Should I really still be in this job?
If you’ve been asking yourself this question as we approach the end of the year, it’s a good moment to do a career assessment.
If you’ve been wondering, should you quit your job, it’s a good moment to do a career assessment.
Considering whether to leave your job, stay, or change direction can bring up guilt, fear, curiosity, or a mix of all three. Taking time to step back and look more closely at what’s going on often brings more clarity than trying to force an answer.
In particular, it helps to work out whether what you’re struggling with is this specific job, or the type of work you’ve been doing altogether. Many people conflate the two, and it’s an easy mistake to make. But confusing a job problem with a career problem can lead either to unnecessary upheaval, or to staying stuck longer than you need to.
A helpful starting point:
Job problems tend to centre on who you work with, how the work is structured, and the conditions you’re operating in.
Career problems tend to show up when the work itself no longer feels engaging or meaningful, even when those conditions improve.
Step one: create thinking space before seeking answers
Without space to think, it’s almost impossible to tell whether you’re reacting to a difficult phase in a particular role or responding to a deeper misalignment with the work itself.
Nancy Kline’s work in Time to Think is a useful place to start, because she makes a deceptively simple point: the quality of your decisions depends on the quality of your thinking, and most adults do not give themselves conditions in which good thinking can happen.
Career dissatisfaction often gets examined in rushed moments. On a Sunday evening. In the car after a bad meeting. At 3am when your mind is already exhausted. None of these are good conditions for sound judgement.
Before analysing anything, the first step is to slow the process down.
Nancy Kline introduces the concept of the incisive question, as part of her ‘Thinking Environment’. It’s designed to surface and remove untrue assumptions, which is particularly useful when you’re trying to work out whether you’re in the wrong role, or the wrong line of work entirely.
Ask yourself one or more of the following:
- If I were to become the chief executive, what problem would I solve first and how would you do it?
- If I knew that I was vital to this organisation’s success, how would I approach my work?
- If I were not to hold back in your life, what would I be doing?
- If I were free from the pressure of time, what would become possible?
(See Nancy Kline’s website for more on the thinking environment.)
Step two: ask better questions
Wise and Littlefield, in Ask Powerful Questions, emphasise that the questions we ask shape the thinking that follows. Many people approach career decisions with questions that can box them in.
Questions like:
- What’s wrong with me?
- Why can’t I just be grateful?
- What’s the safest option?
These questions tend to produce anxiety rather than clarity.
More useful questions open things up rather than narrowing them prematurely. For example:
- What specifically feels misaligned right now?
- What am I trying to protect by staying?
- What feels risky about leaving, and what feels risky about not leaving?
Notice that none of these questions demand an immediate decision. They are designed to help you understand your situation more accurately before you act.
A job problem often shows up in answers about people, pace, pressure, or priorities.
A career problem tends to surface when the work itself no longer holds your interest, even when conditions are good.
Step three: assess energy, not just logic
One of the most practical contributions Simon Alexander Ong makes in Energize is his focus on energy as data.
We are very good at making career decisions on paper. Salary, status, security, progression. We are much less practiced at taking our energy seriously, even though it is one of the clearest indicators of sustainability.
A helpful assessment question here is:
- What consistently gives me energy in my work, and what reliably drains it?
This isn’t about liking every task or avoiding effort. All work involves challenge. The distinction is between effort that feels purposeful and effort that feels depleting.
If the energy drain is tied to a particular environment, manager, or set of constraints, you may be looking at a job issue.
If the drain is coming from the core tasks of the work itself, even in supportive conditions, that often points to a career-level question.
(See Simon’s Life lessons in 22 minutes for more on energy)
Step four: zoom out with a Career SWOT
This is where a practical tool can be particularly helpful.
A Career SWOT analysis allows you to step out of the emotional swirl and look at your situation more holistically.
When people complete a Career SWOT, patterns often emerge. Strengths and opportunities may cluster around certain types of work, while weaknesses and threats may repeatedly show up in particular environments or roles.
This can be a powerful way of seeing whether it’s the container you’re in, or the contents of the work itself, that no longer fit.
Consider:
- Strengths: What skills, experiences, and qualities are genuinely working in your favour right now?
- Weaknesses: Where are you struggling, feeling constrained, or under-utilised?
- Opportunities: What possibilities exist inside or outside your current role that you haven’t fully explored?
- Threats: What are the real risks of staying as you are, as well as the risks of changing?
This helps you look at things more objectively, pushes you to really consider your strengths and what matters to you.
Step five: distinguish between fixing and changing
One of the most important distinctions in career decision-making is this:
Is this a situation that needs adjusting, or one that needs ending?
Ask yourself the following:
- Have I clearly named what isn’t working?
- Have I tried to change the right things, or just worked harder?
- If nothing changed for the next two years, how would that feel?
This helps separate short-term frustration from deeper misfit. It also reduces regret, because decisions made after honest exploration tend to feel more grounded, even when they are difficult.
Step six: resist false urgency
There is a lot of cultural noise around career change, particularly at this time of year. Messages that suggest bold leaps, instant clarity, or total reinvention can make people feel both behind and pressured.
A practical assessment framework does the opposite when considering the question ‘should you quit?’. It slows things down enough for you to move forward deliberately.
You do not need to decide everything now.
You do need to decide whether this question deserves your attention.
If you’re still asking it, still circling it, still feeling its pull, that is usually a sign that it does.
So, should you quit?
Sometimes the most important career decision isn’t whether to quit, but whether to take the question seriously enough to explore it properly.
And that exploration is often what reveals whether you need a new job, or a new direction altogether.
The end of the year can be about asking better questions and setting yourself up to make decisions from a place of deeper self-awareness.
If you’d like support with that process, I have reflective resources on my website, including a Career SWOT analysis, which many people find helpful in clarifying whether they need a change of role, or a change of direction. And if you want to talk it through, you’re very welcome to get in touch.
