[a-priori]

I attempted to start freelancing full-time about 2 years ago but had to call it quits. I had an okay portfolio... more than it sounds like you have, but nothing spectacular. It was enough to allay doubts about my expertise.

My problem was my network. I had only one regular client, a small web consultancy that gave me a couple projects. But they weren't very profitable themselves and so didn't want to pay me much, and were slow to pay even then. Beyond that I had to get work from freelancing job boards, which are a poor way to get good-paying work.

After about 6 months of trying to set up a sustainable business, only getting the occasional small gig and going into debt for the trouble, I had to call it quits. I now work at a consulting firm. I like it because it's a similar experience, but other people bring the work to me :)

My point is that having a network of people who respect your work is important. Ideally, starting out this alone should be enough for you to break even (net of living expenses). From there you can nurture those clients (they're your lifeblood) and try to expand. You should only resort to job boards as an act of desperation to keep your pipeline from drying up.

Good luck!

[a3camero]

Don't underestimate what the parent poster says about "slow to pay". Everyone is. Think months to get paid instead of two weeks like regular employment.

[a-priori]

Yes, dunning sucks. I did two projects for one client and they paid within a week both times. I liked them for that. Most other clients, including the regular one I mentioned before, varied between 4 weeks and 8 weeks.

There's a fine line to toe when it comes to following up on late invoices. You can't let them slide, otherwise you're throwing away money. On the other hand, you can't nag them otherwise you'll seem desperate for money. As a freelancer, you must never, ever give the impression that you're having cash flow problems. Otherwise, whether it's true or not, your credibility goes out the window.

I made the mistake of seeming desperate for payment on one of my last projects when I actually was short on money. There was a minor hiccup in their accounts payable process, and I overreacted. Realizing what I had done was one trigger that told me it was time to pack it in.