Is it cheeky to ask to be paid over the holidays?

Absolutely. You asked them to pay to hold the slot over the summer. They don't want to and I can absolutely understand why. You dropped this on them when that had never been the arrangement previously.
That means you can now go ahead and find some other people to tutor. If you happen to have a spot for the original family in September you can offer that to them and if you haven't, then you haven't.
There's no need for anything to be awkward.

But before you start lessons with anyone else, for goodness sake, get some terms and conditions in place. Re-read the thread and make some notes on what others do. Also, you can google tutors' websites and see if some of them have their terms and conditions on there. Often they do. That will give you a good idea of what sort of thing is normal.

I think you need to drop the idea of getting people to pay over the summer. People do not want to pay for a service they are not using. What you might find is that if you insist on it, even if it's in your new terms and conditions, people will give notice a month before school ends and then try their luck getting a place with you again in September. I'm sure you do a good job tutoring but I very much doubt that you are so good that you are irreplaceable and so good that people would be happy to keep paying you for months just to keep a place with you.

Sorry to hear that @Dogswimmingcompetition but you've got a myriad of excellent advice from self-employed tutors, who have shared their business models, plus all the general advice. You're taking yourself round in circles now. Gently.

You really need to see this for what it is, a business arrangement. I've said it before and I'll say it again, I honestly don't think you're cut out for having your own business, you need to stick to being a full time employee. There's nothing wrong with that, most people are more suited to one that the other.

Why would it be awkward? You either fill the spot with another family and give this family your apologies in September or it's business as usual. It's only awkward if you take it personally instead of as the flawed business relationship it is.

Not if you're professional and turn up and tutor the DD. That's really all they care about. They probably won't give it another thought if you don't bring it up. And you shouldn't give it another thought either. It's June. Just reply nicely saying you understand and focus on your own stuff for the next three months. If you still have space available by the end of the summer (or sooner if you want it sorted), let them know and if they still want you, you can sort arrangements going forward so everything will be clearer. No awkwardness needs to come into it.

What do you mean? You think they will be unhappy because you suddenly tried to get them to pay for work you hadn’t done? I mean possibly, but clearly not unhappy enough to decide they don’t need your services.
what would make it “awkward”?? If you find deciding on, communicating and enforcing terms of service awkward then self employment seems like a difficult option!

You have your answer. Find other employment to fill the time and decide if you have space for them in September.

It's only awkward if you continue to blur the lines. If you make it professional like people have advised then awkwardness doesn't come into it. You're paid for your work and do that work by the terms agreed. You don't make your income stream their problem when you're not working for them and you don't see their money as 'my money' that they owe you. Just agree the hours of work and get paid for those, and arrange other work for the rest of your time. The dad has gone beyond already by paying you for the rest of the term so for you to not go back would be the awkward/flouncy/rude thing. If you have another job by then and can't go back, then so be it. But to just not tutor their DC any more because of this issue you've created with unrealistic pay expectations, that feels a bit off.

Agree with all of this

@Dogswimmingcompetition
Why are you completely ignoring what everyone is saying about how tutoring works?
It goes by term or by block of 10 at a time and is paid in advance, with a notice period for renewing or choosing not to renew.

You can offer holiday tutoring, or get another job. But people don’t pay retainers to keep their spot; they just book for the next term in advance and pay so he should already have booked the next term after summer and paid for it. That’s how people keep their spots with you.

You’ve been given plenty of advice on how to fill the summer time and ways to make money from tutoring during the holidays but you’ve completely ignored it. As you said yourself, it’s quite rude to ignore people.

You're right. There isn't a lot you can do if they breach the contract but I find that it does put some piss-takers off in the first place. Also, you've decided in advance what to do if someone doesn't show up to the lesson, so they then can't complain when they are charged for that lesson. Mine have to pay in advance which means you're not trying to chase people up to pay for the missed lesson they don't want to pay for.

