When’s The Right Time To Quit Your Job?

canstockphoto23612498You’ve tried everything you can. You’ve looked at it from every angle but you’ve decided that’s it.

2015 will be the year you quit your job

And you’re quitting for good. You won’t just get another job, you’re going to start a business so you’ll never have to work for another idiot again (apart from those days when you’re the idiot, but we’ll forget about those eh?)

If you’re gonna quit and start a company when should you be ready with that resignation letter?

The 5 stages in the transition to being your own boss each have their signature type of quitter…

Stage 1 – Dissatisfaction

The “F*ck this I’m out of here” quitter

You’re unhappy. Life seems terrible. You’re not so much dissatisfied as full of hatred for your crappy job. Quitting seems like the only option. You’d do anything to get out of there – even the person cleaning the toilets seems to have a better job than you.

Almost everyone has days like this, but only a select few follow through with the urge to drop it all, burn the bridges and start again. Yes you’ll have a fresh start, a clear diary and no going back, but what the hell are you going to do?

Think for a minute. Would you really be as unhappy if you had an escape plan laid out ready to execute? Could you survive for a couple more months if you could save the cash you needed to start your venture?

Stage 2 – Dreams and goals

The “This time next year, we’ll be millionaires” quitter

Dreams are the antidote to dissatisfaction. Your fantasies and detailed mental pictures about what life will be like on the other side show you that there is another way. If dissatisfaction drives you away from your shitty job, dreams give you something to aim towards.

Big, urgent dreams might force you to quit at this stage. Perhaps you’ve found your calling, and just know it has to be now. But for most of us, quitting at this stage would leave us staring at a blank sheet of paper worrying about how long our savings might last. We need to know how our dream’s going to come true.

Stage 3 – Plans

The “This might just work” quitter

Plans make goals and dreams happen.

It’s no secret that I love a plan, and I think there’s a right and wrong way to make them. Having one fills in the blank sheet of paper, but it might just tell you exactly when your savings will run out.

Depending on the size of your goal and the audacity of your plan to reach it, there might be no other option than to quit at the plan stage.  But could you run the plan alongside your job for a while?

Stage 4 – Action

The “This is working, just watch me” quitter

Almost any business can get started in some form alongside a job. If you can start it, why wouldn’t you work it for a while along side your job?

Eventually, there will come a time when quitting or stopping become the only choices you have. If your business demands time during the working day, then that will come sooner rather than later, but whatever the business, the right time to cut the cord usually falls somewhere in the action stage.

You’ll know if it’s going to work or not, and if a leap of faith is required, you’ll have momentum from taking action to propel you towards success.

But maybe, you don’t actually even need to quit until you’re already successful?

Stage 5 – Success

The “I don’t need you any more” quitter

In the best case, you can be successful before you quit your job – if your side business makes enough for you to live on, virtually all the risk of quitting is removed.

In fact, the main risk you run by waiting until you’re successful is that you wait too long, until you’re “too successful”, and work at two jobs for longer than you need. Setting a low threshold for your initial success helps – perhaps having your basic living costs covered, with a trajectory that will see you hit your major “success” goal in a sensible amount of time.

So what does this all mean?

If you’re sitting at your desk on the first proper working day of 2015 (or any other day) and hating it – what are you going to do about it?

Which type of quitter will you be?


  • Guest

    Thoughtful and well-written article that answers the many stages of “what to do” and how to “get out of there” questions about quitting the job and becoming independent. I was in the “I hate this, can’t stand it anymore, – please G-d, get me outta here,” phase for quite a long time; it was awful. I had started a business project but it was not yet sustaining my living expenses (and I’m a single mom) when the organization began trying to ‘make’ me leave.

    I used to fantasize about handing in my resignation and ‘breezing’ out of there, so I had to remain calm, level-headed and act smart. As I planned my exit strategy, knowing that my basic living expenses were not yet supported by my personal business project, I had to focus on what really mattered – not who said what, and who was wrong or right, but how my basic living expenses would get paid. I had been in the job for 2.5 years, working 40 hours a week and only just scraping by…month to month. I had nothing to fall back on at all.

    It was a challenging time, full of intense negative emotion – and manipulation on both sides – until I was finally let go – asked to sign an agreement with a non-disparagement clause WITH three months severance. It worked out, thank G-d, but I don’t know what I would have done if they’d let me go with two weeks notice, which they could easily have done. For me, it was a matter of standing up for myself and my family and letting them know what I knew that they didn’t want others to know about the organization. It wasn’t blackmail, G-d forbid, or anything like that – but I had to put myself and my family first.

    My internal emotions had to be put on the side. It was very hard. I was mistreated while I was at the job, and their tactics to try and make me leave were despicable. But when the roof over your head is at stake, and you’re the only one that can put the food on the table, you gotta be smart.

    If you are or know someone who wants to quit the job and become independent, give them this article to read – and if you can, help them strategize their exit plan.

    • Rob Young

      Thanks so much for this thoughtful comment, whoever you are :-) Glad it worked out in the end for you.