A Career Story That Might Sound a Lot Like Yours


12/5/202213 min read

With 20-year's of hindsight I think it’s fair to say I’ve had a successful career. Nothing to brag about. I’m not renowned in my profession and I won’t be winning a lifetime achievement award anytime soon. I haven't contributed to major advancements in my field or created anything that will have a lasting impact on people or society. At least not that I'm aware of.

My career has been a success by much more ordinary standards, the kind that most careers are ultimately and realistically judged by. I’ve had good jobs doing interesting and challenging work. I’ve gained expertise and developed professionally. I’ve led teams and worked with talented people. I’ve made friendships I value to this day. I’ve received promotions and raises, and have earned enough money to live comfortably, support my family, and save for the future. I like to think there have been times I've created something of real value for my customers and stakeholders but you would be surprised at how hard that can actually be to know.

To get down to careerist brass tacks, I have a sufficiently impressive sounding job title and position in my company, and my compensation package puts me in the top percentiles of income earners. Again, nothing to brag about, but most people would probably say I've done alright for myself. My career has been successful, and it is progressing as it should.

no smoking sign on grey metal fence
no smoking sign on grey metal fence

There have also been a lot of bumps along the way. To begin with, my career didn’t get off to the most auspicious start. After graduating with a Master’s degree in the wake of the dot-com bubble, I started my career being unemployed. It wasn’t the only time I was temporarily unemployed. During what was later called the Great Recession, I survived multiple rounds of layoffs only to eventually have my job “eliminated”. That’s the, it’s not your fault but you’re still fired version of being fired.

Flash forward almost 10 years and I found my job eliminated once again. This time at the hands of "cost-reduction efforts". Only about a year removed from a handsome signing bonus, relocation package, and being told I was on a succession track, it turned out my role wasn’t so critical after all. I took the unsavory option of being demoted and staying employed rather than taking a severance package and my chances in the job market. Being out of work consistently ranks as one of life’s top stressors. Being demoted might not be as stressful, but it has to be more humbling. Fortunately for me, my periods of both unemployment and underemployment were short-lived. Of course, as a function of working for over 20 years that was far from the end of things.

smiling emoji balloon beside black car during daytime
smiling emoji balloon beside black car during daytime

Over the course of my career I’ve relocated for work twice and worked for 8 different companies. That's a different company every 2 ½ years. New opportunities are exciting, but that is a lot of starting over (see again, life stressors). I have worked countless 12-hour days, and a great many 16 and 18-hours days, not to mention late nights and weekends, which at times were not only regular, but an expected part of the job. I’ve been demoted, passed over for promotions, and not had bonuses paid. I spent over a year in the job market…twice. I’ve worked for terrible bosses. I’ve had other people take credit for my work. I’ve had to fire people. I've seen tears in the office, some of which I unavoidably caused. I’ve had gnarly commutes. I've had shitty business travel and too much time away from home. I’ve suffered office politics. I've endured obnoxious co-workers. I've had snide and passive-aggressive comments anonymously packaged as "feedback". I've been publicly criticized and embarrassed by people in power. I've been treated unprofessionally, rudely, and sometimes bizarrely. I've had too many to-dos. I’ve been stressed out, burned out, overworked, underpaid, and undervalued.

Does any of this sound familiar?

man wiping his tears
man wiping his tears

My sense is I’ve had it better than most, and far better that some. I'm not complaining.

The reality is that if you work long enough, you’re going to have more than just a few ups and downs. Shit is going to happen. You will get fired. You will get demoted. You will lose out on a promotion or raise. You will have conflict with coworkers. You will be overworked and underappreciated. You will have a terrible boss. You will suffer office politics. Your job will make you feel bad. You WILL cry at work (if you haven’t already).

Fair or not, it’s par for the course, and it's largely unavoidable. There is a careerist myth that says that if you make yourself indispensable to your organization you can avoid all (or most) of these negatives outcomes. Being viewed as valuable helps, but it’s no guarantee. If there’s one thing my experience has shown me, it’s that everyone is replaceable. Most employment is “At-Will”. That means your employer can fire you pretty much whenever they want, for whatever they want, barring illegal discrimination.

The upside is that you have the freedom to quit and walk away from a job whenever you want. Being “stuck” in a job is a misnomer because it implies you can’t do anything about your situation. You can do something. Unless you have an employment contract or a non-complete agreement, which are rarely enforceable, you can find a new job whenever you want. If you can’t improve your situation, you can move on.

woman sitting on chair beside table
woman sitting on chair beside table

The point is that even the best careers are going to be filled with their fair share of crap. When it comes down to it, I’ve had far more ups than downs, but the fact that a fair amount of crap is inevitable says something about the experience of working. That might sound a little jaded, but that doesn’t mean it isn’t true. That's okay. No one said a career was supposed to be easy.

