sixtyandme logo
We are community supported and may earn a commission when you buy through links on our site. Learn more

Can Older Adults Overcome Their Programming and Embrace Entrepreneurship?

By Margaret Manning November 03, 2018 Managing Money

What did your parents tell you about the path to success in America? If you are like most of the 50 and 60-year-olds that I have spoken with, the answer is probably “Not much. I had to figure it out by myself” or “They told me to work hard, finish school, get a job with a good company and stick with it as long as possible.”

Millennials, for better or for worse, are much more likely to believe that job-hopping, freelancing and entrepreneurship are the true paths to success. While this is an oversimplification – just ask the 85% of freelancers who creates an Upwork profile but are yet to earn a single dollar – this generational bias towards starting businesses will result in many success stories in the coming decades.

Is Our Financial Programming Holding Us Back?

The data doesn’t lie. In almost every way, older adults are more successful than their younger counterparts when it comes to starting a business. This makes sense when you consider the years of experience that we have, our strong business networks and our financial resources.

So, in my mind, the question is not “Why would older adults want to start a business?” The question is “Why are more older adults not starting businesses?”

The best answer that I can come up with is that our financial programming is holding us back. Because we were trained to build long-term careers, we didn’t invest in our own businesses. Because our parents taught us to value job security, we are nervous about taking financial risks.

Can Older Adults Reprogram Themselves? An Ongoing Debate with My Business Partner

Whenever I talk with my business partner about my desire to help older adults to start their own businesses, become freelancers or try their hand at consulting, I get the same reply: “Honestly Margaret, you’re wasting your time. If someone hasn’t learned how to be self-employed by the time they are in their 50s, they’re not going to switch now!”

I disagree. In fact, I predict that, in the coming decade, you are going to see a massive wave of older entrepreneurs entering the market. There are two reasons for this.

First, we are motivated to improve our financial situations. While most of us have not saved enough money for retirement, we have saved plenty of skills. Once we accept the fact that retirement isn’t going to be the party that we thought it would be, we will settle down and start thinking about how to create a side income.

Second, our generation is already changing society’s views on aging. Unlike our parents and grandparents who were content with “aging gracefully” and staying out of site, we want to continue to be a part of the world. We want to travel, pursue our passions and contribute to society. All of these activities require money – and starting a new business will be an option that many choose to pursue.

Don’t Wait Until it is Too Late – Start Your Side Business Before You Retire

While I firmly believe that most older adults can be successful business owners, my time with Sixty and Me has taught me a painful truth – the second you formally “retire” you will be MUCH less likely to start a business. There are many reasons for this, but, in summary, your contacts will start to cool, your skills will erode, money will be used only for essentials and your confidence may wane.

This is not to say that it’s impossible to start a business in your mid-60s. I did! So did many others! It’s just that it’s so much easier to start a business before you retire. Your contacts will still see you as a professional, you may have a little money left over every month to invest in your business and you will be at the top of your game.

Understanding Your Programming is the First Step

The first step to overcoming your programming is to understand it. As yourself the following questions:

Did you parents encourage you to take a “safe” path in life?

Do you feel like you got stuck on a career path that was difficult to change once you had kids?

Are you passionate about your work?

What are your fears about starting a business? Where did they come from?

Don’t worry if you don’t know what side business to start. For now, it’s enough to dig into your feelings and understand how your past may be impacting your future.

If the only thing that comes out of reading this article is that you finally realize how much your financial programming is holding you back, that’s already a huge win!

If you knew that you would be fired in the next year, would it make it more likely that you would start a business? Have you ever thought about starting a side business? Why or why not? What role, if any, do you think our parents’ perspectives on money play in guiding us down a certain financial path? Please join the conversation.

Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Inline Feedbacks
View all comments

The Author

Margaret Manning is the founder of Sixty and Me. She is an entrepreneur, author and speaker. Margaret is passionate about building dynamic and engaged communities that improve lives and change perceptions. Margaret can be contacted at

You Might Also Like