With a contract I find that the majority of people do actually stick to the terms and conditions and give sufficient notice. There has been the occasional one who has done a midnight flit as it were but if they don't respond within a couple of days I just fill their slot with someone else.

I also agree with you that too much flexibility leads to people taking the piss. If you give the impression that it's some kind of side hustle for pin money then people behave accordingly. Being fully booked and only being able to rearrange a lesson occasionally is a good thing, or giving that impression, even if you aren't completely fully booked.

This level of flexibility tells them that you're not fully booked if you can always change the days. They therefore see that they can mess you around.
There are lots of people talking about contracts. It does come across as more professional but at the end of the day if they drop you with no notice what exactly can you do about it even if you have a contract? It would cost you more money than you would get back. I don't have contracts as such I just ask for 24 hours notice for cancellation. If they don't pay they don't get the next lesson and I move on to someone else. I learnt my lesson when someone cancelled regularly. Once I pointed it out and charged they don't ever cancel again. Even then, if someone has been with me for years and it's sent home sick in the afternoon I don't charge them. If they're new, I might as it stops them taking the p*. But generally, I cannot change days of someone forgets or whatever as I am fully booked.

How did you start working for this family? Did they approach you/ did a friend of yours set it up?

And do you see yourself as staff, as an independent contractor or as friends?

This can skew how you see the world of freelancing. To make a success of self-employment you need a strong business head:

• how can I get enough money for the year?
• How can I absorb sudden drops in income (two of my clients went bankrupt, another’s premises burnt down, things happen!)
• How can I protect myself from risk? (Answer: a contract).
• What can I do to get work quickly? (Agencies are one option)
• How do I ensure I‘m paying NI and tax at the right rate and time - and if I haven’t, can I afford to pay it when they catch up with me and present me with a hefty bill?

When self-employed (language teaching abroad), I tended to have 12 corporate clients a week, many with multiple sessions. I also worked for state organisations, had some different types of work I could do in known quiet periods, and would do holiday intensives and weekend workshops for unis and adult education places. I was signed up to every agency going - they didn’t pay well, but were good for stopgap courses as some money is better than none. I had a website and did leaflet drops.

I‘ve given you advice on what you need to cover in a contract, and pp have also given excellent free advice.

This approach will be what your clients expect. Anything else reflects badly on you and your perceived ability to teach - especially if they haven’t sat in on sessions.

This is all a learning curve for you. You are now self employed. This is your work. You need to have contracts, terms and conditions and rates of pay that work for you going forward. If this family have been treating you as someone doing them a favour - akin to a teenage baby sitter - then that’s because you haven’t had good business practices up to now. Yes putting boundaries and rules in place will lose you clients but eventually it will secure you a sustainable business where this kind of situation won’t happen because you have laid out terms clearly in advance. You have to now forget this family / you have said ‘I need a retainer or your spot is not guaranteed.’ They have not given a retainer so there is the answer. (And ‘let me get back to you on this later today’ is btw a very standard fob off.)

You’re still not getting it.

Asking him to agree to pay a retainer = not the right thing to do.

offering him the choice between paying a retainer and losing his spot = right thing to do.

the second is not asking him to “agree” to anything: it’s just giving him 2 options.

you keep saying you did the second, but then talking about whether or not he will “agree”, which suggests you did the first.

I suspect you can’t understand the difference which is why you’re still somehow feeling that you’ve been wronged here.

Perhaps you got lucky and he asked chat gpt.

You said that you told him “it’s just difficult to take a pause for 3.5 months as it’s hard to offer short term tutoring to a family during this time to then have to give it up in September”, that’s what people are taking issue with, along with the fact you kept referring to whether or not he would “agree”; when there is nothing to agree to, he merely has to make the choice.

I think you're not a real tutor. This is a wind up Mumsnet thread. As you know, tutoring is my occupation now and nothing you describe has been my experience. IF you're genuine, you have a bad business model.

Aye, why bother with asking actual people who either are tutors or use tutors, when you can get the validation you need from AI...