7 Things I Regret From My 9–5 Job

Make the most of your regrets; never smother your sorrow, but tend and cherish it till it comes to have a separate and integral interest. To regret deeply is to live afresh. -Henry David Thoreau

There’s a lot of potential for regrets. And although I think I live a life of minimized regrets, I’m determined to squeeze the most learning, wisdom, and potential out of the regrets I have from my old 9–5 job. I quit about a month ago.

A few things come to mind. First, there’s a principle for a lot of 20-and-30-somethings that it takes a while to find meaningful work, and we’ll probably have to go through a lot of crappy jobs (like say, cashiering at Pottery Barn. Or that sketchy startup that made you email clients under a fake name. Etcetera). You may think you’ve found what you want to do, but then this feeling of buyer’s remorse kicks in, leaving you wanting out. 9–5 work is difficult like that.

Nonetheless, I think I learned a lot about myself, my maturity, and my mindset from my old job. Here are 7 things I regret doing (and not doing).

1. Not sticking up for myself to my boss

“What we fear most if usually what we most need to do.” -Tim Ferris

I firmly believe there are great bosses out there. I mean, there have to be, right?

Great bosses are ones that really care for you. People that are selfless, genuine, and great leaders. I’ve had a few decent ones myself, but my old boss wasn’t one of them.

I’m not here to bash my boss (it’s a bad habit, and I’ve learned from experience it doesn’t really feel that good in the end anyways). I’m here to say that a boss’ inexperience, or selfishness, or lack of vision, or narrow mindedness isn’t a reason for an employee to bow to it.

I’ve been unemployed in the past, and the lack of income, desperation, and constant hopelessness was truly was one of the most traumatizing periods of my life. I get it — if your boss doesn’t like you, your odds of getting fired (or quitting your job because you hate it so much) increase. Generally, it’s not a favorable outcome (although it oftentimes it, just read Pat Flynn’s incredible story that started with losing his job).

However, I chose to roll over in the face of unfair treatment, which I sincerely regret.

I had the power to speak up, say “no, I’m not going to let you do that to me” for the many times I was left holding the bag. I regret letting someone take the credit for my hard work. I regret not standing up for myself, because the potential consequences of my defiance weren’t anywhere as bad as how I felt every day knowing I was being a coward.

2. Not being a part of more diverse projects

“Don’t work to earn, work to learn.” -Anonymous

Tim Ferris, author of the wildly successful book The Four Hour Workweek, frequently discusses success and failure in his podcast. According to Ferris, what people relatively discern as a “failure” usually isn’t a failure at all, given that you learn skills, abilities, and lessons you didn’t know before. How can it possible be a failure if you’re smarter than before?!

In the future of my business StuffGradsLike, I see myself making income on webinars, online courses, and virtual community connections. My 9–5 job had constant opportunities to learn the skills I need to master these environments, but I didn’t want extra work, so I never learned! Hey Anthony, did you want to learn how to set up a webinar online? Oh, it’s too much work? Ok then, see ya!

I kick myself when I think back to the lessons I could’ve already known while I was getting paid. It would have saved me the trouble of researching it now (with the added bonus my workdays would’ve been that much less boring).

If there are projects at your job that will teach you marketable, unique, high-demand skills, get on those projects. Even if you have to keep asking! You’ll be glad you don’t have to read a dozen articles on how to coordinate a webinar.

3. Staying there too long

Winners quit all the time. They just quit the right stuff at the right time. -Seth Godin

I had the unique opportunity to receive a 100% tuition-paid-for Masters degree through my employer (which I jumped on immediately), that was one of the main reasons I stayed. I often lamented to my wife as she politely listened to my whining for the nth time, “If I wasn’t getting my Masters, I’d have quit so long ago!

For me, that benefit was simply too good to pass up, and I was in a place where I gladly would’ve stayed at a job for 2 years while I received a free Masters degree. But that wasn’t always the case for many of my coworkers.

It amazed me how people could be stuck in the notoriously-difficult sales department for years, without ever (actually) trying to change jobs. More shocking were the people who had chosen to not receive their free degree, when they could’ve had it years before. “You know, I just never wanted to do all the work,” they say casually. “But I think I’ll enroll soon, maybe next year.” Hm.

I was determined to receive my free Masters in Psychology, pay off my student loans/car, and reach $10,000 dollars in savings while at my job. I did all three! After that, it was time to go. If I stayed any longer, it would have just been wasted time, the only resource I can’t replenish.

4. Spending way too much $$ eating out

Eating out at restaurants is by far the biggest way I overspend my hard-earned money. It still is.

Do you know how much a plane ticket is from San Diego to New York city? About $400 bucks round trip. How about San Diego to Peru? About $500. To London? About $800.

If instead of paying $12 for lunch, I saved it, here’s how long it would take me to save up for a plane ticket:

  • To New York City: 33 days
  • To Peru: 42 days
  • To London: 67 days

Instead of buying lunch (because I was too late to meal prep on Sunday evenings), I could have saved that money to travel the world. And it would’ve only taken me like, 2–3 months.

