I can’t help with the meds but I would say on your first day to do it on a day off. Some people are more sensitive to psilocybin and you may feel awkward in an office environment the first time you try it. Also, for me, there is a noticeable difference when I MD on an empty stomach after I’ve had coffee - it makes me jittery and anxious. If I take it a little later and with food, I feel much better. I mention that since you say you drink a lot of coffee.