All of our scheduling stuff is done on calendar days
Work for dropping next months schedule:
9th: put in preferences for next month. Takes a hour the first time, then every month about 10 minutes to copy the template and make some small tweaks.
18th: next month schedule is loaded, spend 10 minutes (max) putting trips into the pilot "trading board"
22nd: Load next months trips into trading software. Runs every day at 0800 and 2000 starting in the 23rd of the prior month. Usually will have to reload the trades before each run from the 23rd until all the trips are gone, usually by the 28th. 5-10 minutes each iteration.
24th: "free for all" training system opens for the next month at 1000. Spend about 10 mins at 0900 loading trades into an optional service that automatically executes trading commands. This gets my undivided attention from 1000-1030. Then I'll look at it a few times a day until my trips are gone, usually by the 28th.
Work for picking up flying. I do this on the day-of and day-before any day that I am willing/wanting to fly:
Before 1000, look at the open trips for tomorrow, add to ballot if desired. Rarely desired. 5 minutes
When I get an alert that a new trip has dropped into "open time," look at my phone to assess the trip. 15 seconds if I don't want it, 1-2 minutes if I do. This happens between 10-100 times a day. I do this because I am very picky about the flights I will accept. If you are willing to be less choosey you can load criteria into the website once a day and just let it ride.
So I look at my phone a lot every day, but I was doing that anyways.
Honestly, the hard part isn't the time, though ironically that's what most pilots recoil at. Pilots want predictability and stability. Get the schedule and don't think about it. That's certainly an option.
The hard part is risk tolerance. What if there's no trips to fly? What if you can't drop to zero? What if the senior pilots take the trips? What if I don't get paid?
No pain, no gain. The bigger the hub, the better the options. The closer you live to the airport, the better. Flying weekends means better trips if you're junior since the senior pilots want weekday stuff. The more flexible you are the better.
If I was willing to fly more and be away from home more I could have made $350k I think. Instead I was home a lot, flew very few hours and made $270k.
But be honest with yourself about your risk tolerance. Statistically speaking you will not do what I do. And if you don't, it's still an amazing job with great pay and lots of time off.