‘Should I quit?’ is a question many people ask themselves about their jobs at this time of year.
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.
Considering whether to leave your job, stay, or change direction can bring up feelings of hope, fear, curiosity, or a mix of all three. Taking time to step back and gain perspective on your situation more objectively can bring some clarity when you’re feeling overwhelmed.
It’s especially important to distinguish whether you’re unhappy with your specific job or with the type of work you do. Many people conflate the two because it can be difficult to tell which is actually causing the dissatisfaction.
Confusing a job problem with a career problem can lead you either to make unnecessary changes or to stay stuck in a bad situation longer than necessary.
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.
Think of it this way: your job is the container – the manager, the schedule, the office, the compensation. Your career is the contents – the specific tasks, the industry, the knowledge you create. You need to know if you’re unhappy with the container or the contents.
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 I 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 my 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: notice what energises and depletes you
Flow states – when you’re fully absorbed and time disappears – reveal important truths about fit. So does the opposite: work that consistently drains you, even when you’re performing well.
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 but about the distinction 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 Alexander Ong’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?
Looking at things more objectively pushes you to really consider your strengths and what matters to you.
Step five: distinguish between fixing and changing
Review the outputs from the previous steps and look for patterns: .
Job problem indicators typically cluster around:
- Environment, manager, or resources (SWOT Threats/Weaknesses)
- Poor working conditions (Energy Drains)
- Answers about pressure, pace, or people (Questions)
Career problem indicators typically cluster around:
- Different types of work (SWOT Strengths/Opportunities)
- The core tasks themselves (Energy Drains)
- Answers about meaning, interest, or purpose (Questions)
Now ask yourself:
If I were to give a title to the core conflict revealed in all my answers, what would it be? (e.g., The Conflict of Under-Utilised Creativity or The Conflict of Toxic Management).”
Step six: resist false urgency
Messages that suggest bold leaps, instant clarity, or total reinvention can make you feel pressured.
Taking time to assess your job and career slows things down enough for you to reflect and then move forward deliberately. With deeper self-awareness, the choices you make become more purposeful. Foundational self-knowledge is the starting point for change.
Reflection isn’t passive; it’s active mining of your past experiences for the wisdom required to build the future you want.
Taking time to assess slows things down enough for you to reflect and then move forward deliberately, while also giving you time to address practical considerations like finances or timing.
So, should you quit?
The end of the year isn’t just a calendar deadline; it’s a natural checkpoint for assessing the year you’ve just lived and setting the intentional direction for the next. This exploration is what reveals whether you need a new job, or a new direction altogether.
Ask yourself the following:
- If nothing changed for the next two years, how would that feel?
- Have I clearly named what isn’t working?
- In the past, have I tried to change the right things, or just worked harder?
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.
