> ...to the tune of hundreds of thousands of dollars over the years missed completely.

Whoa, whoa, whoa. You're doing something very wrong if you've lost track of $100,000s of payments.

Keep in mind that it's over 20 years. Happens in dribs and drabs like this: get really busy, forget to invoice project for a while, realise you're months behind and so put off invoicing because clients won't like receiving them late, later it gets, more awkward and easier to avoid it gets. Or the business is sold or collapses. Or you don't chase up unpaid invoices for so long it's unlikely you can convince them to pay. Every client harasses you to get the work done. Very few harass you about the invoices. You start invoicing and then the calls come in or urgent emails. You plan to do it from home at night but then life/kids happen and you're exhausted. I forgot to invoice one maintenance client for a year and threw away five figures. Would've been handy money that year.

In the early years, aggregating staff time sheets was manual and easy to put off. We ended up building https://usepunch.com to handle that which is a massive help.

In web development and with 100+ clients, it can be quite difficult to track things like hosting and domains when they're spread across multiple providers, renewing at different times of the year, etc. We ended up building an internal web-app that interfaces with Xero to help manage this, but this was 18+ years in...

And yeah, I can appreciate I've done something very wrong. I've found that all too easy when spread so thin.

"it's unlikely you can convince them to pay" why not simply use some factoring service that charges you some minor % for never caring about missed payments again? There are multiple out there (I am EU based) that have APIs, a decent interface, etc.

That administration mess is exactly why I stopped freelancing.

I had similar problems, but on a much smaller scale. I thought I had a good relationship with one client and that invoices were being paid on time, but then I found that around £10k had been overlooked by AP over the course of a few years.

After that I phoned after every invoice - which was a pain in the ass for me and for AP, but the money (mostly) arrived on time.

It's really, really easy to miss how important admin and cashflow are. They're boring AF, but also too important to ignore.

Even worse is the realisation that sometimes you are going to be paid late, sometimes you are going to be offered partial payment, and sometimes you may never be paid at all - and these are all absolutely normal in business and you should expect them and have contingencies for them.

As a rule, any freelance work where you rely on timely payment from a single client to cover your outgoings is incredibly risky and dangerous and can easily become very stressful - because you are literally flirting with financial death.

It's not a mess unless you have some weird hangup about billing people and agreed-upon rate for an agreed-upon service. I freelanced full-time for 3-4 years, at one point with dozens of active clients, and never missed a billable hour. It's not difficult if you have a system to track and bill. Yeah it takes time, and it's a grind, and there are times you'd rather just not do it, but to imply that freelancing makes it easy to miss hundreds of thousands of dollars in billables, which is a non-trivial percentage of most folks lifetime income, does not jive with my experience in the slightest.

You did 3-4 years with dozens. I am at 20 years and more complexity. For a number of years, I managed staff and interns - just keeping interns busy chews up a lot of time. I had a co-founder to start with, and was then solo running it from then. Once you have staff but not the scale to get help managing that, it gets seriously difficult. When I started, things like Toggl didn't really exist. I used to print out and manually sum hours from staff per client/project and per month. And then create dozens of invoices each month manually in MYOB, an awful and miserable interface. It was a huge timesink. I couldn't outsource it because I was the only one with true knowledge of each relationship - what to bill in what way, which clients were sensitive, etc.

I'm not saying it's impossible to do it OK, I'm saying it's easy to get it wrong and fall behind. I mentioned the idea of an opinionated business framework to a friend (freelancing very occasionally 1-2 years) and they said "Oh YES, absolutely." And that's for someone who'd send 2-3 invoices a month, not 50+.

It's not just about missing invoices. Freelancing didn't really satisfy me to be a one man business army. Having dozens of active clients sounds like a horror movie to me. I also worried much more as a freelancer than as an employee.

It's great that you could do it.

FreshBooks is $50/month and you can automatically send invoices and schedule reminders. This is a solved problem.

ok and then they ignore the freshbooks invoice

Then find better clients or charge up front. Freelancing is tough but invoicing and getting paid should not be one of the hard parts.

You take them to court. Try to go to small claims. I've got a suit against someone for non-payment I filed 10 years ago - it's still on the court backlog - but it was too large for small claims.

And then you learn to spot warning signs, and avoid clients/projects like that again in the future. Getting some deposit up front is often a good thing, but also not something you can always manage. I've done work for govt agencies - that's generally not going to happen, but once I have a contract or PO, I've got a pretty high confidence the money will come through - it just may take weeks or months to get paid.

This is right. This is what many businesses do. It's better to demand cash upfront, period.

If they don't take those terms, then they don't get your services.

If that means you have to wait tables until you find a few legit clients, then so be it.

> It's better to demand cash upfront, period

In my experience the vast majority of businesses will not entertain the idea of cash up front, period. I bet that you wouldn't either. If you were building a house, and the builder demanded cash up front, you'd laugh in his face.

Finding good clients is important, but if you demand to be paid in advance, get used to waiting those tables because you're going to be doing it a long time. Note: you will not be paid in advance for waiting those tables, either.

This is 100% untrue. I’ve been a freelancer for 11 years and I’ve coached literally hundreds of others. I never, ever work with a new client without getting at least 25% upfront. Never. It’s 50% if the contract is smaller than $20k. And I also never really get any pushback. By the time we’re talking payment terms, they’re sold.

If you’re doing work for clients upfront without a deposit, you are taking a huge risk. Which is probably why out of more than $2 million billed, I’ve only had a single client not pay me, and that was a startup that went under completely.

This could be something built into the hypothetical framework I mentioned. As in, the default quoting template for your industry has x% upfront payment terms, and you deselect that option after a strong warning. All my quotes asked for 20% up front but then I almost never bothered invoicing it until I was finished, so I would need something that auto-invoiced the 20% when the client clicked "Accept Quote"... ;`(

Then the time-tracking component would strongly warn against commencing work until the invoice was paid, etc.

So, basically, a very opinionated business framework web app.

> If you were building a house, and the builder demanded cash up front, you'd laugh in his face.

That's how a lot of builders work - if you're having a custom built home, you're going to need to put down a deposit.

I typically require a deposit and set a payment schedule although I'm doing most of my work on UpWork now. UpWork is nice because they handle all the billing and payment hassles and I get a weekly transfer to the account of my choice. It's worth the 5% cut.

How much does one make through upwork though? my fee is approximately $100 - $150 an hour, I just don't see that on these various services.

I'm paid every night in cash when I wait tables. If someone tries to walk out without paying, the burly manager would stop them.

It basically happens in real time, but a weekly check is still tolerable compared to net-60.