I'll keep mine simple. How do you go about finding paid gigs?
This is the all-important question, the most elusive concept for bands and artists worldwide! As you may have suspected, there are no concrete steps that I can outline to get you paid, but I have some solid tips to get you in that direction.
1. Make friends with every single band member, sound guy, venue owner, bartender, roadie, merch person, etc possible. These are all people that, even if you think their band isn't great, could be the one to message you asking to fill a spot for a paid show or a tour opportunity. Some of my best paid gigs I've played have all been from that circumstance, a chance encounter that I made sure to connect with, and got hit up out of the blue. The more people you add on social media or keep in touch with, the better chance you have of that happening. Keep in mind that social media social media adds only matter if you post consistently about your music in a non-spammy way (I could write a book on that haha).
2. Don't waste time with low quality sites like Craigslist. I have found a RARE couple of cool opportunities through there but it's really a needle-in-haystack game, but instead it's needle-in-poo-pile game on sites like CL and others similar to it. Not really a direct piece of advice but this will save you time for sure!
3. DON'T PAY TO PLAY. By doing so, you set the standard of "I will pay you to have the chance to play on stage with no guarantee of anything good coming from it, and will likely lose hundreds". I've watched some of the emerging underground bands get pay to play offers and consistently turn them down, sticking to their morals, and after they continued to build themselves up over time, those SAME venues come back around and want to pay THEM now.
I can hear the keyboard warriors from here: "John we can say no but there are 1,000,000 other bands that will say yes so the venues will never learn". Ah, but you are wrong good sir. These venues pay to play with bands of low value because they know there's no other way to have them in without losing money, but they DO pay bands where they see they have draw and will make their money on tickets and booze. Playing free, while not great, still allows you to make friends with everyone that night, and you at least are mostly breaking even. You shouldn't have to go $500 into the hole to play to your friends.
4. Have a reason for venues to care. Or, should I say, have a reason for LISTENERS to care, and then use that buzz to make the venues care. I'd recommend checking out Building a Storybrand by Donald Miller to learn about creating a great narrative behind your music. If you can bring in 30-50 people at a venue for free repeatedly, you have demonstrated your value (bringing them drinkers) and can then leverage that into asking for payment, even if it's small to start.
Remember, venues need to see a REASON to pay you in the first place. Nobody cares that you play from the heart, are driven, have something to say, blah blah blah. That doesn't entitle you to anything. What people love, iiiiiiiiis .......... moneyyyy!! Once you can prove a track record of X number of people at your shows with ticket sales to back it, you have some clout. Get crafting your stories!