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Can You Change Careers After 50 or 60? You Bet!

How to change careers after 50 or 60

“Life is what happens to us while we are making other plans.”
— Allen Saunders:

Do you resemble Allen Saunders’ quote? 

Did your dreams for life not match your experience? 

Here’s what I dreamed of doing in my 20’s:

after 55 you should have work you love

The year was 1969.  I was 13 years old when the movie Easy Rider hit the movie theater. 

It was the typical Rebel Without a Cause genre with the added effect of a cross country journey on the open road. 

I was hooked and immediately began plans for a similar journey in 5 years directly following high school graduations. 

What I actually did in my 20’s:


By 20 my dreams were replaced with a different life path…

Here’s what I actually did:

  • I married my high school sweetheart…
  • had 2 kids…
  • bought a home…
  • …and settled on a career that would provide sufficient income to support what was supposed to be the “American Dream.”

I believed replacing the open road for a back yard, a camp fire for a barbecue, and a Harley Davidson Motorcycle for a John Deer ride on lawn mower was the key to finding happiness. 

The problem I had is that my career in sales while economically rewarding was otherwise not very fulfilling. 

What I didn’t realize at the time:

I was typical of the average Boomer… the majority of us hated our jobs.

Gallup Poll finds 70% hate their job:

Gallup has been diligently measuring employee satisfaction rates all over the world. In their most recent survey for 2014, over 80,000 adults were surveyed, resulting in a staggering statistic: nearly 70% of American’s hate their job.  Employees have shouted from the rooftop that in order to love their jobs they need to find purpose, meaning, feel useful and use the skills they were given in a positive way.

That’s why so many of us dream of the day that we can retire. 

Because we see retirement as the day we can actually stop doing something we hate to do. 

But do we really want to stop working for 30 years to go play golf? 

The answer is overwhelmingly NO

We just want to finally do something we “like to do” instead of something we “have to do…”

In fact… most of us NEED to keep working…. but…

Americans seek meaningful work in the second half of life

A MetLife Foundation/Civic Ventures:

Survey conducted by Peter D. Hart Research Associates, Inc. from February to April 2008, involving 1,063 phone interviews and 2,522 online interviews.

Income and benefits are important now but will become even more important to boomers in the years ahead.

Younger boomers (79%) are more likely to say they plan to work longer because they need the income and benefits than pre-boomers (64%). Given the disappearance of traditional pensions, the escalating costs of health benefits, and the lack of adequate retirement savings, it’s easy to understand why.

Those in encore careers are having a good experience. Their message is that the encore career is, on balance, fulfilling and worth pursuing. More than eight in 10 of those in encore careers (84%) say they either get a “tremendous amount” of satisfaction (38%) or “quite a bit” of satisfaction (46%) from their encore careers. A similar percentage (94%) of those in encore careers say that it is “definitely true” (54%) or “somewhat true” (40%) that they have seen the positive results of their work and know they are making a difference. The vast majority indicate they have the income, benefits, and flexibility they say they need.

See full report:

What the heck is an Encore career?

The phrase “encore career” was first made popular by Marc Freedman, the founder and CEO of in his book Encore: Finding Work That Matters in the Second Half of Life.[1]

An encore career is work in the second half of life that combines continued income, greater personal meaning, and social impact. These jobs are paid positions often in public interest fields, such as education, the environment, health, the government sector, social services, and other nonprofits. Encore Fellowships, created in 2009 by the nonprofit, are designed to transition highly experienced professionals from the corporate sector into encore careers in the social sector.

What if you don’t know what you want to do as an Encore career?

Good question…

I asked exactly that same thing. 

Here is a resource that I found very helpful:


Life reimagined is a tool provided by AARP that helps you discover (or uncover) the career path that would be best suited to helping you find real happiness and fulfillment in your 3rd chapter of life. 

The website also offers video interviews hosted by Jane Pauley that show boomers actually living the dream. 

Here’s one of my favorites:

Top 7 Regrets of People Who Are Dying

Here’re the top regrets of people who are dying and how we can use them to live a more fulfilling life.

  1.  I wish I had lived my own life rather than how society taught me to live.
  2.   I wish I discovered my purpose earlier.
  3.   I wish I had taken more risks.
  4.   I wish I had taken better care of myself.
  5.   I wish I’d allowed myself to love.
  6.  I wish I had touched more lives and inspired more people.
  7.  I wish I had been a better partner or parent.

The question is…

Is it too late to make the changes to eliminate these regrets? 

The answer is NO…

…you probably have 20 to 30 more years left in an Encore career if you start today…

Encore Careers: Civic Ventures Study Finds Transition Is Tough

Laura Rowley

Financially, more than two in three respondents who are already in encore careers experienced gaps in personal income during the process. One quarter said they earned no money and 43 percent said they earned significantly less than they had at their previous jobs.

Of those who experienced time with little to no income, nearly four in five respondents experienced a gap of six months or more; 36 percent said their income gap lasted more than two years.

At 50, Rogers was laid off after 18 years as a director of software engineering for a corporation. She had been an active volunteer with the Alzheimer’s Association and wanted to move into the non-profit sector, but was rebuffed for lack of experience.

Rogers attended a three-month program focused on helping seasoned professionals transfer to the nonprofit sector, followed by a two-month fellowship. That paved the path to her new job, in which she helps 220 families in one of Connecticut’s largest and lowest-income housing projects with employment, education, childcare and other issues. “The transition wasn’t easy — my husband and I had a substantial reduction in income for 14 months,” Rogers said.


Now for the bad news:

Just as in the example above most of us boomers will face financial challenges with launching an entirely new career.

Whether it’s:

  • the cost of going back to school
  • the cost of living with a reduced income while training, or
  • simply doing something that has low economic benefit in exchange for high psychobiological benefit

The simple fact is, we will probably need to draw on our current assets to support our transition.

In most cases your home equity might be the most valuable resource you have in your arsenal.

(Unless you have a large chunk of cash sitting in the bank or a generous pension from your previous career). 

Liberating your home’s equity could be the catalyst to launching what I call BoomerLife 3.0.

BoomerLife 3.0 is where you finally live the life that you’ve always imagined.     

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