Going Steady with Your Boss – 20 Reasons Your Job Is Like a High School Relationship

September 25, 2007

Several decades ago, people built a career-long relationship with their employers.  Now-a-days companies are all about the bottom line and our employer relationships are more like bad high school crushes.  How many of these 20 reasons can you relate to?

1) Every person has an image of their ideal job in their head; many people spend a lot of time searching for the ideal job but never find it.

2) Somehow all your friends seem to know when you’re in the market and everyone knows this “perfect job” that they want to set you up with.

3) The interview is like the initial phone call. You don’t have enough time to really get to know the employer and what they’re all about in an hour.  Based on what you learn in that short time you set your first day(te) and hope for the best.  If it doesn’t work out, oh well, there are other fish in the sea : )

4) The early relationship is only based on mutual benefits. You’re attracted to their salary and benefits and your knowledge of AJAX or DB2 is what really excites your perspective employer.

Honeymoon Phase
5) The first day(te) is the most exciting part of the relationship.  Everything is brand new.  There isn’t any hard work, you’re still spending all your time learning about the employer, not arguing about client requirements and whose needs are more important.

Reality Check
6) Once the honeymoon phase wears off those quirky habits of your co-workers stop seeming so harmless and start becoming annoying.  Eventually you feel comfortable enough with them to let them know what you really think of their habits.

7) At least one weekend a month is ruined by “quality time” with your job, paging you for extra work or working overtime to help “maintain customer relationships”.

8) It never fails, your clingy job always comes up with something it wants you to do at 5:30 on Friday afternoon instead of going out on the town.

Green With Envy
9) After a while every day(te) starts to feel the same.  You start to wonder, where did the passion go?  You catch yourself sneaking peeks at sexy jobs on Monster.com.

10) The grass is always greener.  Did you hear about John?  He hooked up with this awesome new job with a bombshell company.  They have cool new technology and hot stock options!

Self Doubt
11) You make yourself believe you can change your job.  Sure you don’t like the way things are but if you “talk about it” with your boss you just might be able to salvage the relationship.

12) You think about venturing out after other jobs but aren’t ready to risk it.  You already have a decent catch, if you leave now, where will you get your health benefits?  What will you tell your friends when they ask which job you’re working steady with?

Death Throes
13) You begin complaining about your job behind its back to your friends.

14) You really want to check out the other available jobs but you can’t at work with your boss hovering over you and the proxy server blocking your view of job sites.

15) You start lying to your job because you can’t bear to spend another day(te) doing the same boring thing with the same boring people.  You call in sick an hour before the day(te) begins so you can spend time looking for other jobs.

Break Up Worries
16) You can’t decide whether you should ask for your ring back, I mean your two weeks banked vacation, when you leave.

17) You feel guilty when you think about leaving the relationship.  Senior prom, I mean the end of the quarter is coming up.  What will they do without you there?  They need you, maybe you should stick around at least a while longer.

18) You start to doubt your decision to move on.  What if I don’t like the next job?   What if I miss the old one?  Will they take me back if I admit I was wrong?

19) You decide that today’s the day to end it but you chicken out part way through the day(te).  You just couldn’t find the “right moment”.

20) You feel SO GOOD after you finally break it off!  You wonder why you didn’t do that a long time ago!  You can’t believe you stayed with that loser job for so long!  Now, on to find the next job and start the same dance all over again 🙁


Will this article help you save or earn more money? Get others like it simply by entering your email address below. Your email is used only for delivering daily money tips and you can opt out of delivery at any time. Click here to see all your free subscription options.


Ben Edwards, the founder of Money Smart Life, saved up enough to buy a Nintendo back when he was 12 years old. When he used the money to buy shares of Wal-Mart stock instead, he knew he wasn't like the other kids... His addiction to personal finance has paid off for his family and now he's helping you to afford the life that you want. Check him out on the web at Google Plus, Twitter and Facebook.

All posts by


5 Responses to Going Steady with Your Boss – 20 Reasons Your Job Is Like a High School Relationship

  • Fred

    Yeah, I guess the only real difference between a high-school crush and a job is that the chance you and your kids could be out dumpster diving for breakfast after you break up with your girl/boy/friend are pretty slim.

  • Ben

    mapgirl, sounds like you and I both work in the tech industry : )

    Thrifty Penny, sorry to hear the honeymoon is over. Hope the job gets more interesting.

  • Thrifty Penny

    I am currently working at my first job out of college, and I agree completely! The honeymoon phase is gone…I’m in the “green with envy” phase.

  • mapgirl

    Scary! I have a post drafted about #9 that’s going to go up later today. Weird psychic connection Ben!


  • Can Losing Your Job Mean Finding Happiness? » Money Smart Life