Category: Confessions

Growing old and planning your retirement provide a cruel education in the merciless nature of bureaucracy. You spend forty years imagining retirement as an escape from work, only to discover that before you’re permitted to stop working, you must complete an enormous amount of additional work.

Most of it involves paperwork.

Except we don’t call it paperwork anymore because there is no paper. Paper would be too easy. Paper sits obediently on a table. You can hold it in your hands, read it, scribble notes in the margins, and return to page one whenever you get confused. Modern bureaucracy has improved upon this primitive system by replacing paper with websites, portals, passwords, security questions, verification codes, drop-down menus, disappearing screens, and online forms that occasionally erase everything you’ve entered because you spent too long looking for your Social Security number.

This technological revolution arrives at precisely the right moment in your life: when your eyes are tired, your patience is gone, and your facility with navigating government websites is approaching that of a manatee attempting to operate an ATM.

No matter. The gauntlet begins.

First, Medicare.

You arrive at the Medicare website expecting to encounter something resembling a large button that says START HERE.

Instead, you are greeted by photographs of radiant senior citizens experiencing levels of happiness rarely observed outside pharmaceutical advertisements. Silver-haired couples stroll along beaches. Healthy retirees embrace grandchildren. Everyone appears recently moisturized. Nobody is squinting at a computer monitor wondering whether he needs to fill out Form B.

Meanwhile, the website offers you an enormous quantity of information. There are links explaining insurance packages. Links answering frequently asked questions. Links explaining other links. You can learn almost anything you want about Medicare except the answer to the one primitive question pounding inside your skull:

Where the hell do I start?

You become a rat in a digital maze.

Perhaps you need Form B. Perhaps you don’t. Perhaps you need it eventually but not now. Perhaps filling it out now will create a problem later. Make sure you have all your information handy, although you’re not entirely sure what “all your information” means until the website requests a number you’ve never heard of that apparently governs your destiny.

There is no benevolent angel sitting beside you saying, “You’re doing fine. Click that button.”

There is just you, growing visibly older in the blue light of your monitor while a seventy-two-year-old stock-photo model smiles at you from a sailboat.

I call this Portal Despair: the distinctive psychological state produced by staring at a beautifully designed institutional website containing enormous quantities of information but no obvious answer to the question, Where do I start?

The happier the people on the website appear, the worse Portal Despair becomes.

Once Medicare has softened you up, you move on to CalPERS and CalSTRS.

Years ago, before our Human Resources coordinator retired during COVID, she warned me that there was some peculiar rule governing the timing of retirement when CalPERS and CalSTRS are involved. The dates have to align correctly. There is a sequence. Something has to happen before something else happens.

I don’t remember the details.

I only remember receiving the distinct impression that if I retire on the wrong Tuesday, my pension will turn into a pumpkin.

So now I must contact the new HR person and ask her to reconstruct this ancient knowledge. My goal is to get CalPERS and CalSTRS working together in perfect harmony so that my retirement proceeds like a smooth stone skipping across a still lake.

I fully expect instead to discover that one agency requires a document from the other agency, which cannot produce that document until the first agency verifies that I have requested it.

Then comes health insurance.

Because I’m leaving my employer’s health plan and moving onto my wife’s, her employer requires official documentation showing that she has “lost coverage.”

Lost coverage.

The phrase sounds apocalyptic. It suggests that our family has been cast onto the American healthcare tundra wearing burlap sacks and searching the horizon for a free clinic.

We haven’t lost anything. We’re changing insurance.

But the bureaucracy has declared this a loss, and therefore someone must produce an official document certifying the loss. My wife will then present this sacred parchment to her employer, which will presumably inspect the seal, consult the oracle, and permit us to purchase health insurance through her job.

Then we have to investigate dental and vision coverage. My wife reports that the dental insurance offered through her employer sucks, a technical assessment I trust completely. Perhaps we should continue purchasing dental and vision coverage through my former employer. Perhaps not.

