Ask These 4 Questions When Planning Your Next Career Adventure

The real question is, will your epitaph be ‘I wish I had spent more time in the office?’,
or is there something bigger out there calling you?

– The Hero’s Journey, Dilts and Gilligan

The decision of whether or not we want to continue working in some form after our ‘official’ retirement age, is a very personal one. However, research has shown that those who continue to live active working lives after retirement stay healthier longer. Who doesn’t want that?

Know that you have earned the right to be selective in what you do next.

You are no longer fresh out of college with little work experience.  Be open to what your gifts can enable you to do, and listen to your heart about what makes you happy. Elizabeth White ( reminds: “Radical reinvention is not for most people. But lots of us want to build on our past careers and use our knowledge, skills, and abilities to serve new purposes in late middle age and beyond…”

There are so many options available today for ‘second act’ careers, and they don’t always mean staying employed, in the traditional sense. Depending on your resources and life goals, you can,

  • continue working in your field of expertise
  • branch out into a whole new field
  • start your own business
  • bring your skills and value to another organization
  • or volunteer your time where it is most needed

When deciding which option is best for you, consider the following questions.

1. Do I want to use my existing skills or try something totally new in the second half of my life?

You may be a butcher, a baker or a candlestick maker, but is there a way to pivot from your current profession and create a different arrangement? I think moving into a completely new career path might be too much for most of us, but moving sideways from your current role might turn out great for you. For example, a teacher might move into mentoring teens, or an attorney into advocacy work for the under-represented.

Or, perhaps you had your fill of your occupation and want to open a new path for yourself. Despite disliking your work now, there must be some reason you got into it, right? Figure out what originally drew you in and how that skill/interest can be applied elsewhere.

2. Do I want to pursue a long-held dream or passion, or fill an immediate need I see around me?

This, of course, isn’t an either/or choice. You can always pursue a long-held dream after filling a more immediate need. Passion may be overrated as a job requirement, but when you consider your career, I think it is central.

My overall advice always comes down on the side of finding something you really enjoy, not merely continuing with what you’ve been doing just because you’re already doing it. Ask yourself: What would you do if you could not fail? Your answer may hold the clue.

3. How much time and involvement do I want in my family’s life?

Changing your work arrangement can provide the time to reclaim your life and relationships that matter to you or pursue new relationships you may not have had the bandwidth to enjoy in the past.

Your situation may work best by being home more; others don’t have the same responsibilities, and have more flexibility.

4. How much money do I need?

You may be in a position where money isn’t as much a factor; or, you can see your idea generating a helpful income stream to supplement your savings, pension or social security. Do you have a preference for working on salary or by project, by the hour, or on commission?

Either way, stay clear-eyed on what you need. Don’t hide your head in the sand when it comes to finances. This will only blind you to other possibilities.

These four questions are only the beginning. Transitioning is not like flipping a switch. Rather, it is a process. Understand that this is just the next step in a longer journey. Know that these are not your final life decisions, but just the next decisions in a series moving forward.

So, what form do you want yournext career to take?

Peter Spellman helps people discover their next calling through online courses and coaching. Find him at