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What one specific thing do you feel helped elevate your playing

Used to get into the only jazz jam/open mic session int town at a club when I was underage. The BL didn't allow Real Books on stage. You had to go by ear (or memory). He would help you out a little though telling you the song title and the key, and would shout out changes (in numerical format) if he knew you were struggling. I was abysmal in my first couple outings, but it made me work my a$$ off to get better.

Also, just a sense of never being good enough. I'm never content in my playing and always searching for ways to get better. That drives me always find another level.
 
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As far as recently I'd have to say finally finding a decent compressor. Now that all my notes from low to high are articulate and stand right out. This has forced me to be sharper & more precise. It's even helped with timing. There is much less room for error.
 
Two things come to mind that elevated my playing considerably:
1. Joining a band with musicians that are way better than me

2. Jamming with typical jam-session musicians.
First time was not great, i felt stressed and struggled to come up with something beyond the roots before the theme would change. Third time, i had a few pocket-moments. Many times later, the dread was gone and i enjoyed myself the whole session.
 
Talking about this at work today. Some answers I hadn't thought of. Made me want to learn those things. So I figured, I'll keep it going on here. What one thing did you learn that stands out. That took you from beginner to intermediate or advanced. That once you had it down you knew you had elevated your playing ability. Ready? Go!

Being wise enough to know if I wanted to indeed get better, I would have to put some time into it. Drive and determination help you stay the course. As soon as I think I've got it, reality rears it's ugly head, reminding me that I don't...

... rinse, lather, repeat...
 
Talking about this at work today. Some answers I hadn't thought of. Made me want to learn those things. So I figured, I'll keep it going on here. What one thing did you learn that stands out. That took you from beginner to intermediate or advanced. That once you had it down you knew you had elevated your playing ability. Ready? Go!
For me, two things, playing along with a good drummer first and foremost and secondly playing live. Having a great drummer whose meter is dead on helps you to drop into the groove and lock the pocket which is the magic we are looking for as bass players. Playing live you have to stay on your game, so I find I practice more and you are not sitting on your butt, but playing standing up and moving around, so you hunt for where to play bass lines on the neck to ensure you get to the notes you need in the most efficient way. And of course performing live you get the creative juices flowing where you and drummer are let loose to groove a little and where you can feed off of the other performers as well. RTS
 
- make recordings of yourself
- learn a sax, trumpet (or any other instrument) part or solo
- imagine what part you could play first, try to hear it in your head, try to sing or hum it and only if you can hum it....thén try to play it. This keeps you from letting your fingers do the same thing over and over again.
- get a keyboard, learn about chords and inversions
- as an experiment, try forcing to limit yourself sometimes, like 'no note on the first beat' or 'no 4th or 5ths'. It opens up new doors, both rhytmically as melodically
 
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At the suggestion (ok…pushing) of a friend, auditioning for and getting a place in my university's concert chorale.

That's where I learned about a huge variety of different music and styles; something about the importance of good arranging; how to follow a real conductor; the benefits of being able to sing for instrumentalists; why you absolutely need to stay healthy if you're doing any kind of music; and most importantly, how to really listen to yourself and the musicians around you when you're rehearsing or performing.

The single best thing I ever did to make myself a better bassist was to put down my bass every so often in order to sing in a 100 person concert chorale.

There's only one drawback. Once you've done it, you'll develop an understanding and some slight degree of sympathy for all those flaky vocalists you're going to end up dealing with. Because you'll know how it feels to be out there just by yourself making music - with no instrument or amp to hide behind.

Good thing we can always fire the drummer and not feel guilty.

tl:dr - learn to sing (as in actually learn)
 
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I couldn't pick one definitive thing, but lately the biggest was becoming much more aware of up- vs. down-strokes (playing with a pick), and how leading with a counter-intuitive up-stroke can sometimes be the "right" choice timing-wise. But also, how sometimes flipping to the "wrong" rhythm can be the right choice feel-wise.

Right now this is still something I usually work out as I'm writing a complicated part, but I'm hoping to get better at feeling it on the fly.