How many spots ahead do you book when you're trying to gig regularly?

I’m trying to get more consistent without turning the calendar into a hostage situation. If I only book week by week, the useful nights are often full. If I book loads a month ahead, I end up with three late ones in four days and regret every decision I’ve made. Do people keep a rough number of gigs booked ahead, or just grab good spots when they appear and sort the diary afterwards?