7 Careers That Might Leave You Second Guessing Yourself Forever


The day-to-day misery of working hits all of us at some point regardless of what it is we are doing with our lives.

A job — whether it’s engaging or totally mindless — will eventually grind you down and make you question everything you thought you knew about yourself.

In essence, nobody can truly enjoy and feel comfortable in what he or she does 100% of the time — that’s just mentally impossible; you’re bound to have a breakdown whether you’re selling shoes at the mall or trading stocks on Wall Street.

With that said, there are some jobs out there that propel this internal struggle faster than others. And, to make matters worse, the speed at which these jobs crush you isn’t the biggest problem you must face — it’s the duration at which this doubt lingers in your head for; like, I’m talking about forever.

Here are seven careers that will leave you second guessing yourself constantly for the next decade:


Whether you’re a musician, a writer, an actor, or a painter, being an artist allows you way too much free time in your own headspace. And once that monkey mind starts churning, it never stops.

Will anybody like this song? This short story I wrote is trash. Man, the play I was in sucked — less than 10 people showed up. Why would anybody pay $500 bucks for this piece of art?

The doubt never goes away and, like plate tectonics, its always shifting and springing up at you at the least opportune moments.

And while you may be your own boss and create your own schedule, you’re not exactly living the dream because tomorrow’s success is never (I repeat: NEVER) guaranteed. You have to be willing to constantly reinvent yourself and mold your talents to satisfy others’ needs and tastes, even though you have absolutely no idea what those might look like next week or even next month.

This means as much as you enjoy being free and living in the moment, that moment is persistently being siege by pressure and panic of an insecure and volatile future. No matter how much you love what you’re doing, you’re next pay check — no matter how small or how big — is directly correlated to you’re ability to create the next big thing.

The sad truth is that the next big thing may never come your way.

Bank teller

I have no statistical evidence to support this claim but I think bank tellers have the highest rate of suicide amongst any profession, which says a lot considering the above tangent about how much it sucks ass to be an artist.

While not as unstable of a profession (unless its 1929 or 2008), bank tellers do have a ridiculous amount of free time to contemplate the meaning of their work and how it fits into the bigger picture of life. Seriously though, have you ever thought about how little these people do now with the advancements in online banking?

Whereas a musician can help people escape the irritation of mindless everyday life and provide them with a spiritual boost, a bank teller does the complete opposite — he or she is a brutal reminder about how everything comes back to the bottom line of your bank statement.

I’m sure there are other careers that are equally soul depleting and unrewarding, but this one definitely pays the least and puts you on a direct path to second guessing what it is you’re doing with your life.


A different variation of bankers, salesmen easily could have led off this list. Just think about how awful it is to sit inside a Best Buy or Walmart trying to hawk a product that nobody wants. Or, even worse, sitting at a cube all day and cold calling people like a programmed machine attempting to sell software or data to people who don’t have the slightest idea what you’re talking about.

Regardless of which side of the spectrum you fall on — corporate or the opposite — you’re going to draw estranged looks from adults and children alike. And, if they can’t see you, their voices on the other end of the phone will serve as your hourly reminder of how pathetic your existence is.

Nobody takes a salesman seriously because they know you tried to make it in another career but failed and had to settle. Living with that knowledge can just about eat a man alive on the inside. And this is exactly why becoming a salesman is a terrible idea. Avoid it if you can.

Note: Even if you’re naturally good at swindling and convincing people to do things you want, then this is something you don’t want to do. It will only leave you second-guessing who you are, what it is you’re doing and why you’re doing it when you can be doing just about anything else with your particular skill set. 


News reporter

Unlike the weatherman, who gets to paid to make wrong predictions daily, being a news reporter comes with an inherent cost — if you screw up at any point and act recklessly, then you could be facing a libel or slander lawsuit. And, not to ruin the surprise, whatever company you’re working for is most likely not going to support you in said lawsuit if they think it’s a lost cause. Most likely, you’ll be out of a job, out of a career and definitely out of any feasible way to pay off your lawyer — basically, the worst case imaginable.

