Should I Leave My Well-Paid Job? 7 Crucial Questions To Ask Yourself

By Laura @ IWMLB Project | Help! I'm so burnt out

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Jan 16

“I’m miserable, stressed and exhausted, but my career pays really well, am I mad to want to leave my job??”


The question whirls round and round in your head. Pros and cons for leaving battle each other like Darth Vader and Luke Skywalker in the eleventy millionth Star Wars film.

Weeks and months go by and you still don’t have an answer.

“I’ll stick it out to the end of the year, I’ll google ‘should I leave my job’ 100 times and see what everyone else says.”

If you’ve been struggling with this dilemma for a while, I’m going to put it out there now.

You already know the answer.

You are just worried about the consequences of leaving.

I know, because I did exactly the same thing. It took me many, many, many, MANY, months to finally leave a toxic work situation.

I had so many fears like:

  • Will I ever earn the same money again?
  • Am I throwing away my career? 
  • What if my business doesn’t work out?
  • What if I can’t find any consultancy or freelance work?

And on, and on.

Funny thing is, it’s actually all worked out rather well. Not what I had planned necessarily but it has all worked out.

I now freelance 2 days a week back at my old company (without the senior management job title, and working on a much smaller team, it’s actually completely do-able).

The rest of the time I work on this blog.

So, you want to leave your well-paid job? (I am assuming you do or you wouldn’t be reading this!). Let’s go through 7 questions to ask yourself to help you make the decision.

should i leave my job?

Should I Leave My Well-Paid Job? 7 Crucial Questions To Ask Yourself

Why Do I Really Want To Leave?

I saw a great definition in an article once. It said you needed to work out if it was your job that you didn’t like or your career.

It’s My Job

If you’ve always loved your career but have a new boss who gives Hannibal Lector a run for his money, perhaps it’s the situation, not the career choice that’s the problem.

In which case, the answer would be to talk to HR or leave that particular company.

It’s My Career

On the other hand, you could be in a career (like I was) where the higher up you go, the more stressful it gets. 

Also, you may have found like I did, that the higher you climbed the ladder, the less you got to do of the stuff you actually enjoyed.

You don’t ‘do’ the job anymore, you sit in endless, frustrating meetings and deal with your team’s HR issues.

If that’s the case then it’s the career that is the issue. And that’s okay. If you’ve been in a career for 5 to 10 years, that’s a good ole stint. 

I can’t think of anything else (apart from a relationship/friendship) that I would want to do day in day out for that length of time.

If the average working life is 45-odd years. 4 careers at 10 years each is more than acceptable. And you will be learning so many transferable skills to help you transition each time.

I Don’t Know Which One It Is!!!

Where this gets a bit muddled is if you are in a bad work situation but aren’t sure if it’s the job or the career.

If you are burned out and exhausted, often you can’t see the wood for the trees. It gets very overwhelming, and the more you try and force the answer, the more confused you get.

I know, because I’ve been there.

In that case, the only way (in my humble opinion) you are going to get your answer, is to take enough time off that you can get over the burnout and think clearly.

If you can take an extended holiday, take a sabbatical (unpaid leave) for a few months or leave your job and take a career break, this will be invaluable in helping you make the right decision.

Another option would be to go part-time if your company will allow you to.

Obviously, you need to make sure you have the money to do this, if you don’t, I would start saving ASAP.

(I have a course coming out shortly that will help you do this.)

Is The Money You Are Paid Worth The Trade-Off?

When I was thinking (procrastinating, stressing, freaking out etc) about leaving my corporate job, one of the things that helped me the most was to ask myself………

……’what is more important?’.

I realised that I could have been offered a £20k, £50k, hell a £100k pay rise and it still wouldn’t have made any difference.

The hours I worked wouldn’t have changed, and if anything they just would have got longer with more responsibility and more stress.

In the end, my mental and physical health were more important than the money I was paid.

Do I Have Enough Money To Leave My Job?

Now, I am not saying you should write your resignation letter and staple it to your bosses face the minute you have finished reading this blog post.

You need to make sure that you have a solid financial plan in place.

You need to know how much you spend every month (perhaps foregoing some ‘nice-to-haves’ for a while you start your business or whatever it is you want to do).

You also need to know how much of a financial buffer you need. I personally saved 12 months of expenses before I quit. I do also have 3 rental properties that bring in a bit of income so I knew I was good for a while)

You can accelerate your escape fund by learning how to save more and also increase your earnings.

Could you rent a room in your home or sell all your clutter on eBay?

