I am currently a freelance bartender. Now while I realize that sounds almost like a euphemism for "unemployed", I am very much employed. NYC is one of the few cities in America where freelance bartender can actually be a viable work option. Basically it works like this:
I'm currently employed at three different companies. One of them is a staffing service and the other two are banquet and event spaces, where I'm technically an independent contractor. Every week, usually around Thursday, I get a set of text and phone messages inquiring about my availability for the following week. Occasionally, they will ask as far ahead as two weeks. The trick here is to respond to the messages as quickly as possible. I usually take each booking as it comes in, even though the temptation is to wait and see which is the best offer. There are variables, one company pays more for an hourly rate, another is usually better for cash tips, and the third provides me with the bulk of my work. But in my experience, playing one off the other can blow up in your face. You run the risk of pissing off a booking manager and then the calls could stop or become of a lesser quality. So I (usually) operate on a first-call first served policy. It also doesn't hurt my reputation as a desirable employee to have to turn down booking managers because somebody snatched me up first.
The calls and messages can last through the weekend, and usually by Sunday night I know my schedule for the week. If the week isn't already full, you can sometimes book a last minute shift. In that case, it's equally crucial that you respond to the call as quickly as possible. The booking manager is looking to fill a slot and be done with it, so they won't wait on a call back. The person who calls first gets it.
I usually don't know what event I've booked for, unless it's at a concert venue. Obviously, those are based on ticket sales and advertised. I find out when I arrive if it's a wedding, a corporate dinner or an industrial. Industrials are showcases that a company puts on for a new or revamped product. Phones, cars, watches, electronics.
I usually wear a tuxedo to most events, and I have two complete tux outfits. If I'm not in a tux it's all black shirt, shoes, pants and tie.
Basically, what happens is I arrive at the venue, change into my work clothes and report to a banquet manager. He or she gives me a verbal or written rundown of the event including start times, end times and any special requests. This can include specific drink requests, to signature cocktails created just for the event. I also need to know how many people are expected and what kind of bar package they are paying for. It can be open unlimited, beer and wine, of occasionally just a juice bar. I recently worked an event where the bar was just champagne and bottled water. At that point, I go off and move a bar on wheels in to place, fill up a beer bin on wheels with beer and ice, and wheel in all the rest of the supplies I need.
At the end of the event, everything gets wheeled back where it came from. I do an inventory if it's required and clean up all my empty boxes and bottles. I check out with the banquet manager, then I punch out and go home. I usually make between $100 - $200 per event for this work. Once in a while I make less, and I often make more. Figure on average $125, and if I do 5 shifts a week, that's about right. A very very good week is double that. Rare but sweet.
I love the unpredictability of it, I love the variety. I love working with different people and meeting all the different guests. I love talking to people from all over the country and the world. I usually love seeing all the live shows for free, even better, I get paid for it. I don't love the fact that it's feast or famine. I can be crazy busy for weeks and then only book one or two events for an entire month. (Although this is where having 3 jobs mitigates that problem fairly well.) I don't love working a lot of midweek corporate events and not making any money above my hourly rate. And you would think I would love getting my regular rate and only being asked to run a "bar" that serves juice, soda and water but that's actually the worst. It usually makes for a boring event and it's guaranteed there are no tips. So while I'm horribly overpaid for pouring Diet Cokes, I earn my hourly rate by plastering a smile on my face and pretending like it doesn't suck.