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What is your most difficult challenge in playing bass.

I guess for me, it's creating the motivation (time, willingness, whatever) to take my playing in a different direction. I was pretty OCD about study when I first started, so I have a decent handle on playing more or less what I want in the generes I play. But when it comes to improvisation, I'm pretty stuck in my comfort zone.

Plus I suck at slap.
 
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This is interesting. Can you describe some of those situations? Personally I've never been in a rock, blues or R&B band that didn't want the bass loud enough to peel paint off the walls. Jazz is a little more subtle, but not by a whole lot.

I play a lot of big band and musical theater pits. While the bass is necessary, few people realize the negative impact if it was absent. It's been years since I've played any church gigs, but the same was pretty much true there also.
Rock, blues and R+B fair a little better, but while you might be peeling paint with the volume, chances are the guitar and even the drums are louder.
How about solos? You get as many as the guitar player? Do they last as long? You ever have to explain to someone just what a bass is? I know there are some bands that tolerate a bass player as a showboat, but are there more than the bands that have a showboat guitarist? And just why was that movie called, "Standing In The Shadows of Motown"? (but I guess that was the whole band). Speaking of Motown Macca often mentions the bass in all the songs as being something he admired, but it was years later that he actually knew the name Jamerson, and eve then, he was a little surprised that all those tunes came from the same player.
It goes back even further. It was Benny Goodman that said that the whole band was built from the bass up. He knew, like many musicians know... but not the general public. Do you know the name of Benny Goodmans bass player? (hint: it was his brother mostly)
And then there's the meme, "you aren't really a fan of the band unless you know the bass players name".
Check out your own memory (no fair Googling). From 1951 to 1964 name the bass players in the major acts. Macca was one of the first names known to the public.
 
I'm still new at this (playing less than a year), so the details of what feels hardest at any given time changes every couple weeks. Really, though, in the big picture, it's mostly issues of technique: working on getting pick playing to be equal to fingers, speed, details like ghost notes and hammers, just keeping everything smooth. There's so much stuff to learn—and I haven't even really started on theory. I have recently started trying to keep the gear craze to a minimum to focus on just playing. (Have only bought one pedal in 2020, yay progress!) I just don't know how you experienced folks manage to keep everything straight.

It's all good, though, the challenge is part of what makes it fun.
 
I play a lot of big band and musical theater pits. While the bass is necessary, few people realize the negative impact if it was absent. It's been years since I've played any church gigs, but the same was pretty much true there also.
Rock, blues and R+B fair a little better, but while you might be peeling paint with the volume, chances are the guitar and even the drums are louder.
How about solos? You get as many as the guitar player? Do they last as long? You ever have to explain to someone just what a bass is? I know there are some bands that tolerate a bass player as a showboat, but are there more than the bands that have a showboat guitarist? And just why was that movie called, "Standing In The Shadows of Motown"? (but I guess that was the whole band). Speaking of Motown Macca often mentions the bass in all the songs as being something he admired, but it was years later that he actually knew the name Jamerson, and eve then, he was a little surprised that all those tunes came from the same player.
It goes back even further. It was Benny Goodman that said that the whole band was built from the bass up. He knew, like many musicians know... but not the general public. Do you know the name of Benny Goodmans bass player? (hint: it was his brother mostly)
And then there's the meme, "you aren't really a fan of the band unless you know the bass players name".
Check out your own memory (no fair Googling). From 1951 to 1964 name the bass players in the major acts. Macca was one of the first names known to the public.

Ahh I see... These are all things you have zero control over.

I'd never dismiss how you feel about stuff, but personally, as long as I kept getting gigs, I wouldn't waste any time thinking about this. If I'm not getting gigs, then it becomes within my control and therefore worth worrying about.

