No Picnic: The Broken Maze of Medicare and Retirement

My transition into retirement has felt less like a celebration and a lot more like a battle. To be honest, the amount of self-advocacy I’ve had to muster over the last several weeks has been one of the most emotionally and mentally draining experiences of my life.

I am exhausted. Medicare and Social Security are supposed to work together as a safety net, but instead, Social Security leaves us feeling insecure, and Medicare treats us carelessly. The enrollment system doesn’t care about a person’s peace of mind; it cares about burying us in paperwork just to prove our basic eligibility.

The public agencies, insurance providers, and plan administrators who maintain our records fail to collaborate as partners. Bouncing applicants endlessly from one program to another, they are fueled by a toxic culture of buck-passing. Upper management gaslights us with bureaucratic, conditional “non-apologies” for their own service gaps. Because leadership refuses to own the problem, frontline staff are enabled to operate with staggering indifference, leaving vulnerable applicants with zero recourse for lost filings and mishandled inquiries.

The Systemic Flaws

The architecture of these programs is fundamentally broken, defined by:

• Unrealistic deadlines: Timelines do not align with an agency’s actual capacity to meet with applicants. For example, Social Security advised me to schedule an in-person appointment to review my IRMAA surcharge, but their first available slot was three weeks after my appeal deadline.
• Threats of lifelong penalties: Applicants face permanent financial punishment for an agency’s own poor recordkeeping. When Providence’s insurance plan administrator, Collective Health, took over in 2026, they lacked access to prior records, making it nearly impossible for me to obtain necessary proof of continuous coverage.
• Inconsistent terminology: Fragmented systems use different language, forcing us to endlessly re-explain our situations. Neither employers nor past providers understood what Medicare and Moda Health meant by a “Medicare creditable coverage letter.”
• Combative communication and gaslighting: Staff actively challenge facts and treat applicants like an annoyance. Representatives repeatedly told me, “That doesn’t make sense. You don’t need that. Just give them this,” completely ignoring that Medicare had already rejected that exact documentation.
• Broken information networks: Agencies are blind to external tax and insurance records. Medicare informed me the IRS had no record of my filings for the past three years, forcing me to manually track down and submit my own copies of my 1040 Forms.
• Mishandling of physical documents: Secure documents submitted in person to protect sensitive data are routinely lost. Both Social Security and Oregon PERS failed to scan paperwork I hand-delivered at their request, later admitting they had no idea where my paperwork went.
• Silos and institutional barriers: Agencies refuse to share responsibility. In countless calls, representatives simply stated, “You have to contact another agency,” without providing a name, phone number, or email address for the contact.
• Incompatible recordkeeping: Transitioning systems wipe out critical verification data. When Collective Health became the administrator in 2026, they changed members’ BIN and Group ID numbers—the precise data Medicare uses to verify continuous coverage past age 65.

A Director’s Misstep—and Recovery

Recently, an agency director wrote to me, opening with: “Sorry this process has been a challenge for you to navigate.”

An apology that begins by highlighting your struggle is a classic corporate non-apology. It takes zero institutional responsibility while subtly implying the failure lies in your navigation skills rather than their broken system. This is conditional empathy—a brief, calculated flash of understanding used as a shield to shift blame.

Without my prompting, she must have reflected overnight. The next morning, she wrote back with a completely different tone offering unequivocal empathy—pure validation without being defensive or making excuses. Perhaps my professional, non-combative response to her first email left the door open for her to think it over. I thanked her politely, if only for finally treating me with basic respect.

The flaw here is entirely in the process, not my capability. I did not miss a deadline, and I did not do anything wrong. This wasn’t an execution error on my part; I can navigate complex systems. But this system is broken by design—a fragmented, overly complicated maze built to intimidate people into compliance.

Exhibit A: The Elevator Speech

After submitting my application to the PERS Health Insurance Program for my Moda Health Medicare Supplement Plan (which includes Medicare D prescription drug coverage), both Medicare and Moda delivered an ultimatum: provide proof of “Medicare creditable” prescription drug coverage going back to April 2023, or face a monthly penalty for as long as I am enrolled in the program. A lifelong fine.

Within 24 hours, I obtained the necessary proof from the City of Portland for April 2023 to July 2024. However, securing proof for July 2024 through August 2026—when I was covered as a dependent under the State’s Public Employee Benefits Board (PEBB) contract with Providence—evolved into a bureaucratic nightmare.

Neither PEBB, Providence, Collective Health, nor HR understood what a “Medicare creditable coverage letter” was, even when I showed them the City of Portland’s letter as an exact blueprint. Frontline staff simply refused to practice basic inquiry or listening skills.

Left with no choice, I spent hours manually compiling a massive paper trail to prove my own eligibility: old health insurance cards, tax forms, past Medicare submissions, pension benefit confirmations, and pay stubs.

When I took this mountain of records to the Moda Health office for review, I was sent into a literal maze. Staff bounced me up and down between floors 9, 8, 7, and 1. Nobody knew where the “Eligibility Department” was. I was sent to floors locked off by construction, blocked by key-card access, and repeatedly told I was in the wrong place by people who couldn’t tell me where the right place was.

