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AUTHOR: DrLefty on 7/23/2025

As I shared a few weeks ago, I’m in the process of moving the money from my workplace retirement accounts at Fidelity to my rollover IRA at Schwab.

This, like other aspects of my retirement transition, has had its bumps in the road. Fidelity will only mail a check to your home, no electronic or direct transfers, so I called them a couple of days before we left San Diego last week to begin the process. The phone call went smoothly, and we had already completed the process of transferring my 403B account, when the agent said, “Oh. You can’t roll over your 457 or DCP accounts until you’ve been separated (he actually said “terminated,” which I balked at) for 31 days.” So now I have to call again next week to do the other half of the transfer.

So I paid $25 to have my check from the 403B expedited and got a UPS notification that it would be delivered on Monday (7/21). I (wrongly) thought someone would have to sign for it, so I made sure someone was home all day, though it didn’t arrive until 8:40 p.m.—and then was just tossed on our doorstep with a doorbell ring. The envelope made it clear that it was financial papers. I hate the idea that such a large check could have been sitting in front of our condo if we hadn’t been there (or worse, in front of our building—some UPS drivers don’t bother looking up the code to get in).

On advice of the Schwab rollover specialist, I hand-delivered the check to the local Schwab branch yesterday rather than putting it back into the mail. The guy there told me it should get deposited into my IRA by this afternoon and then I’d have to decide how to invest it. We talked for a couple of minutes about the upcoming August 1 tariff “deadline” and whether it might be prudent to hedge my bets for a couple of weeks by just putting the funds into a money market account for now. He said that’s what he would do if he were in my shoes. His argument is that the market has already corrected upwards, assuming Trump will again not go through with the tariffs, and it’s not likely to make another big jump if Aug 1 comes and goes without much drama. It could go down if Trump actually follows through this time, though. My husband, who keeps up with this stuff way more than I do, agrees with this analysis.

Any thoughts?

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Jack Hannam
2 months ago

My experience was similar when I retired seven years ago and chose to roll my 401-k over into an IRA. In my case, I happened to look out the door to see a large envelope sitting on my front porch step. It contained a check for a large sum. Not only was a signature not required, but not even a doorbell ring. Even the occasional case of wine delivered by UPS requires a signature!

R Quinn
2 months ago

I guess we were lucky. Fidelity was our 401k record keeper so when I rolled it into a IRA I just clicked on the website and it was virtually instantly transferred.

R Quinn
2 months ago
Reply to  DrLefty

Yup, and we transferred all other holdings from other brokers plus two individual stocks from separate record keepers and two annuities. IRA online, the rest one visit to local Fidelity office and signed a few papers to allow transfer. Never had to deal with the other organizations.

I can understand your situation. My son in law works on Wall Street and has similar restrictions.

Rob Jennings
2 months ago

When my wife and I retired the only choice our megacorp gave us was to snail mail our life savings in regular mail. When it arrived I did not recognize the return address and at first thought it was junk mail to put through the shredder…Astounding. I raised a similar question about timing with our FA at that time and he immediately invested it saying any small gains or losses would be a blip long term. What I have learnt since on this and similar questions is time in market beats market timing. Good luck.

Rob Jennings
2 months ago
Reply to  DrLefty

I understand and I am aware of the Wall Street recent history. Good luck.

DAN SMITH
2 months ago

Dana, 8/1 could be deja vu all over again for us. We had about 70% of our savings sitting in cash on 4/1. On 4/2 I had to decide how to invest; dollar cost average or just jump right back in? I chose the former and am the poorer for it. I did put about 20% of the money in at the right time, and have been sitting on the rest. 
If I get another opportunity I will not hesitate to get fully back in. 
So I agree with the advisor and your husband; let’s see what 8/1 brings.

Stacey Miller
2 months ago

Congratulations on exiting on your own timeline! Enjoy doing all the things you’ve planned, plus plenty of impromptu delights!

Last edited 2 months ago by Stacey Miller
John Redfield
2 months ago

1) Will Fidelity do an electronic transfer from your Fidelity 403B into a Fidelity Rollover?
2) Will Schwab do a electronic transfer from the Fidelity Rollover to a Schwab Rollover? Might avoid the check dance. The company receiving the money generally has more favorable policies for transfers.

I am investing my wife’s funds from selling her house in a modified dollar cost averaging. 4 installments of investing this year – Jan., Apr., July and at year end. Caught the April low, but looks like a July high. We are both retired for over 10 years and got married about 4 years ago. Her money will stay her money.

David Powell
2 months ago
Reply to  DrLefty

This is the part which should be illegal. Fidelity, and all other stewards of tax deferred investments, should be required to do an electronic, in-kind transfer of your assets to the new custodial brokerage, assuming no holdings are proprietary.

1PF
2 months ago
Reply to  David Powell

should be required to do an electronic, in-kind transfer

Agreed. It’s the *safety* factor that is paramount.

