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

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

By Jamie Matthewman
January 14th, 2015

How do you know when it’s time to quit the day job? This is a big question in a mans life. If you’re in this position, thinking about quitting the 9-5 to embark on a new journey of discovery, you’re probably feeling some trepidation.

Whilst exciting, you’re probably also tinged with a sense of uncertainty, if so I know how you feel. I felt like this for quite a few years and discovered that breaking free isn’t necessarily easy.

A regular paycheck is difficult to walk away from, it’s comfortable and well known, which is not surprising considering work takes up the biggest chunk of our day.

Ironically Harvard Business Review research, highlighted men with children work more hours than childless men. In America the average man with children works 8.7 hours, those with a higher education, a strong work ethic and high ambition work over 10 hours per day.

This flies in the face of a recent UK study, which found most men would like to work less hours, but worry what others will think and questions being raised about their commitment to their job.

It found that 70% of fathers who do opt to work part-time, worry that society attaches a stigma to the part-time working dad. Over half were concerned to be seen as the “weaker partner” because they had sacrificed their role as the main breadwinner. And just over one in ten worried about negative perceptions among colleagues.

Society has us believe that to be a man you have to be a model of hard-work and high-achievement; working long hours has historically been seen as the heroic thing to do for men. The expected thing to do, with many office cultures having the tacit rule that leaving the office late is a sign of integrity and commitment.

Will Today Be Another Day You Pretend to Be Happy at Work?

“Work is love made visible. And if you cannot work with love but only with distaste, it is better that you should leave your work and sit at the gate of the temple and take alms of those who work with joy.” ~ Kahlil Gibran

With this level of physical and psychological investment, we better be sure this enormous stake of our short and precious lives, brings us rewards beyond the financial. Things like enjoyment, fulfillment and satisfaction, but the truth is 70% of US workers who Gallup surveyed, either hate work or are completely disengaged with their jobs.

In most businesses, people are simply a commodity, exchanging their bodies and mind for money to turn the cogs of commerce. Mostly undervalued, underpaid and unaware that life holds greater riches.

As I look back on my own story I see the madness in what’s now an outdated paradigm. I spent 14 years working in business. It wasn’t the worst career in the world by any stretch. It paid the bills, allowed me to travel and buy some nice things. Some days were better than others, yet there was always something missing, I never felt inspired.

It was just a job I become OK at. But I was never ever going to truly excel because my heart was never in it. I was pretending I wanted to be there and Impersonating someone I wasn’t.

What if You Need the Money?

“I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.” Steve Jobs

I need the money

If your days are spent in a place of work you don’t want to be, with people you’d rather avoid, doing work which leaves you empty and stressed, you know it’s no fun. But what do you do if you need the money?

You can look for another job which for a while might offer you relief, but it’s unlikely to last if you want out. You could stay and ‘make the most of it’ – I’m all for making the best of things, but it’s a risky strategy that could keep you trapped. The end result is you die with your music still in you!

“Everyone has been made for some particular work, and the desire for that work has been put in every heart.” Rumi

I don’t doubt you can find a sense of satisfaction in any job, even cleaning toilets, but should you just make do? Should you settle and ignore that innate drive that’s urging you to become more?


Nelson Mandela or Gandhi I’m sure could have found contentment keeping loos spotless, but like you they were driven by something bigger. They chose to fearlessly follow their hearts at times in history when the world needed their love and to witness their courage. Thankfully a job didn’t stop them doing what really mattered.

But the fact is simple economics mean that most men will never make the leap. All of that worrying about what other people think comes at the expense of so much. The sense of duty we’re instilled with to be the provider can often cloud joy and dumb down the desire to live authentically.

Don’t Let a ‘Job’ Get in The Way of Living An Inspired Life

“The economics of the future are somewhat different. You see, money doesn’t exist in the 24th century…The acquisition of wealth is no longer the driving force of our lives. We work to better ourselves and the rest of humanity” Captain Jean-Luc Picard

So that’s the BIG dilemma. Do you carry on living a lie because you’re getting a regular paycheck or take a leap of faith towards doing great work. Do you follow that idea that keeps you awake at night or stay stagnating in a life of mediocrity?

In my experience, whilst maintaining your financial responsibilities is important, the more you wake up to what really matters, there comes a point when you just can’t fake it anymore. No longer can you lie to your boss everyday, trying to be enthusiastic when actually you don’t give a fuck.

No longer can you tolerate that sense of disappointment when the alarm signals another day of your short life will be lost to work that really doesn’t matter. You begin to see the worlds gone mad and you’re no longer willing to spend each morning, frantically rushing, embroiled in a crazy commute of miserable faces. People on a mission to get somewhere they really don’t want to be.

No longer are you prepared to sacrifice your life for a job that’s sapping you of the chance to live a bigger, more inspiring adventure. It just doesn’t make sense.

Time For More Important Work

“The work you do while you procrastinate is probably the work you should be doing for the rest of your life.” -Jessica Hische

However if your journey’s anything like mine, breaking free won’t be easy or straight forward. It will require you to let go of old ideas and perhaps material things you may now think are important.

If you’re fortunate to be in a financial position that allows you to quit tomorrow great, but if not, for your own sanity, you may have to decide to make the best of it for now.

Every experience holds a lesson and a gift. The biggest may well be about finding out you’ve more courage than you ever knew and the strength to ignore the naysayers (often family members!), who may tell you you’re crazy, selfish, lazy or just plain stupid to follow your heart.


Creating an inspired life is going to take a shift in thinking and a bucket load of effort. I would like to say it’s easy, and in many ways it is because it doesn’t feel like work, (that’s when you know you’ve got the golden ticket) but it’s going to require more of who you really are to show up.

This is a journey of epic proportions, one that will test you, challenge you, bring you to your knees and help you soar like an eagle. Creating big changes in your life is by no means the easy option, yet neither is mediocrity, they both take the same amount of effort.

The difference being – one inspires you, gets you running out of bed each day, the other saps you of energy as you ignore what really matters to you most.

So I am curious where are you on your journey? Are you finding escaping the 9 – 5 hard work or is it the best thing you’ve ever done? Be great to hear about your experiences or questions in the comments section below…

Jamie Matthewman

About Jamie Matthewman

Jamie is the founder, main contributor and editor of The Inspired Man.

2 thoughts on “How Do You Know When It’s Time to Quit The Day Job?

  • Great article. I escaped the 9-5 corporate grind 8 months ago and have no regrets. Yes it’s hard, there are ups and downs, but I am embarking on a journey that is in line with my goals in life, and that in itself is rewarding.

    Thanks for the post.

    • Hi Richard, thanks for the comment and it’s great to hear that your escape is going well. It sure feels good doesn’t to be living your life in accordance with what matters most. It isn’t necessarily the easiest path to take but certainly as you say, it’s the most rewarding! The very best of luck to you.

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