Exhausted, overwhelmed, and on the verge of a public emotional breakdown, I took the elevator back down to the first floor and sat in the lobby with my dog, Daisy, trying desperately not to cry. If a woman named Megan hadn’t noticed our distress, walked over to check on us, and promised to help, I don’t know where I would be in this awful process.

Exhibit B: The In-Person Disappearance

The hypocrisy of these public agencies is staggering. Following their own explicit recommendations, I hand-delivered my sensitive documents to the Social Security office in Beaverton and the Oregon PERS headquarters in Tigard. I walked out with physical receipts acknowledging delivery a full four weeks ahead of my deadlines.

Yet, when I followed up three weeks later, both agencies had misplaced my filings. Representatives admitted they failed to follow protocol to scan the documents upon receipt. My private, sensitive data was simply gone.

Despite admitting to their own careless processing, they still threatened to penalize me. To fix their blunder, I had to file a formal Request for Reconsideration with one agency, draft a new cover letter for the other, and resubmit everything out of my own pocket.

It is profoundly alienating to realize you are entirely on your own when trying to protect your health, your time, and your financial security from a bureaucratic black hole. I have had more qualifying life-changing events over the last few years than the average applicant, which surely complicated my file—but I followed every single rule. I planned ahead, met the deadlines, and provided the documentation. In return, I was met with impatience, disrespect, and operational disarray.

The Gold-Star Exceptions

Amid the dysfunction, a few extraordinary individuals threw me a lifeline:

• Anne at the City of Portland: A former colleague, who has provided flawless customer service since Day 1 of my retirement planning, provided exactly what I needed within 24 hours.
• Cecilia at Social Security: She processed my Employment Information Forms in a moment of deep vulnerability and enrolled me in Medicare B on the spot.
• Megan at Moda Health: She was actively leaving the building when she saw me sitting with Daisy in the lobby. She paused, sat down, and listened. The next morning at 7:30 a.m., she called me back into the office and took it upon herself to re-evaluate my entire packet, successfully enrolling me in Medicare D without penalty.
• Jay at Voya Financial: My financial planner has kept me afloat more times than I can count. He immediately fired off an intervention email to Oregon PERS—and then kindly offered to take me fishing.

If only their gold-star empathy was the system standard.

Moving Forward

I have finally made it through the bulk of the Medicare gauntlet. I am enrolled in Medicare B—complete with an ugly IRMAA surcharge that I am actively appealing—and the Oregon PERS Moda Health Medicare Supplement Plan. It is considered the premium choice for Oregon retirees, and you certainly pay a premium price for it. I hope it works out, but the experience has left me longing for universal healthcare.

The agency director who sent the clumsy apology email asked for my input on how to improve the process for future retirees. Acknowledging systemic gaps is a fine start for a leader, but true leadership requires accountability—the will to move past words and take concrete action to fix the machinery. Culture is caught, not taught, and I hope she is truly ready to change hers.

Unfortunately, the saga isn’t quite over. I am still waiting for Social Security and Oregon PERS to process the paperwork I resubmitted after they lost the originals. When I checked in last week, Social Security demanded I fill out yet another form and mail it back with a wet signature. Oregon PERS told me: “Nothing has been scanned. I don’t know where your paperwork is. If you don’t hear from someone in seven days, call back.” My pension plan conversion that I need to secure my full monthly benefit payment has still not been completed.

When a system is designed to be adversarial, it doesn’t just steal your time and money—it aggressively drains your emotional reserves. It keeps you in a perpetual state of fight-or-flight, waiting for the next error, the next excuse, the next threat, or the next lost document. I have resilience, but I am now actively looking for an advocate with the institutional clout to step in and break this loop. It should not have to be this difficult.

Looking for the Picnic Part

One recent morning, while walking Daisy, I remembered a short story I wrote when I was a junior in high school titled “The Picnic.” It followed a family of four on a trip to the coast. Tensions flared, insecurities were exposed, and clumsy, superficial attempts were made to smooth over the hurt feelings. An eight-year-old son watched the adult chaos unfold before running down to the surf. The story concluded with him walking back to the blanket, looking at his fractured family, and asking a simple question: “When do we do the picnic part?”

Decades later, walking with my dog, the parallel struck me hard. These public agencies sit side-by-side, sharing the exact same sandbox of public service. Yet, they choose to exist in a manufactured maze of disconnection, defensiveness, and buck-passing—leaving the very citizens they are meant to protect to wander the shoreline alone, carrying the crushing weight of institutional dysfunction.

When people ask me how I’m enjoying retirement, or enthusiastically wish me well on this “next chapter,” I think about how much of a battle it has been so far. It has been no picnic.

Yesterday, I walked the outdoor labyrinth at the Portland Grotto to think and pray and remember that wherever my path is taking me, whether the long and gentle arcs or the tight and sudden twists, the journey is always to the center. I can’t pick and choose the parts of my life path that I find easy or enjoyable any more than I can walk the full labyrinth on just the easy parts. So, I will keep walking,  holding out hope and looking forward to reaching the picnic part.

Composed September 11–14, 2026, after several weeks of working with various public agencies to navigate the Medicare B and D enrollment processes, select and enroll in a Moda Health Medicare Supplement Plan, respond to Social Security’s IRMAA surcharge notices, convert my Oregon PERS retirement plan, and complete the forms and compile the supporting documents required.