20 Questions

Questions to Ask Yourself Before Quitting Your Job

Thought-provoking questions that help you evaluate your current job situation, identify your priorities, and make an informed decision about whether to stay or leave your current position.

1

What specific aspects of my current job are making me want to leave?

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Why this works

Helps identify the root causes of dissatisfaction and reveals what specific issues or problems are driving the desire to quit.

2

What do I value most in a job and how does my current role align with those values?

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Why this works

Reveals your core values and priorities while showing how well your current job matches what you find most important in work.

3

What are my long-term career goals and how does this job fit into that plan?

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Why this works

Shows your career aspirations and reveals whether your current job is helping or hindering your long-term career development.

4

What would I miss most about my current job if I left?

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Why this works

Reveals the positive aspects of your current role and helps identify what you value and enjoy about your current position.

5

What are my financial obligations and how would quitting affect my financial stability?

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Why this works

Shows the practical considerations of leaving and reveals the financial impact and security implications of quitting your job.

6

What are my alternative options and what would I do if I quit?

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Why this works

Reveals your backup plans and shows what alternatives you have available if you decide to leave your current position.

7

What have I learned from this job and how has it helped me grow?

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Why this works

Shows your professional development and reveals what skills, knowledge, and experience you've gained from your current role.

8

What are my concerns about staying and what are my concerns about leaving?

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Why this works

Reveals your fears and concerns about both options, helping you weigh the pros and cons of staying versus leaving.

9

What would I need to change about my current job to make it more satisfying?

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Why this works

Shows what improvements you'd want to see and reveals what changes would make your current job more appealing and satisfying.

10

What are my strengths and how are they being utilized in my current role?

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Why this works

Reveals your professional strengths and shows how well your current job is leveraging and utilizing your key abilities and talents.

11

What are my weaknesses and how is my current job helping me improve them?

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Why this works

Shows your areas for growth and reveals how your current job is helping you develop and improve your professional weaknesses.

12

What is my ideal work environment and how does my current job compare?

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Why this works

Reveals your work environment preferences and shows how well your current job matches your ideal working conditions.

13

What are my relationships like with my colleagues and how important are they to me?

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Why this works

Shows your social connections and reveals how important your workplace relationships are to your job satisfaction.

14

What are my work-life balance needs and how is my current job meeting them?

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Why this works

Reveals your work-life balance priorities and shows how well your current job is supporting your personal and family needs.

15

What are my learning and development needs and how is my current job meeting them?

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Why this works

Shows your growth aspirations and reveals how well your current job is supporting your learning and professional development.

16

What are my compensation and benefits needs and how does my current job compare?

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Why this works

Reveals your financial priorities and shows how well your current job is meeting your compensation and benefits expectations.

17

What are my job security concerns and how stable is my current position?

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Why this works

Shows your security needs and reveals how stable and secure your current job is and what risks you face by staying or leaving.

18

What are my career advancement opportunities and how is my current job supporting them?

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Why this works

Reveals your advancement goals and shows how well your current job is supporting your career progression and advancement opportunities.

19

What are my personal and professional values and how does my current job align with them?

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Why this works

Shows your core values and reveals how well your current job matches your personal and professional principles and beliefs.

20

What would I do differently if I could start over in my current job?

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Why this works

Reveals your regrets and shows what you'd change about your current situation if you had the opportunity to start fresh.

Best Practices for Job Decision Making

Expert tips and techniques for getting the most out of these questions.

Best Practices

Be Honest and Self-Reflective

Take time to honestly assess your situation, values, and priorities. Be truthful about what's working and what isn't in your current job.

Consider Both Short-term and Long-term Implications

Think about both immediate consequences and long-term career impact. Consider how your decision will affect your future opportunities and growth.

Seek Input from Trusted Advisors

Talk to mentors, colleagues, or friends who can provide objective perspectives on your situation and help you think through your decision.

Question Sequences

The Values and Priorities Sequence

1
What specific aspects of my current job are making me want to leave?
2
What do I value most in a job and how does my current role align with those values?
3
What are my long-term career goals and how does this job fit into that plan?
4
What would I miss most about my current job if I left?

The Practical Considerations Sequence

1
What are my financial obligations and how would quitting affect my financial stability?
2
What are my alternative options and what would I do if I quit?
3
What are my job security concerns and how stable is my current position?
4
What are my compensation and benefits needs and how does my current job compare?

Common Pitfalls

Don't Make Decisions Based on Emotions Alone

While emotions are important, don't let temporary frustrations or anger drive your decision. Take time to think through the practical implications.

Don't Ignore the Financial Impact

Consider the financial consequences of leaving, including lost income, benefits, and potential career setbacks. Make sure you can afford to leave.

Don't Rush the Decision

Take time to thoroughly evaluate your situation. Don't make a hasty decision that you might regret later. Consider all your options carefully.

Decision-Making Templates

The Values and Priorities Approach

1
Step 1: Start with: "I need to understand what's driving my dissatisfaction..."
2
Step 2: Ask: "What specific aspects of my current job are making me want to leave?"
3
Step 3: Explore: "What do I value most in a job and how does my current role align with those values?"
4
Step 4: Connect: "What are my long-term career goals and how does this job fit into that plan?"

The Practical Considerations Approach

1
Step 1: Begin with: "I need to consider the practical implications..."
2
Step 2: Ask: "What are my financial obligations and how would quitting affect my financial stability?"
3
Step 3: Explore: "What are my alternative options and what would I do if I quit?"
4
Step 4: Connect: "What are my job security concerns and how stable is my current position?"

Further Reading

"The Art of Decision Making" by James Storey
"Thinking, Fast and Slow" by Daniel Kahneman
"The Paradox of Choice" by Barry Schwartz
"Decisive" by Chip Heath and Dan Heath

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