How to Get Out of Job Jail

So I was sitting in my cubicle today, and I realized, ever since I started working, every single day of my life has been worse than the day before it. So that means that every single day that you see me, that’s on the worst day of my life.

— Peter Gibbons, Office Space

I recently read Audrey B. LeGrand’s How To Get Out of Job Jail: Eight Ways to Have the Career You’ve Always Wanted. I was immediately attracted to her book due to its title. The concept of “Job Jail” really resonated with me, because ever since I entered the work force, I’ve felt trapped.

According to LeGrand, there are many reasons why you might be in Job Jail. You want to change career fields, but potential employers believe that you’re over- or under-qualified. You want to get promoted, but your position doesn’t give you the right opportunities or necessary skills to truly advance. You want to do work that’s more rewarding to you, but you’ve taken your career to the point where you can’t afford to walk away from it.

No matter which situation you might be in, the underlying feeling is the same: helplessness. You’re unsatisfied with where you are. You know that you’re unhappy. You believe that you have no control over it. This is Job Jail.

Being in Job Jail means that someone else is in control of your future. Getting out requires you to regain that control. LeGrand spends eight chapters identifying areas of personal improvement that will help you eliminate the feeling of helplessness, regain control of your career path, and ultimately “break out” of Job Jail.

The book begins with an introduction questionnaire. It’s designed to determine if you’re on the right career path, or if you’re in Job Jail. At first I believed that this “Job Jail Quiz” was unnecessary, because surely anyone wanting to read a book entitled How To Get Out of Job Jail must believe that they are already in it!

After taking the quiz, though, I realized that taking the time to answer these questions really sets the tone for the book. It gets you thinking about whether or not you do your work with enthusiasm. It makes you wonder if the only reason you’re doing this job is because it’s comfortable. It causes you to see if you love talking to people about your job, or if you’d rather talk about something else instead.

In short, the intro helps determine where you stand. It causes you to recognize that you’re unsatisfied, makes you acknowledge that something needs to change, and effectively asks “Now what are you going to do about it?”

For me, it quickly became clear that I must rewrite my resume. As a writer, I tend to be long-winded when providing my work history. Consequently, my resume includes every last detail of my job responsibilities, regardless of how unnecessary those details may be.

LeGrand states that a well-crafted resume will successfully summarize your accomplishments in a quick glance. She uses the acronym CARS to help you remember to hit the important points of your job accomplishments, while still being concise:

  • Challenge: The problem that sparked the need for action
  • Action: What you did in response to the problem
  • Result: The consequence of your action
  • Scope: The impact of your result on the business

A successful resume will combine these points consistently, giving the impression that you are a resource person who can provide creative solutions to professional challenges. An example of a job description using CARS might be:

Developed an Internet Content Filter using Free Software that fully replaced a malfunctioning Subscription Product. The Free Content Filter is being used by all 200 staff members across nine Library Branches, and saves the Library System $30,000 annually.

Although the chapter on resumes was thoroughly informative, I didn’t find all of the chapters in How To Get Out of Job Jail to be equally helpful. One topic I was especially interested in was Entrepreneurial Skills. Sadly, the chapter dedicated to this topic was only eight paragraphs long. It had a questionnaire that basically said “If you answered ‘Yes’ to most of these then you’d do well as an entrepreneur.”

The lack of follow-through on the subject was disappointing, because entrepreneurs already know that they have an innate desire to carve their own path. Entrepreneurs are looking for far more than this acknowledgment — we want the details on how to harness our craft and get started, so that we can succeed in creating and maintaining our own business.

That being said, I don’t mean to dismiss the value of the book entirely. I simply want to emphasize that mileage will vary.

Put another way, reading How To Get Out of Job Jail (or any self-help book for that matter) is not a solution to your dead-end job situation. It is a collection of guidelines that can help you along in your quest to escape from it. Ultimately, the work required to create positive change in your life is left for you to do.

Which brings us to an interesting point: The only thing that separates us from our dream job is the “in-between” work.

Maybe you need to rewrite your resume. Maybe you need to take night classes to gain additional education or qualifications. Maybe you need to focus on your presentation, interview, or communication skills. Although we already know what must be done, we choose to invest our energy into other things. We often don’t want to do the “in-between” work that will affect career enhancement, as we would rather distract ourselves with things that are more fun.

As already indicated, mileage will vary because every self-help reader is in a different spot with a different perspective. I’m grateful for having read How To Get Out of Job Jail because I now realize that my resume sucks. I instinctively want to write an autobiography, but my resume needs to be a snapshot of my most important accomplishments.

