<prompt> Human: Hello!As the title states, Ive recently switch jobs and i am looking into what I should do with my old 401k. I am 29 and have 100k in my 401k. Would it be financially smart to move the 401k into a Roth IRA? Does that somehow by-pass the rule of contributing 5500 a year?x200B;Clarification - Should I pay the taxes now in order to roll it into a Roth so that I dont have to pay the taxes later?x200B;Thanks.Assistant: Rollovers dont count as contributions to your IRA, so yes, it bypasses the 5500 a year rule.If your 401k was a traditional 401k youll be on the hook for taxes on the rollover if you go with a Roth. You can roll a traditional 401k to a traditional IRA tax free though. Sometimes your 401k will have a mix of both traditional and Roth contributions, in this case you can split them into traditional and Roth IRAs. Human: Sorry I guess my main question is, would it be worth paying the taxes on it now and rolling it into a Roth so that I wouldnt pay taxes on it in the future when I withdraw it. Im assuming Ill be in a higher tax bracket when I retired.Thanks!  <response>: I struggled with this question myself .Youre basically betting on where you think federal tax brackets will be in the future who freaking knows and where you yourself will fit into these future brackets again, who really knows. I chose to not pay the taxes now, but there isnt really a wrong answer. 