Should I stay or should I go?

Kate Bishop
6 min readJul 29, 2021


How do you know when it is time to leave your job?

For many people it will be because they are climbing the career ladder and want to leap up it quicker than their current company can facilitate.

For others it will be due to a complete career change or for an offer they cannot refuse.

However, for many of my clients (and, in the distant past, for myself) this is a very hard decision to make. We may feel that we are no longer enjoying our role but that could just be a blip right? Or perhaps we have been there for so long we feel we have invested so much of ourselves that we don’t want to ‘throw it all away’. Or, and this is one of the most common reasons, it’s the people — oh yes our job is dull or super stressful but our colleagues are our friends and we don’t want to leave them.

If you are struggling with this choice then career coaching may benefit you hugely as it allows to assess your situation analytical, think through different scenarios hypothetically and address the main obstacles you will face in each one.

This question is even more pertinent now with the looming ‘Great Resignation’ theory here in the UK. Analysts believe that, come September, a huge amount of people will resign to either jump ship or start their own business.

So how do you really know? And how can you be brave enough to take that leap or change where you are now for the better?

Photo by Tim Mossholder, Unsplash

To start with, we need to understand what is work is to you?

Is it a means to an end in that it affords to you the lifestyle which you want to lead? Perhaps it gives you the 4 P’s; position, power prestige and perks?

For many of people it means they can work for their 5th P — their purpose — that what they do has meaningful significance to them and brings them fulfilment.

If you are in the former camp then you may want to ask yourself:

  • Are you being compensated fairly enough for your efforts, knowledge and experience?
  • If not — what would make you stay?
  • How many opportunities are there to grow in terms of your seniority and income in your current company?
  • If limited then how can you create these opportunities?

If, after honestly answering the above questions and really doing your homework into what your organisation can recompense you for then ask yourself what else is contributing to you wanting to leave?

Be honest here — brutally honest.

Perhaps purpose is what drives you in your work and you currently feel that you are not fulfilling it. Maybe you are bored and feel stuck in your role with limited opportunities to develop your skills or move upwards. Or you feel that there is more out there for you career-wise.

If this sounds familiar then it is time to take a full audit of your organisation and to really find out the facts by asking:

  • What opportunities are there here for me?
  • Are these opportunities enough for me to stay and if so for how long?
  • What needs to change for me to feel motivated by my work again?
  • Are my values mirrored here?
  • What is in my control to make this change happen?

If there are limited opportunities then consider what you can do to generate more — create a mentoring scheme, put a business case forward for specific training, understand what volunteering options are available.

This sounds like a huge task to take on, however, chances are many of your colleagues probably feel the same so use this as an opportunity to create the perfect opportunities for yourselves and enliven your work and learning again.

For many employees they are often told “yes — go for it” only for their request for training, extra support, secondment to another department be blocked later on down the track. If your company keeps on giving you empty promises then you may want to understand why — lack of budget, organisational change, different management — but essentially it is probably time to move on unless they can guarantee a timeline and end date of when you can do the things you have asked for.

Photo by Jeshoots, Unsplash

If you are still unsure then let us take a deeper dive into what is going on with a few more questions:

  • What is not working for you?
  • How can this be improved?
  • Are those improvements enough for you to stay?
  • If so — what now needs to happen by whom and by when?
  • If you were let go tomorrow how would you feel?

Now if you answered that nothing is working and nothing can be improved by anyone, ever ask yourself and you would be skipping for joy if you got fired what the hell are you still doing there?!

  • What are you sacrificing if you go?
  • What are the repercussions if you leave?
  • What problem(s) are solved if you depart? How will they reappear in another role/company?
  • What are the opportunities elsewhere?
  • What is holding you back?

A classic fear of failure may be the answer here and if this is the case then do take a glance at my previous piece on this.

Often we need the fear to drive us forward to make a decision, to enact change, to go for it. When we work outside of our comfort zone then great things happen as we are actively stretching ourselves to make tricky decisions, take a leap of faith and work out how to overcome the challenges in our way.

Before you start resigning left, right and centre — you must assess the reality of your situation.

  • Have you got a job to go to?
  • If so, how much does this new job offer you compared to your old one and is it enough?
  • Does your new role and company meet the needs that are currently not being met?
  • Are you nearly ready for a change; emotionally and financially?

Why nearly? Well rarely feel completely ready, despite several years down the track saying to ourselves (and anyone who will listen for that matter) “I should have left years ago”

Chances are, if you have been deliberating over this question for some time then you are nearly ready and now need to ask yourself what is blocking you from making this decision?

It’s highly likely that now you have answered the above questions you now know what you must do so you can now focus on your career plan, whether that is to remain where you are and work to take hold of all the opportunities available to you or to exit amicably, smoothly and confidently.

When we are disillusioned with our work, company, team or manager (or all of them plus more!) we often find answering these questions hard so be brutally honest with yourself.

Essentially this is all about respecting yourself — if your job or organisation no longer serves or values you then you have the choice to leave and move onto somewhere which does.

If you are struggling then it may be time to call in a career coach like myself who can enable you to look at your dilemma objectively, ask even more insightful questions and work with you to assess each potential route to take so that you have a crystal clear picture of what you could do and you can then make the right decision for you. Get in touch today if you want to talk more.




Kate Bishop

Kate is a renowned career strategist, confidence guru & coach on a mission to make everyone’s Mondays feel as good as Fridays.