I grew up in a time when it was popular to “keep up with the Joneses.” This term comes from a 1913 comic strip which depicted a family intent on climbing the social ladder and accumulating material possessions to keep pace with their neighbours doing the same thing. It birthed conspicuous consumption, our demand for status goods and likely spawned our mania for credit card debt.

Keeping up with the Joneses meant: a safe, secure job, home ownership, a bedroom for each new child, new model cars, a gourmet kitchen, social respect and admiration. The intent was to work at one job for 40 or more years, retire to your rocking chair and then die.

We were programmed to follow this “success formula” - until it drove some of us to depression and despair. Many of us spent decades climbing the social ladder, reaching the top and then finding it was leaning against the wrong wall.

Our “gourmet kitchen” was filled to overflowing with every kitchen gadget that came on the market - in shades of orange, gold and turquoise. My father did his best to keep up with the Joneses. His fatal mistake was delaying his dream of a leisurely cross-Canada drive with my mother until his scheduled early retirement at age 60. He died at age 57.

Life is Short

Life is indeed short and it may be later than you think. If you are living a life of quiet desperation, now is the time to make alternate choices that allow you to live on your own terms.

3 Alternate Paths for Midlife Reinvention

There are three paths Baby Boomers are increasingly walking so they can live their own dream before they die.

I’ll be sharing examples of people I know from the Island I live on - because all three thrive on Gabriola Island.


Creativity is the ability to make something new or think up new ideas. It’s also a skill that will be needed for the future of work. If a machine can replace us, it will. Creativity separates us from machines.

Women who have made a satisfying midlife career change know that creativity is their “secret sauce.”

We are all creative. Our education system, jobs, family responsibilities and society tend to dull it down. Many of us have just not had time to make full use of our creativity - until now.

How can we harness our creativity?

Two important psychological shifts happen in midlife:

  • We recognize our time is limited and we can’t live forever.
  • Our Inner Soul craves expression. We feel an urge to be creative and leave behind some kind of mark that shows we were here.

Women who heed the call of creativity are rewarded with more fun, physical and mental well-being, connection with others and an outlet for self-expression.

The Gabriola Senior Citizens Association mandate is to maintain a socially and physically healthy lifestyle. Some of their activities include: Painting, Quilting, Photography, Live Theatre, Weaving and a Discussion Group. The Palette People meet in their building. They enjoy a creative art environment where members come together to develop their artistic skills using watercolour, acrylic, oil paints or mixed media. There is likely something similar in your own neighbourhood.

How to Cultivate Creativity

Write it out. Keep a journal of notes and doodles. Over time, your writing will give voice to your inner creativity and help you focus your ideas.

Share your ideas in a conversation. Brainstorm ideas with others.

Trust your instinct. Try on the bold and inspired ideas you come up with. As Thomas Edison of lightbulb fame told us - there’s no such thing as failure. We’re just discovering what does or doesn’t work.

Allow your creativity to be expressed through you - as only you can express it. As the always irreverent, Brene Brown says, “Midlife is when the Universe grabs your shoulders and tells you, I’m not f**king around. Use the gifts you were given.”

Say, YES to your own creative expression and encourage others to shine their own light. Experiment with creative mediums until you find one that speaks to you and allows you to tap into your emotions and express what you have to say. This is how you can leave a legacy.


Women age 55+ are the fastest growing group of entrepreneurs. A growing number of midlife women have turned to self-employment so they can finally work at something they enjoy and can set their own hours.

Many Boomers have grown disillusioned with big business. They feel the pinch of age discrimination and realize if they want a “job for life,” they’d better create it for themselves. It also allows them to have the freedom to create the lifestyle they want and fulfilling work to support it.

Self-employment provides the opportunity to express more of who you are, to use your favourite skills and is a chance to use more of your creativity.

Small is Beautiful

Midlife women know they don’t need to create a million-dollar business. They also realize financial planners have hoodwinked us into believing we need millions in our bank accounts and sold us high-priced products to line their own pockets. We’re wiser now.

Financial security comes from having more than one source of income. Many choose fulfilling work to fulfill a lifelong dream and to create an income to top up their pension plan.

Creativity and self-employment go hand-in-hand. Self-employment is the best path for self-knowledge and self-expression. It allows you to tap into your heart’s longing, values and interests and to create something that wouldn’t exist without you.

I’m surrounded by women who have combined their creativity with entrepreneurship. On my small Island, there are women who write and sell their own books, paintings, photography, jams, baked goods, liquorice, pottery, weaving, jewelry, glass art, clothing, felt work, cheese-making classes, yoga, singing lessons and many other pursuits. The only limit is their own imagination.

Inner security and peace of mind come from knowing you are doing what you love and understand how to support the life you want to live.

How to get started

Get rid of stuff that keeps you feeling trapped. We all have stuff we hold onto that’s not necessary. It is consuming “energetic space” in your life. Sell stuff you don’t use or enjoy - or give it away to someone who can use it.

Spend some quiet time in nature to get in touch with your heart and intuition along with what you really want from the next stage of your life. Let nature be your guide. Career change will not progress on a linear path. Stay open to the unexpected. Be pleasantly surprised by serendipity. Re-assess the direction you are headed as new information comes to you.


The #1 dream of many Boomer women is to have more time for travel and adventure. We are tired of working most of the year and squeezing in a 2 or 3-week vacation a year. We crave new experiences and are trading “more stuff” for “more adventure,” and want an opportunity to pursue our creative interests.

Savvy women have combined travel with creativity and entrepreneurship. They enjoy the best of all three worlds.

My Island attracts hundreds of tourists each year. We have thriving enterprises in local B & Bs, kayak tours, sailing and fishing excursions, a world-renowned Retreat centre, bike rental, local craft fairs, annual events that include three days of Live Theatre, concerts with local and off-Island musicians, Salmon Barbecue, Concert on the Green, Book Talks, and many other year-round events.

Some of us are taking our Portable Employment ideas on the road with us as we travel off-Island. We’re using travel to broaden our perspective, reframe our views on life, learn from other cultures and creative entrepreneurs around-the-world.

You can do the same

You can combine Creativity and Entrepreneurship with your own Travels.

I’ll be hosting small group Artful Living Retreats on Gabriola Island to help you do this. Group size is limited to 6 women.

If you would rather opt for a Retreat-in-a-Box experience that you can do anywhere in the world at your own pace, access to my Online Course & Step-By-Step Coaching program on how to Save & Make Money While You Travel includes 30 interviews with folks who are already living this lifestyle.

 Let me know if you’d like more information.

A version of this story first appeared on Sixty and Me. ]