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Want to Start a Business After 60? Ask Yourself these 6 Questions First!

By Margaret Manning April 23, 2014 Managing Money

Women over 60 have a strong independent streak. When we were younger, we used the word “freedom” in a carefree way. It defined a lifestyle. We were free to wear bohemian clothes, free to travel cross country or to choose unconventional lifestyles.

Now, in our sixties, freedom takes on a new definition. We must focus on surviving and shaping healthy and meaningful lives.

One of the specific challenges that we face as we search for independence is how to make money as we transition from the careers that have supported us in the past.

As I wrote in a previous article, instead of trying to break through the glass ceiling in our 60s, it may be time to build an entirely new house. In other words, it may be time to start our own business. Unfortunately, many women simply don’t know how to go about starting a new business. I certainly didn’t when I started Sixty and Me. The good news is that there are several simple questions that you can ask yourself if you want to start a business in your 60s or beyond.

What Skills do You have? Which Ones do You Still Need to Develop?

You may have a fabulous business idea, but, before you print your business cards, take a hard look at the qualities that venturing out on your own will demand.

Did you develop business skills in marketing, operations, sales or management during your career? Do you consider yourself to have good technical skills? Perhaps you have a strong network of people that can help you to get started. No matter what your background, creating a list of your skills is a great place to start.

Equally important is being honest about the skills that you still have to develop. The good news is that it has never been easier to learn new skills online. For example, offers design, presentation and business courses for a small monthly fee. Be honest with yourself. Then get out there and start building your skills.

How Independent Are You Really?

As women over 60 we have created structure in our lives. We have learned lots of way to handle routine tasks with our children and in work situations. Our personal identity has been shaped in relationship to family and colleagues.

Most importantly we know where to turn for advice and help and have enlisted experts along the way to lean on. When you start a business you are on your own. You have to hold yourself accountable for mistakes and responsible for problem solving.

Before you start a business, it makes sense to mentally prepare yourself for the road ahead. Nothing is mentally harder than building a business from scratch – and nothing is more rewarding when you succeed.

Do You Have a Valuable Business Idea?

Career coaches often encourage you to do what you love and to follow you passions. There is definitely some truth to this. After all, if you don’t care about your business idea, you probably won’t stick with it when the going gets tough.

At the same time, if you want to build a profitable business, you need to sell something that people actually want to buy. One of the best ways to test your idea is just to get out there and start talking to your target audience about it.

Many people are afraid to talk about their idea because they think that someone will steal it. In reality, this is pretty unlikely. The far bigger risk is launching something based only on your own assumptions.

Do You Like Wearing Different Hats?

To start a business, you have to plan to take on different roles and responsibilities. You may need to work on PR and marketing one minute, product design the next and then deal with accountants or operational issues. There are also all those unpleasant tasks that someone took care of when you were in a “proper” job.

Of course, there is a positive side to wearing all of these hats. When you succeed, you will feel a sense of achievement unlike anything that you have experienced before. In a way, starting a business is like raising a child. You love your company, warts and all.

Can You Support Yourself in Startup Mode?

Starting a new business can be extremely stressful. You don’t know when the first orders are going to come in. If you are launching a product-based startup, your business may not be profitable for at least three years. It is important to approach your new venture realistically and to not waste money on anything. Ask yourself how many scarves you will really have to sell to pay the electricity bill.

How Do You Handle Rejection?

Your business is your baby and you have spent sleepless nights nurturing it. No one likes to be told that they have an ugly child, so it’s easy to take rejection personally. As an entrepreneur, you’re going to receive lots of bad news – from banks, customer, reviewers and shops. If there is one trait that separates successful entrepreneurs from unsuccessful ones, it’s resilience. Successful entrepreneurs get knocked down, but, they keep standing up again.

Asking these questions will help you to prepare for life as an entrepreneur. Go for your dreams, but, keep your feet (and your ego) firmly on the ground. I firmly believe that women over 60 are underestimated in many ways. So, let’s get out there and prove that we can build businesses better than anyone else!

What do you think is the most important thing to ask yourself when starting a new business? Are you an entrepreneur? Please join the conversation.


If you are wondering what to do in retirement, watch my interview with Nancy Collamer.

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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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