I would’ve avoided eating out as much when I worked my 9–5 job, so I could travel the world instead.

5. Not putting in enough work for my side-business

“Too much dreaming leads to too little doing.” –Hustle: The Power to Charge your Life With Money, Meaning, and Momentum

I was very busy outside of my 9–5 job. In my last year there:

  • I was working full-time
  • I was in full-time grad school
  • I obtained a professional craft beer certification (just for fun)
  • I started a craft beer podcast (just for fun)
  • I published my 2nd eBook

I actually don’t regret my time before/after work, because I was being productive and investing in myself. But if I had nothing else to do besides sleep in in the mornings and watch TV after work, I would sincerely regret not putting in extra work to build my other income streams.

Tim Ferris discusses how many individuals have a misconception that their “job” and their side-business cannot coexist. These are not mutually exclusive projects, and it would actually be irresponsible to simply quit your paying job to work on your side-business, essentially throwing yourself in the deep end of the pool without a flotation device.

Instead, Ferris recommends you put in a lot of work to your personal project as you’re getting paid at your day job, and only quitting to work full-time on your project after you have a sustainable stream of income.

That freedom to work full-time (and get paid) on projects you’re passionate about is worth waking up early and staying up later during the week!

6. Gossiping

I am actually a huge gossip at work, I’ve discovered.

My team environment was often very negative and dysfunctional; the office politics, constant gossiping, and trash-talking behind backs was toxic. I regret partaking in it.

When you have a bad boss, or when you’ve been wronged at work, or when coworkers do obviously-stupid things that make things more difficult for you, it feels like you’re going to explode if you hold those feelings in. You have to get it out! Watching Office Space 3 times in a row just doesn’t cut it anymore. Surely someone must be told how so-and-so did this and he-or-she did that stupid thing. They deserve it!

Well, let me tell you from someone who has indulged that trash-talking-the-boss; you never really feel that justice has been “served,” that the person in question receives their rightly deserved punishment. All you feel is dirty and more depressed.

Gossiping feels good at first — there’s a sense of camaraderie, and you’re actually doing a service by commiserating and bonding with others, helping each other get through the day.

It never lasts, though. And after a while, you’ll find yourself driving home with your wife telling her all about how stupid and foolish that one coworker acted today, and your wife will look over to you right in the eye and (rightfully) tell you what a jerk thing that is to say. And you’ll realize you’ve become an office gossip, who hurts people behind their back to feel better about yourself and others.


7. “Drinking the Kool-Aid”

My company was a difficult place to work, and everyone knew it — the management and CEO weren’t popular, the working conditions were stressful, and worst of all, the cafeteria salads were like, way too expensive.

However, the company did start making a lot of changes for the better. It was the small things — free doughnuts on Tuesdays, more frequent carpet cleaning, opening up free Wifi, more lenient holiday hours, etc. I thought the company was making great strides, slowly but surely, in increasing the goodwill between employer and employee.

But not everyone thought so — some people still harped on the company for being incompetent and a difficult place to work. The phrase people used around the office was that “they drank the Kool-Aid,” which described the individuals who accepted their job sucked, it would always suck, and the company was a terrible place. Period.

I regret not speaking up about what I actually thought, and instead quietly went along with the complaining.

I don’t want to do that anymore. At my job, with my family, with friends, with anyone. If I have an opinion, I’m not going to think or say the opposite just to get people to like and accept me. They wouldn’t even be accepting the real me, anyway.

What I learned from these regrets

I don’t have to live with these regrets for the rest of my life.

So I blew the opportunity to stick up for myself to my boss. That sucks. But the next boss I have won’t have the opportunity to push me around.

No more gossiping or trash-talking behind any coworker’s backs, because that’s not the person I want to be. Also, I was spending $2 every morning, Monday-Friday for coffee (my coworkers were spending like $4.50 on their lattes and mochas). After realizing how much that comes out to over time, I decided to brew my own coffee from home. Lesson learned, son.

Looking back at your 9–5 job, you probably have a lot of regrets too. Some of them might be small — wishing you hadn’t spent so much on food/coffee — or some of them might be pretty big. I wish I hadn’t become a person that gossiped behind people’s backs, I wish I would’ve had a backbone and stand up for myself. I wish I didn’t complained about problems as much, instead of finding solutions, and following others’ toxic mindsets instead of having a mind of my own.

It’s alright though, because next time will be different.

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  1. Kevin Hoelscher says:

    Not learning more earlier in my career, that’s my regret, now I’m always trying to learn more, to read more. But it took me several years to build up that appetite. I’ve realized that the more I learn, the more confident I am in my work, which makes work much more enjoyable.

  2. Fantastic, honest and candid. These are lessons that anyone can take to heart, myself included! Something else I have learned is to not let myself burn out. I work in a place where a lot of OT is worked, which I’ll do occasionally, but I believe it’s so important to not give all of yourself over to work, because personal life, family life, etc. will suffer. And if those suffer, you suffer, and work suffers as well. I’m still learning the art of giving my fullest effort to work, but still protecting myself and everyone else in the process.

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