How Do You Know When It’s Time to Quit Your Job?

It’s tough making the decision to quit your job, especially now with the unemployment so high. So, how do you know if you should stay or go?

Some people try to stick out a job they don’t love out of fear they’ll get labeled as a “job hopper” or have trouble finding the next gig (after all, most recruiters prefer to hire people who are already employed). Others find that leaving a stressful job frees them up emotionally and logistically to find the next job.

I left my full-time copywriting job two years ago to focus on freelance projects. I had some concerns, but it felt like the right time, because I was getting so many freelance writing projects that I had to turn many of them away due to my day job. Other times I’ve left job because there was nowhere for me to advance in the company or because the corporate culture wasn’t a fit for me (those times I had new jobs before I left or within a day of giving my resignation).

Here are four common reasons why people quit their jobs. Remember, though, everyone’s situation is different, so only you really know when it’s time to move on.

1. You’re so stressed, you find yourself popping Xanax like candy.

No job is worth sacrificing your health. But before you throw in the towel and give notice, it’s a good idea to talk to your boss about your workload. Maybe you can delegate a few of your responsibilities to the office intern or find a way to streamline your to do list. It’s also smart to see a therapist or career coach if stress management is an issue to help ensure that it doesn’t follow you in your next job. Despite budget cuts on budgets, some larger companies still offer on-site counseling, yoga, or workshops on coping with stress. If your company culture just isn’t conducive to a reasonable work-life balance or if you’re stuck with a toxic boss, it may be time to move on. The tough thing about this situation is that it’s hard to hold down a demanding job and job hunt, so some people who have a decent cushion of savings and reasonable expectations of finding a new job consider leaving their current position to focus on finding something better.

2. You’re asked to do something illegal or ethically wrong.

Hopefully you’ll never find yourself in this position, but if you do, it’s a good reason to say sayonara and search for greener pastures. For instance, I know people who work in social media and have been asked to falsify testimonials or pose as customers on popular blogs and forums. Although some companies employ these techniques, they’re not considered a best practice, and they’re nothing to brag about in your next job interview. Most of the people I know in this position have since moved on, because the request made them uncomfortable and showed that the company’s values were at odds with their own.

3. You see the writing on the wall and sense that your company is headed for disaster.

If you hear rumors of lay-offs or downsizing, you could stick it out and hope you aren’t among the newly unemployed or use that severance package while you search for your next job. But if things are more dire than that – like if your company is headed for bankruptcy or a major corporate scandal – you may want to get out before the s— really hits the fan. Recruiters like to say that you’re most employable when you’re already employed, so start job searching and building your network now.

4. You’ve built up your side business and you’re ready to focus on it full-time.

I wouldn’t recommend leaving your day job simply because you want to write the Great American Novel or dream of finally starting your own widget business. Freelancing or starting a business are both a lot harder than they look! If you’ve been doing it for awhile and you have a plan, though, these can be a very rewarding way to escape your cubicle and build something out of your creative passions. Don’t make this jump simply because you’re unhappy in your current job. Many freelancers start writing, designing, or coding on the side, then eventually transition to part-time employee or jump into full-time freelancing with both feet. However, if your company has a policy against moonlighting, you may have to re-negotiate that part of your contract or find another job that’s more flexible.

When did you know it was time to quit your job? In retrospect, are you glad you did? Why or why not?

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Susan Johnston is a freelance writer/blogger who has contributed to publications including The Boston Globe,’s blog,, and Yahoo! HotJobs. Her own blog,, covers tips on productivity, brainstorming, and more for fellow writers.


  1. Web design portfolio on the 11th October

    nice article. the temptation to go full time freelance is big but without the consistency of work, it can be a dangerous move!

  2. melanie brooks on the 11th October

    I quit my job at a staffing agency when they weren’t able to match my salary to all of the extra duties I was being saddled with due to layoffs. I found something else, first, but was relieved to go.

  3. Aaron Bailey on the 11th October

    Best reason to quit: You are no longer challenged at your job and find yourself becoming “stale.” A job change will shake up your life and allow you to re-shift professional and personal priorities.

    • martha torres on the 16th November

      I could not agree more!

  4. My Life My Trip on the 11th October

    Hi Susan,

    Thanks for sharing this. For me, I thought i’ve built up my side business and ready to focus on it full-time. But still struggling. I need more time to adjust.

