You're Stuck in a Loop - It's Called Your Career


1/4/202313 min read

As I wrote in a previous post, the cycle of work and spend can create a loop we get stuck in. There’s a different loop as well. It’s hard to notice because it’s right in front of us every day, hidden in plain sight. It’s the 9-5. It’s the routine. It’s the daily grind. It’s going through the motions without imagining other possibilities. It’s the career itself.

If your mind wanders too far down the path of questioning your career, there’s something in addition to careerism that reels you back in, something more nefarious - toxic positivity. Every time I expressed doubts about my career and the course it was setting for my life there was the constant refrain to look on the bright side, count my blessings, and practice gratitude. Some of that came from family and friends trying to “put things in perspective”, but mostly it was my own self-talk correcting me…limiting me.

brown eggs on white textile
brown eggs on white textile
Stuck in a Different Loop

Even though I knew there was more to life than work, I still viewed work as an obligatory fact of life. Given that, I was resigned to do two things. First, I wanted to keep playing the careerist game at least to some degree, but second, I wanted to make the most of my time outside of work. I believed I could balance those two objectives and didn’t consider them mutually exclusive.

I worked hard and pursued career advancement, but I also paid close attention to work-life-balance. Even when I was in stressful jobs that required long hours, I felt grateful I mostly had my nights and weekends free. I took advantage of my jobs’ paid time off (PTO) policies, consistently taking at least a few long vacations each year.

At one point I even arranged to take 3 weeks off for my honeymoon. When I shared that with a Brit I met on the trip, he was more than impressed and earnestly asked how I had managed to pull it off. He knew enough to know 3 weeks for a U.S. worker was unheard of. I felt pleased with myself, almost proud. I knew I had worked myself into a pretty good situation.

Relatively speaking, I was in a good situation. According to the US Travel Association, in 2019 55% of U.S. workers reported not using all their days off.

Survey company Qualtrics found that in 2021 only about a quarter (27%) of U.S. employees used all their allotted paid vacation time, and when they did take time away, half (49%) said they worked at least an hour a day. Fear of falling behind on work, fear of letting down a team, and pressure from coworkers were the top reasons employees gave for not taking all the vacation time they had.

I had managed to set aside that careerist guilt, and I was long past feeling like my job should be my passion. I viewed work as primarily a means to an end, and I was fine with that. We all have to eat is what I told myself. My jobs not only paid the bills, but I had enough left over to save and invest, which I did. I wasn’t what you would call a supersaver, but I was diligently plugging away, saving about 15-20% of my income just like every retirement planner tells you to.

For the most part I’ve always been a decent saver and have lived within my means, so I’ve never been too worried about whether I would eventually be able to retire. I always joked, albeit with considerable envy, that if I could retire tomorrow I would. But that’s why it was a joke – it wasn’t realistic. Early retirement wasn’t an option, but I knew it would happen for me some day in the distant future if I kept doing what I was doing. After all, by most standards, I was doing all the right things.

Things were working just well enough, until they weren’t. It wasn’t until I found myself in a bad job that I became acutely aware of how truly stuck I felt. Not stuck in my bad job per se, but just stuck. Dreading going to work every day wasn’t pleasant, but after brushing up my resume and starting the job search process, I knew it would only be a matter of time. This too shall pass. For as much as I was hating my job at the time, most of the day I was getting paid to look for a new one, and that wasn’t all bad. Yes, technically that is stealing from my employer and no I don’t feel a bit bad about it.

silhouette photo of man standing near mirror
silhouette photo of man standing near mirror

As anyone who is a true careerist will attest, job searching can be exhausting, but it can also be intoxicating. On the one hand you have to deal with constant rejection, but on the other hand there is the thrill of the hunt. If your current company doesn’t recognize how valuable you are, plenty of others will, and they will happily pay more for your expertise and experience.

Recruiters compliment you on your resume. Interviewers validate your sense you are a talented professional. The little dopamine hit you get from seeing a message from a recruiter, or the unexpected reply to your resume from the blackhole of an applicant tracking system keep you hooked and looking for the next hit. Being sought after, being wanted, affirms our professional identity.

Beyond the ego boost from our resume being praised, or being flown across the country for an interview, we also get to indulge in what is almost a spiritual experience for a careerist – the quest for the perfect job. This could be the job that catapults my career. This could be the job that gets me the title and salary bump I was looking for. This could be the job where I finally get to make my mark on the world! With every job application and networking email we send, hope springs eternal.

