Why Your Career Hasn’t Turned Out the Way You Thought it Would, And What to Do Next

My first job out of the Army was a dream come true for a striver with OCD tendencies.

The job came with several shelves of active case files and a rigid/hierarchal reporting structure – perfect for an ex-military officer. The pathway to promotion seemed to be clearly laid out, just waiting for someone like me to forge ahead to success.

Nobody can learn and implement a system like me. I looked forward to a rapid climb up the corporate ladder with the high salary that would naturally follow. After all, I was leaving the Army behind and striking out in the world of business, where ability is quickly recognized regardless of rank, where hard-chargers move to the front of the line.

(Allow me a brief, indulgent smile as I fondly recall my younger, naïve self.)

I dove in, doing what I do best:

• I documented dozens of processes and pinned them to my cubicle walls.

• I created a checkout system to ensure that no paper file would ever go missing.

• I even hung up my scissors and stapler so they would be instantly available without cluttering my desk.

And, of course:

• I worked long, hard hours to get every bit of documentation and reporting precisely right.

Meanwhile, Andrew in the next cubicle spent all day playing fantasy baseball.

In the presence of a master (scammer)

During those initial months of hard work and long hours, I never heard Andrew work on his job-related tasks more than one hour a day. The rest of the time he was on the phone discussing batting averages and earned runs.1This was WAY before online fantasy sports or even the use of spreadsheets to manage stats. In 1991 it was all newspaper box scores and paper and pencil, from what I could tell. Not being into sports myself and not wanting to sound dumb, it took me several months to even figure out what this guy was up to.

Andrew spoke to me only once: “Hey. I just heard something that will make your files stand out.”

Me: “What do you mean, ‘stand out?’”

“You know, without any extra work. Look, I just heard three top managers saying that they prefer the file prongs bent inward rather than outward.”

He demonstrated with a file:

Guidance from the paper-file era

“I’m going through all my files right now and changing them.”

One year later, Andrew had climbed two rungs up the corporate ladder. I was still organizing my case files and updating my process lists in the same cubicle.2And for the record, bending my file prongs from out to in made no difference at all for me. What? Of course I tried it!

It became a recurring life theme: Diligence and attention to detail, mastering the rules made up by other people, overdoing and over-documenting…while shortcut-takers who played by their own rules passed me by.

Sound familiar?

Part 1:
Why The Career Success Rules You Were Taught Growing Up Didn’t Work in the Real World

In which I explain how your education set you up to fall short of your career aspirations without ever quite figuring out why.

A world of rule-followers

When it comes to pursuing a purpose in life, there are three types of people:

• Those who play by other’s rules
• Those who refuse to play by any rules
• Those who play by their own rules

Most of us are a mix, but if we break people down by the category that they mostly are, it looks about like this:

Long after my experience with Andrew – far past the time when I should have learned my lesson – I was dismayed to realize that I’d been a rule follower my entire life.

I fooled myself every step of the way. I thought that over-mastering processes and extraordinary attention to detail meant I was sort of making my own rules as I went along. But I wasn’t; I was just being an uber rule follower as I did exactly what management wanted. I was a cubicle dweller stuck at the side of a river in a swirling eddy, watching make-your-own-rules people speeding by in the faster current.

How does this happen? How do we become obsessive rule-followers, forever faithfully executing the directives from other people? Two reasons:

1. It’s in our genes
2. It’s the way we’re conditioned from birth

About number one: you and I come from a long line of rule-followers that stretches eons into the past. For much more on that, read my article, You Talk Like a Lone Wolf, But Act Like a Sheep. How to Break Away from the Herd and Achieve Your Goals.

As you’ll learn from that article, given our genetic heritage we don’t require much programming to become a devoted rule-follower.

Which brings me to number two, conditioning.

All humans (very much including myself) LOVE systems, and systems are what we use to train educate our children in the supposed ways of worldly success. By the time we step into adulthood, our conditioned responses are nearly automatic.

How does the conditioning process work?

The conveyor belt to success

Growing up is all about learning the rules – social, academic, financial, and more – that allow us to survive. But we’re taught something else in addition to the rules: It’s ingrained in us that mastering the system leads to success in life.

