Hydraulic brakes >> tubeless.
Hydraulic brakes will fundamentally improve your ride, your confidence, and lower your life insurance premium by thousands of dollars per year.
If you already have tubeless-compatible rims, it is an easy and inexpensive "upgrade" anyway, but unless you are pinch-flatting all the time, it isn't going to be as life-changing an experience as getting hydraulic brakes (assuming they are Shimano and not SRAM).