re: Am I over thinking this...Roth v. Traditional IRA

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Why would I want to pay taxes now at a higher bracket than have to pay the lower tax penalty when I retire? Especially if I am wanting to advance at work and make more money. Am I wrong for thinking this way?

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No, you're on the right track. But nobody truly knows what tax rates will look like in 30 yrs, so most people try to do both pre-tax and post-tax retirement investing to lower the risk. It's usually through 401k + Roth, but you can do the same with a tIRA, you just won't get any sort of match.