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7 Qualities of a Good Entrepreneur That Will Help You Start a Business in Retirement

By Hilary Henderson July 20, 2023 Managing Money

In a previous blog, I offered some points to consider when you decide to become an entrepreneur in retirement. This time I would like to look at the qualities that make a successful entrepreneur.

It is not a failsafe guarantee, and I am living proof, as I sold one business successfully, only to have the next one liquidated.

If you google the topic you will come up with many suggestions. I would like to present the 7 qualities that I think will stand you in good stead as you set out on your entrepreneurial journey:

Decisive and Action-Oriented

There are going to be many decisions you will need to make, not only as you get started, but along the way, so an ability to sort the wood from the trees and make clear decisions as well as action them will be an advantage.

As the entrepreneur, you will dictate the direction of the business, so everyone involved will be looking to you to make decisions. Wavering indicates indecisiveness and will leave people feeling insecure.

Self-Disciplined, Self-Starter

When you decide to start your own business, you need to realise that nothing will happen if you do not do it. Entrepreneurs tend to be natural self-starters, but the discipline to keep going despite distractions is essential.

Many who have been in the structure of corporate life do not realise the social distractions that pop up when you are not working to a rigid timetable.

As an entrepreneur, you will also need to get things done outside office hours, even if it is only to catch up with backroom chores, such as keeping the books up to date!


If you do not have a passion for your product or service, it is going to be difficult to keep going during the tough times. The road to success is seldom straight, and it is your passion that is going to keep you on that road when it twists and turns.


Perseverance is the ability to continue on despite setbacks. You started the business and you believe you are on the right road.

It may involve improving your service delivery or fine-tuning your product, but you need to be able to go back to the drawing board every time you get feedback, to keep ahead of your competition.

Assertiveness and Confidence

The quiet, withdrawn person will find life hard as an entrepreneur. You will need to push your product and you will have to demonstrate complete confidence that you are doing the right thing.

Any visible hesitation and you will lose credibility. That does not mean you can’t have a failure of confidence with your close friend, but ideally never in front of your client.

Willingness to Learn

Seldom do we get things perfect the first time with our product, service, and delivery. A successful entrepreneur learns from their mistakes, listens for feedback and then acts on it. You also need to analyse your competition and learn from what they are doing.

Courage and Risk-Taking

If you are frightened of risk, then perhaps entrepreneurship is not for you. The successful business thrives when you are doing something new and are playing out there ahead of the competition. You will need to tread the path not yet followed if you really want to be successful.

All of this takes courage and of course some measure of risk-taking. A word of caution. I refer here to well-considered risk-taking, not blindly following your gut.

Personally, I feel the above 7 attributes will take you a long way on your entrepreneurial journey. Good Luck!

Let’s Have a Conversation:

What do you think about starting a business in retirement? What attributes do you think make an entrepreneur successful? Which of them do you lack and which do you have abundance of? Please share 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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