Social Security Alerts, News & Updates
Retiring Teacher Faces Social Security Roadblocks Before Move

Ah, the joys of retirement planning! Because nothing says “congratulations on decades of molding young minds” quite like a bureaucratic maze designed by people who apparently believe clarity is overrated when it comes to Social Security benefits.
When “I’m Retiring” Somehow Becomes Lost in Translation
One brave educator recently shared their delightful adventure in the r/SocialSecurity community. Their master plan? Finish teaching in May 2025 and start collecting Social Security benefits in June 2025. Revolutionary concept, isn’t it?
Shockingly, the Social Security Administration—the same folks who never miss a payroll deduction—couldn’t quite grasp this straightforward timeline. Despite the teacher explicitly stating their retirement date, their benefits were promptly suspended because they were “still employed.” Multiple calls to check Social Security eligibility yielded different answers each time, because consistency would just be too convenient.
To add a cherry on top of this bureaucratic sundae, the teacher plans to move to Costa Rica. Because navigating Social Security retirement wasn’t complicated enough without adding international relocation to the mix.
The Problem: Apparently Calendars Are Confusing
The issue, it seems, is that the Social Security Administration operates in its own special dimension where time works differently than for the rest of us mortals.
Since our teacher friend works until May 2025, June becomes their first “non-service month.” This means:
- Their first payment arrives in July—not June
- The Social Security application process becomes needlessly complex
- Their application status remains uncertain
And let’s not forget the “grace year” concept. It’s just like it sounds—except not at all. It means they’ll apply a monthly earnings test rather than an annual one when determining Social Security eligibility. How gracious indeed!
The Solution: Persistence and Paperwork (What Else?)
A kind soul on Reddit offered a solution that involves—surprise!—more bureaucracy:
- Call the Social Security Administration again (because the first three calls were just for practice)
- Request a “work notice” for 2025 (a document you probably didn’t know existed until now)
- Make sure this notice shows June through December as “non-service months”
- Clarify in writing that teaching work has ended (because saying it verbally multiple times wasn’t enough)
Following these perfectly reasonable steps should result in Social Security benefits being unsuspended. Maybe. Possibly. We’ll see.
As for Costa Rica, the teacher simply needs to inform the Social Security Administration of their new address. Though they should verify countries where retirement payments can be sent—because of course there’s a list.
The Moral of the Story
This heartwarming tale reminds us that even when you plan meticulously for retirement, the government has special ways of making you question your life choices. Despite doing everything by the book with your Social Security application, our teacher friend still encountered obstacles that would make Kafka nod in recognition.
The good news? With enough documentation, phone calls, and perhaps a small animal sacrifice, these Social Security issues can eventually be resolved. For anyone approaching retirement, consider this your warning: start early, document everything, and develop a high tolerance for absurdity. It’s going to be a bumpy ride through the Social Security system.