Nine Questions to Help Build a Bridge to a Semi-Retired Career

Invariably, when I speak with people of a “certain” age, generally 50+, about the concept of semi-retirement, they LOVE the idea.

And, it has never occurred to them before.

The culture of the sixties and seventies, when Boomers came of age, oriented toward a very traditional work/life agreement.

Pick a job. Do it your whole life. Retire.

While this worked well for the older portion of that generation, as well as previous ones,  it has faltered a great deal for the more junior Boomers.  As a result, more and more people expect to have to work in some capacity well into their sixties and even seventies.

Why not create a NEW model that combines working with greater blocks of time off to enjoy life?

For many, the challenge is how to get from where they are now to where they want to be.   The first step is to identify the obstacles and the stepping stones for each individual.  These nine questions should help you get started and begin to shine a light on your path to a better work/life agreement.

Grab a blank sheet of notebook paper and jot down your initial answers.   Try not to over think – this is about what you WANT your life to look like.   We will work on the HOW next.

  • Do you want to work the same job for nine or ten months?
  • Or, do you want to do project type jobs, perhaps a quarter at a time?
  • Do you want to do the same job/jobs every year?
  • Do you want to work where you live now? Or, is there a specific place you want to be?
  • Do you want to combine work and travel?
  • Do you want/need steady reliable income?  Or could you work in bursts, stowing away a large payout and then living off that?
  • Do you have any physical limitations?
  • Do you have obligations of time or money you have to work around?  What are they?
  • What changes do you need to make to work toward this goal? Pay off debts?  Give away or sell belongings?  Get children grown and launched?  Take a class or obtain a certification?

At first, these questions seem very simple.   To an extent, they are.   The single biggest factor in deciding to live a semi-retired life is deciding to DO it.   After that, it’s a matter of setting your own boundaries, and the options are really limitless once you let yourself examine them.  And questions tend to beget questions.

Answering them should help create a framework for avenues to pursue.     The first step is the scariest – take it anyway!


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Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

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