Entrepreneurship After 50: Courage or Insanity

Published on January 26, 2019

As posted in She Owns It

If you want someone to hire you after your 50th birthday, you may need look no further than the reflection in the mirror.

The smile on my face was beginning to head south and I knew it was time to make a run for the door. I was attending a luncheon with a large group of women 50+ whose lighthearted conversation was totally out of my comfort zone. About to make my excuses, someone finally asked a question that caught my attention and deserved an honest answer. Sitting back down and rubbing my hands together to dive into an interesting debate, I was in the mood to be the nay in a room full of yeas.

The Question

I decided raising my family was more important than a career. So I temporarily put my plans on hold until the kids were old enough to fend for themselves. Is it too late to go back to school, complete my education and apply for work?

This woman did what many of our generation were told we were supposed to do. Her question was relevant and to be taken seriously. Unfortunately, what she received were platitudes.

Of course! You’re never too old to educate yourself or start a new career. What a great idea!

The Bad News – Ageism

I decided to play the devil’s advocate and tell this woman the truth. No, it was not a good idea. Not if that education was in order to get hired. Face it lady, you are too old. Take a look around at job sites such as Indeed, Glassdoor and Workopolis and sift through jobs for older workers. It shouldn’t take long to find that Walmart greeter position.

Age discrimination is alive and well in North America. No one is going to hire you. You will hear excuses such as: you are over-qualified, you’re not a good fit, we’ll get back to you. Hilarious – they won’t. Take a look on LinkedIn for photos of “meet our new team”. How many faces do you see over 45 besides the owner?

What those HR recruiting algorithms are telling you is that you are over the hill and too much money. They are looking for two 20-somethings at half your expected salary.

The Good News – Why are You Applying for Jobs to Make Someone Else Rich?

Are you feeling brave? Have you considered taking all that life experience and work ethic and employing yourself? If so, consider joining the club of crazy entrepreneurs! At your age, you probably have a pretty good idea of what you want to do (baker, home stager, barber, dog trainer) and willingness to pore yourself into your passion.

You are never too old to set another goal or to dream a new dream.

~ C.S. Lewis

I’m a Late Bloomer. Until I was in my 50s, I worked at jobs I had no passion for but paid well enough to raise my kids. When the time came for them to fly the coop, I did too. I disengaged my life’s autopilot and decided it was time. There was no shortage of well-meaning friends telling me I might be a touch too old as they looked forward to retirement in warm places. What they didn’t know is I’d spent all my money raising kids and didn’t have two cents to rub together. So ignoring their kind advice, I formed a plan.

…Two roads diverged in a wood, and I— I took the one less traveled by, And that has made all the differenc.

~ Robert Frost

With one credit card to my name, I borrowed money to go back to school to become certified in tourism, took every available free and not so free on-line course, researched destinations, tours, hotels and suppliers, and reached out to anyone who could help me get into the business. I attended networking events, spent my own money to travel to trade shows, and read industry magazines on the bus to and from work.

There were days I thought I was out of my mind. So I would ask myself this question: If I don’t do this, what were my options?

  • I live no better than I am today, keep buying lottery tickets and eventually die.
  • I keep going and see if I can create some magic. What did I have to lose?

Fast forward 10 years and I now consider myself pretty successful as an independent Virtuoso luxury travel consultant. Over time, I narrowed down my niche and love what I do. I also find time to write articles, blogs and get started on my book. But more importantly, I work for and love my boss – me, myself and I. The sounds emanating from my home office consist of chirping birds in the tree outside my open window. What a life!

The Bottom Line

I recommend you start by reading Jane Park’s insightful article published in Forbes.com Are Entrepreneurs Really the Happiest People on Earth? It might help you decide if you’re up to the task.

So how much do you really want success after 50? It can take a year or 10 before things click. Being an entrepreneur is not for the faint of heart. Be careful – you are about to find out the stuff you are made of. For me, I learned more under pressure about courage, people, business and what I am capable of. My life is still an adventure in progress but it sure beats busting my butt making someone else rich.


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