Dr. Seuss’s best-selling book, “Oh, the Places You’ll Go!” is a favorite gift for recent college grads, but what happens when you’ve been to most of those places and you’re ready for that last job before retirement? Wendy Wilsker explores what to consider as you look for your “last” job.

By Wendy Wilsker
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It’s crazy to believe that my friends and I are at an age when the next job may be the last – or second to last.  While some of our parents may have worked well into their 70s, most people consider 65 the age at which they may consider retiring.  We start to wonder, “Where did the time go?”

Looking for a job in your 50s requires a bit more reflection by looking back before you can look forward.  As I have done personally and recommend to peers, at this age, we know what we enjoy, what we are really good at, and what we hope never to do again.  Our next job is less about the title and where we may sit on the organizational chart, and now it is more about what is fulfilling and meaningful. 

By now we have learned to overcome whatever obstacles we have faced. We have fought for promotions, built up the courage to ask for certain titles plus a salary raise, and for sure made some mistakes along the way. Financially, we have saved and paid for college and kids' activities. Ensuring the security of retirement savings and health benefits has become a larger priority over annual compensation. But for most of us, we are not done working and still have that fire in our belly for our next opportunity. Here are some things to consider as you seek a new job in your 50s:

  1. What is your “swan song?” Is there an organization whose mission is a passion of yours? If you could work for that organization, would you accept a lower salary?
  2. What do you love to do that you wish you could do all day? Do you want to spend time managing and coaching or do you want to “be out there” doing the work for others? Many fundraisers who have become managers miss time with their donors, so maybe a “Gift Officer” role is more preferable instead of managing a team.
  3. Is it time to think about a different kind of role? I know many non-profit professionals who have recently transitioned from Chief Development Officer to CEO. Is it time to be on that platform, sharing your voice and vision?
  4. Might you want to live somewhere else? If your “nest” is empty, maybe you can consider a relocation – take the time to think about those dream locations.

Lastly, maybe it’s time to do something entirely different. A friend of mine has always loved to coach others. Finally, she stopped “winging it” and took some classes to become a certified coach.  Now she has a “side gig” role, coaching a few mid-career professionals.  Her goal is to transition this role to full-time within a few years when she has greater financial flexibility.

Looking ahead can be scary, for sure, and there is also a freedom and confidence that comes with thinking about a new job in your 50s. When Dr. Seuss wrote, “Oh, the Places You’ll Go!”, the book was geared for college graduates pursuing their first job, but what if we wrote a new version for pursuing your last job? 

More Blog Posts by Wendy Wilsker

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