Here’s To The Terrible Bosses

For the average Joe or Jane, working a 9 to 5 job can be a real drag… because the reality isn’t 9am to 5pm anymore.  Most people I know put in at least 10 hour days now.  They get-up around 6 or 7am, and then commute for at least half an hour (and some even more than an hour) to work.  They don’t usually leave work until 5:30 or 6pm either.  It’s pretty normal for the average person to put in a 10 hour day these days.

Working through lunch is a normal occurrence too.  The era of leisurely hour long lunches is long gone.  Most people I know eat at their desk and answer emails/work at the same time.  Then there’s the hours after work when you’re expected to answer emails and otherwise be on-call.

Almost nobody I know works 9-to-5 anymore.  It’s more like 8am-to-6pm and then ‘online and answering emails’ from 9pm-to-midnight.  That’s just the way it is now.

Yep, working can be tough.  Doubly so if your boss is a horrible person.  They can make your life a living hell!  Imagine working extremely long hours for someone you don’t really like hate.

I’ve certainly had my fair share of horrible bosses over the years.  Working for some of these terrible people really made me hate our modern work culture.

Today I thought it might be fun to share some of my “horrible boss” stories that helped set me on the path toward Financial Independence.

I hope you get a good chuckle at my expense…


Mrs. Every-10 Minutes

Back when I was still fairly fresh out of college, I got to experience what it’s like to work for an extreme micro-manager.  I’m calling her “Mrs. Every-10 Minutes” because after giving me an assignment she’d check-up on me every 10 minutes.  Literally.  Every 10 minutes she’d walk by to see how I was doing on the task.

Mrs. Every-10 Minutes:  “Hey, how’s it going on that task I assigned you this morning.”

Me: “Well, it’s been 10 minutes.  I’ve started reading the documentation to learn how the process works.”

Mrs. Every-10 Minutes: “Well, try to hurry it up.  I’d like that task done before noon today.”

Me: “OK.  I’ll do my best.  I don’t know how the process works yet.”

Mrs. Every-10 Minutes: “Oh and by-the-way, I noticed you were a couple minutes late this morning.”

Me:  “Err, yeah I think I might have been a few minutes late.  Traffic was bad this morning.  Sorry.”

Mrs. Every-10 Minutes: “Well, it reflects badly on me when you’re late.  Start leaving earlier so you’re here before everyone else.”

To be fair, I don’t think it was just me.  I think she did this stuff to all her employees.  She really liked to crack the whip.  When she wasn’t in meetings, I think she literally walked-around and continuously pestered her employees.  Like in a circle, so she could continuously be prod us every 10 minutes to work harder.

I think it was actually harder to get stuff done when being interrupted that often.


Mr. Handsey

Mr. Handsey was a boss I had one summer during high school.  The job was a dishwasher job at a the nicest restaurant in town.  (I grew up in a small town)  Anyway, I was pretty grateful to have the job.  There weren’t many good-paying jobs in that town, but I think I made about $8/hr washing dishes and doing food-prep.  It was decent money back then (for a high school kid).

Anyway, Mr. Handsey was just that — “Handsey”.  He was a gay man that liked to touch a little too much.  He’d always be doing stuff like rubbing me on the back, touching, putting his arm around me, or unwanted hugging.  It wasn’t overtly sexual or anything, but it was pretty uncomfortable.  I didn’t like it, but I did like having a job.  So I didn’t say anything and just put up with it.

Thanks boss, but keep your damn hands to yourself.

How do you tell your boss to get his damn hands off you?  Especially in a small town without a lot of job prospects.  I know, it seems like pretty tame stuff in this #MeToo era, but men sometimes have to deal with this stuff too.

It was icky and made going to that job icky too.


Mrs. Backstabber

Mrs. Backstabber was probably the worst boss I’ve ever had.  On the surface, she pretended to support my career like a good boss should — giving feedback, putting me in touch with the right people, and even letting me attend college classes that (I thought) would be helpful for my career development.

In every interaction I had with her, she appeared to approve of the work I was doing.  She seemed like a good boss.