But a career should be worth it.

At some point in my career, I guess I started to question if it was worth it. Sometimes difficult roads lead to beautiful destinations. But sometimes they lead to dead ends. And sometimes they just keep going with no end in sight.

difficult roads lead to beautiful destinations desk decor
difficult roads lead to beautiful destinations desk decor

Personally, I never hated my job. Okay that isn’t true. At one point, for a brief period, I hated my job. Fortunately, that was short lived. The bigger problem was that over the course of my career I never loved my job. I always tepidly liked my jobs. In the religion of careerism, that creates a lot of dissonance. Whenever I’ve heard people say they are “passionate” about their job I never thought they were being sincere. It always felt like something people said to convince themselves they liked working, when in fact they would rather be doing something else. I was always a career atheist in that sense. If given the choice, I knew I would rather be doing something other than working a 9-5 job, but I was on the road that kept going with no end in sight.

Something Else

Perhaps as a counterbalance to the culture of careerism, pop culture has produced countless tv shows, movies, cartoons, memes, and mottos, all about how much work sucks. Dilbert, 9 to 5, The Office, Horrible Bosses, Workaholics, Parks and Recreations, Severance…in my view it’s no accident that many of the most popular media come in the form of satires and dark comedies. It’s almost as if we know our last resort is at least to laugh and commiserate with our favorite tv and movie characters about the predicament we’re all in.

No one does the “work sucks” trope better than the 1999 classic, Office Space. At the risk of doing the least original thing in world in a blog about work, I'm going to offer up my take on Office Space. Original no, but relatable yes. There' a reason it's still popular and has maintained its status as a cult classic 20-years later.

Although it is inconceivable to me that anyone would not be familiar with the movie, allow me break down a quick scene for you. Peter, the main character, is discussing what he and his friend would do with a million dollars. For historical context, in 1999 a million dollars was considered enough f-u money not to have to work. What would Peter do with a million dollars? In his own words, “Nothing. I would relax, I would sit on my ass all day…I would do nothing”.

Not to give away any spoilers or key plot points, but as opposed to doing nothing, Peter sleeps in, takes Jennifer Anniston out on a date, goes fishing with his buddy, watches Kung Fu re-runs, and remodels his office. That seems more like doing something than doing nothing. That seems like doing more of the things he really wanted to do, but couldn't, because he had to work.

For comedic effect, the line was written beautifully. Saying he would do nothing is funny, but saying he would do something else is what he really meant. Do you know what your something else is? Have you ever stopped to think about it? If you didn't have to work, how would you fill your time? What would you do with your life? Would every day be like the weekend? What is your beautiful destination at the end of the road? What is important enough that all the hard work and sacrifice would be worth it? What activities are so interesting and intrinsically motivating that the hours race by?

But We All Have to Work

At this point you might feel tempted to say, but that was a movie and Peter had a shitty job. Who wouldn't want to do whatever they wanted all the time and not have to worry about work? That's not reality. We all have to work. You have to pay the bills somehow. Besides, my job is great. I really do love my job. Really? Would you rather be working at your job, or any job for that matter, instead of having the time and freedom to do all your favorite things whenever you wanted? Do you love your job that much?

girl in white crew neck shirt
girl in white crew neck shirt

If you say yes, I won’t call you a liar, and I won’t blame you. I get it. Your mental antibodies are busily fighting an idea pathogen. It’s a scary and unsettling thought to be forced to admit you don’t love your job. After all, in our careerist culture loving your job is one of the most socially desirable things you can possibly do. Maybe you’re one of those lucky few who truly does love your job. In that case I would still ask - if you didn’t have to work for a living would you keep doing it for free? Would you continue to do the same thing even if you didn’t get paid a single cent?

Compensation is an appropriate word for the salary and wages that come from work. Technically compensation means providing monetary value equivalent to, and in exchange for, work performed. Commonly though, we compensate someone to make up for loss, damage, or injuries. When we compensate someone, we pay them for the service and work product they provide, but we are also compensating them for the loss of their time. Time, I would argue, they would otherwise be spending doing something else.

person holding U.S. dollar banknote
person holding U.S. dollar banknote

If you can honestly say you would do your job indefinitely without being compensated, then I sincerely and truly commend you. You can probably stop reading this because most of what I have to say won’t make sense to you. For the rest of us, being totally and brutally honest, we work our jobs because we have to. To a lesser, but substantial degree, we work our jobs because our careerist culture makes us think we’re supposed to. Who would you be if you weren't the professional you are? Our jobs provide both the means, and the meaning.