I had done this drill many times before, and I was decent at it. If my current job wasn’t ideal, I would go out and find the next better one. Even in the worst job markets the talented careerist has abundant professional opportunities. You might have to pull up stakes and relocate, but to advance our careers, those are the sacrifices we make.

two women sitting beside table and talking
two women sitting beside table and talking

But this time felt different. Going through the process this time, I realized it wasn’t the job I wanted to escape, it was all of it. I realized that, even if I had a “good” career, I didn’t want to spend the prime years of my life as a middle management office worker. Even envisioning what I could potentially achieve in my career didn’t change how I felt. Breaking into an executive or c-suite role would just mean running longer on a bigger, fancier hamster wheel. My career progression wasn’t the problem and finding a job that was the right “fit” wasn’t the problem.

I realized no amount of making myself invaluable to my organization or being highly employable in the job market was going to change the fact that as long as I was dependent on a job, I wasn’t in control of my own destiny. I came to realize that, somewhat ironically, my modest career success and relative financial security had made me complacent and unquestioning about my career and my future. Even though I didn’t know exactly what was next, that realization was everything. At a minimum, what I did know was that I felt trapped in my career of 9-5 jobs. If not trapped exactly, I felt like I was stuck in a loop.

There is a reason why people refer to quitting work as getting off the hamster wheel. Most people are just trying to get through the day, but especially for careerists, work is demanding. Work is…work. Work ensures you are busy all the time. It’s not just the time commitment, it’s the mind share work occupies. It’s thinking about work when you’re not there. It’s worrying about appearing productive, regardless of if you really are. It’s the constant effort to maintain our standing in our organizations, and our status in the careerist pecking order.

That state of perpetual busyness can give you short-term, tunnel vision. As opposed to living an examined life, you’re thinking about how to stay one small step ahead of what your job demands. What do my boss and coworkers need from me? How many meetings do I have tomorrow? What do I need to prepare? How many emails haven’t I responded to? How can I get done what I need to get done just to win a little time back for myself? Oh good, the weekend is here. I think this can wait until Monday.

The work is always there, and as we careerists like to say, the reward for good work, is more work. As opposed to considering if the work is fulfilling, or even that essential, you end up working for the sake of working. We’re busy staying busy. Work takes on a life of its own. There is an inertia to it, an inescapable momentum that drives us forward, compelling us to do the same routine of work and career, day in and day out, week after week, month after month, year after year, even when we know it’s not necessarily making us happy.

I knew when I was happy and when I wasn’t. During the average week my happiness spiked at 5pm on Friday in anticipation of the weekend ahead. By the time Sunday evening rolled around my mood would start to dip. Getting back into the routine of work on Monday was never as bad as I dreaded, and the work week would predictably come and go with its countless trivial irritations offset by its share of minor victories.

On a good day, with the little time I had left over after work I would exercise, walk the dog, try to eat something healthy, watch a show with my wife, and go to sleep not necessarily exhausted, but pretty tired. The cycle would repeat each week, broken up by the too short weekends and the 1-2 long vacations each year that I lived for, and told myself I was lucky enough to get to go on. This was my loop, and I was stuck.

Count Your Blessings aka The Positivity Trap

If this is starting to sound like complaining about a mundane life lacking in variety and excitement, it’s not. I have a good and happy life. I’m a creature of habit and enjoy some amount of routine. I believe contentment is found in relishing the small moments of our day to day lives. A quote I like and tend to agree with is, “how we spend our days is of course, of how spend our lives”.

When you take a moment to think about just what that quote means, it can fill you with comfort, knowing that if you spend your days being present, mindful, and grateful, such will be your life. But thinking about how you are actually spending your days can also fill you with existential dread. It can make you painfully aware of just how fleeting the time you have is. As Socrates, and long running soap opera both said, “like sands through the hourglass, so are the days of our lives”.

No matter how much gratitude I practiced, when I thought about the grains of sands slipping through the hourglass of my life, too many of those grains consisted of 8-12 hours of work every day, week after week, year after year. But toxic positivity tells us to shush up and count our blessings when we’re having those doubts.

When there are poor, starving, and homeless people in the world isn’t it an overly indulgent, first-world problem to complain about work? That’s true, to a degree. I was lucky enough to be born in a wealthy, industrialized country with high standards of living. Being born here I’ve had opportunities other people in the world just don’t have. Every year, people die trying to come to this country. I’d say I’m extremely fortunate in that respect.

man in gray hoodie lying on gray concrete floor during daytime
man in gray hoodie lying on gray concrete floor during daytime
boy holding cardboard box
boy holding cardboard box

I’ve also benefited from being raised in a loving, stable, middle-class family. If I was born in a different place, or to a different family I have no doubt my life would be, well…different. It could be better, but chances are it could be much worse. Complaining about work might not be a luxury afforded to me.

