I know how hard it is to feel like your role as mom is to solve all of the baby's problems and that you should have all of the answers. My son had a difficult time with any transition. From boob to bottle, bottle to no bottle when it was time to stop taking the bottle and switch to a sippy cup, and our most difficult switch - sleeping alone. My story for you is a little off subject but might shed some light.
When my son Kai was born the nurse in the hospital somehow talked me into holding my son while he slept and didn't encourage me to lay him down in the bassinet. I being so exhausted would of course fall asleep with him on my chest and we napped/slept like this the whole time we were in the hospital. So naturally when we got home my son would not sleep alone. He would honestly cry for an hour straight if we tried to lay him down so we would hold him during his naps and he slept on my chest (me propped up with pillows) during the night. I think when most people think about co-sleeping, this is not what they are referring to. It was insane but I somehow did this for six weeks all because my husband and I were so exhausted, we all just needed sleep at all costs.
Eventually my husband had to go out of town for a week when Kai was about 7 weeks old. My friend graciously came to stay with me while he was gone. After a day or so she watched this behavior and expressed her concern that I was not getting enough rest sleeping with him like that. She was right! She and I talked about ways to get him to sleep alone and kept trying different things but as he cried and cried she quickly realized what I was up against. So one evening she watched him while I went to teach a dance class and when I came home two hours later he was sound asleep IN HIS CRIB. I couldn't believe it. She said that she got him to fall asleep rocking him and then laid him down and he fussed but she kept comforting him till he fell asleep. Sounds simple but my husband and I had tried this over and over to no avail. I think the difference was that my friend was pretty determined to make this happen and he sensed this and complied. It was then that I realized that although he was used to things happening one way it was going to be up to me, dad, whoever to teach/guide him towards something new. And usually the way to do it was going to be through firm guidance.
I now have no problem dealing with his resistance to something he thinks he doesn't want especially if I know that it is something he needs to learn or something that is healthier for him or whatever. This might be one of the most important lessons I learned early on -- which I have to still remind myself of all the time. They need us to show them the way even when they are still as young as your son. Be consistent, be compassionate but know that you are in charge. He will follow your lead as soon as you take command of the ship.
By the way we are potty training right now.... reminding myself of this story is exactly the ammo I needed!
Best of luck to you -- you absolutely deserve an afternoon to indulge in whatever you desire...
D.