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What You Need to Know: Retirement from Teaching

Updated: Aug 12, 2022

Paul Ruez, M.Ed. Formally of Oceanside High School Once a Pirate Always a Pirate (Ret’d 6/11/21)

Notes from a Veteran on Educator Retirement Planning:

Retirement from Teaching: These bits and pieces are my personal notes, opinions, suggestions, etc. and in no way represent CalsTrs, Social Security, Oceanside Unified School District, Congressman Mike Levin, or anyone else’s toes I may be stepping on.

Some of this may have changed by the time you read it. Remember when we were kids we wanted to be “older?” Ha, times change as you reach these chronological benchmarks along your life and career journey – mandates and opportunities also change. If you’re a young pup just kicking up stones as you map and engage in your life-career journey, this discussion will still have some value. If you know others who are approaching retirement, please share this information as they begin their educator retirement planning.

Planning for Retirement for Teachers Tip 1: Register in CalsTrs

Where to begin with your educator retirement planning: Call 800-228-5453 or visit If you are not on CalsTrs, check the system you are in.

800# support – have your login info and plan on waiting at least 3.5 minutes to get through the initial phone messages. Remember you have to accurately complete the Service Retirement Application to retire. FAX and or mail it in AND then call and verify receipt. No emails.

Use their Benefit Calculator

800# support can help walk you through this. It really works! And save screen shots because I was not able to get it to “remember” the calculations and did not want to totally start from scratch when I came back later to continue using it.

  • Their Counseling sessions can do likewise – bring your laptop. Attend more than one. Ask questions and save your notes.

  • Have your accurate last three years pay stubs.

  • Have your unused sick days data.

  • Check your Supplement Fund – this is separate from the main benefit fund. Supplemental builds as you do paid work beyond your contract classroom work like after school classes, tutoring, etc. Districts may contribute to this amount – check yours. If you have years to go in your career, check this out and do more work that builds this account.

When you retire you’ll need to decide on how to “take” the Supplemental Fund income. There are choices – review with your CPA. I rolled mine into a Roth and paid the tax upfront. I did not need the money, so a higher performing Roth generates tax free returns which meets my future needs. Know your financial needs and do what meets your needs.

If you have a spouse – consider taking the reduced option so that if you buy-the-farm first, they will get your retirement. You can choose different percentages. What happens if they go first? Ask.

Attend several of the counselling sessions and keep asking questions – there are answers. This does really make sense.

ALSO attend the counselling sessions offered by your district.

Social Security

Another part of to look into for your educator retirement planning is Social Security. Visit to learn more.

I worked through the Oceanside office where I received professional and useful information. 855-287-4793. When it comes time to sign and submit forms, you will need a FAX or make an appointment and hand deliver. Save copies of your FAX documentation. If you FAX, be sure to wait about 4 days and call and verify that they actually received it and have it on file. It will not have been “processed” but all you are checking on is whether they received it AND that your information is correct. The District gave me 2 forms (Request For Employment Info & Application for Enrollment in Medicare Part B) which documented my start and stop dates working for the district AND requested enrollment in Part B Medicare. Both need to be signed and FAX’ed or delivered. Yes, call and verify receipt.

Back the Truck Up

If you have some miles on your tires and are still on the clock for your school, consider this. When I hit 66 (yes still teaching and “back then” this age got me full Social Security) a counsellor at the Oceanside Social Security office suggested I turn on Social Security.

First of all – for you to get any money, you need enough Social Security Work Credits.

If you do not have enough Work Credits – unless something has changed, or you have some extenuating circumstance – you probably don’t have any money in that pot to grab. How about your spouse? ASK. Call and check your and your spouse’s Work Credits. Set up your online account:

So let’s say, like me, you have enough Work Credits. I turned Social Security on and started receiving monthly Social Security payments – WOW a raise! Yes, this is taxable money but it’s money. So, in my case I got about 6 years of these payments before retirement!

Once you retire and start collecting your pension a dark cloud hovers over your Social Security income stream. It’s called the Windfall Provision which pretty much cuts this income stream in half. Thank you, President Reagan, this was another misstep in your attempts to save the economy which did not help the middle class. Personal opinion: there are other pieces of the tax pie to cut which do not take money away from the middle class, education, etc. But then, who has the horsepower in our system with the ability to grab the money? It’s not you and it’s not me.

