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

Please, please don't message him again, you're just going to come across as really desperate and very, very unprofessional. It's up to the family to decide what they want to do, if you badger them they'll lose all respect for you and won't want to have anything to do with you.

You say you're not badgering but that's exactly how it will come across if you contact them again.

Go ahead and make alternative plans, it's not like this family needed you for lessons for the summer so feel free to take on other students.

You are though. You've asked for an unprecedented retainer at short notice.
By all means tell them "let me know by Monday or I will offer the spot to another family". But they haven't "left you in the lurch" - they've done exactly what they did last year, and had no reason to think anything else was supposed to happen. It is very unprofessional to ask for a retainer at such short notice, with so little time to think about it, and if I were them I'd be looking for a new tutor anyway to be honest.

It would be really rude to message again. The lack of response is the response. Would be very unprofessional to start badgering them for money for nothing at short notice.

You need to stop hoping for this family to support your business and start making decisions.

How do you want to work it?

They book a term at a time, and need to confirm renewal 4 weeks before the start of the next term and pay the full term on confirmation? That means you know ahead of time who is staying on and have time to fill the spaces. They’d book the term starting in September before the summer holidays begin.
You can then run “summer school tutoring” as an extra.

They book a block of 10 lessons at a time and need to confirm renewal and pay when they have 2 lessons left?

They book week to week and can cancel without warning? Book week to week but need to give 2 weeks warning?

You need to work it out. You can negotiate separate options for people if you want, and if this guy had wanted permanent tutoring then he would need to pay a summer retainer so you don’t fill the gap.

You were given advice on here to try and book in some summer tutoring. Have you started advertising any of that? As I said, there is a high school girl round here who tutors and she runs “summer school” and tutors a few groups once a week during the summer. I think she does a primary group and National 5 (GCSE) groups in her specialty subjects.

Sorry to hear that. Protect yourself going forward with a contract. Introduce a contract for this client from September. Once you have contracts in place you will find that clients won't mess you about so much and drop you earlier than planned.

I do think this is a different way of looking at tutoring than I've ever seen before. Tutoring is effectively a zero hours contract. You provide a service for payment and when that service isn't required you don't get paid. I've never known a tutor have a retainer. Child minder yes. Tutor no. If I was this family I would say fine maybe see you in September.

And what else have you done to start trying to build an income over the summer? (After all the suggestions you were given)

See what today brings; you might hear something.

You said what I suggested, that either he pays a retainer or you won’t hold the spot?

but you then refer to it in another post as a “request”. Which is what I’m getting at. What have you requested? There is no request to make, unless you are requesting payment. Which you shouldn’t be. You should be saying, you have 2 options; which would you like? The ball is in your court, not his. Either he pays, or you get other clients and they lose their spot.

If you get the bulk of your income from this family- what will you do if you just don't hear from them again? Can you realistically fill the slot?

It honestly doesn't look like you'll hear from him. Though I hope I'm wrong. As others have said lots of good advice for your business going forward and everything is a learning curve. Hopefully you'll not have this type of situation again

Of course it is your poor planning, you do not have a contract or clause in place for this, therefore they are completely within their rights and allowed to choose. YOU now last minute want them to pay you for providing no service. That is your poor planning. I wouldn’t be impressed and I wouldn’t keep you on for that reason.

It is poor planning. They did the same last year so you should have foreseen this same scenario happening and broached the subject with them a lot earlier.
You've never mentioned this as being an issue before and you don't seem to have a notice period that parents are aware of either so that means that under the current system any family can stop, any time they want.

Even under a system where they have to give a month's notice, or they have to pay until the end of the summer holiday, or they have to pay a retainer to keep their place, any one of your families can give notice and that means your financial planning also has to be good to cover any times when you have fewer students which could happen if two or three give notice at the same time (eg. at the end of the school year when they don't need lessons any more). You can then take on new students but sometimes even if you have a waiting list, the people waiting can't come in the slots you have free, or people don't want to start until September.

If I was the Dad in this scenario I'd be pretty pissed off that you suddenly sprung this change on me without notice and were asking to be paid a retainer over the summer to keep the place which comes across very manipulative. Pay up or you lose the slot. It's fine to have that as part of your terms and conditions when people sign up because they can then decide whether to start the lessons or not, but it's mighty annoying if a tutor does that last minute as you have done.
If it were me I'd be ringing around tutors to see if I could get a place for the child for September and only if I couldn't would I pay your retainer.

Of course it's poor planning. You've worked with them almost 3 years and left it until the very last minute to have this conversation. They're doing the same thing they did last year, so it isn't a last minute change.

Yeah, I wouldn’t say he sounds positive & if I was him I wouldn’t be impressed with you asking for more money last minute for your own poor financial planning so on that basis I’d be happy to stop using you anyway

OP, as you don't have a contract in place you don't have a leg to stand on asking for current clients to pay you over the summer when they don't need you.

Get a contract sorted asap and look to take on new clients for the summer. Unfortunately this is a lesson to learn about running a business and agree that you shouldn't be so reliant one one client.

Hi OP. I might be wrong but it sounds like you have asked this client to pay you over the summer and are waiting to see if he agrees, possibly explaining that you need the income? If so, I feel there is something that you still haven’t quite taken on board. You needing the income is neither here nor there, and not relevant to your discussions with the client. You need to put a very simple choice: to hold your spot for September, you will need to pay a retainer fee of £X. If you wish not to pay this then I cannot hold the spot and may have committed to other clients come September but you are of course more than welcome to get back in touch late August and I will let you know my availability.

apologies if I have got this wrong!

It's a good idea, as others have suggested, to read through the posts again for advice on how to boost your income for the summer, and how to set clear expectations with all your clients.
The following threads, coming up in the similar threads section, also contain very useful advice. Worth reading through and taking the advice on board.

https://www.mumsnet.com/talk/am_i_being_unreasonable/5224671-when-would-you-expect-to-get-paidwhen-would-you-pay?reply=140343789

https://www.mumsnet.com/talk/am_i_being_unreasonable/5033763-would-it-be-fairer-to-be-paid-for-these-days?page=1