My clients keep ghosting invoices and I'm so fucking done

It is a real pain, but you are approaching it with the same attitude that is causing it. Don't email gently to "check in". Don't beg. Don't start soft and build up over weeks.

If a payment is late, call them directly that day and be firm. Not mean or harsh, just firm. "Hi, your payment did not come through, please take care of it so I can start working for you again." And then stop working with them until it does.

To answer your question, no. I would never pay for an automated service to email payment reminders. Because emails are ignorable.

I have only worked as a contractor where I was officially working for a third party company and they had a contract with the client. But I didn’t get paid when I wasn’t on contract and working full time for consulting companies (or departments) where I was a full time employee with benefits and got paid regardless of whether I was on the bench.

Either way, I have never known clients to pay in advance and now I’m high enough up the food chain to know that every company has trouble from time to time getting clients to pay. But that’s never been a “me problem”. The company I work for has sales, accounting and legal to worry about it. I get paid on time regardless. The trade off in getting paid less per hour is well worth it.

I still wonder if most people doing “independent consulting” wouldn’t be better off taking your bog standard enterprise dev job working 40 hours a week or working full time for consulting company.

When I was a contractor I had set deliverables for projects and written agreement on payments for these milestones. One project might have 5-6 milestones.

95% of the time it worked well and the milestones gave an opportunity to review progress with the client, perhaps even a change of direction. On several occasions it lead to extensions (more features) or new projects in the future.

As a self employed contractor (cloud infrastructure), who got badly burned in the past, the key was to have deliverables which were self contained but still required the next chunk of work to be of any use in the bigger picture.

The financial loss for me was only the most recent deliverable should the client decide to ghost me. I did happen unfortunately.

From my perspective, I liked working on multiple sequential deliverables rather than one final one. I appreciate that infrastructure might be more flexible than other areas and often contractors only have one final deliverable.

I have charged clients first before I start. Most in full, some in part.

The question "why would they trust me to deliver?" is a good one. And there are two answers:

1. How you sell will determine their trust level. In my sales deck, I have testimonials, case studies and the outline of our full process. By the end of the presentation, when I tell them the price, they expected $10,000, but it's only $4,000. I ask them to pay the 4k now. Or, pay 2 payments of $2,500.

2. If the prospect asks us to do ALL the work first, then invoice, I say the following: "if we do all the work first, it means that you have no skin in the game. In the past, that hurt my business because people would disappear after my team spent 300 hours working. For that reason, it's not our policy to do all the work first. We have 2 options."

Then, i end off by saying: "if that's a deal breaker, I understand and I will happy send you the plan for what you should do next if you want to go at it without our help"

If you do multiple projects for each client, stall the work you're presently doing for every client that pays late. Let them know upfront that unpaid invoices immediately make you halt all work on the next stages of the client's project.

As for the AI solution you're suggesting, it's probably too easy for people to automate that kind of thing, so it might be a tough sell if you're charging $49 for it. But who knows.