The system tells us to do THIS, and THAT will result. It’s always some variation of:

Get good grades → go to the right college → get the perfect job

Easy-peasy, step-by-step.

But there’s a problem with this pseudo-knowledge that we absorb from both conscious instruction and subconscious experience:

when we are growing up, success is mostly built in.

(I’m talking here about our perception of success, which for the human mind just means moving forward toward some [often hazy] goal.)

And “move forward” we do, from birth to early adulthood. The process of growing up is a long conveyor belt. We are plopped onto one end of this conveyor belt shortly after birth like a lump of raw material making its way through the assembly line in a factory.

At each stage of manufacture, we are progressively formed into nearly identical copies of the standard functional member of society.

And what do children absorb as they go through this process? I mean, besides their multiplication tables and the hidden meaning behind To Kill a Mockingbird?

Children learn that no matter what they do, they move forward, ultimately achieving their full glory.

Yes, glory: their penultimate achievement of finally attaining the starring role in the movie script of their young lives, otherwise known as being a high school senior.3Grade 12, about age 18, for my non-American readers. Anyone who sees their high school classmates still reminiscing about their glory days on Facebook knows what I’m talking about. (Cue Springsteen.)4Now I think I’m going down to the well tonight and I’m going to drink till I get my fill. And I hope when I get old I don’t sit around thinking about it, but I probably will. Yeah, just sitting back trying to recapture a little of the glory of. Well, time slips away and leaves you with nothing mister but boring stories of…glory days.

Even the non-popular kids and non-athletes who didn’t achieve the pinnacle of high-school fame still got to play king of the mountain for a year. Their mountain may have been smaller, but they were still standing on the top.

Let’s zoom in on the end, the stage in the process that is remembered so fondly by so many:

At the end of the high-school section of the conveyor belt, some people hop onto the “college extension” conveyor belt…which for many students – but not all – is more of the same.

And every step of the way, every person becomes more convinced that they, and they alone, were the ultimate driver of their own fates. Indeed, each traveler on the conveyor belt thinks, “I did it my way.” (Cue Sinatra.)5I planned each charted course, each careful step along the byway. And more, much more than this…I did it myyyyyy way.

Conveyor belt wisdom

This is what you learn in the Academy of the Conveyor Belt:

If you master the systems built by other people, you get ahead.

What you don’t realize is that you are almost guaranteed to “get ahead” anyway because the design of the system will keep pushing you through.

You think it’s all causation:

“I learned the system and my knowledge and hard work moved me ahead.”

But there is only a weak causal connection. In reality, you just have to learn enough to not fall off the edge of the conveyor belt in order to stay on track.

Some people move ahead a bit faster (e.g., spelling bee champ, prom queen, shot put finalist, Phi Beta Kappa member), but it’s like using the “walking” side of the flat conveyor belts at airports instead of the “standing” side. All are being transported to the same destination. Some appear to have more success than others, but that success usually differs only to a degree.

A few fall off the sides along the way, but the vast majority make it to the end. For many the end is age 18, for others, it’s 20 or 22-ish depending on how much college they go into debt purchasing.

So, we learn this false lesson of causation:

“Mastery of existing systems and rules will naturally make me successful (and even happy). All it takes is hard work, and I can be anything I want to be.”

Although the “be whatever I want to be” thing has never been true,6e.g., wishing to become a star NBA player would never have been in my 5 foot 10 cards. Or a career based on singing. Or a multitude of other talents that I don’t possess, no matter how much I may want to. “be something that is good enough” has been an almost automatic achievement in the past.

In the past, with only a little effort, a young adult could make a short jump over a narrow space to a career conveyor that carried them all the way to the end. (“End” meaning retirement, death, mid-life crisis, whatever.)

Relatively few failed to make the jump:

And now?

The end of the line

What happens at the end of the birth-to-graduation conveyor belt now?

The world of work has changed with the erosion of labor protections and an increasingly competitive, increasingly global marketplace. Employees cost money – lots of money. Corporations large and small have worked diligently to figure out how to turn as many of their staff into low-paid, interchangeable parts as possible.

This trend of commoditizing and devaluing human labor has eaten its way up the food chain into the ranks of skilled professionals, devouring unskilled laborers, skilled laborers, and technical experts along the way.