  5. Joshua Riddle on the 11th October

    I think it is important to think about personal satisfaction in work. Many years ago I quit a full time job with great pay and overtime and traded it for a part time but much more pleasing job. I was a much happier person because i enjoyed going to work. I think that in the end it is about figuring out what YOU want to do and finding the ways to make that possible, through planning first but then ACTION. Sure, it will be scary because its ne. However, you might find yourself happier than you have ever been. You won’t know until you go for it!

  6. Abhijit on the 12th October

    I quit my job from a multinational company when I found that the work and work culture is not suitable to me. Indeed it depends on individual experience whether to stay or quit a job.

  7. Ed G on the 12th October

    All good reasons, the first 3 are reasons to start a 100% effort job search RIGHT NOW.

    I was going to add “lack of challenge” but @Aaron beat me to it.

  8. Jessica Bosari on the 12th October

    I figured out it was time when my toddler fell at daycare and needed stitches. I was overjoyed to have the chance to spend the day with him, stitches and emergency room and all. It’s pretty bad when you are more happy about spending time with your kid than worried about his injury. That was the day I realized I wasn’t spending enough time with my kids and needed to take telecommuting seriously.

  9. Marko -- Calm Growth on the 12th October

    Oh jeez, I have met all of these reasons. :-O

    I will quit my job in a few days. I’m not kidding, things have gone out of control there, and I’ll have to put an end to that… Thanks for sharing this great article Susan… 🙂

  10. GJ on the 13th October

    I always said the only way I would go freelance was if I lost my job. Well, I was “freelanced” 12 years ago and haven’t looked back since. I’ve been offered full-time employment numerous times, but luckily I haven’t had to take it. I have an advantage in that my wife has always been employed full-time, so benefits have never been an issue, but she changes jobs every 4-5 years. If you are looking for a new full-time gig, the best time is always when you have a job like Melanie said.

  11. jeanettte vieira on the 13th October

    When I realized that I was working harder for somebody else’s dream than my own.

    • Lili on the 19th December

      Thanks Jeanette,
      this reason sounds much stronger to me. I feel like I’ve met my own thinking today. I take it as my Christmas gift. Will soon implement.

  12. Exidium on the 14th October

    Well, I got out my last job due yje lack of understanding of my work: I was hired to make some website programming in an agency, but my former boss would fight me everytime I was “wasting my time, writting stupid nonsense text” at note pad…

    I think I gotta send that to “clients from hell” : )

  13. Simon MacDonald on the 18th October

    I’ve always found internal bleeding to be a good indicator that it was time to quit. I wish I was joking. Please learn from my mistake people.

  14. Rox on the 19th October

    I had a day time full time job together with an online job which was still part time that moment. When I felt that I’m getting sickly and I did not like my team leader I decided to quit. I realized that I could have great money on my online job (when going full time) than with my day time job. Yes, I resigned and I focused on my online job. If you think that you can make more money on your sideline job, don’t hesitate to resign if that full time job is low compensated.

  15. jordan on the 2nd December

    I’m right in the middle of this process, I’m working freelance on the side (takes tons of time!) but I’m not getting enough income yet to match my day job. I guess I’ll wait a little while longer and find maybe a new outlet or two for my video editing before putting in my 2 weeks.

  16. Samantha Gluck on the 1st June

    You know it’s time to quite and go freelance when your boss begins pawing at you relentlessly and cooking up schemes to get you to go on business trips with him that have nothing to do with your expertise (that, among other things).

  17. Doris Pardon on the 8th March

    I work for an amazing charity for children who have had the most dreadful lives. It offers advice and counselling – and I work co-ordinating the ‘drop-in’ – its the most emotionally draining and underpaid work I have ever done. I have nightmares about the kids and am exhausted when I get home to my 4 year old. I am also an artist and photographer with great business ideas – and when I do get a freelance job, 2 days covers two weeks worth of salary for my day job. But, I am petrified of giving up regular money, especially in this climate. … My husband is so behind me giving it up as he sees how it effects me (lots of tears) … And although I am scared, I will do it. If there is one thing I have learned in life, its that whenever I have been brave, life is enhanced… and if it all goes wrong, I will get a temp job to pay the bills. Good luck everyone and thanks for your posts.

    • Pooja Lohana on the 8th March


      Your story is touching and powerful. You’re doing a great job by supporting those kids. And in that you should feel proud about yourself.

      Hope it will be easy for you from here on.


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