Generating career possibilities with AI
Are you contemplating a career change or craving a significant change at work, but you’re stuck on the specifics of what that might be?
Maybe you’ve been doing research on LinkedIn, talking your partner’s ear off about how much you want a change,
and even having a few informational interviews…
But then you get overwhelmed. And stop.
The activity below is designed to help you generate and notice career possibilities.
Suggested prompt for generating career possibilities
Copy and paste the prompt below into your preferred AI tool.
I’m currently working in a role related to [briefly describe your work or context].
I’m curious about possible next directions in my career, but I’m not trying to make a decision yet.
If helpful, here’s a bit more context about me (optional):
- Types of work I tend to enjoy (e.g., mentoring, analysis, creating, leading, problem-solving)
- Work environments I usually thrive in (e.g., collaborative, independent, structured, flexible)
- Something I want more (or less) of in my work right now
Act as a thoughtful career mentor with experience across professional, academic, and mission-driven work.
Your role is to help me generate possibilities and notice patterns, not to evaluate or rank options.
Generate a set of career directions I could explore, grouped into four categories:
- Obvious possibilities: natural next steps that build on what I’m already doing
- Ambitious possibilities: directions that would stretch my skills, scope, or visibility
- Pivot possibilities: paths that use transferable strengths in different contexts
- Dream possibilities: imaginative “what if” directions that feel energizing or meaningful
For each possibility:
- Write 2–3 sentences describing what the work might involve
- Note the kinds of people I’d likely work with
- Include what might make this direction engaging or satisfying
Include at least one option that may feel unconventional but aligned with how I like to work.
If details are missing, make reasonable assumptions and clearly state them.
After generating the list, ask me two reflective questions to help me notice which possibilities have the most energy for me.
What to do next
Once you’ve generated your list of career possibilities, take a moment to notice:
- Which ideas you keep rereading
- Which ones spark curiosity
- Which category feels most alive for you right now
If one possibility has energy for you, consider talking it through with someone you trust
(for example, a friend, mentor, or coach) to help you choose and take one small, time-bound next step,
rather than letting the momentum fade.
Credit: The above activity was inspired and adapted from Squiggly Careers’
How to Design Your Future Career Using AI
.