This is not your grandparents – or even your parents – job market anymore. Increasingly, it takes perfect alignment of the planets and stars to move smoothly into jobs that you imagine to be in your “dream” category.

Some people get to hop on the next conveyor belt if their skills line up precisely with the needs of the job market. Some marry into the next belt and jump with someone else. Random, almost-uncontrollable factors:

• parents
• wealth
• location
• timing

…combine to give some people a conveyor to a future that is pretty darn good, if not exactly what they wanted:

The lucky few along for the ride of their lives

This is the real-world manifestation of “privilege.” Race, wealth, and the social status of families play a huge role in determining peoples’ paths through life…and the beneficiaries of this privilege very rarely acknowledge or even recognize their built-in advantages. As the saying goes, they were “born on third base and thought they hit a triple.”7An American baseball reference. When a player is on the third base of four, they are just one short sprint from reaching the safety of “home” base and scoring – with only limited danger of being tagged out of the game. Getting to third base is the real challenge, and they’ve skipped right over that part.

Yes, there will always be people who pulled themselves up by their own proverbial bootstraps, but bootstrappers still need timing and luck. An orphan who becomes an electrical engineer still requires there to be a shortage of electrical engineers in order to jump right into her chosen career.

Here’s how the rest of our lives look:

The not-so-fortunate along for the struggle of their lives…plus (spoiler alert) one brave person setting off on her own

On the non-charmed side of the landscape, there are a few conveyor belts, and most of us end up on one or two during our lives. Some are fast, some are slow, and many of them end before we are ready to get off.

But our training keeps failing us. We apply the rules that we were taught, that were supposed to work for our entire lives, but someone else seems to be rolling the dice and directing our moves. We keep ending up in the wrong location at the wrong time. Like luckless players in a cosmic game of Monopoly, we’re forever doomed to land on Boardwalk, which we’ve never owned and never will.

Bottom line: The system will no longer save you.

Hard-wired by a broken system

Society puts a lot of effort into getting their kids launched.

We instinctively know that we must give our kids the best chance at a successful life. Parents have passed on their knowledge to their children for eons. It’s what we do, it’s what we are programmed to do for the survival of the species. So, we build systems to pass along what we’ve learned.

But systems are inherently flawed.

You see, a system is just a structure based on past experience. It comes with a built-in assumption that what worked in the past will continue to work in the future. And it often does, right up until it doesn’t.

When change happens incrementally, systems function well and last a long time…sometimes for generations. When change happens fast, systems break down.

And the “birth, to adulthood, to career, to living the good life” system is pretty much broken. This system is teaching history lessons about what used to work, rather than strategies for success in our ever-changing future.

If you are a product of this system, the damage has already been done.

It took me many years to understand this: the systems of my youth had hard-wired my brain to expect that specific actions would lead automatically to specific results. I just had to follow the rules and try hard enough.
One advantage of age over youth: only experience reveals how the system really works (or doesn’t). Click To Tweet

Considering your path to success

This article is not about:

• Pointless calls for the system to reform itself and start training kids “how to think.”8I despise article conclusions that come down to saying, “I’ve identified the problem. Now all you people in charge of this problematic situation need to get together and figure out how to do a better job.”

• People who never made it out of the end-of-conveyor-belt pile

• People who hopped on the express conveyor belt and are on their way

This article is about:

People in the vast middle, wandering in search of the next conveyor, still thinking that if they can just figure out the system, they’ll find it.

What is it? It’s the conveyor built precisely for you. It’s the dream job with an excellent boss and a team atmosphere and no slackers and great benefits. It may not even be a new job, but a new position with your current employer where your skills will finally be recognized, where promotions and raises will follow and give you a sense of meaning and accomplishment in your life.

Sorry to be the bearer of bad news, but no one is working on a conveyor belt just for you.

Seriously, though, the situation faced by so many is this: trying to find another conveyor belt or hoping the current one doesn’t end abruptly.

It’s not a good feeling when the rules don’t work the way they are supposed to, when the lessons we learned don’t apply anymore. That feeling is called insecurity when you’re talking with others about it. When you’re alone with your thoughts, the feeling is called fear and comes with side dishes of anger, disappointment, and hopelessness.

Is there any way out of this situation? Yes, as long as you don’t think there is an easy way out.

