You've finally been able to get some nods from people around you. You're a good bedroom/hostel/car park/aux cable DJ. You're looking at earning from this craft you have a hold of. You're assessing the situation now and realizing maybe you'd want to be employed by an establishment - you are tied down by a club/bar/pub and have your weekly events there only... or maybe not. You'll book your gigs at your own pace - you want to be freelance.
Let me help guide your choice by weighing the pros and cons of being a freelance or resident DJ from my experience in the industry.
To start off, the profession of DJ'ing is still for the most part freelancing anyway. You'll almost always have time to work around doing other private gigs, even if you happen to lock in a residency... it depends on what you agree to anyway. But let's get into it.
Freelance
You're not tied down by any client or establishment. You book and execute your gigs independently. Working without a residency can be so freeing, I won't lie.
Flexibility
The level of Flexibility is PEAK! No one on your neck for any demands. You manage your own bookings, clients, workload. You can take on gigs at different establishments or clients only by the booking agreement. Absolutely no strings attached. You also get way more time on your hands to do things that you may not have had the time to, if you didn't have this amount of flexibility.
More Exposure
With the amount of flexibility you have, there are more chances that you may get higher exposure. Since you're not restricted to one establishment, you have a wider variety of venues and types of events to tackle. You also get to learn to play and curate your music in different ways than you would have if you didn't have that amount of flexibility.
No Taxes
You're not an employee, so no payslip, and no taxes. You show up, do your gig and move out. You get paid what you negotiate. No long stories.
Work Inconsistency
Work is not always present as a freelancer. There's no steady constant earning and playing time for you. It is possible to have a good patch and have constant bookings at a point, but that condition, while solid isn't permanent. Job security is pretty much a myth.
Expensive
It may be more expensive being a freelance DJ since most of what you spend is mostly out of pocket. You buy and maintain your own gear, promote yourself, and put in work to secure your gigs.
Residency
Job Security
Your job is secure. You're scheduled to show up at an agreed time to show up and perform. You run your shift and leave. You have this fixed. This is great because, unlike the freelancer, you don't have to go out and find a gig to keep busy. On the flipside, your paycheck is going to be taxed.
Benefits
You're an employee, so you receive benefits from your employer. This could range from health insurance to wellness programs, pension plans, and leave days. All this depends on what you agree on with your employer, but having benefits could be a great motivator to stick with a residency.
Limited Flexibility
You didn't think having employee benefits and a pretty secure job was going to come with your freedom, right? That's right. Your flexibility is now limited. You're required to be at your post, rain or shine, on your performance days. To some extent, your exposure is limited as well. You're going to be playing in the same venue, and will therefore be exposed to people who attend the venues you work at. Venues most likely, also don't allow their DJs to play at any competing venues.
This could also impact how and the music you play. You get used to what makes the crowd happy, so you keep giving it to them. It is possible to plateau in a venue you get used to if you don't challenge yourself.
Gear Maintenance
The DJ gear at the venue you're working at would probably be maintained by the venue. Speakers, controllers, or CDJs are all off your hands. You only show up with your PC and kill it and you're out.
As the post starts, it's very possible to still freelance with some resident positions hanging in there. That has been the best combination for me so far. I haven't held a very strict residency yet, but I've had the freedom to do events at competing venues and done other private events in the same 24 hours. I have also experienced dry spells and the harsh realities of how difficult things can get when everything is on your hands. However, choose what works for you. Everyone is different.