Get 20% off the new Gentleman’s Journal Clubhouse membership. Limited time only.

Here’s how to know when it’s time to quit your job

Are you whiling away the hours in a dead-end job? We asked the experts on when, exactly, you should call it a day and quit...

Quitting’s never nice. But, sometimes, it’s necessary. Unfortunately, however, it has been ingrained in us — socially and spiritually — to believe that quitting is somehow shameful; an embarrassing ‘last resort’ that displays a lack of fortitude, ambition, drive and direction.

Not so, gents. Quitting before you’ve given something a good is, of course, a little premature. It’s the equivalent of reading just one page then setting the book down; taking one sip before pouring away your cocktail, heading home after one day of your holiday. After all, it pays to persevere a little.

"It may be time to get yourself out of that environment..."

And, when it comes to jobs, quitting is not something to be ashamed of. If you’re feeling stifled or held back; if you’re feeling demotivated or as though you’ve eked out every last shred of life lessons you could learn from that particular role, it may be time to quit. If you’re struggling to breathe in a toxic environment, bashing away at a ‘dead end’ job while you figure out what you really want to do or secretly wish you were launching your own company: it may be time to get yourself out of that environment, double quick.

But we know it’s not as simple as merrily quipping, “Just quit!”, as we look on from the sidelines. That’s why we’ve sought the advice of two life coaches, who can share their considerable expertise on when to take that redefining (albeit terrifying) career plunge; and we’ve broken down their advice into a few handy questions that might give you the clarity you’re searching for.

1. Do you love your job?

It’s a simple one, really. By ‘love your job’, we don’t mean: ‘Do you spend each weekend counting down the hours until you can be back at your desk again?’ Few people feel that way (and if you do find yourself clockwatching at weekends, we’d advise availing yourself of some of our activity guides…). Instead, we simply mean: do you feel yourself thriving? Do you enjoy spending time in your workspace? Do you have a sense of purpose?

The question of loving your job was posed to us by Life & Business Coach Jake Smolarek. “If I ask ‘Do you love your job’ and you say, ‘No’: it’s time to leave. ASAP,” says Smolarek, frankly. “If you say it’s ‘ok’, it’s time to start at least thinking about changing it for a either a ‘great’ job, or an ideal (dream) job; or to start working on your own project, or hustle.

"Having a 'safe' job isn't that safe any more..."

“If you have a job that you’re not enjoying, and you’re working 8, 10 or 12 hours a day; you [could] eventually burn out,” Smolarek continues. “If you’re working on something you really love, you could work for 14 or 16 hours a day; because you love it!”

And Smolarek is clear when it comes to toxic workplaces: “If your work or job environment is toxic for you, the time to leave is now; no matter what the consequences may be. The pandemic proved that having a ‘safe’ job isn’t [always necessarily] that safe any more. Take care of yourself first!”

2. How well are your needs being met?

This is a question posed to us by Accredited Enneagram Practitioner, Psychodynamic & NLP Master Coach Nick Hatter, whose book, The 7 Questions, is currently available to pre-order.

“What differentiates us from an inanimate object (like a rock) is the fact that we have certain needs that must be met by our environment if we are to be physically healthy,” Hatter explains. “According to the Human Givens model of psychotherapy, we all have a need for connection, belonging, self-esteem, a sense of competency, meaning, purpose and autonomy (a sense of control), as well as financial security. We also need some fun and laughs!”

"Are there enough fun and laughs on the job..."

So the big question, for Hatter, comes down to whether or not these basic needs are being met by your workplace. If not; it may be time to quit that particular job. “Does your company’s culture feel supportive?”, he posits. “Do you feel that you belong? Are there enough fun and laughs on the job? Does your work feel meaningful and purposeful? Is the job meeting your need for financial security? Do you feel you have enough freedom and say in your work?

“If the answer is ‘no’ to any of these questions, it might be time to move on. Not getting your needs met could lead to you developing a mental health crisis.”

3. What do you want to achieve?

This question comes to us courtesy of Smolarek; and, needless to say, we’re not talking about minor achievements like clearing your email inbox by end of play on a Friday (though depending on how many emails you receive, that may not be a minor achievement at all). We’re talking about what you want to achieve in life; and Smolarek has some intriguing thoughts on how to work this out.

“What is your vision?”, he emphasises. “I have a model that I’ve created, and I use it to help my clients: it’s called V-GPS, or Vision-GPS. The acronym is V for ‘vision’ (or a dream); G for ‘goals’; P for ‘plans’ (or a planning process); and S for ‘system’ (or procedures, or routines).

“Most people don’t plan their lives,” Smolarek continues. “They plan their holiday, their wedding…and that’s usually it. We [all] need to have a vision. If your job isn’t bringing you closer to that vision, you need to change it. Or start working on a side hustle; or anything else that will actually bring you closer to what it is that you want to achieve.”

4. Will you have any regrets?

Regrets are a tricky business. Often, the fear of the horrifying concept known as living with regrets is the principal factor that prevents people from quitting a job they really, seriously need to quit.

This question is proffered by Nick Hatter: and he posits a deeply thought-provoking way to see regrets in a whole new light.

“Often, what we most regret is [what] we haven’t done,” he says. “If you do the following calculation:

80 — your age x 365

“This is [approximately] how many days you have left to live: in the best case scenario,” he explains. (Feeling spine-tingling chills? Us, too…) “You don’t have to wait for a terminal diagnosis to start living. This sounds morbid, sure; but think of this as an ‘existential cattleprod’.

"Small steps is how mountains are climbed..."

But don’t despair just yet: Hatter has some tips on how to use this (somewhat terrifying) idea to galvanize you into action when it comes to quitting your job, in order to keep those regrets at bay — and he suggests starting with the small steps. “Starting and building a company, or changing jobs or career, can seem like such a daunting task,” he acknowledges. “We see the mountain and think: ‘There’s no way I can climb that. It’s too high!’ But the good news is: you don’t need to climb the mountain. You only need to take the first step forward.

“Small steps is how mountains are climbed. So the next small step might be to incorporate a new company, or create a blank document and add the title ‘CV’. Before you know it, you’ll have momentum: and you’ll be well on your way to a more fulfilling life.”

5. What is most important to you?

This final question was put to us by Nick Hatter: and it’s a pretty crucial one, gents.

“This is such a simple and underrated question that I recommend to my life coaching clients,” Hatter explains. “It works for small decisions, such as what to eat for dinner — and [for] big decisions, such as whether you ought to leave that job, or start that company.

“Is it leaving a legacy? Is it making meaningful contributions? Perhaps it’s your health or your family? [Regardless,] find out what’s most important to you and align your actions according to that.” We couldn’t have said it better ourselves. Happy quitting.

Thinking of starting a business? We asked 18 businessmen to define the term ‘entrepreneur’

Become a Gentleman’s Journal member. Find out more here.

Become a Gentleman’s Journal Member?

Become a Gentleman’s Journal Member?

Like the Gentleman’s Journal? Why not join the Clubhouse, a special kind of private club where members receive offers and experiences from hand-picked, premium brands. You will also receive invites to exclusive events, the quarterly print magazine delivered directly to your door and your own membership card.

Click here to find out more

Further reading