The babysitter problem (and what it has to do with starting a side business)

Asking people to pay you for something you love feels awkward. Here's how to take that moment out of the equation.

The babysitter problem

You get home. The kids are alive. The house is mostly intact. Everyone had a lovely evening.

And then comes the moment that nobody quite knows how to handle gracefully.

The babysitter is putting her shoes on. Whether you're counting out cash or fumbling with a bank transfer, there's always this brief flicker of awkwardness that nobody mentions and everyone feels.

It's not weird because of the money. It's weird because caring for someone's kids feels like the kind of thing people do for the love of it. The cash makes it feel transactional in a way that doesn't quite match the warmth of the evening.

Most of us have felt a version of this on both sides of the exchange.

The people pleaser problem

I talked to someone recently who has a skill people would genuinely pay for. She said she couldn't start a side business because she'd end up giving the product away. She's a people pleaser. She knows it about herself. Asking someone to pay her for something she loves doing feels wrong somehow.

I understood exactly what she meant.

The discomfort isn't really about the money. It's about that specific moment of asking. Looking someone in the eye and naming a price for something you'd happily do anyway. It changes the feeling of the thing, even when the thing itself hasn't changed at all.

You don't have to do that part

Set the price once, on an order page. The customer sees it before they decide. They pay before they collect. No invoice to chase, no cash at the door, no moment where you have to look someone in the eye and ask.

The transaction happens quietly in the background. You both get to focus on the thing itself.

Your customer gets to feel like they chose you, not like they were charged by you. And you get to feel like you're doing the thing you love, with the admin handled somewhere out of sight.

The babysitter problem, solved. (Incidentally, if you are a babysitter, Picklo works for that too.)

If you've been putting off starting because you know you'll end up giving it away, this might be the thing that changes that.

usepicklo.com