Beyond the place of my birth, the time of my birth was also fortunate. Think about it. As a Gen Xer it’s a luxury of my generation to be able to complain about work. Our grandparents and their grandparents worked much longer and much harder for much less. Add to that, our grandparents’ jobs usually didn’t have very good working conditions, and may not have been very safe.

As recently as 20 years ago no one cared if you were “engaged” at work. Now, today’s workplaces are geared toward making the employee experience as rewarding as possible. In fact, it’s a big business and part of many professional’s job description.

Work used to really suck. People toiled endlessly. They barely eked out an existence. They died. And today, many people are still in the same boat. Ever read an argument in defense of sweatshops? For many people in the world, working in a sweatshop is actually their best option.

The Cards We Are Dealt

So, have some perspective and count your blessings, right? Yes, of course. Count your blessings. Feel deep gratitude for what you have. Have the humility to know your accident of birth boils down to luck. But also recognize this - in the lottery of life, luck isn’t evenly distributed, and it never will be. We all have to play the cards we’re dealt to the best our ability, and to our highest potential.

Whatever luck we have been afforded in life; we have to define what the best version of that life is and strive to achieve it. Just as it is counterproductive to compare yourself to those who have much more than you do, it is counterproductive to compare yourself to those who have much less. You alone are the yardstick to measure yourself against. Doing a little better today than you did yesterday is what counts. As Jordan Peterson said in rule #4 of his much acclaimed 12 Rules for Life, “compare yourself to who you were yesterday, not to who someone else is today.”

This is an area where some people have a real mental block. They have internalized the notion that it is somehow wrong to dream bigger, or even to just dream different. If you desire more when some people have less, that somehow makes you ungrateful or “privileged”, a word people like to throw like a dagger.

I guess I just see it differently. I think it is ungrateful not to strive for your best life, whatever that means to you. That doesn’t mean living a self-absorbed life. I think it means, in the Socratic sense, living an examined life. It doesn’t make anyone noble or virtuous to deny they want a rich and fulfilling life, just because others many not have the same opportunities they do. To paraphrase a famous poem, it simply means not becoming vain or bitter, because there will always be greater and lesser persons than yourself. It doesn’t mean you shouldn’t strive. We all have to play the cards we are dealt.

jack of diamonds playing card
jack of diamonds playing card

Even if becoming disenchanted with our careers is a first world problem, why shouldn’t we take that feeling seriously? In a previous post, I questioned if “Career” should rank higher than helping others, community involvement, civic mindedness, and doing good when it comes to what brings people meaning in their lives. I think most of us would say that doesn't feel quite right. It does make me wonder if people truly value their career over these things, or if they are just honestly admitting they don't have the time and energy left over for them. Do you think people who work 50 and 60 hour weeks tend to be generous with their free time, or do they hoard it? Does focusing on my career which is an expression of my identity tend to make me more human-centered or more self-centered?

What if the people had the opportunity to stop toiling in the corporate world and invested more in their communities, even on a small scale? What kind of a community would that be? What would happen if people stopped worrying about their next raise, and instead worried about their relationships and developing their moral character? What if the prestige of being a good human and helping others outstripped the prestige of a promotion and fancy job title? What kind of a society would that be? What kind of a world would that be? Wouldn’t it be better if more people took their first world problem a little more seriously?

There is something deeply misguided about coming to believe that, in spirit of gratitude and mindfulness, you somehow owe it to the less fortunate to focus on your career. What if instead, you focused on the less fortunate?

person standing wearing red shirt
person standing wearing red shirt
woman in white t-shirt and blue denim jeans sitting on brown cardboard box
woman in white t-shirt and blue denim jeans sitting on brown cardboard box

I’ll stop waxing philosophical and simply say that despite how you might feel, and despite what others may have told you, you’re not wrong if you want more out of your life than your career. You’re not wrong if you feel like you are stuck in a loop of a 9-5 job and you want out of it. It doesn’t mean it’s a bad loop. You just may have the nagging sense there is something more. You should pay attention to that feeling. You should give yourself permission to play the cards you are dealt. You should give yourself permission to get unstuck.

In Summary...
  • There are many forces that keep us stuck in the loop of our career: 1) the feeling we're doing all the right things, 2) the quest for the ideal job, 3) the busyness of work itself, 4) toxic positivity

  • Playing the cards we are dealt isn't leading a self-absorbed life, it's leading an examined life

  • Focusing less on career provides an opportunity to focus more on doing good in the world