Phyllis:

There is nothing wrong with projects that take a year or more to complete.

But milestones that "that take several months or longer to complete" (to quote the moderator's original post) are a bad idea for freelancers.

For example, a project involves writing a book with 10 chapters, and each chapter is expected to take 1 month, then structuring this as a single milestone is a bad idea.



It would be better for the freelancer to break this down into 10 separate milestones, one for each chapters. Or 10 separate fixed-price contracts.

And it would be even more advantageous to break each chapter down further, into separate milestones, such that a freelancer is getting paid for her work more regularly.

As a freelancer, if a client pays me this week for the work I did this week, and pays me next week for the work that I do next week, that is better for me than waiting for "several months or longer" to see if maybe the client releases payment to me. Who knows what will happen over the course of those several months?

In pointing out something like this, I'm not advocating that Upwork change its rules or user interface to prohibit freelancers from working on milestones that take many months. I'm simpy pointing out what works best for freelancers.

This works best for clients, as well. As I client, I would rather set up a relatively short-term task for a relatively small amount amount of money. What if I set up a really large milestone for 3 months of work, and in the end, I'm not happy with the work? Then do I need to fight with the freelancer over who gets the money? It would be better to know within a few days that a freelancer isn't a good fit for my job, and then the amount of money involved isn't as significant. Maybe I can simply let that freelancer keep the money and hire somebody else.

Moreover, if I'm working with a freelancer who I know absolutely is doing tremendous, wonderful work for me, I would rather have that freelancer getting paid on a regular basis while working on my project, as opposed to working for months at a time before seeing any reward. I think that will lead to a better outcome.