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AUTHOR: DrLefty on 7/01/2025

Well, I tried to stay up until midnight to pop a cork, but it just wasn’t happening. So today I woke up as a retired person!  If you’ve read my articles from 2024 on the topic, you know this didn’t sneak up on me.

My road through the logistics of retiring from two university systems and applying for Medicare went…somewhat smoothly. I was pretty meticulous in my preparation. I attended webinars for both systems last year and put the application dates on my calendar. I had a Zoom meeting with an advisor from one of the two systems to make sure I was doing everything correctly.

My retirement application from my current/most recent employer was finalized May 15, and I’ll get my first pension check on August 1. (I just got my last regular paycheck, as we’re paid in arrears.) My Medicare application process also went smoothly, and that coverage also begins today. (I turn 65 next month, but since my birthday is on the first of the month, I got to start Medicare on July 1.)

But there’s one glitch: My retirement application from my previous university system is still not finalized, even though I submitted it on March 3. The hold-up is that I have reciprocity between the two systems. That’s a good thing, but it makes the process more complicated. They had informed me that because of this factor, my final pension calculations could take longer, so I didn’t worry about it…but then last week I realized “wait, I’m only a week out; I should have heard something.” So I got on the phone, and indeed, there was a problem, which turned out to be lack of communication between the two systems. I’ve been on the phone with both several times and messaging with the first system. They all assure me that it will get worked out and that if my first pension check from that system is late, I’ll be made whole retroactively. But it’s a nagging piece of unfinished business that’s dampening my glee a bit today. (And it’s not a small issue. This pension from my first employer is going to represent more than 50% of my retirement income.)

I guess the take-home message is that no matter how carefully you plan, something can still go wrong. But I know I’m in a position of privilege having pension income at all, so I’ll try not to worry about it too much, although I’m naturally wired for fretting.

My next task, which I may actually tackle today, is rolling over my workplace retirement accounts (403B/457) from Fidelity to my Schwab Rollover IRA (already in place from my previous job). (My husband wants/needs me to do this because of his independence audit for the accounting firm he works for.) Again, I planned for this—I spoke to a rollover specialist at Schwab, who sent me detailed instructions of what to tell Fidelity when I call them. Fingers crossed that it goes more smoothly than my pension experience!

On a happier note, we have a nice dinner out planned tonight, and the bubbly will get cracked at some point today! I’m RETIRED!!!

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Richard Hayman
1 day ago

Congratulations, Dana. But…. I surely hope you retired “TO something”, not just “FROM something”. If so, what is it?

Last edited 1 day ago by Richard Hayman
mytimetotravel
1 day ago
Reply to  DrLefty

That sounds like a full time job. Maybe more than one. Relax!!

Mark Eckman
1 month ago

Congratulations!

I had similar hurdles when I retired with 2 pensions, a rollover 401k, HSA contribution timing, and other issues. All went smoothly, except the rollover. Since I went from work and home ownership to retirement and full time RV travel, getting the check to the correct address was quite a challenge. But it did work out. Next month, all these worries will be gone.

Debbie D
1 month ago

Enjoy! I retired on May 30th this year. It has been wonderful doing what I wanted to do each day.

SCao
1 month ago

Congratulation! It is a big life milestone. Wish you a happy and healthy retirement!

AVINASH PRASAD
1 month ago

I retired too on July 1! Congratulations to the both of us!

William Dorner
1 month ago

Congrats Dr Lefty. Keep planning, be patient, all will work out in time. My mantra is One Day at a Time. There will always be some bumps in the road.

Doug Burke
1 month ago

Congratulations on your retirement.

stelea99
1 month ago

Just found this a minute ago….Congratulations, You have passed the finish line and all you have to do now is to wait for your Blue Ribbon!! When I retired on Aug 1 of 2001, I had already submitted requests to get $$ from various company retirement funds Xferred to Schwab. It took until the middle of February 2002 before it all got accomplished. Over than period, the market dropped, so when I finally was able to buy some funds, I thought that I had gotten ahead….oh well, the market kept falling until the end of the year…..

OldITGuy
1 month ago
Reply to  DrLefty

I’m surprised that Fidelity won’t do the rollover directly to Schwab and “in kind”. I wonder if they’d do it “in kind” if you did a rollover into a Fidelity Rollover IRA? If so, then you should be able to immediately do an electronic transfer of an IRA from Fidelity to Schwab. That should then be an ACATS electronic transfer of “in kind” so you don’t have to be out of the market and there wouldn’t be any paper checks.

Nick Politakis
1 month ago

Bravo

Mike Gaynes
1 month ago

Mazel tov!

Linda Grady
1 month ago

Congratulations, Dana. Hope you enjoyed a lovely dinner last night and are having a relaxing time in SD. When I retired 10 years ago, I also had a trip planned that departed the very next day, and enjoyed it even more, knowing I didn’t have to return to to work.