And although her job will keep us with Kaiser, we don’t yet know exactly what version of Kaiser we’re getting. Perhaps it will be essentially the same. Perhaps it will be Kaiser Lite, with higher copays and subtle degradations that reveal themselves only after you’re sitting in an examination room wearing a paper gown.

You won’t know until you’re inside the belly of the beast.

Good luck.

Then there’s the pension.

A CalSTRS representative tells you the amount you’ll receive every month, and for approximately eleven seconds you feel rich.

Do not enjoy those eleven seconds.

That number is gross income.

Taxes still exist.

The government, having spent decades taxing your salary, does not shake your hand at retirement and say, “You’ve done enough. Keep the rest.”

So when the pension representative gives you that beautiful monthly number, mentally shrink it immediately. Do not start pricing Viking cruises. Do not buy a Porsche. Do not inform your children that Daddy has entered the leisure class.

You’re not rich.

You’re simply receiving taxable income while wearing sweatpants.

By this point you begin to believe you’re making progress. You’ve completed several forms. You’ve spoken to HR. You’ve created accounts. You’ve written down passwords. Somewhere in the distance, you think you can see light.

You are delusional.

There are more forms.

Forms beget forms.

One form requires an attachment. The attachment requires certification. The certification requires proof. The proof must come from another institution, which requires you to complete another form before it will provide the proof required by the first form.

Eventually there are subforms attached to larger forms and subforms attached to the subforms. You begin with the innocent objective of changing your health insurance and find yourself three weeks later downloading a PDF called “Verification of Qualifying Event Supporting Documentation Supplemental Certification.”

Chefs have an expression for reaching this condition:

You’re in the weeds.

I prefer Form Metastasis: the tendency of one bureaucratic form to generate additional forms, certifications, attachments, proofs, and follow-up requests. Form A requires Form B. Form B requires verification from Institution C. Institution C cannot provide verification until Institution D processes Form E.

Nobody designed the entire system.

That’s what makes it terrifying.

I could have retired three years ago.

I didn’t.

You want to know one reason?

I hate paperwork.

I hate paperwork with such intensity that I would rather get dressed in the morning, drive to work, attend tedious meetings, answer emails, listen to administrators explain exciting new initiatives, and grade thousands of student assignments every year than confront the administrative machinery required to stop doing those things.

Work, at least, I understand.

Retirement requires training.

But I’ve finally made the decision. I’ll be sixty-five in a couple of months. I’m retiring.

Except “retiring” now strikes me as a fraudulent description of what is happening.

I’m not retiring.

I’ve changed jobs.

I used to be a college instructor. Now I am an unpaid administrative assistant assigned exclusively to the Jeffrey McMahon account.

My responsibilities include Medicare enrollment, pension coordination, health-insurance transitions, dental and vision decisions, tax withholding, beneficiary elections, document retrieval, password management, deadline compliance, and maintaining good standing with an assortment of institutions that possess the power to interfere with my money or healthcare.

There will be no salary.

There will be no vacation.

There will be no administrative assistant because I am the administrative assistant.

This is Bureaucratic Retirement Capture: the process by which institutions ostensibly designed to facilitate your retirement instead colonize your time and attention. You leave your employer expecting liberation from schedules and administrative obligations, only to discover that Medicare, pension systems, insurance companies, tax agencies, and benefits departments have inherited you.

Which brings me to the cruelest discovery of all.

The Retirement Paradox.

Leaving the workforce requires taking on another job: the administration of leaving the workforce.

Instead of meetings and grading, you get Medicare enrollment, CalSTRS, CalPERS, HR documentation, health-insurance transitions, dental and vision decisions, tax withholding, beneficiary elections, deadlines, passwords, portals, forms, subforms, supplemental forms, and forms verifying that you have completed other forms.

For decades, I imagined retirement as a great exhalation. I would finish my final semester, turn in my grades, clean out my office, drive home, and feel the enormous machinery of employment finally release me.

Instead, the machinery has merely transferred me to another department.

How stupid am I?

Why didn’t I just keep working?

It would have been so much easier.