I’ve never been able to do it. I always drop off to sleep around 3 or 4, even with the best intentions to stay up all night on Shavuos. Of course, it is the men who are required to stay up; the Torah has mercy on us women who have work schedules, a house to maintain, and children to take care of, and are exhausted by the beginning of the holiday. Nevertheless, many of my friends and I exert ourselves to try to keep the custom of staying up all night and learning on Shavuos. The times I have spent in all-night (or somewhat all-night) learning sessions at shul have been an inspiration. Everyone prepares some word of Torah to share. Converts to Judaism tell the story of their journey to the Jewish faith, which is appropriate for Shavuos, because we read the Book of Ruth, the righteous convert and grandmother of King David, on this holiday. However, for the last few years, my child has kept me at home on Shavuos and out of the synagogue or women’s study groups, so I usually end up falling asleep with my head in my book. It is so much better to learn in a group, but my child is my first priority!
The custom to learn Torah all night on Shavuos is derived from the story that the Jews fell asleep before receiving the Torah. It is strange, after looking forward to such a great event, simply to go to sleep at that moment! However, Kabbala explains that the sleep of the Jewish People at this time was not due to a lack of care or concern, G-d forbid, but because they were trying to reach a higher level of consciousness, and went to sleep on purpose to reach this state. However, G-d wanted the Torah to be given and lived in this world and not in an exalted dream state, so it was necessary to wake them up. It is a delightful paradox that Jewish mysticism keeps reminding us how to live in this world and not on a cloud!