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The Older Entrepreneur: Is It Ever Too Late?

By Rosemary Cass June 17, 2023 Managing Money

Is it ever too late to start a business? The data shows that the highest rate of entrepreneurship worldwide is in the 55-64 age group and the over-50 age group is twice as likely to be successful.

Sometimes people newly retiring from a fast-paced career find retirement to be too slow. They miss the stimulation, the purpose, and let’s face it, often the money! Many of them take an avocation, something they enjoy and have always wanted to spend time doing, and turn it from a hobby to a business. I’ve been dipping my toe in those waters, and I’m certainly not alone.

I always wondered if I could have made it as a journalist or writer, something I loved to do, and on those stressful days running my business, I dreamed: “If only I had become Barbara Walters or Anna Quindlan, how different my life would be!” So of course, after I retired from the 25-year long career that put food on the table, I was eager to give it a try.

Do the Numbers Matter?

There’s a big difference between starting a business at age 50 and at age 70, however. The 50-year-old still probably needs to earn a living, maybe support a family and is probably not financially able to retire yet.

On the other hand, the 70-year-old, already retired person is probably looking to fulfill a dream or earn some side-hustle money. They’re eligible for Medicare and Social Security. There’s less at stake and so the stress is much less.

That 50-year-old needs to think long and hard and do a lot of research. Entrepreneurship is hard work and high risk. Don’t let anyone tell you different.

The Benefits of Entrepreneurship in Later Life

But if you’ve found the right niche and put together a good plan, sought advice from the many available resources and are willing to do the work, there are many rewards in success.

Those include:

  • Doing something you love
  • Having a flexible schedule
  • Being your own boss
  • Making more money

Some Great Later-in-Life Stories

Not everyone started like Bill Gates or Mark Zuckerberg as a teenager in their garage.

Vera Wang

Vera Wang was 40 before she started designing clothes.

Martha Stewart

Martha was earning a decent living with a catering business, but she was 50 when she signed the Martha Stewart Living deal.

Ray Kroc

Ray was 51 and selling milk shake machines when he bought a little hamburger business and grew it to the McDonald’s chain.

Leo Goodwin

Leo founded Geico Insurance when he was 50, after concluding that insurance could be sold directly to consumers instead of through brokers.

Grandma Moses

Grandma Moses painted her first picture at the age of 76. She turned to painting because arthritis ended embroidery. She went on to paint more than 1,000 paintings, 25 of them after her 100th birthday.

Colonel Sanders

My favorite story! The Colonel owned a gas station and during the depression started cooking and serving truckers in the back room. When he lost his gas station at age 66, homeless, with only his perfected chicken recipe to his name, he tried to sell the recipe. He was rejected 1,009 times! The rest is history.

What Qualities Does the Older Entrepreneur Bring to the Table?


Older and wiser, right? You’ve been around the block. You know that you need a good business plan, some good advice, and money. Most important of all, you know what you don’t know and need to learn.


You’ve failed before and you know how to accept the set-backs and bounce back.

You Know Yourself

By now you’ve figured out what you love doing and what bores you, how you want to spend your days. You’ve heard the saying, “Do what you love and you’ll never work a day in your life.” Not sure I buy that 100% but at least you know what you love.

A Network

You know a lot of people and they know a lot of people. When you identify a need, you know who to ask.

Age Is Valued

No, not as much as it should be. Age discrimination still exists. But it’s better than it used to be and in some areas is actually a plus. For example, according to Entrepreneur, investors look for and value the older entrepreneur.

Financial Security

This might not always be the case but it often is. If you’ve reached retirement age you might have retirement savings and be eligible for Social Security and Medicare.


Remember that young you, full of self-doubt, little life experience? What a difference as we age! Now we know we can do anything!

Let’s Talk About Purpose

Why do this? You’ve worked hard and now you want to rest on your laurels – just play, travel, read, do nothing at all. There’s nothing wrong with that and if that makes you happy, go for it! That’s purpose in itself.

But for those of a different personality type, who need to always be stimulated and have an exciting reason to get up in the morning, this might do the trick. The important thing is to have purpose in your life. Purpose of a sort that makes you happy.

In my conversations with seniors, I find purpose is key to a richer later life. That can be so many different things – volunteering, the arts, learning new things, time with children and grandchildren, travel – the list is endless. And several things, not just one, can be on that list.

But if the idea of starting your own business excites you, follow the Nike ad, just do it! It is definitely not too late.

Let’s Have a Conversation:

Have you been wondering if you can become an entrepreneur in your 60s and beyond? What skill/hobby would you explore as a business? How prepared are you to launch this new opportunity? What do you still need to learn and figure out? Please share in the comments!

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The Author

Rosemary Cass, an entrepreneur and former publisher of a magazine for the over-50 population, wants to enrich the lives of older adults by inspiring them to find purpose, learn new things and explore the arts. She blogs to that end at and also, a blog dedicated to grandmothers.

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