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5 Qualities You Need to Be a Successful Entrepreneur in Retirement

By Hilary Henderson September 24, 2019 Managing Money

Research shows that the number of people planning to leave a traditional “job” and instead go with self-employment is set to rise exponentially by 2020. In many economies, the lack of jobs in the formal sector is driving this trend.

This means that boomers intending to work for themselves in retirement, setting up as entrepreneurs, will need to join this stream. Therefore it is essential to arm yourself with the necessary qualities to ensure success.

Starting up a business can be tough, but when you are older and competing with the generation X-ers and millennials who appear to have all the social media knowledge and can speak the “language” of the 4th Industrial revolution, it is necessary that you are aware of your own strengths and leadership skills to make it in the 21st century.

So what qualities will stand you in good stead as a more senior, more experienced member of the entrepreneurial workforce?

Ability to Stay Focussed

The generations that come after us like to flit from industry to industry and are intent on climbing the ladder, seeking the perfect job and the perfect life balance.

We boomers were taught by our parents’ generation to stay focussed, and this will stand you in good stead if you enter the world of entrepreneurship later in life.

It is so easy in the instant world of social media to get distracted, but in order for your business to succeed, it will be important to follow a strategy and not get side-tracked.


Psychological resilience is the ability to “bounce back” from stressful or negative situations. This is not an inborn trait, though some people find it easier than others to pick themselves up from perceived failure and stress.

Resilience is a frame of mind, it is the choice to push through and overcome when faced with a negative event.

As an entrepreneur you are constantly faced with ups and downs, successes and failures, and it is the ability to rebound from the knocks that will make you successful.

Some people feel that having a thick skin is essential, but we want to be authentic and hear the needs of our customers, so I feel it is of more value to be resilient.


Going into business on your own today is all about seeing the gap and being creative. The traditional jobs and businesses of our youth are disappearing, and it is the creative mind who takes the gap that is most likely to succeed.

It is not about telling yourself that you are a teacher and therefore you need to stand in front of a class. It is about exploring the creation of online courses or webinars, setting up a YouTube channel, or blogging, thus utilizing your teaching skills “outside the box”!

You don’t need to set up a retail store today. You can distribute products online so that the customer receives the goods directly from the manufacturer with you facilitating, by-passing the need to hold large stocks of inventory.

Have a Strategy

Because of all the distractions we experience by social media, it is easy to get side-tracked. Now, more than ever, it is essential, if you want to be a leader, to have a strategy. If you are uncertain, engage a mentor or strategist to help you think it through, but then stick with your strategy.

Having said that, no strategy should be cast in stone. Yet it is important to have a plan that stops you from taking every diversion that is offered and helps you to stay focused.


A passion for what you do, or loads of enthusiasm, will be of great value. If you are planning self-employment in retirement, I hope you have been able to choose a business that you feel passionate about.

Maybe you have spent years in a profession that your parents chose, or working in an industry that paid the bills but left you plodding along, unenthusiastic about Monday mornings.

Now is your chance to find something that really ignites you. If you have that, the ups and downs of entrepreneurial life are so much easier to negotiate.

Remember, you already have the wisdom developed over a life-long career; hopefully, the necessary resilience and EQ as well. So you simply need to focus and be enthusiastic about what you are doing. Now is your chance!

What qualities do you think could be added to this list? What has helped you be successful as an entrepreneur? If you aren’t doing business for yourself yet, what is stopping you? Please share your thoughts in the comments below.

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The Author

Hilary Henderson is a Retirement Coach She brings to her coaching her experience as an Occupational Therapist as well as an entrepreneur. Her mission is to help people find relevance, purpose and meaning in their retirement years. Facebook is one way to reach out to her.

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