Five Steps to Find Your Dream Job for the Last Third of Life

A wish for fulfilling work can roar to life at any age. It often seems a promise we must keep. So, we hunt and hunt and hunt, and often are still hunting for the “dream job” in our 50s and 60s.

Many howl with pride that they have found and do “the work they are meant to do.” We try not to hate them.

Many continue to seek “purposeful work” while others have determined their lives will go on forever without a hint of this elusive and mysterious phenomena.

If you’ve bombed at finding the dream job your entire life or settled in to a less fulfilling career for one reason or another, you’ll want to take another crack at the dream job thing.

Why? Because authorities on people in their eighties – the “new old” – champion pithy sayings backed by solid research on how to get the best from a life of longevity.

Might it surprise you that this is advice heard in speeches when you graduated from your university and still advocated for fresh-faced graduates today?

Here is the “if-you-didn’t-get-it-before-let-me-tell-you-again” list for a happy and well-lived life:

  • Find meaning and purpose.
  • Go after your dreams.
  • Try something new.
  • Set out in a different direction.
  • Get out of the rat race. (Too early for you to understand as a graduate, perhaps.)

Many baby boomers leave their careers behind only to find themselves, once again, on the chase for meaning, purpose, and the fulfillment of dreams – often all encompassed in the “dream job.” Others occasionally contemplate the idea of “what will I do later on” but it seems fuzzy and complicated so they stop.

To discover a “dream job” at fifty or sixty seems daunting, but is it much different from when you were twenty or forty? Is the best approach to discover paths for meaningful work for a seasoned professional similar to the approach best used for a workplace newbie? What, if any, advice given to the young applies for a late-in-life expedition for a dream job?

These questions burned in my soul.

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What’s Best for a Sixty Year Old Dream Job Seeker- Well Worn or Contemporary Career Advice?

In the midst of my struggle to find a career path at sixty, an invitation appeared for Penelope Trunk’s online seminar, “Get Your Dream Job Now.” Serendipitous? Perhaps. And also irresistible.

Penelope Trunk is a successful, talented, and popular blogger; her account on Twitter, @penelopetrunk, has 128,288 followers. As a street smart, whiz kid, she uses her web savvy skill to cull extensive research and dispense advice to loyal fans in their 20s and 30s who adore her counter intuitive life/career instructions. She reminds me of a naughty Mouseketeer.

Over 200 of us tune in to watch Penelope fidget in the beginning of a content-loaded seminar but eventually settle in to a performance of enviable passion, off color language (not so enviable) and reproach.

Trunk uses the popular and valuable Myers-Briggs personality assessment (I am MB certified) as the be-all end-all for one participant who identified his dream job of film editor and his personality type. “If you are an ENTJ you can’t do that job. You will never be happy.” (End of conversation.)

Skeptical that Trunk’s advice for a twenty-year-old audience holds any meaning for a person who is old enough to be a grandparent to any of them, I am surprised by one particular hunk of wisdom. (You’ll find this later in the post.)

Finding a dream job is not a new topic of conversation for any generation. In a Google search for “career advice” on Amazon, long-standing books such as, “What Color is My Parachute?” and “WishCraft” remain relevant and anchors the 31,164 resources.

No one, not even Trunk, can claim the success of author, Richard Boles who for over forty years with 10 million copies sold, annually revises his book and keeps up with trends. In his latest edition, – no surprise here – Chapter 13: The Three Secrets of Finding That Dream Job of Yours.

But good advice – contemporary or well worn – truly tailored to those embarking on the dream job trek at 50-plus was missing for me in my journey.

And it was missing for millions of others – until now.

The Five Forever Rules

Based on a firm foundation of the research on aging, longevity, wellbeing, happiness, interviews and experiences of people who learned to continue career success or find different kinds of work success after 60, there are now a number of cairns to mark the way.

The dream job rules below aren’t really rules, but principles to guide you to work important for your future. I used the descriptor “forever,” not as a novelty but as a way to underscore intentionality of what must be done against the reality of time.

Forever means “for all future time,” but in this life stage there is less time ahead than ever before. The use of “forever” is a reminder of this often unspoken truth.

