I decided when I was a teenager, I would get a tattoo if something I said 10 years ago still rang true. Now, the things that ring true are not something I care to have on a tattoo.
The only tatt I've really liked was someone that got their cycling bib shorts tan line with an ink line and a couple of emojis. They had a little tattoo line with a smiley face on the tan side and a frowny face on the shorts side. I've seen a few on the back of someone's calf while riding. I thought it would be cool to do something cheesy with the flex, but that would take a lot of work to map out exactly where things move around while walking versus riding. The calf was kinda cool because we were on the same shop racing team and even in the mix of 50 dudes fighting it out on bikes, I could pick out that tatt from further away than numbers or jersey. Racing is like trying to test your mental abilities when they are 95% missing in action. So something simple like that is ideal. I did a VO2 test once. I pushed until I felt like I was very close to passing out during that test. It felt like my heart was pounding out of my chest and my vision was blurring. A week later in a criterium race I managed 12 BPM higher and I didn't even notice. Knowing how wild things get with racing, the VO2 test was the valid mental state, and being brain dead in the race just went undetected.
Anyways, I'm somewhat undecided on tatts. When I did airbrush graphics, I drew out a sleeve but never was successful enough to afford it.
More seriously though, I don't really regret any of mine. Like I said in another comment on this post, my attitude towards tattoos is that I know the designs might not look perfect to me forever, and on a purely "technical" level even with touchups old tattoos do tend to look, well, old. So, for me, it's not about getting the perfect piece that I'll love forever, but getting something that's interesting or important or whatever to me right now, and which will serve as a marker or reminder of this period in my life and the context in which I got it.
So do I have tattoos that I wouldn't get now? Yes, absolutely, but there's no regret there – I was a "different me" when I got them, and they tell me a story about the time they're from and who I was at that point (and who I still am in a way)
I wish I was cool enough to commit to anything like that, so to me not only are they beautiful images of self-expression, they indicate a very attractive, almost wreckless, authenticity and confidence in decision making that seems really refreshing compared to my own insecurity.
For me I think the trick with getting tattoos is to realize that they won't be "perfect" forever, because styles and preferences change, both mine personally and in general. I think of them more as markers of some period in my life, of some context – this one's design was drawn by that crazy girl I dated for a while, this one I got in university because of that one class, this one was right after I split up with so and so, this one I got because I read that one book, this one was my friend's idea, etc. etc.
Some pieces can be timeless and I've got a few that I feel fall in that category, but some definitely look like they're from a different time and were made for a different me, and that's OK.