Let’s loop back to Andrew, the fantasy baseball ladder climber.9No matter how far I wander, I always close my loops.

The Andrew method

Andrew was not a genius. He was just a guy who had a natural instinct for figuring out what the real rules were. In my company at that time, the pertinent rule was “appearances matter more than substance.”

Modern-day “Andrews” never expect that assigned daily tasks will bring the success they crave. They seek out another way, make their own rules, and weasel their way to the front of the line (or, the front of the conveyor belt).

Andrew’s approach is a big piece of the puzzle because it’s a “get real results” method. But don’t be fooled…it’s not necessarily a “get real happiness” method.

Long-term, Andrews may end up as unhappy as anyone else. But at least they’re mastering circumstances to get where they want to go.

That’s the essential attitude we want to harness, but with less gut instinct and more intention. We start by unlearning the unrealistic – or even harmful – parts of what we’ve been taught in the Academy of the Conveyor Belt.
A path established by someone else will never lead to your destination. Click To Tweet

Part 2:
The Difficult (But Not Impossible) Process for Changing Direction in Your Career and Life

In which I destroy any notion that changing your life will be a simple matter of applying a few easy tips, and instead provide a difficult (but doable) pathway forward toward your personal goals.

Rules don’t lead to ultimate outcomes

Here’s the equation we’re taught:

Following a Rule → Result → Happiness

Applied to real life, this is how the equation we are taught reads:

Hard Work → Promotion → Happiness

Here’s how this works out in reality:

Jan works 60 hours a week, plus at least one day on the weekend. Jan “gets ahead.” She is given more responsibilities, slightly more pay and a small promotion after two years. According to the equation she was taught, her hard work (paying her dues) and the resulting outcome should make her happy.

Here’s her expected outcome:

Expected “happiness” outcome

Jan gains more control of her time so she can take a one-week vacation without feeling guilty. She signs up for a cooking class and has a couple of non-work-related dinners with friends each month.

Actual “unhappiness” outcome

Jan now works 80 hours a week and 1-1/2 days on the weekend. She gives up unused vacation days every year. But if she can hang on for another year or so, a senior manager position might open up, and then…

Jan keeps working the “rules → results” math correctly – according to what she’s been taught during her time on the conveyor belt – and wonders why the last part, happiness, is always false from her perspective.

The problem is that it’s not an actual equation, because…

There is no reality where conveyor-belt wisdom holds true.

Following the rules, working the plan that’s provided, and getting whatever you want is a false lesson that we’ve all learned on our journey on the conveyor belt of early life.

The actual “get results” process

Following a rule that we learn in our formative years may or may not achieve the result we expect, and the result (whatever it is) may or may not result in happiness.

In Jan’s case:

Hard work is not an automatic predictor of a promotion or even a pay raise. And a promotion is not a certain predictor of happiness.

This is a distressing realization. Humans don’t like to admit that forces beyond our control, rather than our own efforts, may significantly influence our lives.

When we try to follow this equation (rules → results → happiness), it doesn’t work for this simple reason:

We are following someone else’s rule to achieve someone else’s result, and expecting it to lead to our happiness.

You didn’t think all those rules you learned during the conveyor belt years were designed specifically for you, did you? Of course they weren’t. Remember:

• Systems must be generic enough to push the masses along, and…

• Systems are unavoidably based on knowledge from the past, not knowledge about your future

No matter how well-meaning your teachers/mentors/parents were, they could not tailor the system specifically to achieve your happiness needs.

And when the equation fails, the little voice in your head keeps parroting the only “wisdom” it knows. The voice just keeps saying:

“You’re failing because you aren’t trying hard enough.”

But! You can unlearn the ingrained mental equation of your conveyer-belt years…and no math is necessary.

Driving the process backwards

I’m a big fan of backward planning. I was first taught the concept in the Army, and it’s pretty simple:

Start with the time at which you must accomplish something, then calculate how long each of the preparatory steps will take until you arrive at the time you must start.

It’s related to scheduling, of course, and everyone does it to a certain extent. But it can be applied to achieving life goals as well.

Instead of following a rule to get a result that is supposed to lead to happiness, you decide what makes you happy, then figure out what result will achieve that happiness, then figure out how to change or apply the rules to get your result.10 “Rules” include systems, ways of getting things done, as in “the rules of the game” for situations in your life or your job.

