Can WitnessWork plan my month for me?

Yes. During setup, if you log hours and have a monthly goal, you get a quick preview of the Assistant: pick the days you usually go out and it spreads your goal across those days for this month, or next month if fewer than seven days are left. This month's plan starts on the 1st, so the days that have already passed get plans too: log the time you already spent on them. Days you've already logged time on are left alone. Tap any day to change its plan with the slider, or to plan a day yourself. Tap Add to my schedule to save them as plans on the Schedule tab, where you can change or delete any of them, or tap I'll plan later to continue without plans. The weekdays you didn't pick become off days, so the Assistant won't suggest plans on them; change this anytime in Settings → Preferences → Plans → Availability. After setup, you plan on the Schedule tab by tapping any day, and the Assistant there suggests plans whenever you're short of your goal. Plans are saved with your other records and don't count toward your report; log the time you actually spend. Kingdom Publishers who don't log hours, and anyone without a monthly goal, skip this step but can still add plans from the Schedule tab.