Find Your Dream Job after Fifty – Five Forever Rules

  1. Think old. Not what you want to hear perhaps, but age is not a weakness in the quest for a dream job, but rather a certifiable strength. With past jobs and experiences you’re able to crystallize what you “do not want to do” or “don’t want any more of” articulated likely with more zest than at any other time in your life. You have lived many years – you have a past – and know the underbelly and            fragility of life. With a cadre of experiences on which to draw – and a new sense of finite future – you’re in the best position ever to begin to create fulfilling work.
  2. Get crystal clear on “me first decision-making.” Put yourself first is not a new message, yet over and over we put others needs above our own and eventually the results are a kind of bankruptcy of the self. In the spirit of putting yourself at the center of your wheel of life means actions and outcomes align to meet your needs and wants. To begin the act of living your life as if it were your own at any age is an extraordinary step and one that comes in a nick of time as you determine a future of work.
  3. Don’t choose a dream job, choose a dream lifestyle. Straight from Penelope Trunk’s advice to her young audience, make this yours. One non-negotiable differentiates this life stage for you – freedom. You want freedom and you can have as much as you like. Design a life where high priorities – like your work, your garden, your grandchild, your book club, your writing, your living in third world countries – meet measured time. Trunk was relentless in her seminar about the need to be realistic about how much time chosen “dream work” takes. Her advice to individuals who dream of “startups” and “being a lawyer” is, “Well, okay, but you can forget having a life.”
  4. Don’t do what you love if you don’t have the potential to make money. Your financial security may be as solid as an iron skillet but that’s not the point. Most of us have always liked to get paid for our work. Why change this part of the dream job just because it sits at the end of your career arc and not at the beginning or middle? And realistically, not one of us has a solid financial future so why would you want to go to a dream job every day only to worry about dwindling retirement funds? Where ever you invest your talents and time in the future, look for remuneration possibilities. Your finances will be in better shape and your working identity will thank you.
  5. Define your career with slashes. Multiple selves are who you are late in life. Rather than confine your definition of work in one word, Marci Alboher, author of Encore Career Handbook: How to Make a Living and A Difference in the Second Half of Life, advocates the package or portfolio approach: Activist/teacher; traveler/blogger/author; Consultant/gardener.The slash method, especially effective during the transition phase before a final sort for a dream job happens, asserts we are not one true self but many selves.  We have identities in the past and present- but most important – are those waiting for us to discover in the future. Joy in late-life design is found in incorporating the multi-dimensions of who we are; no single word answers again – ever. 

Don’t start your dream job search by writing your life story, a list of your strengths, a mission statement or mind-mapping passions. (Oh, how I hate these ideas for re-imagining a third act!)

Do start a new conversation with yourself about how your future might be. Think about it – a lot. And start now.

Invite others to join in and soon you’ll have a group of people you can talk to and learn from. It’s a fail-safe way to energize the hunt for your dream job, find it and flourish in it.






About Barbara Pagano

Barbara Pagano,Ed.S., author and speaker, influenced over 3,500 executives in organizations to achieve higher performance. She is now on a mission to help individuals extend their career arcs and craft lifestyles of productive longevity.
This entry was posted in Productivity, Reconstuct Retirement and tagged , , , . Bookmark the permalink.

8 Responses to Five Steps to Find Your Dream Job for the Last Third of Life

  1. Carol Zink says:

    I retired at age 60 because I could financially. It was too early. But I was exhausted after 14 years of teaching high schoolers. I love many aspects of teaching, but was ‘burnt out’. Now I want to go back to work, but after interviewing for a teaching job (an all day process), I realized I do NOT want to teach full time (and maybe not even part time). But I feel/think that all those years of gaining valuable experience should not be thrown away. So how can I take that experience (and my other life experiences -raising kids, volunteering, and work experiences in the Navy and in the software marketing and sales) and put it to constructive use? I’d like to teach people who want to teach (but I don’t have a MEd or PhD in Ed, and I do not want to go back to more school!!!).

  2. Pingback: Why You Must Dare, Dream and Work…Forever » The Inventive Life Post50

  3. Pingback: The Aimless Post60 Tribe: Failing to Grasp the Meaning of Their Decade » The Inventive Life Post50

  4. I am struck how each one of you shares optimism and high hopes for a third-act future! Whether it’s just moving forward or the “Last Hurrah,” we’ll carve new ways of being productive in our long lives. Thanks for your comments.

  5. Dee Dee Kincade says:

    I am one of those that lucky individuals that found “the work they were meant to do”, early in life. And then I followed up with pursuing a passion afterwards. Now that my passion is waning and I need a change, these rules are a reminder on how to find my next passion. Because I know anything else just will not do.

  6. Sara Fountain says:

    After enjoying having been “retired” for a year, I am feeling ready for The Next Hurrah. I am inspired by the Five Forever Rules and look forward to living many more of my dreams.

  7. James Mullis says:

    I am early in the Life Post 50. The Five Forever Rules are sound advice that have lifted my personal outlook in times of great volatility!

  8. Geoff Sobeck says:

    Great article! The ‘Five Forever Rules’ I plan to read daily. Thanks so much for the inspirating and thought provoking information.

Would love to hear what you are thinking.