We spoke to serial entrepreneur, Caroline Jackson who’s built a portfolio of diverse businesses in midlife. They include an Indian restaurant, a company making bras for women with small breasts (Little Women) and a dive centre in the Canary Islands!

1. What made you decide to do what you do?

I had stopped working in 2006 to take the opportunity to go to university – at 40 – which I had never thought about but my circumstances had changed so drastically following meeting my now-husband that I could afford to be a mum to my 5-year-old AND fit in degree study at my local uni. I saw that through to a Masters degree and our circumstances flipped again when we sold our business. I’ve never been one for sitting around doing nails (or whatever the colloquial equivalent is) and I followed my passion and invested in British manufacturing.

I couldn’t have chosen two worse companies to invest in – one (attempting to save horn button manufacturing in the UK) was a money-laundering scheme run by a convicted criminal – thankfully now in jail; and the other, attempting to build a luxury British handbag brand from a long-established white-label manufacturer was run into the ground deliberately by the owners – with no recourse to me and my investment and directorship. A sorry tale.

Anyhow, being one who keeps her chin usually up, I was talking to a friend of mine who was selling her online lingerie business due to ill health and it seemed a very attractive proposition with my previous retail buying experience, my husband’s tech ability and both of our entrepreneurial spirits!

Caroline Jackson

2. Why did you wait until you did to do it?

I think I’ve answered that above – I’d been a freelance IT contractor for years, specialising in business and procurement analysis and interim management solutions, and had spent a long time travelling all over the country to service the contracts I was involved in.

3. What are you hoping to accomplish?

With LittleWomen.com I want to build a brand that becomes a household name for women with small cup sizes and – equally importantly – that women who aren’t our cup sized customers know about us and tell their friends about our specialism.

With my other businesses I just (!) want them to succeed, to flourish, to offer quality employment to people and to do good in the world! I’m a director of a tech app that can and will revolutionize shift management and save companies (including my beloved NHS) millions of pounds/dollars/euros; with my restaurant, I want to bring Nepalese food products, spices and flavours to people, and to serve great food in the restaurant itself.

Related: Millie Lingerie – Beautiful Bras After Breast Cancer

4. How did you make the change? What or who helped you?

Money – having access to it has certainly enabled me to move into areas of business that I perhaps wouldn’t have started on my own from afresh.

5. How did your family and friends react?

All positively – with the minor exception of my dear dad who asked why I bothered…… He’s nearly 90 so I can forgive him. I have learned though that, even if your friends and family support you, it doesn’t necessarily mean that your product or service is right for them to buy, or (being brutal) they expect discount or freebies – sounds harsh, and obviously, each situation varies, but a startup is a small and tender thing that needs as much cashflow protection as possible – friends and family should accept that and not try to blag.

6. How has your life changed having gone down this path?

I’m certainly very busy. Ridiculously not-at-home busy, but having my son fairly self-sufficient when I started this hands-on stuff, and a very supportive stay at home “I’m trying to be retired here…” husband has helped. I’m also frequently outside of my comfort zone and making decisions and choices in a grown-up voice when realistically I haven’t got a scooby doo. I also admit that I find the need to be pretty much full time in the office (especially in times of short-staffing) is quite pressing as my independence is curtailed. With physical product to ship and staff to manage it’s not really practical or possible to do all of the job from the sofa.

7. What advice do you have for women considering a similar life change?

I know that my situation is quite different to most if I’m honest. However, I’m a serial entrepreneur and think (no, I KNOW) that I have to work for myself – and if another woman feels the same way then once she has the bug it’s going to be hard to stop her. If I was advising someone standing on the edge of a major life change in a business sense, I’d advise them that the most important thing (apart from their idea) is to be sure that they have thought through what their support requirements are – family, friends, money, time and that they can tick most of the boxes if not all. Startups are scary, at almost every stage and support is one of the key things that can give you the strength to go on.

8. What are you proud of and what keeps you inspired?

Hmm, that’s a hard one because the businesses I’m currently involved in are all pretty much at start-up phase. I’m proud that I employ people with (hopefully) meaningful reasonably paid employment. I’m proud of our awards – for the app and the restaurant, and I am proud that I’ve taken Little Women from a homespun lifestyle business into the brand arena, but there’s so much still to do and to achieve that I don’t think of it in pride terms.

What keeps me inspired? I don’t know. I believe that every single woman is beautiful whatever their size shape or style and those who are petite of cup should be able to buy beautiful lingerie! If I’m ever feeling less than energetic or pro-active I go and have a read of some of our testimonials and realise that we are doing a VERY GOOD THING here and I need to keep on keeping on.

9. What do you love most about being the age you are?

Not sure I really do – I have the body of a weak and feeble 50 something and the mind of a 14-year-old…. No, seriously, I like the fact that I have made various conclusions about areas of my life – relationships, principles to live by (always fluid of course) and self-knowledge to a degree. I also don’t have to conform to anything. I really don’t. If I do, it’s my choice.

10. What do you hate most about being the age you are?

Not being 14, not having achieved the things I wanted to do which relied on physical youth, seeing opportunities that my overprivileged son has that were (and never will be) available to me, the educational potential that I haven’t realised.

11. What do you know now that you wish you’d known in your twenties?

That my parents don’t know everything, and their way wasn’t necessarily the ‘right’ way; that I’m actually really intelligent but never fulfilled my intellectual potential; that you don’t have to like family members; that whatever someone might think of me is none of my business…oh the list goes on, but that’s the beauty of having some degree of self-awareness.

12. What are the most important business and/or personal lessons you’ve learnt along the way?

If you don’t NEED to do something then don’t – the answer will often work itself out; give freely with no expectation of return; for heaven’s sake do more due diligence than you can imagine you need before you leap into anything; people are always very happy to relieve you of your resource if you let them – again, so many more I should go write a book.

13. Do you have a mantra that has guided you more than any other?

Be straight with people.

14. Which woman do you most admire and why?

Ah, too many to name. Marie Curie for scientific genius and ability to put her discoveries out into the world regardless of getting credit for them is in my mind today for some reason!

15. Is there anything people consistently misunderstand about you?

Most people hate me until they get to know me. It’s been the story of my life and I have no idea why. I don’t THINK I’m monstrous, but people really take against me.

16. How can Mutton Club readers find out more about what you do?

I’m happy to be messaged or emailed or, well, anything. I’m just an ordinary woman from North London.

Little Women Bras

You may also like: From Empty Nest To Starting A Business – Inkpots Founder Gill Pawley  and From Music Marketing To Being A Chef – Claudia Cevenini

Last Updated on February 2, 2023 by Editorial Staff

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