Repeal the Windfall Provision!

There have been attempts and recently Congressman Mike Levin has voiced his concerns about the injustice of this Windfall Provision. About 5 Town Hall Meetings ago a teacher called in and raised the issue. He expressed his desire to see this changed. If you share this view, contact his office and ask for a progress report on his efforts to get it changed: If you have a group, get them involved in this.

Your School District- be careful

As you continue to work on your educator retirement planning consider this- If you have valuable work parked on your school Google Drive and Google email, start NOW and make thoughtful and careful decisions about backing up your files, folders, photos, videos, emails, etc. onto your personal HARD DRIVE.

Hopefully by the time you choose to part ways with your school, Google will have refined their technology but right now they offer backup software called TakeOut. For me it was not user friendly.

Other Options

Another option is: You can also right click on what you want to save and click Download. I suggest renaming those folders first to read EXPORT before whatever name it already has. Once it appears on your personal computer as “downloaded” move it into a folder you make onto your personal hard drive. I named mine “Export G-Drive Folder” on my PERSONAL Hard Drive.

Because I had most of my curriculum development and other valuable resources on my hard drive before the school mandated using Google, I already had pretty good back ups.

Because I paid the money to join Google One, I get access to Google support and 2 TB of storage. For free you get 15GB. Both Google and one of my senior district techs suggested that I just change “Ownership” of what I wanted to keep. How? Right click what I wanted to keep, share it and in the dropdown, click change Ownership. This may work for you but there was NO dropdown available to me that offered an Ownership click option.

Save Yourself the Frustration- important note

This is important: The above represented about 6 different back and forth exchanges with the techs. All involved spending my time “trying” what I was told. None worked. Literally 10’s of hours was spent trying to follow their suggestions on various other how-to questions. VERY frustrating indeed, and I’m not done yet. No one was willing or able to do a screen share and just show me.

In the course of asking these how-to questions of Google, my personal Google email at this time has about 80 exchanges = way too much time down the drain. This does not include other emails on my school account before it was shut off. This represents a LOT of wasted time.

Alternate Option

Another option for you is to Google: backup google drive to external hard drive as discussed.

And, there are techs in the community who, for a fee, will do it for you. Just make sure you know what want you, so when it’d done, you know you have want you want. Ask for references.

Protect Your Google Mail

In the Google TakeOut program I believe there is a download for mail. I did not try it. There are many choices, click only what you want. I suggest trying them one or two at a time and seeing how they work as opposed to clicking all at once. You can go back and do it many times as you like for the different categories.

For email threads which have personal, sensitive, crucial, etc. data, you can forward it to your personal email address.

Email Shut Off Headaches

Without notice I found that emails sent to my “old” school email receive this reply; 550-5.2.1 The email account that you tried to reach is disabled.

So, someone receiving this might think… Oh, he got fired or died.

OK here we go again, more stuff to deal with.

I’ve asked Google (more time spent in the Q&A maze) and other techs I know, and all I hear is that Google does not provide a way for a forwarding address to be sent to people trying to reach me (or you when you leave).

If you have spent years connecting with other professionals, students, parents, etc. wouldn’t it make sense to have them receive an auto reply with your forwarding information? I would think so because this reflects on both you and the school. But no, “blame the teacher” and its my fault for not giving ALL these people my forwarding info in advance. Hey, hold the show, over the past year I included a forwarding address and phone in my signature block. But still, that’s not going to reach everyone.

Google suggests, for people who want this Forwarding Information feature to be available, to send a Feedback suggestion.

Get a group together and help them submit a feature change suggestion.

Your Important Data on the School Website

Ok, here we go again. In my case the site changed webmasters and without notice (at least that I knew of) my access to changing my website was locked. Then the district changed the web platform from Schoolloop to Blackboard. I had written Schoolloop and asked if I could still gain access to my web pages in which I had invested a lot of time and had shared the links with other educators, students, parents, VIP’s and others over the years. They wrote back and said yes, but I could not make changes. Then my links went dead. I wrote, and Schoolloop amended their original reply by adding that because the district had terminated the contact with Schoolloop, my links were now dead – game over.

