a challenge to man and presents a problem for him to solve, the question of meaning of life may actually be reversed. Ultimately, man should not ask what the meaning of life is, but rather he must recognize that it is he who is asked. In a word, each man is questioned by life; and he can only answer to life by answering for his own life; he can only respond by being responsible.

Life is not about finding yourself. It is about creating yourself. The good news is you can get better at it through hard work and seeking guidance from others who are further along.


It is easy to feel like there is some conspiracy preventing us from career (or life) fulfilment. Turns out, it’s just takes a long time, a lot of hard work, and some humility. Sometimes it feels unnatural, like forcing yourself to focus on the long term. Sometimes you get bad or inapplicable advice. But if you decide you want to get more out of life — if you really make up your mind — then you can do it.

So on one hand, have a little compassion for yourself — you’ve likely been trying your best. To think you can rewrite your past decisions is an illusion. On the other hand, there is every reason to believe you can learn from the past and do better in the future.

All you can do is learn, commit to something based on what you now know, do it, learn some more, commit and do some more. As Chris Sommer says, “Dealing with the temporary frustration of not making progress is an integral part of the path”. Half of the battle in becoming a standout individual is making the decision to actively try to succeed.

One thought on “Career Conspiracy Theories

  1. I didn’t realize you were writing another article James! Were you working on it here? Talk later today? I miss you!

    Sent from my iPad



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