How to Rollover a Complicated 401K

Rolling Over a Traditional and Roth 401K Plan

I have 2 types of accounts in my 401k from my previous employer – a tranditional 401k and a Roth 401K. After doing some research and weighing my options, I have decided to roll over my 401k into  Vanguard due to the lower fees and a variety of investment choices. I still do not feel educated enough to trust my 401k funds to a fully self-managed account with individual stocks and bonds, so the fund option is still appealing to me at this stage in life. Hopefully, one day I will have the time and knowledge to invest more specifically and strategically. For now, I plan to put some research into the  funds, diversify wisely and monitor my investments.

How a Roth 401 Works

Some organizations allow you to invest all or a portion of your “after-tax” dollars in to a Roth IRA type of 401K, called a Roth 401K. This can be good for some investors because the earnings will not be taxed at withdrawal. The withdrawal rules can get tricky, with options such as the 5-year rule, but I do not plan to withdraw (or otherwise called a distribution) any time soon.  There are many more things to consider to fully understand the Roth 401K, and it does vary in rules from the Roth IRA. I recommend going to as a starting point for information or consulting your financial advisor. Another interesting point is that employer matching funds cannot be contributed to the Roth 401k – they have to go to your traditional 401k. I didn’t even realize this. Apparently the laws allowing Roth 401Ks will be re-evaluated in 2011, so they may not be available forever.

Here Are My Steps to a Complicated 401k Rollover

  1. In order to roll over my 401k, I had to sign up for 2 new accounts at  Vanguard, both a traditional IRA and a Roth IRA. The folks at Vanguard were quite helpful on the phone.
  2. I then had I believe 3 different phone conversations with someone at Fidelity discussing the process of rolling over my Roth 401K. At one point, he was convinced that the earnings on my Roth 401k would have tax implications because of my rollover. He said because I didn’t have the account open for at least 5 years, the earnings could be taxed. This made absolutely no sense to me as the whole point of a Roth 401K or Roth IRA for that matter are that you put after tax dollars into them in order to NOT have to pay taxes on the earnings in the future. Or at least that is MY understanding of them. A rollover should still be a tax-sheltered process and should not count as a distribution. After much debate, he agreed with me and initiated the request.
  3. Mailed documents have been sent to me that I now have to send to my former employer for approval. I find this odd since I no longer work there, why would they care about my rollover?
  4. After these documents have been processed they go back to Fidelity and then Fidelity will cut me checks for the rollovers addressed to my Vanguard account.
  5. I have to send the checks with a cover letter and instructions that I create to Vanguard in order to process the funds.
  6. I then will have my money in a Money Market fund temporarily that earns basically nothing until I figure out what funds to invest in.
  7. I invest my funds into a new portfolio, in 2 different accounts, the Traditional IRA and the Roth IRA.
  8. Then, now that I am self employed, I figure out if I want to contribute to my new Vanguard accounts on a regular basis or find out more about SEP and Keough plans.
  9. Pass out from exhaustion.

If you find this of interest, here’s a few resources on Roth IRAs and 401K rollovers:

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