I know I promised no more math, but to summarize:

happiness ← result ← rule

We just have to let go of the misinformed notion I mentioned above that…

Following someone else’s rule (based on their past experience)

In order to achieve someone else’s result (based on their self-interest)

Will lead to our happiness (repeatedly disproven by our past experience)

When you work the equation forward, you are giving control of the ultimate outcome (your happiness in life) to those who establish the rules. When you work the equation backward from your desired end goal, you are deciding to take control of the rules or systems yourself.

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It’s still a difficult process

If happiness was easy, then everyone would be happy…including you.

You shouldn’t take anything I say to mean there is a process that involves less work in achieving your goals…unless “less work” is your goal. Instead, we want your hard work to be in pursuit of your own goals rather than the goals of others. But it’s still hard work, and it won’t get any easier if you put it off.

So: What rules or systems can we master that will lead to a result that will lead to our satisfaction? Let’s begin…

What makes you happy?

The most significant question, of course, is what will make you happy…or at least, happy-er (aka “satisfied”). Getting to that answer is way beyond the scope of this article, but we can at least narrow it down. A few guidelines to help you work toward your own answer:

First: Focusing on short-term income will always lead you right back to doing whatever you can for “the man” to rack up hours and climb the ladder. If true happiness for you equals:

• A new car
• Larger house
• Awesome vacation next summer
• Etc.

…then yes, the result you need is more money, and the way to achieve that result is do whatever your job asks of you and volunteer for more.

Congratulations! Your life activities are perfectly aligned with your happiness! You can stop reading now.

I’m not saying that your old clunker car doesn’t need to be replaced, or that you don’t need a larger house for your growing family, or that you don’t deserve an excellent vacation. These things might even be necessary, depending on your circumstances.

But you and I both know that any happiness you get from these short-term, money-based achievements will be fleeting. When the dust settles, you’ll still be at your same job, focusing on the next short-term happiness goal.

And after a few years or decades of obtaining these short-term goals, you still won’t be happy if these have been your only goals all along. I’d put such items more in the category of “objectives” and save your goals for big picture, long-term items.

I think that “happy” goals are best stated in circumstances, rather than money-based possessions or activities.

Happiness goals that drive results (an example)

So, let’s cover a few examples. Back to Jan and her busy-but-unsatisfying life. If Jan were working her own process, she might define happiness this way:

Jan likes what she does, and she’s good at it. She finds fulfillment in most of her daily tasks; there’s just too many of them. She wants to take all her vacation without feeling guilty, she wants to stop working on weekends, she wants time in the evening to take classes, and she wants time for a social life. She’s not really interested in climbing the corporate ladder right now.

These aren’t particularly long-term goals, but for now, that’s as far out as she wants to plan.

What result does Jan need? More time.

How will she bend the existing rules to her own needs? I’m going to split Jan into four people who are working under four different sets of conditions.

Jan 1 changes her job

Jan 1 realizes that her current job can meet her needs, but she needs to make some changes. She has a co-worker who is struggling, and Jan is covering for her; that has to stop.

Jan 1 has become the only expert on a few processes that no one else is trained to do; it’s time for others to be developed and accept some of this load.

Jan 1 never says no, ever, to anything asked of her and can’t stand the silence when volunteers are requested for new projects; she vows to be the last one to speak at least 50% of the time in the future.

Jan 2 changes her boss

Jan 2 realizes that there is no way she can achieve the result she needs while working for her current boss. The pattern of overwork has been established, and there is no way to undo it without suffering dire consequences. Her company is a good place to work – she just lost the boss lottery.

Jan 2 decides that she’ll start posting for other positions immediately, but only after using her contacts to learn if they are a good fit. She also makes a plan – just like a student moving to a new school – to establish a new work personality that is not so susceptible to overworking. (Perhaps Jan 2 starts by reading my article on how to avoid the overwork trap: You’re Great at Your Job. Which is Why Your Boss and Coworkers Are Slowly Killing You

Jan 3 changes her company

Jan 3 realizes that her desired result can never be achieved at her current company. The corporate culture is built around overwork, and everyone is drowning in tasks.

