I don't screw up too much anymore. I'll occasionally mash a line the wrong way or shade something a little wrong, but it's nothing that's unfixable for the final product...... however, when I was first starting out I was terrible and reckless.
I used to drink a lot while I was in my early 20s, so generally that was a bad thing. Thankfully the shop I was starting out at was owned by my Uncle, who owed my mom a favor, so I was cut a ton of slack for being a total drunk idiot.
I remember one day I had come in, quite drunk, not really even walking straight. Usually they kept a needle out of my hand when I was like this, but it turns out we had a scheduling error so my Uncle somehow talks me into inking this guy. He just wants a quote on his upper back. "Not all who wander are lost." I remember the quote well. None of my friends let me forget about it. Anyways, this thing should have been simple. Easy. Nothing fancy about it. But not for drunk me.
The details are a bit fuzzy, but I remember grabbing a random ink color and just going for it. I remember leaning in very closely to the guy's back, hunching over in an insanely uncomfortable position and propping myself up by a wobbly arm because my legs had decided to turn to noodles somewhere along the way. But my arm had of course landed on the far side of the table, so I was pretty much leaning on top of this poor sap. It had to have looked hilarious, but I was way too drunk to even realize how awkward it probably looked...
To top it off I was getting closer and closer into the guy's back like I was inspecting it. I recall very clearly that I was almost leaning my head on his shoulder as I guided the needle along his back, freehanding this tat. It wasn't a big tattoo by any means, and I was careful to avoid his other ink that was on his back. He asked me a few questions, to which I think I just mumbled some gibberish in reply. My lips were literally against this guy's back. So I'm pretty sure feeling them move was enough to shut him up. I was too drunk to even think at this point.
So finally the tat is done, and I'm pretty much on auto-pilot. I really just want to take a smoke break. I'm fucking tired. The guy gets up and asks to see a mirror to look at his new ink. I give it to him and just sort of zone out until I register that he is now screaming at me.
So the tattoo had come out perfectly. No typos, no issues. But because of the awkward position in which i had tattooed him in, it was upside down and crooked. To top it off, I had used pink. Of course, I didn't register anything wrong with this until I was sober the next day and my uncle had called to tell me I should take a few weeks off and get my act together.
TL;DR - I was a drunk 18 year old who drunkenly got a bit too personal with his client and ended up tattooing it upside down and in pink. Got my act together within the month though.