Here’s how I typically like to work:

I review a contractor’s portfolio. Either it makes the cut or it doesn’t. I don’t buy the cheapest. I buy from someone whose past work demonstrates they can do what I want. Usually I find people I hire by searching on my own or asking for referrals (the one exception being the music reviewer who does writeups for me monthly, who solicited me).

If their portfolio is adequate, and I’m reasonably impressed by their conduct when we discuss a project, I hire them. We cover all of the project details, talk about price and delivery times, and once I have the information I need, I pay them and they deliver when the work is complete.

There are a few reasons I prefer paying up front. For instance:

1. It means my end of the bargain is finished. I don’t have to worry about doing anything – just receive and review the work.
2. I don’t have to worry about payment processor issues – if there’s a problem, we know up front (see the example below for the latest horror story).
3. In my experience, I’ve noticed two things. When I pay after the work is complete (generally on the contractor’s insistence), they have a faster turnaround, because they want to get paid. When I pay up front, I’ve already shown that they can trust me and that I have the ability to live up to my end of the bargain – in that case, I find the contractors are more eager to please and they focus more on quality (which in the end is what I’m most interested in) – they know keeping me happy as a client means they might be able to get more work (also being paid up front, which they often find they like even if they’re not used to working that way).
4. If I’ve already paid up front, I have more leverage when it comes to ensuring other terms are met (if I haven’t paid yet, people seem less worried about upsetting me, missing a deadline, etc., because in their mind I haven’t really lost anything yet – and this has happened with small and quite large ticket projects alike).

Why I’ll keep paying up front in the future:

I made a mistake with the coder I hired recently. Because he generally did a good job with the work itself, I’m not going to name names. In short, I wanted to pay up front, and he insisted I wait and pay after the work was delivered.

We agreed to payment terms (in this case via Paypal). He noted that I should contact him before sending payment, because his business partner manages the account. It might sound strange to some, but I work with a lot of firms, and it’s not uncommon that the person I’m dealing with isn’t the person who directly manages the Paypal account, credit cards, bank account, checks, etc. I didn’t think much of it at the time.

Work was finished and delivered. I was ready to pay. He tells me there might be a problem, and that his business partner won’t let him use the account to accept payment (so obviously some honesty issues there about them actually being in business together, and needless to say I’m not happy about it). He proposed a different payment processor. If we were doing an upfront payment as I asked for, I would have simply said no (with this particular suggestion) and found another coder.

The other payment processor was a nightmare. They sent a receipt that funds were transferring, and they put the hold on the funds in my account. They ended up canceling the transaction because of some problem on the contractor’s end (said he wouldn’t be able to accept payment, but they couldn’t tell me why for privacy reasons).

I ended up spending a half an hour on hold just to reach someone, received form emails when I was promised a personal and detailed response, and to put it mildly all hell broke loose. It was crazy just getting them to release my funds from hold and answer simple questions.

So the coder asked me to send the money via Western Union (I generally don’t do this). I set up an account with them online and tried to send the payment. I got an error message telling me to call them. I called them (more time wasted on the phone). They told me they couldn’t verify my address with the credit report they checked (which was bullshit, because I check my reports regularly and as of last month every one of them had my correct and updated contact information – the two reps I spoke to could barely speak English to begin with and kept spelling my street name wrong no matter how many times I repeated it, so I’m sure the issue was in what they were entering). They canceled it (but to this point haven’t released my funds again, which they also immediately put on hold with the financial institution).

I let the contractor know he would be responsible for any additional fees incurred because of the change in agreed upon payment terms, and he was fine with that. I also made it clear that I’m not processing the payment again (they want me to go to a Western Union location and go the manual paperwork route now) until they release the funds from the first attempt (after dealing with their customer service people who were absolutely atrocious, there’s no way in hell I’m trusting them with double the payment in their control).

It’s been far more of a hassle than it was worth, and looking back it all stemmed from me not insisting on paying up front as usual. I doubt I’ll make that mistake again.

So folks, don’t be afraid to ask for up front payments for your freelance writing work. Buyers don’t all take issue with it, most will compromise if they really want to work with you, and it’s the seller’s right to set their terms (you don’t tell your doctor, plumber, or any other service provider when you’ll pay them – they tell you). And in the end, it just may be in their best interest after all.