Top Ten Signs that You are Ready to Divorce Your Job
March 19th, 2008
Are you in a career or job that you simply hate?
Someone recently emailed me and asked, “How do you know when is the right time to leave your corporate position or your job?”
My first thought, is that leaving your job that you have been in for two, five, or ten years is a lot like a divorce in many ways. Not that I would have any idea what going through a divorce is like, but for many people, even if they can’t STAND their career it still defines who they are, much like a long-term relationship.
I think the thought of separation [from a job] and the act of following through with the split can be a lot more difficult than most people imagine. Additionally, some people cling to their job (or marriage) like a life raft and are tremendously afraid to let go. Really, it comes down to the following. You have a burning desire and goal to be doing something else and the only reason you’re not is because fear, or a sense of job security, is holding you back.

image source: amazon
I don’t really have a specific answer for exactly when someone should “divorce their job.”
For me, the decision was easy. When I originally went back to university I had the unfortunate [but now seemingly fortunate] happenstance of working for a pharmaceutical manufacturing company. While I was employed there I learned everything I needed to know about the sometimes ugly face of corporate life. What I witnessed on a daily basis was backstabbing amongst colleagues, deceit and strategic power plays, and individuals hoping to advance themselves up the corporate ladder, not on the merit of their work, but by scheming and underhandedness.
Now let me put in a little *disclaimer*
I am sure that there are TREMENDOUS companies to work for. In fact, Fortune Magazine has a whole issued devoted to highlighting the 100 Best Companies To Work For. It’s just during my various twenty years in and out of various offices I did not happen to work for any of them.
So, if you have had enough of corporate life and would like to take a leap and start your own business, or you just want to explore a different way of living then this post is for you. Some people that I run into think that not having a structured job to go into every day is a radical concept. And to be perfectly honest, for some people it is radical. There is ABSOLUTELY nothing wrong with having a career or job, but for those people (who are like me) it can feel like prison.

image source: code_martial
Knowing when to make the leap can be difficult.
There are all kinds of reasons telling us not to; mortgages, bills, kids, tuition, student loans, car payments, you name it…but there are many people who have been successful at this change and if you really want to do it I am sure you can!
Here are my, Top Ten Signs That You Are Ready To Divorce Your Job -
- You have been thinking about leaving your job persistently almost everyday for six months to a year.
- You loathe working for other people in an office environment.
- You really have an inner desire or drive to be your own boss and start your own business.
- You are generally miserable and it is because of your job, or your job is affecting your personal relationships (even on the weekends).
- You requested a leave of absence for three months to take a career break, sabbatical, or mini-retirement and your company said NO even though you offered to take it without pay.
- You would like to travel and see the world.
- Every very year when you come back from vacation you tell yourself I am going to leave my current job and do x,y, and z. Then a week later you are back into the same “treadmill-esque” routine.
- You would like to work from home or possibly telecommute.
- You have a strong feeling that there is more to life than just going to the same job for numerous years and working from 9 to 5.
- Everyday when you are at work (or even out of work) you are feeling claustrophobic or trapped.
Bonus signs!
- Quite possibly you are having panic attacks about your job.
- If you get the feeling like you want to drive your car off a bridge on the way to work that is a pretty good sign that you are ready to move on.
- When you are at work you find yourself doing anything but WORK to keep yourself distracted.
- Your boss is a dickhead!
Now what?
For some, leaving a job might be the most daring thing they have ever done. Also people naturally fear that they won’t have the support of their loved ones, spouse, or peers. That can be a tricky and you will have to make some very personal decisions as to how you will deal with the situation.
Making the switch from the traditional employment norm, or “divorcing your job,” is not always an easy process. I am a fan of a phased approach where you remove yourself gradually and have some sort of plan. I realize that some people are so miserable or pissed that you just want to get out of the situation as fast as possible. If that is the case then try to make sure that you have a financial cushion or backing to help carry you through.
