Should I stay or should I go?

Leaving a job at late in life

Photo by Centre for Ageing Better on Unsplash

On a Sunday evening, as Monday morning approaches, it isn’t uncommon to have feelings that range from apprehension to dread to “meh.” These feelings can give rise to the question: Should I be thinking about leaving? Even when the job is going well, there can still be nagging questions about whether it might be time to move on. While there is often no absolutely correct answer, there are some valid considerations that may help in making the decision:

  • You like the income, but personal satisfaction is lacking. You no longer feel a sense of purpose (the “why”) with your work or the organization. The organization and the culture may have changed significantly. You find yourself saying “this place isn’t what it used to be. . .” The values of the organization have changed significantly and are not aligned with who you are now.
  • It’s hard to let go. Change can be hard. You’ve worked hard to achieve your current income level and it’s hard to walk away from it, even though you could live on less. But the work environment is sapping your motivation.
  • Technology has replaced human contact. Direct human engagement is quite important to most people. Completely remote work, with constant Zoom meetings has replaced the connections created by in-person work. There are people who have been hired in the last two years whom you have never met in person. You miss the human interaction.
  • You are comfortable but you’re not growing. You’re bored and the job is no longer energizing or intriguing.
  • You have enticing interests/passions that you would like more time to enjoy and learn about. There’s more you want to do, such as delving more deeply into hobbies or interests or having time for avocations such as volunteer work.

There could be more considerations with a job that you don’t love (or when it isn’t going well). These include:

  • You question your relevance. You have the sense, or some clear indicators, that you are no longer relevant in the ways you have been. You are passed over for interesting assignments. You recognize that you are out of the political and informational “loop:” you’re not asked for input on decisions, and you don’t get any advance notice of impending changes. Being “side-lined” may be an indirect way of the organization giving you a message that it is time to move on.
  • Tension and discomfort in your relationship with your boss is emerging. You have few if any informal conversations; you have to initiate most of the communication. There may be an age and or generational gap that shows up as disinterest in your experience and skill set.

If any of these points resonate with you, it may be time to consider moving forward to more fulfilling ways to contribute. Consider the following suggestions:

  • Future: Move towards something that energizes you rather than escape from something that is draining you.
  • Environment: What are you looking for? What is going to give you a feeling of accomplishment?
  • Relationships: What would you miss if you leave where you are? People, structure, customers/clients, feeling of accomplishment? How would you like to match who you are, what you are drawn to, what you are expert at with a new approach to contributing?
  • When other stressors or demands are great, don’t make the change. Making a successful job or career change requires a lot of time and energy.

And as Kenny Rogers sang in “The Gambler”:

“You’ve got to know when to hold ‘em; know when to fold ’em; know when to walk away and know when to run.”

Good advice for poker and work!

Marg Penn, Ph.D., has over 25 years of coaching and consulting experience in a variety of settings including academic and corporate environments. Learn more about Marg at