Take a £50K job and pay for childcare?

Look for home based roles, there’s loads, quite a few contract ones as well. If you’re IT, particularly IT support, you don’t necessarily have to be local. It’s an option to select.

You haven’t got a black hole in your CV you’ll be winding up your own company due to lack of trade. It’s not trivial to run your own company.
Tbh though it is a shame you didn’t keep your eye on the ball in terms of your customer base and salary but there you go. You can’t live on 5k so you don’t really have many options. Plus if you don’t mind a lower end salary you’ll have plenty of roles to choose from.

If you can find a home based role you probably can still do the school run (check with employer) as long as 9 year old can entertain himself a bit when he gets home and you need to finish work.

You got lots of transferrable skills through self employment! Most businesses don’t last 5 years so you did really well.
Good luck with your search.

You may be able to get a job working from home, for around £22/25k. Civil service/local authority, to tide you over until the children are older. You may have to travel to do a short day /possibly two days a week in an office perhaps.

You haven't got a black hole in your CV, OP. You've been running a business in that time - loads of transferable skills. Your big client could provide a reference if necessary. I know a couple of people who have moved from self employed to employed and it hasn't held them back. I'm not saying it will be easy to find something that fits around the kids, but I don't think your employment history should be a massive problem.

Reference from big client.

Any chance big clients is hiring? They know you well.

Get in touch with an IT specialist recruiter.

Look at realistic wfh roles.

I suspect that branching out from your current role will be more fruitful and flexible than an entry level job at Tesco.

I agree with previous posters. You've got a strong cv. Think of all the skills involved in running your own business.
You have a good rationale for now wanting to go paye or be part of someone else's business (children older).
Loads of roles are complete remote working or hybrid now (in the office one or two days a week)
Currently (although don't know how long for if we do go into a full recession) it's a great market for job hunters and there are not enough IT candidates go go round so don't take too long thinking, get out there and apply.
Can anyone take a look at your cv and help prep you for interview as it's been so long?

I've filtered the search criteria to IT officer but you can change it to see what else comes up. The charity sector is usually good for work life balance and remote working.

www.charityjob.co.uk/jobs?keywords=IT+Officer&contracttype=full-time&contracttype=part-time&contracttype=permanent&workplace=hybrid&workplace=remote

Universities are usually good for work life balance.
www.jobs.ac.uk/search/it

I feel as though your perspective of what you've achieved has skewed so negative right now that I'd actually suggest a session with a work coach. Though my experience at one remove was that my amazing but depressed friend was eventually told by the work coach that she needed therapy which wasn't exactly helpful!

You've run a business and paid yourself for 20 years! Do you know how many businesses fail in that period?? Now you want a job that is remote only and you can afford to take a slightly lower pay rate to get that.

What sort of job would you actually like? It's still a candidate's market at the moment. Maybe get onto some agencies? Update your LinkedIn and start boosting yourself a bit.

Hi OP, you've successfully ran your own business for 20years and you have no skills? Is that what you think? It's irrelevant what you earn from it and irrelevant what other people earn cos yours was a lifestyle career so stop beating yourself up.

I think you need some career coaching - you may find it's free via your LEP - ask your local council or Google search. Get them to help update your CV with you to win more work or enter employment.

If your field is IT, still loads of IT management jobs that are hybrid working. These roles don't look for specific tech knowledge they need someone who understands the IT sector not an analyst and you'd be ideal as you kniw the sector and have ran your business for 20 years!

Good luck.

Speak to other recruitment agents who specialise in IT. Don’t be apologetic. Ask for fixed term contract options which are remote.

Have a look on LinkedIn. Do you have industry contacts? Explain you’re looking for opportunities and put it out there.

Are there specialist job websites? Have a look, get applying and see what happens.

You can describe everything in your OP in a positive light. For example, you can describe how you ended up essentially working for a single company and how that made you realise that you wanted to be part of something bigger rather than working independently on something smaller.

I'm not sure what I'm asking here, just feeling like I've really underachieved and wasted the last 25 years. And now I must look like a terrible employment prospect with zero real world employment experience, and completely out of touch with current salaries.
OR, you could say I've spent the last 25 years being my own boss and leading my company because it fitted well with family life. Now I'm ready to bring all my transferable skills into the workplace. I am particularly good at customer service, as that was vital in keeping my clients, and I'm very flexible as I've always had to adapt to keep the business going.

At my organisaion the IT staff WFH with a compulsory day in the office each month.

I think it is time to test the water. Do not undersell yourself. You are being very negative, unfairly so.