Sometimes I shudder to think how many people there are out there who, are not only are hesitant to remove themselves from corporate life, but never actually take any RISKs. If you are not a risk taker then of course this a fine path to follow! I just genuinely feel bad for the people that would like to try something different and for whatever reason lack the time, energy, resources, or fortitude to actually go out there and take that risk. If you have an idea, don’t be afraid to pursue it.
A success story
Recently, I came upon a young Australian entrepreneur, Ross Hill, who is getting ready to finish university. Ross left a comment on my site the other day and upon further research I found out that he is already running three or four online enterprises. I must say, I find that terribly inspiring.
As of yet, I don’t know if Ross is making any money online but he is at least attempting to make money online. These are the kind of people who, if you find yourself on the fence about a “career divorce,” then you should be following their sites and stories.
In closing
Seriously, I am not against corporate life, or having a 9 to 5 job. In fact, I am stating right here that I could very well find myself back there someday.
What I am against is people being treated like indentured servants without fair compensation and also I am against people staying in a job or career if they TRULY want to be doing something else.
In essence, the question really becomes, how do we get the corporate world to have a paradigm shift in what they think is fair and equitable treatment of its employees? And how do you support and promote creativity, different types of work styles, while still ensuring productivity?
Editor’s note: if you read my Travel the Globe With Flickr post the other day, I just thought that I would point out that Steven Snell recently posted a fantastic Flickr resource list. Also, please consider signing up for my RSS feed.
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March 19th, 2008 at 2:19 pm
This is a great article, I really like all of the resources that you link to, and appreciate the link to my own!
I am going to print this and keep it handy for the monthly reviews.
March 19th, 2008 at 2:25 pm
Great post, Mark and thanks for the link.
I’ve had lots of jobs in my life and two distinct careers, and even though generally I am a risk taker, I still found
it difficult to leave my corporate job and start afresh. Part of it was knowing that I was leaving a well paid marketing career and I wasn’t sure what else I wanted to do. And part of it was fear about WHO I was if I wasn’t the successful one with the enviable job and bright future.
I ended up retraining to become an ESL teacher and all my fears faded the first day I stood up in front of a class. I loved it! And the years I spent doing that work were probably the best in my employee working life. And this is despite the fact that I halved my pay when I left marketing.
Money doesn’t ease misery, it just gives you the resources to medicate it. I never really missed my old pay because I no longer felt the need to spend money to make myself feel better. I already felt great!
I know this choice is harder once you have a family and a mortgage, but I believe there is always a way to do what you love. Sometimes it just takes more time and planning. And if you don’t have those kind of responsibilities, now is the time for change. The longer you leave it, the harder it gets.
For people who think it’s not possible to halve your executive pay and live, I did that and more. I saved and travelled to Europe, Asia and the Americas while earning $34,000 pa. Over a 4 year period, I spent about 14 months overseas, and I found that the world is full of people like Tim Ferriss. They may not live as well as he does, but they live free and that’s the point of books like 4HWW.
Enough with the rambling. Loved this post.
:) Kelly
March 19th, 2008 at 3:49 pm
WOW … I love those list.
Especially, #5 and #6. Travel around the world is my dream. I told my ex-boss that I want to travel to my Home Town for 2 months. He said no. So I said to him. “Fine. I will come back in two years”
I will add one of my major reason that I quit my job.
“I think I can do better job than my boss did.”
Thank you for the links to those sites.
March 19th, 2008 at 5:44 pm
Mark, thanks for the link.
March 19th, 2008 at 9:50 pm
I’m not sure if I can ‘divorce my job’ without having a job - but I’m trying! Thanks for the mention. I’m making a few hundred bucks a month but would like to increase that to be a full-time wage. We’ll see how it goes.
March 20th, 2008 at 6:04 am
Hi Stephen - I have been reading through you posts lately and thought it was a good time to start linking to some of your practical productivity.
March 20th, 2008 at 6:12 am
Mark,
I’m currently in this very situation. Just beginning to launch my 1st web site. I’ve already been travelling for a year, 3 years ago.
Yet I want more. Each time I go away. I think, I just love this so much. Not so much the places, yet the people I’ve met have just been fantastic.
