Why I will never DM again

I know I should stop thinking about this and move on, but I simply can't. So hopefully venting out and getting an outside perspective on things can relieve some of the mounting stress. I've bugged my friends enough anyways.

It was just one session. A session where I managed to do just about everything a DM shouldn't do when it comes to building up and executing a boss encounter.

The stakes were in place as well as a shocking reveal. There was an in character musical performance that everyone was looking forward to. They had already been through a lot and they just wanted a cool moment to bond and see their characters be the  impressive badasses that they are. I instead humiliated a character mid act and ruined what could have been the most  wholesome moment of the campaign thus far. I thought I was building the menace of this guy. This was my big reveal. The mentor of one the characters was actually jealous of his student and he wanted to destroy this character's public image. Well the party already knew he was a bad guy and were going to fight him regardless so the reveal wasn't needed and all I did was just ruin good moment. With the good vibes good and dead, it was time for combat.

I absolutely can not build a proper fight encounter.

I made a retarded boss fight and ruined several characters' big moments. The fight lasted longer than 4 hours. The minions were to many and had way to much health, especially the mages. I had essentially a high level glamor bard fighting as a boss with hold person as a legendary action.

So in translation, nothing was dying so no one was getting any feeling of achievement in the middle of the fight. There were too many counterspells and no one could touch the boss for 10 rounds. The fighter was frustrated because he was either held or not hitting. The monk was focused and also held. The mages were being Counterspelled and the artificer was stuck on healing duty.

On top of that, this was our first time using roll20 and working through technical issues dragged things out. No one was having fun.

There was so much planning and hype that went into this. I thought I was ready. I tested roll20 to get it working. I had everything planned from them killing the boss to them joining him. The players were hyped. They were planning out attack strategies and one even dressed up for the performance. Only for me to accidently torch everything with my incompetence. This fight was meant to be a huge turning point for the characters. This was the fall of a mentor, the reunion of brothers, and the starting point where the party would gain some major clout, good and bad in the world lore.

Instead, the emotion that was felt was frustration as we all just wanted it to end. I don't why we kept going. I can't even tell why I didn't change or adapt as a good dm should. I knew everyone lost interest so I should have done fucking something to salvage it. Nah, I just plodded along forcing things and being a stubborn moron.

We met up again to hash out where things went wrong. Or rather, me needing them to tell me what they disliked because I was too stupid to figure out the specifics on my own. I knew for a fact that I had royally screwed that one session and thought if I could just fix what I did wrong with my players' help I could maybe move on. Well no, I couldn't. My biggest mistake in the ocean of mistakes I make everyday was that I assumed my campaign was good.

On a deep retrospective, I realized I've been a terrible DM all along. Railroaded encounters, way too easy to way too hard combat, DM vs player mentality, being unprepared, convoluted story, and forgetting important rules/abilities to name a few. The only good thing was some of the role-playing, but that's because I had great players. I even had a player tell me he enjoyed my first ever campaign better. So somehow after getting a book to help nail down worldbuilding and having a year or so more DM experience, I only got worse. That campaign died along with my will to ever DM again (or play dnd in general). I'm too afraid of somehow just being worse and the stress and anxiety that come with it. I truly think I'm doing them a favor even if they don't say so.

Months later, I asked if there was any plot or character ideas that they wanted to hear about but no one had anything they cared to ask about. I really should stop thinking about it but at least once a week I imagine something else that I could have done to make the campaign better.