My price for the product was based on guessing. What about yours?

My pricing strategy involved identifying two competitors and positioning my service below them. That’s the extent of it.

After 6 months, the problem is clear. Customer support requires 12 hours per week, server costs have risen, and my price covers costs but does not account for my time spent working on the project. It is unfair to raise the price because of that, but the majority would certainly understand.

The standard recommendations are quite clear: grandfather early users, give advance notice, introduce additional pricing tiers. These make perfect sense, but do little to change the uncomfortable task of drafting an email. I’ve started writing it many times already, but I’ve deleted it each time.

Have you raised your prices before when you had active customers? How did you deal with them?