Jo Bo
1 month ago
Reply to  DrLefty

Congrats to you, Dana.

Retirement from teaching didn’t seem real for me either until the first fall. Then I was out biking on what would have been the first week of the semester when suddenly the feeling struck that I needed to be in class. The same feeling washed over me multiple times that September, but ceased soon after. I still, however, occasionally dream about arriving late or not prepping for class; those dreams are waning though, now that I’m retired for a few years. Being in or around academic environments continuously since kindergarten, as you may have been, and then retiring, necessitates a rather big mental shift.

quan nguyen
1 month ago
Reply to  DrLefty

Congratulations on your new freedom. From personal experience, our mental habit would not change easily unless we deliberately subject ourselves to new demands or routines for a while. After 2 decades of hospital on-call duties, and despite 4 years into retirement, I still have not escaped the startled / surprised / anxious feeling when I got unexpected night call or text. Just be amused how work life conditioned us. Now that work is no longer a part of our life, we are free to unlearn and recondition ourselves to new happiness. Goodbye the old golden cage, and good ridden.

David Powell
1 month ago
Reply to  DrLefty

That’s one thing I’ve loved about this new phase: booking trips when far fewer are also free to travel. Get ready for lower trip costs (or longer vacations), and fewer crowds.

Michael1
1 month ago

Congratulations!!!

Dave Melick
1 month ago

Congratulations! Keep on writing for HD!

Edmund Marsh
1 month ago

Congratulations! I hope your retirement is all you’ve planned it to be, and more.

luvtoride44afe9eb1e
1 month ago

Congratulations and welcome to your next stage of life. You will have plenty of time to work out the remaining pension issue (ans if you needed something to do) and I’m confident it will be resolved soon.
All the best and keep us posted.

Rick Connor
1 month ago

Congratulations Dana on a well planned retirement. My experience is that transitions form one thing to another here the worst. Once rouge things set it should go smoothly. Enjoy San Diego and you daughter.
Best Wishes, Rick

eludom
1 month ago

Welcome to what’s next.

1PF
1 month ago

Woohoo! Go, Dana! Go, Dana!
👍🎉👏🍾🪅✨

Scott Dichter
1 month ago

Congratulations!

DAN SMITH
1 month ago

DrLefty, congratulations and welcome to joblessness.
I want you to know that I am contributing to your family finances. I have streamed Randy’s music about 13 times now. I calculate that to amount to nearly 4 cents!
Seriously, I hope you guys have a long and happy retirement.

mytimetotravel
1 month ago

Congratulations and welcome to retirement! Maybe when your husband sees how happy you are he’ll want to join in!

baldscreen
1 month ago

Congratulations, Dana, I am happy for you. Chris

David Mulligan
1 month ago

Congrats!

Olin
1 month ago

Congratulations Dana! Your planned retirement was way better than mine and well thought out.

I wish I had spoken to a rollover specialist beforehand, but that doesn’t mean they know everything to think of asking you. Fidelity knew that I had just retired and they hounded me to do a rollover. Pro rata now lives with me forever.

Jack Hannam
1 month ago

I begin my eighth year in retirement today. I experienced minor glitches during the retirement process, but nothing significant. Enjoy the bubbly!

Jeff Bond
1 month ago

Congrats! My experience with Fidelity rollover (maybe 4 years ago) is that they will insist on sending you the check personally. They won’t send it to Schwab.

I rolled out of my employer’s Fidelity 401(k) for a Schwab IRA. I never understood why Fidelity wouldn’t go straight to my Schwab account. I was uncomfortable holding a check that large.

Edmund Marsh
1 month ago
Reply to  Jeff Bond

Yep. Waiting a couple of weeks for a big paper check made the Fidelity to Vanguard rollover uncomfortable for my wife and me.

David Powell
1 month ago
Reply to  Jeff Bond

Yes, same experience here with a rollover from Fidelity to Vanguard.

Fidelity won’t do in kind distributions from a 401k, so they will sell everything and let it settle before cutting the check. You can pay a small fee to have it sent overnight.

When it arrived, I did a mobile deposit of the check to my rollover IRA using the Vanguard app, which was a hoot.

Randy Dobkin
1 month ago
Reply to  David Powell

I have T-bills and TIPS in my Fidelity 401(k), so I asked whether I could roll them over in kind to an IRA, and they said yes, as long as I did the whole account at once.

Last edited 1 month ago by Randy Dobkin
R Quinn
1 month ago

Welcome to the club.

kristinehayes2014
1 month ago

Congratulations!

bbbobbins
1 month ago

Well done. You now have a new full time job of liberating your husband!

David Powell
1 month ago

Congratulations, Dana!

Ben Rodriguez
1 month ago

Mazel tov!

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