re: Invest in Roth IRA or 401k - first job

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Can I set up a Roth IRA, say through Vanguard, that allows for direct deposit/contributions, or will I just have to make a manual lump contribution at some point during the year?

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Yes, and it's super easy.

I have mine set up to withdraw weekly. It's $105 and change. I feel that schedule makes contributing extremely "doable" "easy" whatever. It's the same amount in the long run, but a hundred bucks a week is like going out to nice (not even that nice) dinner once a week. It helps to put it in perspective and prioritize your spending.