My 'guitar regrets' are so strange, yet appropriate, and profound (IMO) that it is unbelievable.
The regret is doing my first performance with an internationally acclaimed band, on a stage before a large crowd at 15 without knowing how to play a lick, really I knew nothing.
It started when I was 5, and my mother made me a singer, for instance in church or with classical pianists, and my dad bought me a ukelele. Then, when I was 10 my friends started getting guitars (in 1965) and I was playing the Surfari's "Wipeout" on their instruments, as well as my ukelele. My dad wouldn't buy me a guitar then because he expected me to be an outdoorsman or a tough guy, and he had bought me a real motorcycle, not a minibike when I was 9... that was a bad idea, I drove it on the streets, stole his car when I was 12, bought my own larger motorcycle when I was 14, and cheated, driving bikes and cars, trucks and vans when I was 15. That's irrelevant, except it was a distraction from music, as were the girls that tagged along.
Now the music fiasco comes in when I was 15 and we had weekly parties, and occasional Coffee Houses where there were always guitars, I would sit in a small group of young 'hippies' and pick a few notes, and whine or howl or hum some bits of a song I had written, or just thought of, and not written, but nevertheless, a spontaneous original. It got to be popular, I didn't think I needed to learn to play just yet, if at all... there wasn't really time, I was in school, working lots of hours at a job, restoring classic cars and building my first race car. Music was just popular culture, it wasn't my hobby, certainly not till the 'incident'.
So, one night a big band came to town and my friends and I went, and stood in the sort of mosh pit, in the first row. My friends pushed me up on stage, and the band let me play? Umm... I remember it well, the band launched into one of their songs, and I just noodled like an idiot and they sure wondered what the hell I was doing. My style was like, I had no clue!!!
My friends liked it anyhow, and I got a sort of cult status thing going on, and we went to bars underaged, and the kids kept pushing me to go on stage and play with every band! I was never turned down. I knew I was cheating, and the bands knew instantly that I was a dummy. It got to be such a routine, that I had to buy a chord book and get a guitar - I learned to cover real songs in full length, was given my own coffee houses to perform, and was given a part in a big stage production, where ironically, I played "Woody" in Finian's Rainbow, acting as a cool drifter dude who carried a guitar to get the girls but couldn't play. I protested that I wouldn't do it, or wanted to play, because hey... I knew at least 5 chords already! BTW, the theatre part was heavy on singing, just no guitar, only as a prop, and it was my own guitar too. Then, a talent scout gave me a TV show for a year, no pay, public TV and for charities, or for businesses that promoted charities, and I continued w/coffee houses. I had a lot of connections, but knew that I was no good compared to the real acts, namely Hendrix, Clapton, Beck etc.
They SO outclassed even local bands (of course, they were guitar gods) that I saw no point in joining bands or in pursuing a career in music, unless I was willing to sit down, and learn, and nooo.... my whole life was about being in motion! I drove everything that had an engine, on pavement, 1/4 miles, dirt (bikes and trucks) and even on water, not to mention snow?
I took my interests in the tech area, and building things into guitars, building sound systems and then guitars themselves.
At the moment, after taking a 15 year hiatus from song writing, I think I want to make a CD or be a recording artist before I am too old. I still can't play guitar, or don't consider myself a player, after doing 40 years' improvising and just getting by.
The thing about me and my music, if there is a thing, is that it has just been a no fear attitude, not quality, just "facing it" - I could only describe as perhaps the attitude of a competitor or a racer where you know you are taking chances, but do it for the rush and enjoyment anyhow and in my case I have worked 40 out of 55 years for charity and that's my way of giving.
Like a bird on the wire,
like a drunk in a midnight choir
I have tried in my way to be free.