At Vanguard, most transactions have been electronic: (1) at retirement, rollover workplace 403(b) and Roth 403(b) from TIAA to V IRA and Roth IRA; (2) RMD from V IRA to V taxable funds; (3) automatic monthly transfers from V taxable money market fund to my bank checking account.

The one exception is each qualified charitable distribution (QCD) from V IRA: Vanguard mails me a check made out to the charity c/o me, and I hand-deliver or mail it to the charity with a cover letter. If the amounts were much larger, I’d be worried, but for now, fingers crossed…

Mike Xavier
2 months ago
Reply to  David Powell

Think about it, they want to keep your money, so they make it difficult as possible to transfer the funds somewhere else. Stickiness and Greediness.

Rachna Condos
2 months ago
Reply to  DrLefty

My husband is retiring from CalStrs this year and I will be following him into retirement in 2026. After reading The NY Times article where Ron Lieber is now in Federal court because his check for the rollover was lost and cashed fraudulently, yet apparently no-one is responsible, I decided I needed to find out if we could do this electronically. Therefore, I contacted Vanguard/Ascensus, which is where our 403bs are held and they will only do a paper check for the rollover. I also contacted CalStrs as we both have large supplemental accounts that we will need to rollover. STRS will also only do a paper check as well. I thought I would have it come to our home so I could stay on top of it but they said they will deduct 20% since it’s not going directly to a bank or brokerage house. All very frustrating and seems ridiculous that we are sending paper checks. I even asked if they can send it by registered or certified mail requiring a signature and tracking and they said “No, it just goes in regular mail.” I asked if I could pick it up from their offices and the answer was “Absolutely not!” I cannot fathom how we are still using paper checks and mail in 2025 to rollover 6 or 7 figure amounts of money!

Last edited 2 months ago by Rachna Condos
Rachna Condos
2 months ago
Reply to  DrLefty

Thanks for that advice-I will contact STRS and ask if that would be a work around since I want to make sure that the check is received and can better be assured of that if it comes directly to me. I can then walk it into Schwab which is nearby.

Edmund Marsh
2 months ago

You won’t know the best move until it’s too late to make it. I like Michael’s comment.

Nick Politakis
2 months ago

I think it could go either way. Just read an article about how the S&P crossed its 200 day moving average and when that happened the returns over the next 12 months were significant on the up side. But we are dealing with an administration that thrives on creating uncertainty and not always implementing policies that help the economy. Needless to say both of those things are bad for stocks.

Nick Politakis
2 months ago
Reply to  Nick Politakis

I forgot to say something about fidelity that would only issue a check and ups that just dropped the delivery where anyone could get it. These important businesses are failing us when they do things like that.

quan nguyen
2 months ago

Here are my thoughts

1 I don’t trust the news – and will not bet my money on it. The efficient market hypothesis dictates that the price is built into all public news. The market already baked the tariff talk into the cake. Time for dessert?

2 With a lump sum of money for investment, my first decision is: Do I want to make one decision now or many decisions over time? Even parking funds in a MM account marks a choice – not a neutral stance.

3 Historical data favors lump sum investing. It beats dollar cost averaging (DCA) 2 to 1 because stocks go up more often than down. On the other hand, a $1 loss feels sharper than a $2 gain feels sweet. Or as Schopenhauer put it: the joy of eating is minor compared to the horror of being eaten. I’ll take the smaller bites.

4 If my asset allocation is 50/50, then 50% would go into fixed income allocation at once. The remainder waits on my courage.

My words come from a deliberate mind, but my actions always follow the gut feeling.

Michael1
2 months ago

That advice may turn out to be correct, but anything could happen in the next two weeks. My default would be to go ahead and invest what I don’t need in line with my preexisting overall asset allocation (to US stocks, international stocks, bonds), and be done.

Another option would be to invest half now, again in accordance with my overall allocations, and plan to similarly invest the other half on say August __. That way whatever happens, as I believe John Yeigh wrote a few years ago, I’d only be half wrong. But I wouldn’t drag it out beyond that. And again my base case would be what I said in the first para.

Good luck and congratulations again 🙂

mytimetotravel
2 months ago

Would you have changed your allocation if you weren’t moving the money?

David Lancaster
2 months ago
Reply to  DrLefty

Then if you are going to invest in a like manner and the market value is not significantly different I would put it all to work now. If the stock portion is not going to be touched for several years what difference does it make. Likewise when you were investing in your 403b did you stop investing when the market was at its peak? I agree with Quan regarding at least put your bond allocation to work at once.

Just ignore my post from earlier today. 😂

David Powell
2 months ago

Not everything is insanely overpriced at this moment. International stocks are up but not wildly so. For those, perhaps re-invest a chunk and put the rest on a weekly or monthly DCA buy schedule.

For bonds, I’d stick to shorter durations. There’s not much premium for holding longer durations right now.

The sticky spot is US stocks. Broad index funds are dominated by a small set of wildly overpriced stocks. If you do choose to wait a bit before reinvesting, that cash can earn about 4.3% from 3m T-Bills, e.g. SGOV.

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