I have two bands now, one jazz/fusion and one Hip Hop/Neo-Soul. If I have to solo in the jazz band, I will. I don't care if I do, or not. I have a rare solo in the R&B band, but again I don't care if I do, or not. That music isn't about that anyway. The only thing I care about is if the band sounds good and I contribute to that good sound. Absolutely everything I do musically is about the music. It never occured to make it about me. I will admit though, my one concession to making it about me, is that when I get recorded, I like the bass loud in the mix, especially when it comes to Hip Hop. Because that's the way it's supposed to sound.

But I can tell you right here and right now, that when it comes to church gigs in a Black church, everybody in the building, absolutely knows the value of the bass. I can easily imagine that in a big band or a pit, nobody is gonna care about you as a bassist. Seems you're just playing the wrong gigs if that's what you crave. I've never had any desire at all to play in those situations. I've been asked a couple times to do theater work and I turn it down without a second thought.
 
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Because I got to a passable point very quickly so I could work out with a band, I have lots of technique leaks. On both hands. On the plucking hand, I'm constantly working to get the two finger groove down good. I learned with a one finger approach, which gets me by most of the time, but some lines really benefit from having the two finger approach. I can use the middle finger OK until I need to move my fretting fingers in opposition to my plucking hand ( I can play C-D (I-M) just fine, but trying to play D-C (I-M) really trips me up. For my fretting hand, I know I don't use my pinky enough. It really only hurts my speed and even then, only on certain lines. For example, I'm currently working on Sweet Emotion which I know would be twice as easy if I could get the two finger plucking right.

Can't use a pick, even though I used to play guitar - I figured that would be my go to when I started, but the string spacing really tripped me up. Also struggle with slap (although I coming to find out it may be my instrument that is giving me so much grief!)

Improv is just not for me. Couldn't do it well when I was playing horns in school, and can't do it now. I can improv walk all day and do tend to do some improv noodling on pentatonics when a blues guitar solo is happening (not always), but I can't put together a melodic line on the fly to save my life.

Theory is no issue for me - learned that in HS and college.

Not too much of a gear hound, but doing music as an established adult is so much easier than it was when I was in my 20s. I can pretty much go and get what ever I want when ever I want. I try to pretend I'm where I want to be gear wise, but there always seems to be something else I want to explore.

Probably my biggest issue is finding enough gigs. As an old guy, I know my days are numbered and just want to gig as much as I can while I can. Somehow, I'm crazy busy this month (5 gigs with 3 groups in 2 weeks!), which I hope continues, but typically starving for gigs, which will dampen my enthusiasm to practice.
 
Keeping my pride and ego as a bass player realizing many people don't even recognize what bass is nor can they pick it out in a song. I once spent a few months painstakingly learning a few very difficult Kansas songs note for note including the original long version of Song for America, The Pinnacle, Hopeless Human, Lamplight Symphony and Incomudro Hymn to the Atman. I've always been a huge David Hope fan and having a good ear I've never had a problem picking out bass lines. Learning these difficult very complex songs note for note has probably been my biggest accomplishment as a bass player. Once I was trying to impress my girl friend so played "The Pinnacle", a 9 minute 34 sec Kansas song followed by "Incomudro-Hymn to the Atman" even longer at 12 mins and 12 secs. After playing them both flawlessly for her along with the CD, she to my disappointment did not seem so impressed. She just gave a look like "What the hell was that"? Knowing she was a big Bob Seger fan I then proceded to play "Old Time Rock & Roll" a song I really really hate! I've never played the song before in my life but it's so disgustingly boring and easy I just played it as likely any average bass player could. After I was finished she looked at me in amazement as if I were some kind of rock star. Go figure! I learned after that incident that the only person you really need to impress is yourself.
 
Just wondering what everyone struggles with the most in bass world. Speed, theory, fills, gear?

Don't get me wrong, I'm always working on improving my technique, but for me, a relatively new player, the biggest challenge by far, has been understanding gear, effects pedals and order in the chain, especially in live situations. It almost seems like you have to be a scientist to get all your amp settings and effects pedals and levels and being heard but not being too loud all integrated well, especially in live situations.

How about y'all?
Changing my strings. I do it fairly regularly but it is a chore... fo' shore!