Jan 3 has it tough because if she is serious about her happiness, she’s going to have to start looking for a job at a different company. She’ll research the culture before making the leap, of course. (Perhaps Jan 3 starts by reading my article Quit Stalling on Your Life: The Real Reasons You Procrastinate and How to Overcome It which includes a segment on finding a new job.)

Jan 4 changes her industry

Jan 4 has it the worst. She realizes that her entire industry is a bad fit for her happiness goals. She, too, needs to find a new job but must branch out to similar-ish positions on a different career track – or even something completely new! Much planning is required. (Perhaps Jan 3 starts by reading my article The Difficult Journey from Point A to Point B: How Goal Achievement Really Works,)

In all instances, Jan has not merely accepted that following the rules set down for her by others will result in her personal happiness. Instead, she has backward planned and taken control of her situation to create or modify the rules for her own purposes.

None of these scenarios is easy for Jan to accomplish. But she knows that unless she does something, her misery will increase.

Jan has stopped hoping to find the express conveyor belt to her dreams and struck off on her own path.

Told you I’d get back to this brave adventurer

Non-work rules affect satisfaction (another example)

I’ve focused on jobs in this article because jobs are the main conveyor belts that we tend to deal with in adult life. But many aspects of our lives are driven by non-job situations, and these often must be considered as well:

• Family obligations that should be renegotiated.

• Social groups, even close friends, who are not helping us achieve our goals.

The list can be as varied as each individual reading this. When you’re dealing with your life, it’s all on the table. Let’s put Jan through another scenario:

Jan realizes that much of the insufficient free time she has is take up by two activities:

• Providing support and assistance for her aging mother.

• A support group for lupus, a chronic condition she has.

(I don’t like to choose easy examples.)

Jan knows that she has been playing the martyr when it comes to helping her mother with cleaning, appointments, and errands. Her brother lives in the same town and will help, but only if asked by Jan since her mom can’t bring herself to bother him (“He’s so busy, you know.”).

So, Jan just does everything and then complains about it, hoping her brother gets the hint. (He never does.) Her resentment of brother and mother is growing as a result, which is not a healthy development.

She decides to take action and makes a deal with her brother: They will split the cost of a cleaning person to come in for one hour each week and will divide all errands and appointments equally. Since mom won’t ask anyone but Jan, she creates a calendar on Gmail and shares it with her brother; it notes all appointments and they agree during a weekly phone call who will cover them.

(Coincidentally, mom is thrilled that brother is suddenly interested in visiting more often. Jan grits her teeth and smiles but says nothing for the sake of family cohesion. She silently chants to herself, “It’s the result, not the method, that matters.”)

As for the lupus support group, her condition has been under good control for a few years. She has served in three leadership positions and is tiring of the commitment and being the one who always volunteers to bring refreshments. She decides to let this one go completely.

Suddenly, Jan has four to eight extra hours a week for herself (depending on the week). She altered the rules without abandoning family obligations and still gained time to focus on her own needs.

Setting your own rules for your own life

It was an arduous, years-long process to learn how to master my own rules in work and life. I fundamentally believed that working extra hard and over-mastering systems would lead to my (ill-defined) goals.

• It was distressing to realize that my greatest strength was mastering rules devised by other people.

• It was painful to think about what “could have been” if I’d applied more of my efforts and time to my own goals.

• It was heartbreaking to realize that the things I had become the best at doing were not enough to allow me to achieve my biggest dreams.

But it was the catalyst for change.

Mastering a system created by other people or organizations is the road to a perfectly acceptable life…. if acceptable is what you are going for. But you don’t have to settle for that.

I don’t know what will make you happy. I don’t know the result you need to achieve that happiness. And I don’t know what rules you are currently dealing with.

But I do know this: if you give 100% of your effort to mastering the rules of systems devised by others, you will never achieve your unique purpose in life.

It’s difficult – sometimes heartbreakingly difficult – to shed the rule-following instinct that was trained into you from youth and play your own game. It can be a monumental task to alter the core of who you are in order to become better at things that matter for your happiness.

But it’s so worth it. Mentally breaking free from perfecting other people’s systems is a huge first step, and you can take it now.

What will your first step be? I’d love to hear it in the comments.

Until next time…remember the OverExamined Life motto: Think about it. A lot. Then do something.

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