Is Working the Same Job for 20 Years a Dream or a Nightmare for You?
Am I the only one who finds the idea of doing the same job for 20 years unimaginable horror?
People thought I was crazy. Perhaps. But I never regretted it. I had the best time ever, and these last couple of years, while broke and without an ounce of stability, were by far the best years of my life.
I never liked “normal” things.
A 9-5 job. A rational car. Doing homework. Two weeks of vacation per year. A vacation spent lying at the beach. Popular sports with a ball. Bowing to authority. Going out dancing. Drinking alcohol. Missionary position. Wearing a suit and a tie. But there was one thing, one idea, I struggle with the most:
Doing the same thing for the rest of my life.
Having the same job for decades. Staying in your lane. Going to the same places. Driving the same roads. Living in the same country, city, and home all your life.
It always felt like stagnation, especially with work. Since our jobs take up most of our time, doing the same thing repeatedly until retirement was always “dying before having to die.”
It’s like finding something you can do with ease and deciding that this is where you shall await death. God forbid you should make a change and inject uncertainty and challenges into your life. Even staying at the same job for ten or twenty years seemed impossibly dull.
Talk about wasting a perfectly good life!
I know this is the normal. For most, this is the goal, the best-case scenario they hope for. To find a good job, wait until retirement and enjoy the freedom.
It's a bad plan in my book, but whatever. It is rational, to a point. Unless you die. I get it. Not only that, it’s praised and sought after by employees.
Yesterday, I saw an ad demanding twenty years of experience in the same job. I mean, what? Are you buying a robot or hiring a person?
Here’s the thing, though. It works.
Well, if you were lucky, made the right decisions in school, found a good employer, and stuck around, you are now what is called a professional. You know your shit. You’re the man (or woman).
Most of my friends and peers who took this “normal” path, combined with some luck and a lot of stability in their lives, are lightyears ahead of us, confused seekers financially. Not only that, they also settled down earlier.
They found their partners ten (or twenty) years ahead of us, and while I chase around my little toddler, their kids are learning stuff in school. They have bought and paid off their first home, and most now own a new or second home (well, the bank does).
The normal is winning.
I am happy for them. I am. But I could never live like that. I just don’t have it in me.
I know it makes sense. I understand why they are where they are. I don’t care. I had a home. I had a job. I had a girlfriend. I had experienced the non-joys of beach frying vacations. It did nothing for me except scare me into running away. Life is just too short, dammit!
I quit my job, sold my apartment, and went all-in on trading and traveling.
People thought I was crazy. Perhaps. But I never regretted it. I had the best time ever, and these last couple of years, while broke and without an ounce of stability, were by far the best years of my life.
Sure, I could have made a few year's worth of salaries more had I chosen stability, but I would have died inside. I already couldn’t sleep as I felt trapped and sinking at my last job.
Life was slipping away again, my time wasn’t appreciated, and I was trapped with a pack of hyenas. Hell no, I must go and went I did.
Was it smart? No.
Would I have lost my mind if I stayed? Almost certainly.
Was it the only thing for me to do? Yes!
Consistency is king in the long run.
Even a person with almost no education but the ability to persevere and keep going will overtake the risk-takers and seekers most of the time. There are exceptions, the big winners, but they are exceptions for a reason.
When you want back in.
I have had to delete a lot of my working experience from my CV, as potential employers were shocked when they saw that I could list a dozen different jobs by the time I was thirty.
Some were my choice, failed explorations, and others were random occurrences that weren’t my choice. A few fallen companies, lousy market timing, choosing a dying industry, expired stand-in jobs, and so on.
Even as a kid, barely a legal grown-up, I worked three jobs simultaneously. I was a key account manager in one company, worked shifts in a shop with completely unrelated products, and spent the weekends as a bodyguard/roady for a locally famous band.
I was also simultaneously studying to become a police detective, practicing two different martial arts, and was already living in my fourth home.
When I was young, I was ambitious.
It drove me forward, and I was making a good pace. At twenty-four, I was driving a good, three-letter car, lived independently in a new city, wore a suit to work (which I hated), and made good money handling businesses in millions.
The titles on my contract and business card were rather impressive if I do say so myself. I heard I had made it big in my hometown’s local bar. It didn’t feel that way, but it was nice to hear it just the same.
I thought I had found my thing, my path.
That was my first real job. The rest were as a student, on contract, or *redacted*. But it wasn’t meant to be. The 2008 financial crisis came and wrecked my employer and my health to pieces.
Until that moment, I was convinced I was destined for great things and was ahead of my peers by a large margin. After that moment, everything changed, and I would never catch up again.
I was lost between hating my old job, the one that broke me, swearing to my doctor and myself that I would never put myself in the same position, and searching for something new. I needed something that wouldn’t cause me stress and would keep me alive. Financially and health-wise. Plus, I was sick and tired of the corporate world. It just wasn’t me.
That period, which is still ongoing, was filled with trials and tribulations.
There was a lot of failure and rejection, with rare, short victories in between. Some of these transitions between jobs, employers, and fields of interest were my choice. Others weren’t. The result is the same, though. A non-linear path of an eternal beginner. A jack of all trades and a master of none. My CV has more holes than Swiss cheese!