I think you’re confused OP. You don’t have any gaps in your CV, quite the opposite. You’ve successfully run and IT business for 15 years and have a vast amount of experience in everything relating to that - contract management, customer management, finances, project management etc etc. Running a business gives you a huge amount of experience for your CV.

You’ve also assumed the £50k job is completely inflexible but you haven’t actually asked. Most jobs can be tweaked for the right candidate. They may even let you work from home. You would need to approach them with a tempting proposition.

As for childcare, can you get a childminder? Or could the 14 year old not pick up the 9 year old?

Another option could be to shake up your business!
So the thing you currently offer is now a bit outdated by the sounds of it - could you turn it into something more cutting edge? Could you develop another product / service? Could you look for different clients - maybe in a different sector or country?

Perhaps you been doing it so long you need a fresh pair of eyes to give you some ideas on a slightly new direction for the business. You could look into getting a mentor or do some new courses to give you some inspiration.

So many jobs are flexible and at the very least hybrid now, thanks to the pandemic. Especially in IT.

Would it be worth using a specialist CV writer to help you put a positive spin on things? I think you're massively underselling yourself, a business doesn't run for as long as yours has without some serious hard work. A CV writer could be a good investment to highlight your transferable skills.

You could also follow The Work From Home Hub on Facebook/Instagram - they post only genuine (so no MLM nonsense) remote or hybrid job roles. Something you hadn't thought of may come up, especially if you can be flexible on salary.

There are so many IT roles out there at the moment, it's an employees market.

Home based roles are common now and there are loads of free courses out there to upskill and refresh your knowledge if you feel you need it.

For the love of all that's holy do not tell any recruiters your current salary as they'll see an opportunity to low ball you.

Agree with others that you need a session with a career coach. You have a view of the working world that is not in line with what is happening now and while there is nothing wrong with that, you need to know your worth

You think there is a gap in your CV - you have been working for all this time, this is not a gap

You have been out of alignment with workplace salaries - well yes but nothing you can do about underpaying yourself now. You need to look at your skills and understand the market rate

You can work hybrid in so many roles now that if anything it opens up more opportunities than you have had up until now

Good luck

OP I mean the kindly (I’m knackered and breastfeeding a 15 month old currently so not at all reasonable) but you’re putting up barriers where they aren’t necessarily any.
Obviously it’s good to be realistic and aware of limitations but firstly I’d stop getting so hung up on childcare issues. I work for a local authority and my team work the most random selection of hours between all of us. The only day all of us are actually working is a Wednesday then there are variations of half days, full days, non working days and condensed hours between us all added to that a mixture of WFH and office based. I’ve not seen some of my team in months.
Also, stop putting yourself down! Running your own business is hard and has lots of transferable skills. Not only do you have to do the job you’re doing, but you’re also doing all the admin, selling yourself and business and some if not all the accounting!
be kind on yourself and have faith in yourself

In your shoes I would look at jobs on Glassdoor and LinkedIn in the 70k salary + region and see what the key skills are.

Upskill anything missing in my skill set.

Then I'd pay to get my cv redone. Look on Fiverr and pay for someone with a lot of excellent reviews. Likewise cover letter.

I'd set up a job search on LinkedIn and Glassdoor and start applying.

Of course you are employable! The only people I know who are unemployable have a poor attitude to being told what to do.

You don't have a gap in your CV, you have been working this whole time.

I'm in a hybrid it/finance role. Like all my colleagues we mainly WFH. In the office once per month for a team meeting. Many people come in for the meeting then leave shortly afterwards.

You say that it is mainstream mature tech. Doesn't this mean more roles rather than fewer? Okay, not at a premium but given you have been underpaying yourself for years it will feel like a premium.

You got this, you need to think about what you really want to do and sign up to linkedin.
You have so many skills running a business.

Spend some time researching linkedin profiles etc and get yourself set up or amend what you already have. You don’t need to use it as social media but it’s really good for finding jobs. It has its own job board.

I have worked in IT (but on finance side) and it’s been really flexible around the children and I have worked from home successfully for 12 years. You can earn way more than £22K!

I'm not in the IT sector but did go from being self employed for 15 years to employed after retraining. I too worked my business around children on a lower salary at times. I am slightly older than you OP and my employers seem to really value my self employed experience and I have moved up a grade within a year, which is not usual. The sole reason is my experience of running a business, which, whilst I may not have the full profession specific technical skills yet, I can organise, plan, problem solve and work well under pressure. Don't underestimate how many skills you have, you won't have an issue getting a new employed role, they will actively want you.