Figure out if it's time for a career change

Most people sit on the “should I change careers?” question for months. They go back and forth, read Reddit threads at midnight, and never actually make a decision. The problem isn’t that they lack information. It’s that nobody’s asked them the right questions in the right order.

This prompt doesn’t tell you what to do. It helps you think through it clearly so you can stop guessing.

Copy this into ChatGPT, Claude, or your AI tool. Replace the brackets with your info.

I'm trying to figure out if I should change careers or stay where I am. I don't want generic advice. I want you to walk me through this like a smart friend who asks hard questions.

**Where I am now:**
- Current role/title: [your job title]
- Industry: [your industry]
- How long I've been here: [time in this role and/or career]
- What I make: [salary, roughly - helps with realistic planning]

**What's bothering me:**
[Be honest. What's making you think about leaving? Is it the work itself, the company, the pay, the ceiling, the industry? List everything, even the small stuff.]

**What I think I might want instead:**
[Even if it's vague. "Something more creative" or "tech" or "I have no idea" are all fine starting points.]

**My constraints:**
[What's non-negotiable? Bills, family, location, salary floor, timeline? Be specific.]

Here's what I need you to do:

1. **Sort my reasons.** Look at what's bothering me and separate them into:
   - Things that are about THIS JOB or company (fixable by switching employers, not careers)
   - Things that are about THIS CAREER (only fixable by changing fields)
   - Things that are about ME right now (burnout, life stage, unrelated stress that might be coloring everything)

   Be honest. If half my problems would follow me to a new career, say so.

2. **Reality-check my timeline.** Based on my constraints and where I am, what does a realistic career change actually look like? Not the inspirational version. The real one. How long would it take? What would the income dip look like? What would I need to do first?

3. **Challenge me.** Ask me 3-5 follow-up questions that will help me figure out if this is a real signal or a rough patch. Things like:
   - "When was the last time you were excited about your work? What were you doing?"
   - "If your current job paid 40% more, would you still want to leave?"
   - "What would you need to see change in the next 6 months to want to stay?"

   Wait for my answers before continuing.

4. **After I answer**, give me your honest read:
   - Does this look like a career problem, a job problem, or a life problem?
   - If it's a career change, what are 2-3 directions worth exploring based on what I've told you?
   - What's the single most useful thing I could do this week to move forward (not "think about it more")?

Rules:
- Don't be a cheerleader. "Follow your passion" is not helpful.
- Don't catastrophize either. Career changes are normal, not reckless.
- If I'm clearly in a bad headspace, gently point that out. Bad weeks are not good times to make big decisions.
- Push me for specifics. Vague answers lead to vague plans.

Tips for better results

• Do this on a calm day, not right after a terrible meeting. Your answers will be more accurate when you’re not in fight-or-flight mode.
• Answer the follow-up questions honestly. The “if your job paid 40% more” question is a good one. If the answer is yes, you’d stay, that tells you something important.
• Save the output. Even if you don’t act on it right away, having a clear written analysis beats the loop in your head.
• If the result points toward a real career change, the transferable skills audit is your next step. It’ll map what you’ve done to what you could do next.

What to do next

• If you’re leaning toward a change: run the transferable skills audit to see what you’re working with, then build a career change action plan.
• If you’re leaning toward staying but switching jobs: the resume tailoring prompt will help you move faster.
• If you’re still not sure: that’s fine. Come back to this in a week with fresh answers. Sometimes the clarity comes from sitting with the questions.