Hmm...
Sitting down with a label discussing a development deal. It was a new label headed by two Nashville musical heavyweights, we had done a CD, they liked it and the label was supposed to be more of an "artists" friendly label subsidized by one of the big guys plus they wanted some local rock artists to put on their label.
However they did not like our singer. They liked his writing, but vocally no. Funny thing is the singer was an incredible bass player. He wanted to be a front man, my band at the time just lost our singer, we get this guy and things take off. The kicker, he's probably the single most talented individual I have ever played with and his bass skills were off the chart sick.
So there's the dilemma. Replace him? Replace the current bass player with him? What do you? So while as a musical career accomplishment that was probably the biggest thing it was also one of the worst. We stuck to our guns, they passed. A year later the singer would go back to his true calling and ended up in a signed band that tour the east coast for the next 10 years.
From a fun standpoint my biggest accomplishment was with the last band I was in, touring over a 2 year period. 160 shows, 35k miles playing music with the coolest bunch of guys I've ever stepped onstage with. Was a nice way for me to end my live playing days. Musically it was my least favorite music I had played but the vibe, it allowed me to walk away satisfied and have more fun memories than all my other bands combined.