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Want to Start a Business After 60? Ask Yourself these 5 Questions First!

By Margaret Manning September 10, 2018 Managing Money

Women over 60 have a strong independent streak. When we were younger, we used the word “freedom” carelessly. In many ways, it defined our lifestyle. We were free to wear bohemian clothing, free to travel where the wind took us and free to choose unconventional lifestyles.

Now in our 60s, freedom has taken on a whole new meaning. Rather than simply defining what we want to do, freedom is all about not being restricted or stereotyped. We want to be healthy, so that we have the freedom to explore the world. We want to avoid people and situations that hold us back. We want to be free of the psychological constraints that society tried to impose on us.

As a result, many older women are no longer willing to put their financial future in someone else’s hands and are making the decision to start a business. In many ways, this is the ultimate act of defiance. It says that we are willing to take risks to ensure our continued freedom.

Over the last several years, I have started several businesses. Sixty and Me, in a way, is a business. My primary goal is to help the community, but, it’s nice to have a little extra money coming in from our premium videos and other services. I also work as a freelance consultant, helping companies to develop their social media strategies. These activities are central to my own plan to maintain my freedom as I get older.

At the same time, while I love working on Sixty and Me and my other businesses, I’ll be the first to admit that it isn’t easy. Far from it! I am working harder now than I ever did during my corporate career. I suspect this is the case for most older entrepreneurs.

So, with so many tradeoffs, how do you know if starting a business in your 60s is right for you? Based on my own experience and conversations with other older entrepreneurs, here are 5 questions that you can ask yourself.

How Independent Are You Really?

Over the decades, we have created routines that make us feel comfortable. We have learned ways to handle our routine tasks – at home and in the office. Our personal identity has been shaped in relationship to our family and colleagues. Most importantly, we know where to turn for advice and help.

Starting a business requires us to step into the unknown and abandon many of our comfortable habits. Are you the kind of person who can get up every day and work, without someone needing to tell you what to do? Are you willing to reach out to others for help, even when it is uncomfortable to pick up the phone? Do you consider yourself to be an independent person? If the answer to most of these questions is “yes,” starting a business may be an options.

Are You an Entrepreneur?

Entrepreneurs have to wear a lot of hats. Especially in the beginning, you will be responsible for every aspect of your business, from product design to marketing, customer support to accounting.

You may have a fabulous business idea, but, do you know how to get people to buy it? Are you creative? Do your eyes glaze over when someone shows you a list of revenue and cost numbers?

As an entrepreneur, you will need to learn to stay calm when you are faced with unfamiliar tasks – and, to be clear, this will happen on a daily basis! So, either you need to be passionate about learning new things, or, you should consider partnering with someone who has complementary skills to your own.

Do You Have a Valuable Business Idea?

Career coaches often encourage you to “do what you love” and “follow you passions.” While this sounds nice, in theory, it doesn’t always work in real life.

Passion is important, but, to make your business profitable, you have something that people actually want. So, by all means, start with what you love. But, also make sure that you are filling a gap in the market from the very beginning.

If you don’t know where to start, here are a few articles that I wrote that can help you to find your profitable business idea.

How to Start a Business After 50: Finding Your Strengths

How to Start a Business After 50: Finding Your Idea

Can You Support Yourself in Startup Mode?

Starting a new business can be extremely stressful – and expensive! You don’t know when the first orders are going to come in or when that first “lucky break” will happen. If you are launching a product-based startup, your business may not be profitable for years. As a result, it is important to approach your new venture realistically.

Before you spend a penny on your new business, make sure that you can afford it. Sit down and make a budget. The last thing you want is to sink all of your money into “the next big thing,” only to find that you don’t have any money for marketing.

In many cases, it makes sense to start small and feel the market out before you invest your hard-earned cash. This could involve starting a blog or getting involved with communities that host your target audience. Or, it could involve creating digital products (such as training videos) at a minimal cost rather than jumping into producing a physical product.

Many older entrepreneurs that I have spoken with have told me that raising money after 50 is extremely challenging. This is all the more reason to build momentum in a particular market before “going big.”

How Well Do You Handle Rejection?

Your business is like your baby. You give it live. You nurture it. You spent sleepless nights, sitting in bed, worrying about its health.

Because starting a business is so personal, it’s easy to let our emotions get in the way. After all, no one likes to be told that they have an ugly child.

As an entrepreneur, you’re going to receive lots of bad news. Banks will reject your loan applications. Customers will fail to pay you on time – or at all, for that matter. Your costs will be higher than you expected. Your taxes will be complicated. If you want to succeed, you will need to learn to roll with the punches. It’s not personal. It’s just the way the world works.

If you are the kind of person who takes failure or criticism personally, you are likely to have a difficult time as an entrepreneur. But, if you are willing to see mistakes as learning experiences and problems as opportunities, you will go far.

Starting a business after 60 can be one of the best ways to ensure your financial future during a time of transitions. This is especially true if you already have specific skills to fall back on. That said, being an entrepreneur is difficult at any age. Older entrepreneurs face all of the challenges that plague their younger counterparts. We also have to deal with age discrimination.

At the end of the day, if you love a good challenge, are willing to embrace risk and know how to find the sweet-spot between your passions and what the market needs, starting a business could be the best decision that you ever make.

Have you started a business in your 50s, 60s or beyond? Are you planning on starting a business in the coming years? What kind of business do you want to start? What advice would you give to the other members of our community about starting a business? Please join the conversation and “like” and share this article to keep the discuss going?

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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

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