Should I stay, or should I go? When job satisfaction starts lowering and signs of distress increasing, one of the first things we explore is whether it is our time to leave. This post suggests 5 questions to help you untangling the many issues that overlap when we are no longer happy with our job.
Embracing a vision for a new job requires clarity of purpose and challenging what does not work—and why.
1. Why now?
When we noticeably lose motivation in our job, it’s often the result of multiple events or disappointments. At times, it may be the outcome of one single and major event, for example, an over-challenging relationship at work or a new reorganisation. A root cause analysis is, in both cases, helpful. Ask yourself, ‘What has added up over time, and how much have I tried to address my issues?’ The aim of this question is not just to plot a chain of events but to start building clarity around the key question: ‘What do I want from my next job that the current one does not offer?’
Exploring ‘why now’ uncovers what’s behind the sense of urgency. Excessive stress and constantly managing issues are, for instance, valid reasons to move on if prospects of the situation getting better are slim. Identifying a key window for career progression we cannot get in our current role is also a good reason to challenge our current job. And equally, why we should stay.
2. What is the thing I like the most?
When we refresh ourselves with our original motivations, we leave a usually sticky mental space and time-travel to refresh ourselves with what we liked in the first place. We applied to that role because we liked, say, working in large transactions, which gave us exposure to opportunities to grow professionally. Or we liked solving a specific type of puzzle. Is it still the case now, or is it time to reconsider what matters the most to us after we have had that work experience?
Motivations evolve over time and go hand in hand with the experience we develop. The more we process our experiences, the better we become at fine-tuning what we enjoy the most. It may be the same thing we enjoyed 5 or 10 years ago, or it may be radically different.
3. What is my main stressor?
When work becomes a heavy burden, we must ask ourselves, ‘What doesn’t work anymore? What is the biggest problem right now?’ Can we single out one main factor, for example, excessive workload? If so, is there a way around this? Constant overwork may have to do with the way we deal with work demands. If our main stressor is a lack of prospects for a promotion, this may have to do with our internal perceptions or objective limited opportunities. Will a promotion truly address the issues?
Usually, we place the greatest emphasis on what doesn’t work with our jobs, and that’s how we build our narratives. Exploring fully what we can realistically do about it allows us to cleanse the lens we use to look at our stressors.

4. What’s my worst-case scenario?
The definition of our worst-case scenario is personal and deeply linked to our sense of inner resourcefulness. Appetite for risk is personal. It’s a dynamic concept that changes with seniority, experience, and periods of life. Having a family or young children usually plays a significant role in this. We feel there are times we can absorb greater risk. But is it true? Or can that perception also be challenged?
For some, job volatility is the worst-case scenario. For others, it’s an opportunity. Sometimes, it’s risking a reduction in salary (for example, on the variable component). Other times, it’s something that can be swallowed if job satisfaction is high. The worst-case scenario may even be finding out the new job is not much different from the one we left. This is a risk we all take when we change jobs. Nevertheless, we do it because one thing we know is that staying will also not satisfy us.
Changing jobs comes with a share of the unknown and a leap of faith. That faith, however, can be substantially mitigated by the best due diligence we can run on the new role, the new organisation, and our likely career prospects.
5. What’s my long-term plan?
This is about re-evaluating the long-term plan in light of the work experience developed so far. Ask yourself, ‘Are my original assumptions and goals still valid? Do I now wish to develop in a different direction? Is this a more substantial rethinking of my career?’ Working on a long-term plan mitigates the risk that the next role will not deliver our expectations. How will a new role offer what we’re looking for in the long run? We do that by looking carefully into all the information we need to find out.
The long-term vision is particularly crucial when we feel too exhausted and overworked to even start looking for a new job. A decision out of frustration is rarely a sound decision. Switching jobs without a solid long-term vision and understanding of where we are heading may bring us back to square one quickly.
These are times when we’ve got to pull together all the strength and resources we have—and we know already it’s going to be hard. However, challenging our long-term plan will more likely lead us to a rewarding position, which will compensate for staying and stagnating.
If you have experienced any of these issues and wish to explore whether coaching may support the next steps in your professional journey, please get in touch.