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Want to Become an Entrepreneur in Retirement? Here Are 5 Important Points You Should Consider

By Hilary Henderson July 03, 2025 Managing Money

Many of us are turning our hands to starting a small business to supplement retirement income. This will probably pose no problems if you have been an entrepreneur previously – though few entrepreneurs retire!

It is those who have dedicated their working lives to the corporates that might have difficulty with changing their mindset.

Having spent more than 20 years as an entrepreneur, I would like to look back on some of the things I feel one needs to be aware of when making the shift from corporate employee to entrepreneur.

Becoming an Entrepreneur Requires a Shift in Mindset

An entrepreneur tends to see everything as an opportunity to be explored or exploited. The employee, on the other hand, works for the good of the company or to satisfy the requirements of an employer. This involves, in many cases, toeing the line or adhering to company norms.

Entrepreneurs usually see the end goal and minimise the obstacles and limitations, whereas the employee is given the company goal and is asked to focus on how to get there.

Ring-Fence Your Retirement Finances

Do not pour your retirement savings into starting a new business. If you need to use some of your retirement capital, structure your company so that debtors cannot get to the rest of your carefully saved retirement funds.

When you are just starting out, that might sound rather negative, but it is foolhardy to risk your retirement savings when you no longer have the time to build them up again.

Time Is Money

When we start out, we tend to do everything ourselves. As the business begins to grow, many entrepreneurs forget that doing everything themselves will lead to burnout.

It is usually cheaper to pay an expert to do certain jobs that you would struggle with due to lack of expertise. For example, if you have never before done any book-keeping, it would save you time and money to pay someone to look after the financial side of the business.

Stay True to Your Values

Our value system is like a compass, if we are aware of what we regard as important, we can use this to steer us in the right direction. Our parents, schooling, and religion play a large, though far from finite, role in forming our values’ structure.

Recently I hit an impasse in my business progress. When I pulled out my values’ structure, I realised that I was not being true to what I value in life and this was at the root of my problem.

The starting point, however, is knowing what you value. There are many suggestions on the Internet to help you draw up a list.

You Cannot Ignore the Internet

Many boomers have slipped through in the shallow waters before the wave of connectivity hit the world and are afraid of the Internet because they do not understand it. Unfortunately, the saying “when in Rome, do as the Romans” could not be more true for this aspect of business.

These days as an entrepreneur, it is almost impossible to survive without some kind of presence on the web – if not a website, then a Facebook or Linkedin page.

I have written a couple of articles on the value of digital marketing, you can refer back to them for guidance.

Telephone directories are diminishing, and print adverts are few and far between. More often than not, if clients want to find you, they will go to the Internet!

Therefore, Be Prepared!

These are some of the first things that come to mind when I think about the adjustment of becoming an entrepreneur.

Successful entrepreneurs tend to be those who take calculated risks, step outside of their comfort zone, and have a clear idea of what they want to achieve.

If this is not you, it does not mean you should not start your own business, it simply means you need to define your product carefully and draw up a detailed description of your target market and start small.

Baby steps are important. Building on each completed stage to grow your business slowly will go a long way to diminishing the risks.

Let’s Have a Conversation:

If you were to start your own business, which niche would you choose? Do you have expertise in that field and how did you acquire it? What do you think you will need to change about your mindset in order to succeed as an entrepreneur? Please share your thoughts below.

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Dee Barrell

Well, thank you for your article, only just joined your site. Being newly single and having more time on my hands, I am discovering my way forward.
My current property business is doing well, I have ran it for 24 years. it only takes up to 4 hours a day to run, and I enjoy it. However I am looking to add another few income streams to my portfolio.
1/ I have just completed a business plan for launching a service to landlords advising them on navigating constant tax and compliance changes here in the UK, surviving the current economic situation, avoiding stress, embracing the challenges and maximising their income. This will be an on-line business where they will be able to download info & free docs, join a landlord forum, pay services for specialist advice, incl tax, accounting, mortgages, financial planning. Etc and learn (from my own experience and designated partners) on how to maximise their profits, and provide the best service for their tenants in their own portfolios. I love everything property, like to help tenants, so will enjoy it and hopefully be able to help both.
Being A little Welsh girl at heart, coming from humble beginnings my passion to make things, craft be thrifty is in my blood. Basically creating safe affordable accommodation, is nice and necessary but simply doesn’t scratch that creative itch…
2/ For JOY…Over the last year I set myself a budget of 3k, bought a load of jewellery components and branded ethical packaging, from Temu ( no vat ) To create and sell branded fashion jewellery on an online shop, ( being aware of Microsoft Lens) one can no longer sell any item easily as consumers take a pic of a product, check on lens, then can see all prices of same product, from washing machines to rat poison which incidentally has done 3 things, it shows the price, where to buy, and WHO is charging more for the same item. It can decimate small businesses in a heartbeat.
So ….to give something back to my community and to help other women. Although I bought the components, 4 local unemployed ladies will have fun learning how to create unique branded affordable designs, making only small limited edition qty’s. Constantly changing to follow seasons and retail calendar, and they will also take part in marketing and launching this small business, using promotions on each key dates, our first Is ready for Valentine’s 2026. Hopefully it will work, and they will be able to use those skills going forward to set up something for themselves.X
( Worked as a retailer for years, so loads of experience in fashion home and jewellery,
before doing property.)

Lynne

What an interesting article. Well, my expertise is Teaching English as a Second Language and for years and years I have spent money on people who promise to make you a 6 figure entrepreneur! Not that I ever wanted to be that, but would have loved to start something through Teachable or one of those websites. Something always held me back or knocked me back. However, I have now found a local man advertising digital skills advice and help and I am seriously thinking I will get him to set me up online and be happy to pay him to do so! I can do the English Course, no problem. It’s all the technology that bothers me. Anyway, even at 75, I am hoping to do a little bit of side hustle (I think they call it) or is it side hassle????? Nice article

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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