22 Questions for Better Career Decisions in your 20s & 30s

22 Questions for Better Career Decisions in your 20s & 30s

LinkedIn News Australia recently asked:

“How long should workers stay with their employer?”

To which I responded:?


Since 62 other professionals felt the same way I did about this, I thought it would be valuable to share how I help clients in their 20s & 30s navigate their careers.?

So here are the 22 Questions I ask my clients to help them decide when to stay and when to leave their employer:

  1. Would I apply for my current job if I didn’t have it and saw it advertised?
  2. What promises have my manager or company made to me that I’m relying on? Have they made promises before and not kept them?
  3. What is my potential upside from my current career path??
  4. What would need to happen for me to make a change?
  5. If I stay on the path I’m on, where will I be in 1 year? 2 years? 5 years? 10 years?
  6. What other opportunities are available to me, either internally or externally?
  7. What is my reason for staying in this role or with this company?
  8. What assumptions have I made about my career? Which of these assumptions need to be challenged?
  9. Who can I connect with that will expand my awareness of what’s possible?
  10. Have I been making decisions about my career or have other people been making decisions for me?
  11. How will I feel if things stay the same?
  12. How much control do I have over my career in my current role??
  13. Do my career values align with the values of my company??
  14. What parts of my job that I don’t like do I believe are “normal’ with my line of work??
  15. What would my manager or company do if I received a competing offer?
  16. What would my work environment need to provide me to convince me to stay? And what would be an irresistible offer??
  17. Will my job or the company I’m working in take my career to where I want it to go?
  18. Who are the key decision-makers in my company that will impact my career? Are their incentives aligned with helping me advance?
  19. What fears am I holding onto about taking my next career step? What’s the worst thing that could happen? How realistic is this?
  20. Do I need more direction with my career, and if so, why am I not seeking that now?
  21. What would I do if my position was terminated tomorrow? (which can and does happen)
  22. If not now, when?


The most important thing you can do to advance your career is to keep asking yourself these questions, rather than letting your career drift and finding yourself in a situation you don’t want to be in.?

And if you’d ever like to go through these questions together (or if you’re concerned with some of your answers), I’m always keen for a chat.


Thanks for reading to the end of this article!

If you're keen to Advance Your Career in 2024, please enjoy my online course which will help you:

  1. Get clear on what you want
  2. Get the job you want
  3. Get paid what you’re worth
  4. Set yourself up for future success

Go for it!



Jacqueline Madsen

Director FYA Solutions | Supervisor Australian Antarctic Division

5 个月

22. If not now, when? There's always a reason to delay, but at what cost, and for what real benefit? Always a fun one to think through. Thanks for sharing these thought provoking points Ben!

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