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When should I buy my second bass?

I've been playing bass for a couple of months now and I've been playing on a Squier P bass. If I say so myself, I think I'm quite good for how long of been playing. I can play some slap stuff like never too much by Luther Vandross and got to be real by Cheryl Lynn and my fingerstyle is getting quite fast. I was thinking about buying a second bass... something a bit more funky and probably a more expensive maybe a MIM Jazz bass. Do you guys think I should upgrade yet or do you think I should keep playing my Squier for a little while?
 
A better instrument will allow you to improve your playing ability even more; so if you can afford it and you really want to continue playing bass, it's a good idea to upgrade your arsenal. But you might feel like you really need a 2nd bass only if you start playing live (as a backup), other than that, you can be just fine with 1 bass ;) So it's totally up to you ;)
 
I can't say there's a fixed answer and there have been lots of valid responses already.

If that's a newer Squier then it's already a fine bass and should last you a long time. Add a new one when you feel the time is right - tonal variation, need a backup for gigging, want to experiment, want more strings, want to use a different tuning, have the money and you simply want one, you find a deal you can't turn down, etc., etc. etc, etc.
 
I've been playing bass for a couple of months now and I've been playing on a Squier P bass. If I say so myself, I think I'm quite good for how long of been playing. I can play some slap stuff like never too much by Luther Vandross and got to be real by Cheryl Lynn and my fingerstyle is getting quite fast. I was thinking about buying a second bass... something a bit more funky and probably a more expensive maybe a MIM Jazz bass. Do you guys think I should upgrade yet or do you think I should keep playing my Squier for a little while?

If you are satisfied with your progress so far than yes... IMO you deserve a new bass.

Going to the MIM jazz is not just an upgrade, it's a completely different bass with different character.
If you think you are a J bass guy, get one. (Funds allowing.)
 
As some others have intimated, do what's comfortable for YOU. If you love your current bass and feel that you're not being limited by it, great. But if you think another bass will allow you to expand musically, then go for it. But do it for the right reasons. No need to buy a second or third or fortieth bass (or a wall of $2k amps and 8X10 cabinets) just because some on TB have them.
 
  1. As soon as you can afford it.
  2. When your well timed purchased will get you a hot chick (or dude).
  3. When you get sick and tired of the gear snobs looking down on you.
  4. When they won't let you into the recording studio.
  5. When Queen Latifah says, "Ewww, I got Squire all over my hands!"
  6. When having a "Squier, Backed by Fender" bass becomes cool.
  7. When you break it after defending your family from a zombie attack.
  8. When someone says "you never can own too many Squiers".
  9. I agree with the poster who said "You should already be on your 8th"
  10. When you think that buying a better instrument will replace actually practicing

Quotation taken from, "From Euphemisms to Hyperbole"