| No. | Item | Definition |
|---|---|---|
| 1. | Am I burned out or misaligned? | Identify the real issue. |
| 2. | Am I idealizing this career? | Check for unrealistic expectations. |
| 3. | Am I seeking change or relief? | Distinguish growth from escape. |
| 4. | Can I afford a pay cut? | Test financial flexibility. |
| 5. | Can I freelance or volunteer? | Gain low-risk relevant experience. |
| 6. | Can I handle rejection? | Prepare emotionally for setbacks. |
| 7. | Can I learn this cheaply? | Find low-cost training paths. |
| 8. | Can I learn while working? | Assess part-time upskilling options. |
| 9. | Can I return if needed? | Check reversibility of change. |
| 10. | Can I shadow someone? | Observe the role directly. |
| 11. | Can I switch internally first? | Explore change within current employer. |
| 12. | Can I test this field first? | Try before fully committing. |
| 13. | Can my household handle this? | Assess family financial impact. |
| 14. | Do I have an emergency fund? | Check financial safety cushion. |
| 15. | Do I need a degree? | Check formal education needs. |
| 16. | Do I need a new career? | Question the size of change. |
| 17. | Do I need a portfolio? | Determine whether work samples matter. |
| 18. | Do I need certification? | Check licensing or credential needs. |
| 19. | Do I need to rebrand myself? | Update your professional story. |
| 20. | Do I want leadership or craft? | Choose management versus specialist work. |
| 21. | Do I want people or projects? | Clarify interaction preferences. |
| 22. | Do I want remote or onsite? | Decide preferred work location. |
| 23. | Do I want stability or variety? | Choose your preferred pace. |
| 24. | Have I outgrown this field? | Assess fit with current work. |
| 25. | Have I spoken to insiders? | Validate assumptions with practitioners. |
| 26. | How competitive is entry? | Assess difficulty of breaking in. |
| 27. | How important are benefits? | Consider insurance, leave, and perks. |
| 28. | How important is autonomy? | Assess need for independence. |
| 29. | How important is flexibility? | Measure need for schedule freedom. |
| 30. | How important is pay? | Set income expectations realistically. |
| 31. | How important is prestige? | Check status as a motivator. |
| 32. | How important is purpose? | Weigh mission against other factors. |
| 33. | How important is security? | Evaluate tolerance for uncertainty. |
| 34. | How long can I earn less? | Estimate transition runway. |
| 35. | How long might the search take? | Estimate job hunt duration. |
| 36. | How long to become competent? | Set realistic timeline expectations. |
| 37. | How long to become employable? | Estimate time to entry. |
| 38. | How many hours are typical? | Know expected workload. |
| 39. | How much debt do I carry? | Measure financial obligations. |
| 40. | How much stress is normal? | Gauge common pressure levels. |
| 41. | How much travel is required? | Check travel expectations. |
| 42. | How risky is this move? | Estimate downside and uncertainty. |
| 43. | How should I frame my story? | Explain your transition clearly. |
| 44. | How steep is the learning curve? | Estimate ramp-up difficulty. |
| 45. | How strong is my network? | Assess relationship support. |
| 46. | How will I gain experience? | Plan practical skill building. |
| 47. | How will I network consistently? | Plan regular outreach habits. |
| 48. | How will I show credibility? | Prepare proof of competence. |
| 49. | Is this a temporary feeling? | Test whether urgency will pass. |
| 50. | What am I hoping to gain? | Define desired benefits clearly. |
| 51. | What am I naturally good at? | Spot strengths you can leverage. |
| 52. | What am I unwilling to do? | Rule out poor-fit duties. |
| 53. | What am I willing to learn? | Gauge openness to retraining. |
| 54. | What are my monthly expenses? | Know your baseline costs. |
| 55. | What are my nonnegotiables? | Set firm boundaries and needs. |
| 56. | What are the growth prospects? | Check future advancement potential. |
| 57. | What benefits would I lose? | Review tradeoffs in leaving. |
| 58. | What companies hire for this? | Identify likely employers. |
| 59. | What do people dislike about it? | Learn the hidden downsides. |
| 60. | What does success look like? | Picture the desired outcome. |
| 61. | What does the market pay? | Research typical compensation. |
| 62. | What evidence argues against it? | Look for disconfirming facts. |
| 63. | What experience is expected? | Learn common entry standards. |
| 64. | What is my backup plan? | Prepare for setbacks. |
| 65. | What is pushing me to leave? | Identify current pain points. |
| 66. | What is the hiring outlook? | Review demand in the field. |
| 67. | What is the opportunity cost? | Consider what you give up. |
| 68. | What is the worst-case scenario? | Face the possible downside. |
| 69. | What jobs am I curious about? | List roles worth exploring. |
| 70. | What kind of work drains me? | Notice tasks that exhaust you. |
| 71. | What kind of work energizes me? | Notice tasks that give energy. |
| 72. | What matters most to me? | Identify top personal priorities. |
| 73. | What myths am I believing? | Challenge false assumptions. |
| 74. | What problem am I solving? | Name the issue behind change. |
| 75. | What salary do I need? | Know your minimum income. |
| 76. | What sectors are growing? | Target expanding areas. |
| 77. | What skills do I enjoy using? | Focus on enjoyable strengths. |
| 78. | What skills do I want to build? | Choose future growth areas. |
| 79. | What trends could affect it? | Consider future industry changes. |
| 80. | What values must my work fit? | Match work with personal values. |
| 81. | What will my resume emphasize? | Highlight relevant strengths. |
| 82. | What work environment suits me? | Define your ideal setting. |
| 83. | Which gaps must I close? | Identify missing requirements. |
| 84. | Which roles fit my lifestyle? | Match jobs to daily life. |
| 85. | Which roles fit my strengths? | Match jobs to abilities. |
| 86. | Which roles fit my values? | Match jobs to beliefs. |
| 87. | Which skills transfer well? | Find reusable strengths. |
| 88. | Who can mentor me? | Find guidance and support. |
| 89. | Who can open doors? | Identify helpful connectors. |
| 90. | Who can vouch for me? | Identify strong references. |
| 91. | Who depends on my income? | Count people affected by change. |
| 92. | Who is already doing this work? | Find people in the role. |
| 93. | Who should I talk to first? | Choose best initial contacts. |
| 94. | Why do I want to change careers? | Clarify your core motivation. |
| 95. | Will I need to relocate? | Consider moving requirements. |
| 96. | Will I need training costs? | Budget for education expenses. |
| 97. | Will this fit my family life? | Check home-life compatibility. |
| 98. | Will this fit my schedule? | Assess time demands realistically. |
| 99. | Will this work suit my health? | Consider physical and mental demands. |
| 100. | Would I enjoy the actual work? | Separate fantasy from reality. |