Bottom line, if what you are putting on the school web is that important, back it up. At least take screenshots. And if you are in the admin arena, yes, advise faculty and staff of the coming change. That did occur at my site. BUT also, be in tune enough with your team to know who has invested heavily in their web content and reach out more strongly to those team members and connect on this important subject. If that happened in my case, I missed it. This is an important part of your educator retirement planning.

Medicare- Healthcare is important as you work on your educator retirement planning

Sill working as you think about your educator retirement planning? If you qualify for Medicare and are not thrilled with your school health care plan, you can stop that plan and start your Medicare.

On the surface Medicare usually seems complicated. As with Social Security you can call and ask questions of Medicare – TAKE NOTES! After a while, it makes sense.

I use this info-only (no sales) resource, and I also use them for other than Medicare things like legal too – all free. If you are already happy with your go-to answer person, use HICAP for a second opinion.

Sophie Exdell (she/her)

HICAP Assistant Program Manager, HICAP Volunteer Coordinator

Elder Law & Advocacy 858-565-8772 ext. 206

Find Your Best Match

Beside the above who are not brokers, there are BROKERS who get paid by the insurance company when they sign you up for a Medicare Plan. The good one’s “match” you with the plan that best suits your medical and financial needs.

Ask trusted friends who they recommend as a Medicare Broker. I’ve asked my doctors – good starters. While docs may not be officially able to recommend, you can ask them who their patients like the most?

I Don’t Want Medicare- What do I do?

Alternatives? If you use a blended mix of the Pharma / alternatives, ask your prospective broker how many clients they have who use this blended mix of the Pharma / alternatives AND which doctors they use. In our pharma-based system it is difficult to find docs who are comfortable with both modalities – pharma/alternatives. For example, I know only one doc (Jeff Pearson, DO – Carlsbad) who takes Medicare and is not afraid to use hormone replacement therapy (HRT) as one of his treatments. There are other docs who treat with HRT but all I have found do not take Medicare. Many establishment pharma docs and their bosses consider pharma ($$$) the Holy Grail and alternatives demonic. Tongue in cheek here (a little) but finding the good docs who know when and how to use both, unfortunately is rare and special. If you have such a doc, pass the word – let me know!

The individual Medicare plan categories (i.e. “G”) are regulated and between the insurance companies are all the same. IMPORTANT: So it comes down to finding a doctor who meets your needs. AND also, some plans have “extras” so keep asking and taking notes.

NEXT: You do need to choose either Original Medicare (pic ANY doc who takes Medicare) -OR- choose Medicare Advantage which are “groups’ like Kaiser, AARP, Aetna, etc. where you can not choose any doc you want, only the ones they offer. – ask/shop/ask/shop, etc.

Change your mind / body? Once a year you can change your plan – ask/shop/ask/shop, etc. Yea, you can change your broker too.

Dental, eye, chiropractic, etc… ASK how much these “extras” cost? It may save money to pay out-of-pocket and not pay the insurance company’s high rates. Do your homework and run the numbers.

Confirm Last Day of Coverage

SCHOOL: Verify the last day of your coverage. BEFORE leaving your school insurance, ASK yourself… do I have any medical / dental work in progress that makes more sense to complete now before my school plan is not available? If you have something major in the works, keep asking until you get an acceptable answer. VERIFY your answers because you do not want to get stuck paying some humongous medical bill because you did not verify and get it in writing.

Dental: Delta Dental may have money left on your account and you could use that money for that final cleaning or cavity that’s been bugging you. Your dental office can verify how much money you have left. You can be able to get this by just calling. If confused, ask your school insurance office for advice.

The above are just bits and pieces for you to noodle on and prompt you to get your own answers. If you find mistakes here, please let me know. I do not verify the totally accuracy of the above – do your own critical thinking while it’s still legal!

Enjoy Your Retirement

Paul taught photography to high school students. A passion that won’t go away even after retirement.

I hope you find this useful as you continue your educator retirement planning .

FYI: This is a link to a much appreciate feature the Osider Magazine (pg. 12) ran on my work. If you are interested in what I’ve been doing, feel free to keep in touch.

Paul specialized in teaching Restorative & Workplace Skills and welcomes opportunities to collaborate. You can email him at:

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