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Reinventing Your Career After 50

A laptop showing the time.

Carl Reiner, the 95-year-old comedian, writer, actor, and director, likes to say “Every morning … I pick up my newspaper, get the obituary section, and see if I’m listed. If I’m not, I have my breakfast.”

In a recent HBO special, If You’re Not in the Obit, Eat Breakfast, Reiner challenges perceptions about what it means to be living in your 90s, and talks with friends who, like him, are thriving in their ninth decade.

Americans are working longer than ever, with nearly 9 million people, age 65 and older, employed. This is more than at any other time since the turn of the century, and double the number working in 2000, according to a new Pew Research Center study.

According to the Shift Commission on Work, Workers and Technology, by 2024, nearly one-quarter of the workforce is projected to be 55 or older — more than double than in 1994.

Reinvention is imperative

Expecting to retire from an organization you’ve been with for most of your career is no longer the norm. Today, the average person changes jobs twelve times during her career.

If you plan to stay employed after 50, it’s up to you to manage your career; reinvention isn’t just for the young.

If you’ve worked in finance and operations but want to become a front-line fundraiser, you might consider joining a nonprofit board where you can take a leadership role in organizing a fundraising event. If your goal is to move into marketing but you lack social media experience, consider taking a course on Coursera or Skillshare. Alexis Perrotta’s article, Get the Experience to Land the Job: Social Media Manager, will give you additional ideas on how to develop social media credibility.

What lights you up?

In my experience as a career coach, I’ve had clients who simply think they’re too old to reinvent themselves. But with people living healthier, longer lives, there’s a good possibility of working for another 15 or 20 years past traditional retirement age.

Instead of focusing on the time that is gone, think instead of what’s in front of you. Ask yourself:

  • What do I get out of work besides compensation?
  • What work would give me purpose?
  • What interests do I have that I have not been able to devote enough time to?
  • What new skills would I like to learn?

Plan accordingly

In their book, Don’t Retire, Rewire, authors Jeri Sedlar and Rick Miners emphasize the importance of “using today to build your tomorrow.”

Although your current job may no longer be fulfilling, quitting without a plan is sure to create unwanted stress and anxiety. It may seem appealing to have nothing on your calendar for a month or two, but that may speak to the need for a sabbatical rather than a permanent break.

Additionally, if you are considering moving from a lucrative career such as an executive director of a healthcare nonprofit to one that pays less, developing a financial plan to get there will help you understand how much you need to save to make a comfortable transition. In her article, 5 Ways Nonprofit Employees Can Tackle Their Finances, author Kimberly Maul offers a number of resources for financial planning.

For some great ideas on how to fund your career change or plan for a pre-retirement transition, check out Vicki Johnson’s article, 4 Ways to Find Funding for Your Career Change.

Consider location preferences

If your post-retirement goal is to winter in sunny climes or travel extensively, those choices will inevitably affect your employment options. What are your priorities and how do you determine them? Here are some questions to consider:

  • Do you need to move closer to family?
  • Do you want to snowbird and if so, where?
  • Do you want to live abroad for a month each year?
  • Do you want to combine travel and work?

If you expect your lifestyle choices to take you away from one location for part of the year, consider the suggestions from Dorie Clark in her Harvard Business Review article, Planning Your Post-Retirement Career.

“Perhaps you could choose a job that only operates for a portion of the year and allows flexibility the rest of the time (such as being a teacher or university instructor). Or you may want to focus on internet-enabled jobs that can be done from anywhere, such as being a freelance journalist or a web designer or a business consultant,” says Clark.

Research your options

Volunteering or moonlighting is an effective way to confirm your assumptions. offers a range of job postings; full-time, part-time, paid, and volunteer that connects professionals with organizations in search of expertise.

If your goal is to combine living abroad and working, check out Unsettled, a startup that organizes 30-day coworking retreats around the world for professionals seeking to combine work, and travel. More resources on travel-work programs can also be found in Volunteer Abroad Opportunities for Seniors and Retirees.

Working in your late 50s, 60s, and beyond is possible if you plan, engage your passions, clarify your geographic preferences, and research your options. For additional ideas on working in your later years, read my suggestions in Staying in the Game Past 50.

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About the Author | Susan Peppercorn is a career coach and writer with a passion for helping individuals go from surviving to thriving in their careers. Through her knowledge of personal branding, hiring practices and social media, she enables professionals to realize their career goals. Susan is founder and CEO of Positive Workplace Partners and author of the soon to be published book, Ditch Your Inner Critic: Let Go of Perfection to Thrive in Your Career.

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