20 Questions to ask Yourself when Deciding to leave a Full-Time Role and Career

Man holding a pen and thinking

By: Nanette Fairley
February 17, 2021


For many baby boomers, stereotypically hard working, the job may have taken a significantly greater part of their life than other generations.  Stepping down then can be hard especially if you like what you do, you’re good at it and derive a sense of purpose and meaning from it.  Also, as we are often healthier than ever before at this age, we may still have the energy we need to achieve.

If you are considering retirement but are really not sure if it is the right move for you, or if you may be impacted by some organisational changes, some navel gazing might be in order.  In my blog, Are you Psychologically Ready to Retire?, I outlined several questions to reflect on that may help you confidently make the decision to leave full-time commitments.  These included:

  • Do I have a plan in place for how I will spend my life post full-time employment?
  • Have I thought about my new identity once I am no longer an engineer, a teacher, a CEO etc.?
  • If in a relationship, have we discussed our plans with each other and found a happy compromise?
  • Am I ready for the upheaval that this transition will bring?  Even positive change can be stressful!
  • Do I have a network outside of work?
  • Am I ready not to have a monthly pay check?

A recent article in the Wall Street Journal added some additional questions you might usefully ask to guide your thinking:

  • How long is it optimal to be in my role? Is it time for a fresh perspective?
  • Do I want more control of my life?
  • Do I want a change?
  • Who am I without a business card?
  • For Type A personalities, how will I meet my need to achieve?
  • What would I rather do? Become an angel investor, for example? Or join a board? Work for a nonprofit? Consult? Teach? Mentor?
  • How will I reinvent my social network to make up for colleagues I won’t see daily?

And finally, some practical questions:

  • What kind of lifestyle do I want to live and how much will it cost?
  • What will a typical day or week look like?
  • Have I saved enough for the lifestyle I want to have at this stage of my life?
  • How much can I afford to spend each year once I leave full-time employment?
  • Where will I live?  In my current home?  In another community?
  • Have I sorted the practical elements e.g. health insurance
  • Do I have any factors I need to plan around? e.g. care for an adult children or aging parents

 In exploring these questions in a detailed and thoughtful way, you will move closer to making a decision only you can make – to step back from a role you may love and do other things.