“Good job on that project” she’d say.  Or, “Thanks for your efforts on that proposal.  I liked how that one turned-out.”

Turns out anything positive from her was just fake.  Complete bull-hockey.

I later learned from other co-workers that she set me up to be the fall-guy for her organization.  Behind my back, every chance she had she told her superiors what a terrible job I was doing.  She set me up to be the reason for everything wrong in her organization.

knife blood
Getting stabbed in the back definitely left a scar.

I got thrown under the bus.  Clearly I didn’t stand a chance with a boss like that, and they fired me a couple of months later.  I even got accused of wasting company resources by attending those college classes… even though Mrs. Backstabber had personally signed-off on my taking those courses.

HR attempted to withhold my final paycheck until the “issue” was resolved.  Thankfully, I had saved all the documentation with her signatures.

Now, a decade later I still have nightmares about the last few months at that job.  I’m still extremely angry about how it all went down… even though I know I should just let it go and move on with life.

Horrible bosses can do that to a person.


Mr. Biltong

Mr. Biltong was one of the toughest bosses I ever worked for, but he was also one of the nicest bosses too.  He was straight-forward and honest in every dealing I had with him.  Unfortunately he was something of a workaholic and expected the same from his employees.  He basically worked 14 hour days — 8 am to 10 pm. Every single day, except for Sundays.

horrible saturday

That’s right — Mr. Biltong frequently asked his employees to work on Saturdays, just like he did.  That got old really fast.  As a parent, weekends are the days when you actually get to spend time with your kids.  Mr. Biltong didn’t have kids and didn’t understand this.  By Sunday I was usually too exhausted from the hard-driving Monday-thru-Saturday schedule to have a lot of fun with the kids.

What made matters worse was the fact that he lived and worked in New York City, and I lived and worked in Seattle.  (That’s 3 time zones apart.)  So when I started working at 8am on the West coast, he’d already have been at it for 3 hours.  I had to hit the ground running every morning (so to speak), in order to catch up to everything he’d done on the East coast.  It was always a mad rush in the morning.

Why not come in earlier, you ask?

My schedule was primarily dictated by drop-off and pick-up times at the kid’s daycare.  Those times are NOT very flexible.  I was also at a time in my life where putting in long hours at the office wasn’t something I wanted to do.

Mr. Biltong didn’t understand this because he didn’t have a family.  For him, life was all about work, and putting in as many hours as humanly possible.  That’s a tough kind of boss to have when you have kids.


Here’s To Those Terrible Bosses

So that’s my list of horrible bosses.  Some were actually pretty decent human beings, and others I wouldn’t save even if they were on fire.

They each made my life a living-hell each in their own unique way, but I really should be saying “Thank You” to all those horrible bosses — they ultimately set me on the path for achieving Financial Independence.

I hated work and wanted a way to escape… so I did.  Financial Independence was the solution for me.  I saved as much as I could, and then investing the money into the very best investments I could find.  It only took 15 years, but I finally made my escape.

These days life isn’t quite so bad.  I don’t work for anyone but myself.  I have a lot more freedom and a lot less stress now.  I get to spend plenty of time with my kids, and I couldn’t be happier.

Have you ever had a horrible boss?  I’d love to hear about it in the comments!


[Image Credit: Flickr1, Flickr2]

14 thoughts on “Here’s To The Terrible Bosses

  • November 13, 2019 at 2:24 PM

    Hi I’m a long time lurker on your blog and I want to say that this is a really big issue in the corporate world. Horrible bosses are far too common, it’s a great wonder that any high quality work gets done at all. My horrible bosses also kicked me up the path to FI. The last one was also a micro manager, yelled at me in the office, embarrassed me and my team during meetings. I worked in the tech department of a Fortune 50 firm and was one of the very few women there. My manager had a boy’s club thingy going on. I knew for sure I wouldn’t make much progress careerwise there after looking around seeing how women co-workers were treated. I’m so happy I don’t work there anymore. I’m thankful for all the personal finance bloggers who showed me the way out of the terrible rat race.