Once you have a clear plan for saving, your situation may feel a lot more bearable as you know you have an end date.

Am I Really Throwing My Career Away?

This is a question that haunted me for ages before I quit.

I’d worked in retail for 13 years. I’d reached a senior management position through blood, sweat and tears.

And now I felt like I was throwing it all away.

The funny thing is, you may find that your new business or new career path actually ends up incorporating a lot of the skills you’ve already learned.

I thought I was walking away from budgeting, forecasting and spreadsheets (my senior role was in retail merchandise planning) and into words and digital with the blog.

What I’ve found is that the first course I have created (due out soon) is actually to help people create their own financial plan or escape fund to make sure they are financially stable before they leave their jobs.

The course is centered around budgeting, forecasting and spreadsheets (hey, that sounds familiar!).

I wouldn’t try and brainstorm which of your skills are transferable as this is just another way of procrastinating 😉 Just know that your previous skills will pop up in a way you probably didn’t expect.

Do I Have All The Information I Need?

One way of preventing yourself from making a decision is to remain unclear about what will actually happen if you leave.

A reader recently emailed me about leaving a job but wondering whether it was the right thing as she thought her maternity benefits were good.

I was in exactly the same position before I left. We were thinking about trying for a baby and I questioned whether I should stick around for the maternity pay.

Once I actually looked into it, I found out that the maternity pay at my work was appalling. I decided I could live without the money (about £4k if memory serves) as it wasn’t worth staying for.

If you get a year’s full pay, perhaps it’s more worth thinking about.

Also, we have been trying for over a year. That would have been another 12 months in my miserable job with no clear end date.

Not saying that will happen to you. It’s just that your body has an annoying habit of conceiving when it wants to, not when you want it to!

The moral of the story is if you are hesitant because you might think you might get certain benefits or you are unsure what your tax situation would be, make sure you find out the concrete details.

Once you have all the answers, you can make a much more informed decision.

What Do I Want To Do Instead?

Ah, the question that paralyses normally rational human beings.

I know I don’t want to do this but what do I want to do??

You may feel like you can’t make a plan to leave your job until you know exactly what you want to do.

So the months and weeks plod on, you get more and more burnt out, and still don’t make a decision.

Here’s my two pennies worth. Get your financial plan on the go. Start saving up to leave and have an end date in mind.

If you want to start a business, then attend the Pop Up Business School if you can (it’s completely free, and amazing).

Test your business idea by joining s0me relevant Facebook groups and offering your business services for free.

Or maybe you don’t want to start a business, in which case you could explore some alternatives like travelling or becoming a freelancer.

Use the time you are still in your job and saving to leave to explore some ideas. But you just remember that there isn’t one perfect business idea or one perfect job that will solve all of your problems.

Just try something new and see where it takes you.

Where Do I Want To Be In 5 Years?

It can be so difficult to see what the ‘right’ decision is when you are stuck in the corporate maelstrom.

Sometimes it’s easier to look further ahead. The one I always use is (and I’ve mentioned this on one of my podcasts) to think about when I am 80 and in my rocking chair (with a gin and tonic obvs).

Will I regret not doing the thing I am thinking about, and how significant will this point in my life seem?

I imagine when I am 80 and looking over my life, I won’t remember the crushing indecision about leaving my job, but I will remember the awesome life I led once I left.

Here is a fab quote from an article in Forbes.

Polk, the hedge funder who stepped away from Wall Street, recalls one moment that helped put him on the path out of his golden handcuffs.

“When I was about two months away [from quitting]…… my twin brother came over and we got into an argument, and I got so overwhelmed, I burst into tears. …….he said, ‘What’s wrong? and I said, ‘I’m so scared about what’s going to happen when I leave this job.’ He said, ‘In 10 years, you’re going to look back and thank God that you left because of all the things you’ve done since then.’

If you think about where you want to be in 5 years (or 10 or 20), it takes some of the emotion out of your decision and stops it feeling so final.

And Finally,

As I said before, if you are asking the question, you already know the answer.

Make the commitment to yourself that this is the year you take the leap. And then get your plan in place.

Sort your finances, build your escape fund, gather information and, get excited about what comes next!

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About the Author

Hi, I am Laura. I set up the 'I Want My Life Back Project' after burning out in a corporate job. I quit in May 2017 and set about getting my life back. I now freelance 2 days a week, run this blog, manage my rental properties and am SO MUCH HAPPIER! All the content on this blog is to help you to get your life back too :-)