Now, imagine you’re in charge of picking out a new employee.
You’re seeing red alerts everywhere. Recruiters told me as much on a few occasions:
Having so many jobs (if they only knew) indicates you get bored quickly, and we risk losing you when a better opportunity comes along.
It shows instability and ambition. We will invest in you, and then you’ll leave us.
You need a leadership role where you will be more challenged (I don’t apply to those for reasons of stress) and have a wider array of responsibilities.
You are expecting a higher pay then we offer (I pretend that isn’t true, but it is).
This job is not a good fit for your personality.
There was no convincing them otherwise, no matter how hard I tried.
They weren’t necessarily wrong. That was especially prevalent in the first years after my burnout when I was looking for an easy, stress-free job with minimum pay. Just enough to get by. That was simply not possible for someone with my background.
I am older now.
I find stability more appealing, but I still can’t imagine doing the same thing for the next thirty years. I want to. It sounds so comfortable and easy, unlike my life up to this point.
My mother, a public servant, always told me: “Find a good public job, stay quiet, and you’re safe until retirement.” Talk about a dream for some and a nightmare for others. She did it, though, almost 45 years on the same freaking job.
Was she happy? Hell no! The only way she survived this far is with the help of a million pills preventing her depression from overwhelming her. I don’t blame the job, but it sure as hell didn’t help.
I have found true love in writing.
Even in this creative endeavor, I keep reading the same advice over and over again.
Specialize.
Choose a niche.
Talk about the same thing forever in a hundred different ways.
Readers love this.
It’s great for the algos.
No, thank you. I’d rather blow my brains out than write only on one topic for the rest of my life! It may be rational from a marketing and reach perspective, but it would kill any interest and joy I get from writing. So what would be the point?
We don’t write for money, although we all desire to be able to live from our writing.
We write because we need to.
We feel the urge to create, tell stories, profess, and strip naked in front of unseen readers who will get a glimpse into our souls.
We desire to help as many people as possible by sharing our lessons and experiences.
Writing is more art than business. Maybe it should stay that way.
I already have four thematically distinct publications on a few platforms, and it’s a nightmare to manage them, much less gain subscribers. I know my readers will come across posts they won’t like or be interested in. It can’t be helped, I’m afraid. I’ve tried separating things into segments, but I feel limited both on Substack and Medium in this regard.
I wish I would be so narrowly focused and passionate only about one topic, but I’m not. I love so many things and find even more of them absolutely fascinating.
Living such a “diverse” life doesn’t lead to a lot of money for most, but it does reward one with inner peace, love, and comfort… wait, no!
What it really does is teach us a lot about life, people, and ourselves. It serves up lessons like you wouldn’t believe and challenges we have to chew our way through that would crumble lesser souls!
I have found a few constants in all that time:
Changing jobs is not the end of the world. Yet, the first few months are challenging and require much more effort. After a few months, though, you’re home-free.
It takes about one to two years to learn all you need about a new job and become completely self-sufficient, however challenging it may be.
After two years, everything you thought would be fun and exciting becomes boring and mundane. Most prefer that in their jobs.
If you don’t change jobs every couple of years, even within the same company, you stagnate. You stop growing and learning new things. You become complacent and comfortable.
Not all people are compatible. Finding a good match is essential. You can be wildly successful if you find the right job and team for you, and a complete failure if you work against your personality.
Stress has little to do with your job or workload but more with your emotions, health, and mind. How you perceive this work, people, and situations makes something stressful or invigorating, especially when thinking about the future regarding your job (fear, worry, and anxiety).
You can move mountains when you’re properly motivated, encouraged, and rewarded. However, if you’re disrespected, ignored, or worse, you can transform from a high-productivity individual to a complete slacker in no time. Sometimes intentionally, but most of the time subconsciously.
It’s not worth pretending to be someone you’re not to get a job, as it will only lead to misery and dissatisfaction on both ends. Know yourself and show yourself.
I am not suggesting one path is better than the other.
If you like stability, security, and comfort over adventure, growth, and purpose, you will be perfectly happy in a “normal” career path. Some people, myself included, will have chosen the more challenging path.
I’m not entirely sure it is a choice, to be honest.
I talked to my dad, a small business owner who has often said that his friends are exactly where he ended up while living a simple, stress-free life, and they worked about half as much as he did. Knowing the end game, they were right. He was wrong.
If he had to do it all over again, though, he would still take the same path full of hardship. Staying in that job simply wasn’t an option for him. He needed more. He had to test himself and see what he was capable of. Staying there was a metaphorical death of his soul.
That’s the thing with giving advice.
We are all so very different that what is true and right for one often won’t be for another. Logic, reason, and rationality be damned!
I hope you chose the right path for you and that it will lead to a life of happiness and success, however you define it.
Which are you, the eternal seeker of new knowledge and experiences or a settler, sitting comfortably with your skill set, following the same trajectory for decades? Do you have any regrets?
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When stability is your biggest fear. There must be another game to play. One in which we make up the rules as we go.
I can relate to this so much.