Are There Really 50 Ways to Leave Your Job, Jack?

Speaking of career choices, I was just reading a comment from Jim on a recent post where I asked readers if they would quit a job if they won the lottery. While some of you said you might very well stay at your current job, Jim’s basic answer was Hell yes! Are you nuts? (I’m sure Jim isn’t the only one who can’t stand his job.)

Well…this got me thinking. How many ways are there to quit a job? I’ve done my share of quitting, but I’m sure there are many many ways to say adios to a boss and job you can’t stand. So just for fun I decided to turn to the Paul Simon song 50 Ways to Leave Your Lover for some help finding an answer.  (I’ll need your help too, btw.)

But first a little mood music from Paul Simon himself:


And now without further ado…here’s my shot at 50 ways to leave your job, with the first few courtesy of Mr. Simon of course:

1. You just slip out the back, Jack

2. Make a new plan, Stan

3. You don’t need to be coy, Roy
(Just get yourself free)

4. Hop on the bus, Gus

5. You don’t need to discuss much

6. Just drop off the key, Lee
(And get yourself free)

Hmmm…that’s only 6 at best. If I’m going to give you 50 ways to leave a job, I’m going to have to dig deeper than the Simon song lyrics. OK…so here are some more ways…

7.  Do something (or do absolutely nothing, including your work) to get yourself fired.

8.  Actually go on interviews and get offered a job. (A daring approach.)

9.  Go back to school and get an advanced degree in your field – or get a degree in a totally new field.

10.  Volunteer and see where that leads, either to a job at the volunteer site itself or as a way to see if there might indeed be a new career in your future.

11.  Cut back to part-time hours (either as an employee or consultant) and explore new possibilities for dream jobs in the meantime.

12.  Take a battery of tests or read books such as What Color Is Your Parachute to see if you can discover new dream career choices  for your future.

13.  Work with a career coach to help get yourself to one of those new dream careers.

14.  Network everywhere you can think of until you find a new job – no matter how long it takes!

15.  Win the lottery.

16.  Just tell everyone you won the lottery and borrow money from them “until the check comes”.

17.  Go to jail for fraud because you followed #16 and there was no check.

18.  Take on some extra part-time work that interests you and see if it opens up career possibilities or sparks other ideas that help you move on.

19.  Start your own business.

20.  Marry into a family with a good business.

21.  Quit without any career planning whatsoever and just run with the wind.

22.  Quit without any career planning and run against the wind.

OK. That last one was just so I could play some Bob Seger:


Looks like I only made it to 22…and that’s stretching it a bit.

Please help me by adding your own ways to leave a job. Maybe we can hit 50 together. Your own real life examples and stories very welcome!

Oh…and in case you’re curious, you can see the original lottery post with some great answers (including Jim’s) here:

So Would You Quit Your Job if You Win the Lottery?

And in case you’re even more curious, here are the  lyrics for the Paul Simon song. Rhyming “crude” and “misconstrued” btw ranks way up there in my song book:

50 Ways to Leave Your Lover

The problem is all inside your head
She said to me
The answer is easy if you
Take it logically
I’d like to help you in your struggle
To be free
There must be fifty ways
To leave your lover

She said it’s really not my habit
To intrude
Furthermore, I hope my meaning
Won’t be lost or misconstrued
But I’ll repeat myself
At the risk of being crude
There must be fifty ways
To leave your lover
Fifty ways to leave your lover

You just slip out the back, Jack
Make a new plan, Stan
You don’t need to be coy, Roy
Just get yourself free
Hop on the bus, Gus
You don’t need to discuss much
Just drop off the key, Lee
And get yourself free

She said it grieves me so
To see you in such pain
I wish there was something I could do
To make you smile again
I said I appreciate that
And would you please explain
About the fifty ways

She said why don’t we both
Just sleep on it tonight
And I believe in the morning
You’ll begin to see the light
And then she kissed me
And I realized she probably was right
There must be fifty ways
To leave your lover
Fifty ways to leave your lover


About the author…

Ronnie Ann, founder of Work Coach Cafe, bases her real-world advice on her many years as an organizational consultant where she helped interview and hire people, added to a certificate from NYU in Career Planning & Development and her own adventures as a serial job seeker. She can also be found on her new blog, and on Google+.


  1. I left my last job because I fired myself. I was the head of HR, and I had to make a list of 300 people (out of 700) who would be cut. I put my own name on the list. Then I broke the news to myself over a very long lunch that included the purchase of a new purse. Then I gave myself a nice severance package (I mean, it was the standard package for my level…I didn’t rig it or anything, but still, it was nice). I highly recommend this approach.

    I heard of someone once who actually wrote “F__k You I Quit” on the bathroom wall. In poop. You have to hate your job a lot to actually pick up poop and write with it.

  2. Hah! I love that you fired yourself, Kerry. I’ve done that a few times myself, but without the severance package. Very cool. As for the other story…ugh. But I know there is great anger out there. Speaking of which…

    When I was in high school, I worked at Howard Johnson’s as a fountain girl. When I finally decided to quit and told my boss, he asked why. Before I could respond, my fellow fountain girl, Roberta, piped up in a rich, booming voice “I’ll tell you why!” And then she went on a wonderfully dramatic tirade of all the things wrong with the job. (Luckily for her sake our boss had a sense of humor.) I’ve left other jobs in my long career, but I don’t think there was ever a more colorful farewell speech…and it wasn’t even mine! (Roberta, btw, went on to a career in the theater. No surprise.)

  3. I eased myself out of my last job because I wanted to go back into business for myself. I sliced my time at the company in half, then a little more, and more until I was finally out the door. While I was cutting my hours, I was building my resume writing business in my non-corporate time. This took the financial stress off of my startup because I knew if I didn’t get enough clients to pay the rent, I could stay with my employer. Luckily, my venture worked.

  4. A great way to leave a job and still keep money flowing and doors open. Thanks for sharing that Susan!

  5. Thanks for the trip back into the late ’70s! Let’s stick with the “Rhymin’ Simon” theme:

    * Tick off the boss, Ross!
    * Keep showin’ up late (or Stop pullin’ your weight), Nate!

  6. Hah! Love it. What fun. Thanks, Rick!

    And to those, I’ll add: “Just whine and complain, Jane!” and “Embezzle some dough, Joe.”

    Any other Rhymin’ Simons out there?

  7. I have done 1,3,6,9,11,19 and 21. I am hoping 21 gives me financial independence.

  8. Hah! Love it. Nice to see you again Marsha. A woman after my own heart. Good luck with any and all the numbers. 😉

  9. I’ve ticked off the boss (many times) and stopped pulling weight…hasn’t worked for me, so I’m back to doing the boss’s job while he continues to have fun doing my job, which he stole from me when he came on board about two years ago. Yep.

  10. Hi Kim!

    Thanks for sharing. It helps people know they aren’t the only ones going through this. I’m so sorry you are in this position. Never too early to start planning for a future move! 😉

    Best of luck!

    – Ronnie Ann

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