  • November 13, 2019 at 4:51 PM

    Fun post. Overall I have had some really great bosses over my career. I have been very fortunate and I am grateful for all of their help over 30+ years.

    Unfortunately in the midst of all of these great bosses, I worked for Satan for 3 years. He was about as terrible a human being as anybody you will ever meet. Let’s call him “Mr. Bullshitter” or MrBS for short. He ruined multiple careers over his tenure including mine. He spoke in vague statements that never made much sense but throw in some buzz terms and he sounded really bright. The truth was, he had no idea what he was doing or what he wanted from the team. So when we delivered something, it was never right. He was a back stabbing reincarnation of Satan. It has been 8 years now since I worked for him. I have gotten to the point that I do not wish him any ill will but I can say this, if I was walking along and saw him bleeding on the side of the road and I could save his life for $1, I’d turn the other way and go buy a Coke from a vending machine instead. 🙂

    • November 16, 2019 at 6:46 PM

      Thanks for sharing your story, and I sincerely hope that your good fortune of working with amazing bosses will continue.

      As for MrBS and all the other horrible bosses mentioned in the article and comments, I really fail to understand the illogical motivation for these types of behaviors. After someone pisses off enough people, it’s almost inevitable that the scenario that you’ve described would eventually come to fruition (in one form or another, literally or not). It’s unfathomable to me how anyone thinks this is a smart way to live life, even for their own self-interest.

      Sorry I went off on a tangent.

      • November 17, 2019 at 3:59 PM

        You are 100% correct. These types of people just do not get it but they EVENTUALLY – they get it in a different way. 🙂

        They may never understand but I do believe in Karma. If you are a good person, good things follow you. If not, well that follows you too.

        All the best!

  • November 13, 2019 at 9:23 PM

    Thanks for sharing such a personal post, Mr. Tako.

    Well there is one thing positive to say for all those horrible bosses – and that is they are the ones at the front lines pushing for the companies that we invest in to generate more profit and send bigger dividend checks our way each year. As an owner, I’m glad to have them around.

    Now on the other side of the coin I’ve had more horrible bosses than I can count on two hands.

    Let’s see – over the past 6 years… there’s the Singaporeans who bought our company and had tens of millions in equity of the company but paid themselves a very low basic salary. We didn’t have equity but our compensation was reflected in salary and they started post-acquisition stating that we made more than them. After working us to the bone they came to us with an offer to cut 60% of our pay and that was the signal to leave.

    Then I worked for a great CEO who retired and later a major backstabber came into the picture and I was out a few months later.

    The last three jobs I’ve had in the past 18 months have been train wrecks. Once was a post on the other side of Asia that I moved out to join, taking the family with me a few months later. It had a six month probation period and after busting my butt for six months they decided they didn’t want to keep paying me so that ended. Then I went to another company that had a sudden change of leadership and I left after a few months. A third company then paid me for the first month but after working the second month they ran out of money (were building a new project and required investor funds that got withheld) so I still haven’t been paid for September and I stopped working for them in early October. It’s been a total disaster.

    However some good things came out of this move – my wife became pregnant with our second child, a son – and he was born in Thailand 4 months ago. We all moved back to Thailand for the birth and I was traveling and working on site half time these past few months and missing my family like crazy during this time. It’s great to be back with the family now.

    This is a good chance to try and get the feel for the retired life and fully living off of investment income. I love the flexibility, as I drop my 6 year old daughter off at school every morning using a bicycle with a child seat and pick her up the same way during most afternoons. I’m just less productive than before, it’s like that since my body knows I don’t need to be somewhere I’m sleeping more hours in the night and napping and generally moving slower through my day. It could get old if this trend progresses.

    I’m also getting addicted to a racing game on my phone (Beach Buggy Racing 2) and find myself playing it multiple times a day!

    Best wishes to you,


  • November 14, 2019 at 1:39 AM

    Oh man….. in the Federal Government where I work “Mrs. Every-10 Minutes” is the main problem. We’re chock full of micromanagers. It’s ridiculous.

    But “Mr. Handsey”? I would have extricated myself from that situation as fast as humanly possible!! Fun stuff!