In the end, it’s a book that can help you sort out what you might be doing wrong, or what you haven’t been doing at all. Like most self-help books, if you read it, it will at least get you thinking about the next steps for improving your life.

For me, LifeReboot has been an experiment in entrepreneurship. I liken the task of writing in my blog to “building an escape hatch” with which I can escape from Job Jail. I earn a bit of money from LifeReboot, and over the years it has earned progressively more. Perhaps eventually it will earn enough to allow me to write in it full-time, and permit me to leave my soul-crushing day-job. In the meantime, I’m opening my mind to other strategies for escaping Job Jail.

So tell me — are you underemployed, or trapped in a career field you can’t stand? Do you have any plans for escape? And for those of you who have managed to escape already: How did you do it? Please leave your experiences in the comments!

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8 Responses to “How to Get Out of Job Jail”

#1 Weekly Travel Blog Links — LandingStanding on 21, Mar, 2011 at 6:04 am

[…] article on LifeReboot by Shaun that probably hits home for a lot of you… how to get out of job jail?  Also, I only need the thinnest of excuses to quote Office Space:  ”So I was sitting in my […]

#2 Will on 22, Mar, 2011 at 9:38 pm

Hey Shaun,

I’m in the middle of launching two businesses right now. Nothing crazy, like a tech start-up. Just simple service offerings:
-I tutor high school sophomores and jr’s in math and writing skills, and
-I coach first-time authors on how to maximize the marketing value of their radio interviews and speaking gigs.

Both businesses are young (I have three clients or less in each), but both are incredibly rewarding. What I like most about it is the sense that I’m doing it all FOR ME. Not for someone else telling me what to do. I don’t make that much per hour when you factor in how much time I spend prospecting. But that will drastically change as I build a client base.

What made the difference for me was having a framework of knowledge for getting started. I knew I had the knowledge and ability to provide the value, I just didn’t know how to go about it. I got that from Ramit Sethi (of and his program on freelancing, Earn1k. Literally, it’s been my ticket to freedom.


#3 Eric on 23, Mar, 2011 at 12:34 pm

Hey Shaun

I really do admire your column because it really does resonate with me. I too was in a jail job! I simply walked away one day and have never looked back. I read Will’s response with a lot of joy. What he had was absolute faith in himself. Our employer keeps us in a job because of faith in our abilities. Often we fail to see this! It sometimes helps to think ‘ What if I got sacked? Would that be the end of me?’

I put up my blog ( specifically to chronicle the walk away from a ‘good’ job.


#4 J on 06, Apr, 2011 at 12:28 am

I had the job of my dreams my whole adult life, the only job I wanted since I was 5 years old. I was in the music industry, both retail and record labels, and loved every second of it. This was my only hobby and my job rolled into one. The industry is dying and there is no place for me anymore and everyday since then has been nothing but drudgery. Now it’s just work for work’s sake and I hate every second of it.

#5 Cyndy on 13, Apr, 2011 at 11:35 pm

Get out of Job Jail? Easy, get laid off. Like “J”, I kicked butt for seventeen years in an industry that, although not yet dead, is in a coma on life support. New home sales. I’m excited about not ever going back. I’ve blown up my life and am starting over.

My passion is working for myself as a public speaker. I’ll take a job-job doing something I can tolerate in a field that holds my interest for a couple of years to regroup while I lay the groundwork. But only I’ll know it’s my temporary plan, so it’s not a job, just a “hiatus” from my real calling.

#6 Patrick Dempsey on 19, May, 2011 at 5:36 am

If you hate your job so much, then why do you stay there? You hired in at your own will and you can leave just the same. Thi about it. Seems to me that you the only one holding you back.

#7 Hemant Kurian on 24, May, 2011 at 11:14 pm

Hi Shaun,
Nice review. Keep it going.

#8 Hazel Porter on 21, Jun, 2011 at 12:04 pm

I was in dead end beauty salons working all hrs god sent, getting no thanks, low pay and was afraid of saying I wanted kids,and to work less hrs in case I was let go. They dont like to have to have girls off for long periods of time or maternity etc. So when I was let go from my last salon as it was not busy, I thought I would work for myself so I took my clients numbers and called them all to offer beauty at home, and have gained some new clients aswell,feels so good to be doing it for myself! I also work 3 days a week in a lovely quiet place making organic skincare. The money isnt great but may improve but I am happy now.

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