OK, so let’s dial it back a bit: worse case scenario aside, why else does it suck to be a reporter or a journalist? Well, let’s see, you’re constantly living in the lives of others; your job is entirely dependent on stuff happening around you, and you never get to create a sense of individual purpose like a nurse or a fireman.

Speaking of fires, to throw some more gasoline on why being a reporter sucks — the job constantly leaves you exposed in the limelight without any of the reward of being famous. Essentially, you can be critiqued, attacked and hated on by anyone in the world and you’re completely unprotected. It’s like being a movie star or a pop singer, except for the fact you get paid dog shit and nobody respects your profession — or even likes you in general.

Oh, and we haven’t even mentioned the invention of the Internet and social media which has threatened the very existence of reporters. That’s right, those crazy enough to seek this out as a career (and yes, I’m one of them) are entering into a field that might not be around by 2025. Yikes.

For good measure, it’s worth noting that the only true time you get respected and honored for doing your job is when Middle East radicals kill you or you expose something as inhumane as a child porn ring. To put it simply, don’t ever, EVER think of becoming a reporter or you’ll be second-guessing yourself until you’re in the grave.


Not nearly as bad as being a journalist or an artist, teachers get their summers off so how much second-guessing can they really be doing? The short answer: a lot. Try dedicating your whole life to trying to change somebody else’s except they never listen to the advice you given them or abide by the directions you put in front of them — that’s what it’s like to be a teacher, everyday for 160-plus days of the year.

Again, I don’t have the stats to back this up, but I’m willing to bet 0.0% of the world’s CEOs would step down from their respective companies if offered the exact same salary they’re making to go teach middle school math. Nobody wants to do that. Why, because only a criminally insane person would want to subject themselves to that much chaos over and over again.

Just think about the repetitiveness of school as a student and try imaging it from a teacher’s prospective: teaching the same material year after year and dealing with the same obnoxious parents year after year. Sounds like hell on Earth.

You need a shit ton of patience and tolerance to last as a teacher, and even if you have those skills, you’ll still be rethinking your career path every morning when you wake up at 6 a.m. to go teach 20 eight year olds state capitols they won’t remember a year from now. That might be the worst part of it all — the difference you think you’re making (remember the nurse or fireman example from above) actually doesn’t matter as much as you once thought it did.

Human resources

This is the inverse of being a salesman; instead of calling people all day long and trying to convince them of something, people who are trying to sell you on themselves are calling you constantly. Can you think of anything more torturous? Resume after resume, cover letter after cover, recommendation after recommendation — no wonder the people who hold these jobs are usually totally incompetent and inadequate at what they do? How could we ever expect our society to fill this industry with satisfied, happy employees?

The answer is we can’t — these may be the people holding the keys to your future job, but really they’re more unsettled in their current careers than you are as an unemployed bane on the economy.

Police officer/prison guard 

A two-for-one special as both of these careers can be lumped under the same umbrella. In case you’re wondering why cops and guards? It’s pretty much in tune with the rest of these disgruntled professions — lack of respect, lack of pay, and more than enough hostile face-to-face interaction with the scum of the Earth.

I guess one positive is that, like being a reporter; no day in the field is ever the same. Unfortunately, that constant change can be unnerving and unsettling — your safety on the job is never guaranteed. Plus, I could imagine that the repetition of the codes and procedures can be quite tedious too. How many times can you really go to the police academy to relearn the basic department policies? Five times would be more than enough for me to consider putting my department-issued pistol against my temple.

Of course, the big difference between cops and the rest of the careers on the list is that you’re making a difference, protecting communities and saving lives, which should be enough to satisfy and carry you into retirement.

However, on the flip side of that, cops today must always be aware of their actions — and more importantly, their attitudes toward certain groups of ‘others.’ Racism continues to plague police enforcement even today — 50 years after the Civil Rights movement — and being under that microscope must be exhausting. People second guessing your motivations, beliefs and intentions all the time inevitably feeds a cycle of self doubt that once powered on is hard to turn off.

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