My kid is embarrassed to ask people for money, what do I do?

Almost every kid is, and it is worth knowing that this is the single hardest part of the whole thing rather than a problem specific to yours.

What is going on underneath is usually one of two beliefs, and they need different answers.

Asking for money feels like begging. A lot of kids have only ever received money as a gift, from people who love them, so asking for it feels like asking for a favor. The reframe that works: you are not asking for money, you are offering a trade. They get a clean car, you get twenty dollars, and both of you come out ahead. Nobody is doing anybody a favor.

Saying the number out loud feels enormous. This one is mechanical rather than philosophical. The dread is not about the person, it is about the four seconds after the number leaves your mouth, and it shrinks dramatically with practice.

What actually helps.

Practice the sentence at the kitchen table until it is boring. Three parts and nothing else: what they do, what it costs, when they could do it. Said out loud five times, it stops feeling strange, because most of the fear was not knowing how it would sound.

Then say the price and stop talking. Most kids fill the silence with an apology or a discount, and that is what actually loses the sale. The pause is uncomfortable for about two seconds and then the person answers.

Start with somebody easy. A neighbor who already likes them, or a happy customer asked for a referral. Cold approaching a stranger is the hardest version and nobody should start there.

What does not help is asking on their behalf. It gets a customer and removes the rep, and it quietly confirms the thing they suspected, which is that they could not have done it.