Knowing When It’s Time to Retire

I’m just not sure this is the right time.” I often hear this statement when clients want to exit their careers and plunge into the next phase of their life. Metaphorically, they are on the high diving board, staring into the uncertainty of retirement. They are anxious, not knowing if they will sink or swim. What is the right thing to do? They continue asking themselves if this is the best time to leap into the next phase of their life. They have distinct reasons for hesitating, usually none of which are financial. 

They are typically burned out, not feeling valued, or just restless. To better understand client concerns, we discuss other significant changes they experienced, such as buying a house, getting married, deciding to have children, dissolving a relationship or marriage, moving to another city or state, or changing jobs or careers. Did they have the same feelings when making those transitions?

Like other transitions, deciding when it’s time to retire is significant and can bring competing thoughts and emotions, such as excitement and fear. We all look forward to it, but when the opportunity is right in front of us, some are afraid to jump.

Looking back on other significant life decisions and transitions, we must understand that deciding when to retire is no different. What helped us take prior actions when uncertain about what to do? Transitioning into the new normal of retirement is a process, not an event, and the first step is to identify what is keeping us stuck and acknowledge that there are ways to feel more confident in your decision.

If you want to jump off the diving board but are still determining if it is the right thing to do and the right time, here are thoughts and questions that may help with your decision.

Forget About Age as the Determining Factor for Retirement

If you believe it is your time to retire because you are of a certain age, that has become an outdated reason and no longer the “rule” or even a good reason. There is no such thing as a career expiration date based on celebrating a certain number of birthdays. If you enjoy what you are doing and it is not affecting your life negatively, then your age should not be a factor. Look at Mick Jagger, Willie Nelson, Paul McCartney, and friends or family members who still want to work despite being a certain age and comfortable financially.

Emotions and Other Signs That It’s Time to Prepare an Exit Plan 

  • Where are you more stressed, at work or outside of work?
  • While talking to others about work, are you complaining more and more?
  • Do you experience SND (Sunday Night Disease)? Does thinking about going to work the following day make you miserable?
  • Do you feel like you are no longer making an impact like you did earlier in your career?
  • Does thinking about work situations keep you up at night?
  • Do you take work home with you – both actual tasks and stress?
  • Has your motivation to succeed diminished? Are you no longer interested in new career opportunities or continuing to learn about new business trends and skills?
  • Do you no longer feel relevant because younger employees are now the majority in the company?
  • Do you want to let go and let others take over, but you are afraid they will not do as good of a job as you do?
  • Has your job caused issues at home with your significant other or other family members?

And then this concern often comes up: “Yes, I’m feeling most of these emotions. However, I am not as financially prepared as I want.”  

Older Woman Reading Something on a Laptop
Taking work home consistently may cause excess stress. 

Questions That May Help You Decide to Retire or Continue Working

  • Have you spoken to a certified financial advisor about your predicament? 
  • Have you spoken to your manager or HR about planning phased retirement, moving into a part-time role, or mentoring new employees?
  • Have you researched other income-making opportunities outside your current work? 

So, is it time to retire? The answer is different for everyone. 

I would be remiss if I did not include this thought-provoking quote: “When time becomes more important than money, then it’s time to retire.”


Sue Mintz

Sue Mintz, Founder of Retirementhood™, is a coach, speaker, writer, and facilitator. She educates and guides soon-to-be or current retirees on becoming the best version of themselves in retirement by planning a lifestyle that is purposeful, healthy, fun, and one that fulfills long-awaited goals. She has been certified through Retirement Options, a division of Career Partners Intl, LLC., and is an Authorized "Now What®" Coach/Facilitator. She is not a financial adviser. For more information about Sue and the services she offers, visit or contact her at

Related Articles

Check Also
Back to top button