Okay fine, you might say. By your standard I don’t love my job, and no I wouldn’t do it for free, but I really do like it. It provides me with challenge, a sense of accomplishment, and camaraderie with others. The work-life-balance is pretty good, and I have some time outside of work for friends, family, interests, and leisure. I’m making money and providing for myself and my family. I might even be doing a little good in the world. What’s wrong with that? And why would anyone work for free? My time and talents have value, and I should get paid for them, right?

Nothing is wrong with that, and yes you should be compensated for your time and talents. Having a career is important and beneficial for many reasons. It checks a lot of boxes on most motivational frameworks, such as self-esteem, belonging, and achievement. A job, a career, an occupation, can all be very meaningful insofar as we use our talents to contribute and give back in some way.

But then again, a lot of things other than a job can check those same boxes. It isn’t the case that a job is the only way to meet those needs. If behind door #1 you have a job that is fulfilling and provides a sense of financial security then that is great. But what if I told you there was a door #2?

yellow metal door close-up photography
yellow metal door close-up photography
Door #2

What if I told you that behind door #2 was a place where you can choose to do your favorite, most meaningful things, without having to rely on a job?

Wait, isn’t that called retirement?

Sort of, but not exactly. Most people view retirement as quitting work altogether. Retirement comes usually when we’re older and we’ve reached a point in our career where we can finally hang things up, call it a day, and withdraw from the workforce. Retirement is a one of our final rites of passage, at the end of a good, long career, and it happens to us when we are older.

If you are an average man in the U.S. that is age 65, and for an average woman that is age 62, according to the Center for Retirement Research at Boston College. The Center’s research also suggests the retirement age is going up. Sixty-five may not be the best-case scenario for many workers. In a 2018 study by Pew Charitable Trusts, nearly two-thirds of workers surveyed said they were likely to work past 65. Many said they would work as long as possible and they weren’t sure when, or if, they would retire.

Why work past 65? Was it because they needed to, or was it because they just loved working so much? Even 54% of people earning a salary of $100K or more said they needed to keep working. As you might expect, the percentage of people who said they needed to keep working continued to increase the less people made.

The outright necessity of work for most people, albeit troubling, probably isn’t that surprising. The reality is most people end up working close to 45 years, and retiring at an age that isn’t exactly young, if they retire at all.

But good things are worth waiting for, right? When the retirement stage of life finally comes, we theoretically start an exciting new chapter of our lives. Unfortunately, it appears this exciting new chapter ends up being spent in front of screens. According to the Pew Research Center, Americans 60 and older now spend more than half of their daily leisure time, 4 hours and 16 minutes to be exact, in front of screens, mostly watching TV or videos. I enjoy my screen time, but being glued to Facebook, stupid cat videos, and surfing Netflix isn’t my idea of a fulfilling retirement, and definitely not the desired fruits of my long, hard labor. Unfortunately, most people retire from something, not to something.

woman in brown button up shirt holding white smartphone
woman in brown button up shirt holding white smartphone

These statistics from Pew and BC’s Center for Retirement Research are not only worrying, but emblematic of a larger problem. Most of us have become resigned to a life of needing to work. We don’t perceive a door #2 exists, and as a result we aren’t being intentional enough about the future. Peter is the hero of our favorite office movie, but we are the first ones to strenuously assert that it's just a movie. We don't ever stop to think about our "something else" and how to make it a reality. We’re stuck in the paradigm of careerism, believing that we not only have to work, but we’re supposed to.

Maybe, just maybe, we’re not dreaming big enough. What if behind door #2 was starting the next chapter of your life sooner? What if it was starting the next chapter of your life much sooner, and with clearer intentions, knowing what you were moving towards, and not away from? Opening door #2 isn't going to instantly change your job or your career, but it is how you can start to build your career off-ramp for when you want it. In order to open door #2 you first have to question the faith.

In Summary...
  • A career shouldn't necessarily be easy, but it should be worth it

  • If Office Space can still teach us anything, it's not that we need to do nothing, it's that we need to do our "something else"

  • Most of us have become so resigned to a life of needing to work that we can't imagine other possibilities

  • You can't start to build your career off-ramp until you believe another possibility, a door #2, exists