  • November 14, 2019 at 4:41 AM

    The biggest issue for me with bosses is trust. If I trust that they have my best interests at heart (and it’s easy for me to suss this out after working with them for about a month), I’m totally devoted. Otherwise, I’m out soon. Unfortunately it’s hard to find bosses like that, which is why I’ve been self-employed the majority of my career.

  • November 14, 2019 at 5:19 AM

    As they say, people join companies but leave bosses.

  • November 14, 2019 at 8:16 AM

    Okay, Mr Handsy was an abuser preying on you because you were vulnerable for the reasons you mentioned. As a research assistant I was also preyed upon by my professor who thought because he bought food sometimes and paid me as an assistant that I should provide other ‘favours’. Can’t use the reference from that person despite a lot of hard work over a few years Those who have worked for government and as I have seen, in many places, the manager is not necessarily the one with the people skills. A recent known racist sexist ageist antisemetic person was promoted to manager, did what he could to get rid of me, then was mercifully demoted while I was home with baby. His sycophant has been moving around from job to job as well. In some cases what comes around goes around

    • November 16, 2019 at 10:51 AM

      Great read Mr. Tako

      I’ve had my fair share of good and bad bosses and it’s funny how having the right manager can make or break a workplace.

      I’ve noticed at a past employer, once my good boss left and was replaced by a bad boss, the workplace dynamic totally shifted.

  • November 15, 2019 at 10:58 AM

    Oh wow, you had more than your fair share of crappy bosses. My bosses weren’t that bad.
    The worst one was when I became a team lead. She was never at work and wanted me to take charge, but gave me no support. People under me were screwing up royally and I didn’t have any authority. Of course, it’s my fault that the project was screwed up. That turned me off completely from the management track. Anyway, I have no boss now and life is awesome.

  • November 16, 2019 at 5:14 AM

    Yes, terrible bosses unite the world – we’ve all had them. I’ve learned A LOT from each terrible boss – all things one shouldn’t do, but lessons nonetheless. And I agree that bad bosses are a great incentive to escape the clutches of the Man – if I had better bosses over the years, I’d probably still be working 9-5 / 8-7 🙂

  • November 16, 2019 at 8:27 AM

    Mr. Tako –

    And sometimes… they can all be one person encompassing multiple traits, woof! Further, it helps you realize and appreciate the money you save and invest, as well as makes you hungrier to get to freedom faster, that’s for sure!


    • November 18, 2019 at 2:09 PM

      LOL, it was a terrible boss that first set me properly on the FI path too…one of those never again moments. Mr. Micromanager liked to push me to move faster, then wanted more indepth analysis. Asked for my recommendation, then decided to do the opposite. Every. Single. Time.

      It got to the point where every time he pressed me to provide a recommendation I’d say something contrary to what I’d truly believed as he was really just looking for something to pick at anyway. In a sense it was a type of self defense, giving him straw targets to rip up instead of my hard work. Before I resorted to that I remember once he completely dismissed my analysis of a particular sector, only to a month later completely agree with the exact same analysis…because it was said by a male colleague whom he respected. By the end of my time there I think that I had gotten a bit of a glimpse of what PTSD would feel like.

      And it was a crap paid job working, of all ironies, in the ethical investing realm. I still remember they introduced annual performance reviews just before I left & there was this personal rating component. I gave myself an overall excellent review, with a couple of areas I’d like to further work on. He tried to argue that I should lower my review “as their standards were higher than the norm” (you see the pattern here…). As I already had 1 1/2 feet out the door I let the conversation somehow segue into asking him how much extra of raise he’d give someone who actually met his “higher than the norm standard”. He proudly said $1,000! I had the hardest time trying not to laugh hysterically at the absurdity of the whole situation, especially as I had just finished getting a new tennant for the second bedroom of my condo at a year over year total rent increase of something like $1,500.

      But he did teach me an incredibly valuable lesson. Doing an excellent job does not equal success, unless it’s a job for yourself. Better to do a very good job, but save your real superstar stuff for where the real return on investment is.


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