I think for many the greatest fear is regular cashflow. Hence my 1st website. I now know my current goal is X£$ per month and to be able to work from anywhere in the world. I just love Fiji. Yet, no off the main island internet the last time I was there. Oh and the Girlie is Japanese…need to build up that visa time!
Thanks for the list… yep 10/10 . Just more motivation to push myself and desires even more.
Happy Travels
A
March 20th, 2008 at 6:47 am
Hi Kelly – Leaving a well paying job is not easy…but I am impressed at how much traveling you managed to sneak in even with a lower paying job. Also, I would think with your marketing background and internet savvy you could make quite a bit of extra income working online.
For me having a [very] structured job is part of the issue, but what really gets me is the disparity in pay. This article http://www.commondreams.org/views05/0510-22.htm regarding CEO pay is a little outdated but it still highlights quite nicely the difference in remuneration between executives and employees.
March 20th, 2008 at 6:54 am
Hi Terence (Internet Entrepreneur Diary) - I really like that addition “I think I can do the job better than my boss.”
The smartest and most qualified person for “the boss job” is not always the smartest, most qualified person :)
March 20th, 2008 at 7:19 am
Hi Ross – I used you as a success story particularly because you have not had a job yet.
I figured, if one person reads this post that is currently unhappy in his/her job and is holding back from making a life change (new job, open business, telecommute, etc.) then hopefully they could find some inspiration in what you are trying to do.
Most people know Trump, Branson, and Larry Page but, here is a person (you), not even out of college yet and you have decided to take control and try to have some entrepreneurial success. Another person that comes to mind is Wayne Liew http://www.wayneliew.com/about/.
Some might argue that it is easier for someone still in university to go ahead and take risks. While there might be some truth to that (no mortgage, kids, etc) is still does not negate the fact that you came up with an original entrepreneurial idea and pursued your vision. People who are stuck in careers that they dislike could learn a lot from young entrepreneurs!
March 20th, 2008 at 9:53 pm
@ Mark
I shouldn’t have joined this discussion as I have not had any experience working nor receiving salaries. However, I would like to make clear about the “greatness” of teenage entrepreneurism.
I can’t say that I am an absolute example for teenage entrepreneur as many kids (not even in their teenage years yet) nowadays is trying their hands on entrepreneurial activities and plans. Also, most of us self-study about stuffs like how to write, boost out productivity, marketing skills and so on, which by right should only be exposed to us when we step into the real working world of competition and “rat race”. It is purely based on interest alone without having MBA professors.
Another thing about us is that we have equal amount of pressure like what most adults are facing as well. We have pressure from parents, our studies, relationship problems and true enough, we are still being looked down by people sometimes just because we are young.
We somehow have this realization at this age that avoiding the rat race is the best thing for us. This is what most realized when they are nearing their retiring age and we don’t want to be in that position.
To sum things up, we don’t need to do this as we can well be playing with computer games and flirting around at clubs all day. We do this purely on the grounds of passion and for self-actualization. This is a big statement but as a teenager, we can say that we are able to hold the sky up even if it falls.
March 21st, 2008 at 9:15 am
Hi Mark,
I bounced from “real job” to “real job” for a couple of years after high school, and nothing felt right. I just couldn’t imagine working my whole life on someone else’s terms.
When I was 21 I went to Brazil for a few months and my view of life was forever changed.
I met a woman who is now my wife, and when she mentioned that she had a 1 month vacation…I knew that my “get a real job” path would never be the same.
From then on, have worked for myself as a personal trainer. I make my own schedule, vacation when I want, and can’t imagine ever getting a “real job”.
Best,
Coop
March 28th, 2008 at 9:38 am
Hi Coop - apologies, don’t know how I missed this comment…
What were you doing in Brazil? It’s pretty amazing if you have been able to avoid a “real job” since you were 21!
March 28th, 2008 at 11:53 am
No problem Mark.
I went to Brazil for 3 mos with a buddy of mine…just for fun. I had ideas of parrots and bikinis. I “experienced” the the bikinis, but not too many parrots.
My goal now is to phase out my one on one training, and create online products…and move to my own “tropical escape”.
Best,
Coop