How do I chase customers who won't pay without freezing up?

You can send the invoice easily. It is the chasing that freezes you, because now it feels like confrontation, and part of you does not want to be the bad guy. That hesitation is decent and human. But letting it stop you does not spare anyone; it just quietly costs the business and leaves the debt hanging. Reframe what chasing actually is. You are not attacking anyone. You provided something, payment was agreed, and you are following up on a promise the customer already made. There is nothing shameful in asking to be paid for work done. Most late payers are disorganized, not hostile, and a clear reminder is often a relief to them too. Make it easier by removing the improvisation. Write one short, polite reminder message you can reuse: state what is owed, the due date, and a simple next step. Send it on a set schedule rather than waiting for courage. When the words are ready in advance, the freeze has nothing to grab onto.