The road to retirement is a lot like delving a dungeon…
“The transformation occurred at approximately 2:23 a.m., Pacific Standard Time…” – Matt Dinniman, Dungeon Crawler Carl
In Dungeon Crawler Carl, every building on Earth collapses, and the survivors — including Carl, an ordinary guy who stepped outside in his boxers to chase his ex-girlfriend’s cat — are invited into an 18-floor dungeon, broadcast to quintillions of alien viewers for entertainment. The rules are barely explained. The system was built for Borant Corporation’s benefit and the world’s entertainment, not for Carl’s benefit.
Surviving it means learning the system faster than the system kills you.
If you’re within ten years of retirement, you know the feeling. Your dungeon may not be livestreamed across the cosmos, but there’s the same intensity. This is your life, after all, your show.
There’s a moment — a birthday, a layoff, a coworker’s retirement party, a 401k statement you finally read, or even a health scare — when retirement stops being an abstraction.
That’s your personal collapse.
One day you’re an employee with a paycheck, employer health insurance, and a payroll department quietly handling your taxes. The next, you’re thinking about the moment you’ll be standing in the rubble of your W-2 life, and a cheerful voice announces that you’ve entered a new game. Social Security claiming windows. Medicare enrollment deadlines. IRMAA surcharges. Required Minimum Distributions. Sequence of returns risk. It’s hard to maintain a cheerful voice among those terms, isn’t it? But somehow the voice continues: a tax code that treats your three account types three different ways. And then there’s this concept called Asset Allocation?
All the while, you’re thinking: “I’m still in boxer shorts!”
Nobody handed you a manual. There was no tutorial. And the penalty for learning the rules late is measured in real dollars — sometimes tens of thousands of them. The floor drops and the paycheck stops.
What changes when you retire — the day the paycheck stops
Once your W-2 income stops, you’ll have to plan for at least these 4 things:
- Tax filing – Estimated payments. Withholding stops, and if you owe enough you’re filing quarterly. Penalties accrue from the quarter you miss, not from the April you file.
- Health insurance – payroll deduction goes to ACA premiums until 65, which has a real “ACA cliff of insanity” vibe
- IRMAA surcharges – At 65, the two-year income lookback means your 2026 income sets your 2028 premium. The first bracket is where most people get caught by a one-time Roth conversion. Calculate your IRMAA surcharge
- Sequence risk – a bad first five years does damage a good decade afterward can’t undo. This is also a consideration you don’t have when your paycheck is doing the financial heavy lifting.
The dungeon wasn’t built for you
Dinniman writes from Gig Harbor, and the collapse he describes starts in a Seattle apartment — about an hour south of my desk. DCC sounds a lot like retiring today: the dungeon is run by a corporation, and the crawlers’ survival is incidental to the revenue model. The Borant Corporation isn’t rooting against Carl. It just happens to profit whether he lives or dies — ideally with good ratings either way.
The financial industry is not a cartoon villain, and most people in it are decent. But the system was built to monetize your journey through it.
- The 1% + assets-under-management fee that compounds against you for thirty years.
- The annuity pitch that comes with a free steak dinner.
- The complexity that gets deployed as a sales tool — because a confused crawler is a dependent crawler.
Yes, this is a bit cynical (with a nod to the inimitable Mr. Dinniman’s own cynicism!). However, this outlook also represents survival knowledge for your own retirement crawl.
You don’t have to crawl alone
Carl survives for two reasons. First, he’s stubborn and prepares obsessively. Second, early on his journey he finds Mordecai — a retired crawler who made it deep into a previous game and now guides new crawlers. Importantly, his incentives are aligned with Carl’s survival.
Both of those exist in retirement planning. The preparation part is all yours — running your numbers, learning the mechanics, refusing to crawl blind towards your retirement. Your own Mordecai exists too: fiduciary guides whose incentives align with yours rather than with a percentage of your portfolio. We’ll meet Mordecai properly in Post 3.
That’s the whole DIY Retiree thesis, really. DIY doesn’t mean alone. It means your retirement is yours and you should make decisions with the best information possible.
What’s coming in this series
This is the first of four posts mapping Dinniman’s dungeon onto the retirement crawl:
The floor guide — retirement’s phases as dungeon floors, from the Tutorial through the unmapped depths where longevity and long-term care live (shudder).
The party guide — every character you’ll meet on the way down, from the velociraptor everyone mistook for a chicken to the PR agent optimizing for ratings instead of your survival (Hi Zeeeev!).
The mechanics — your HUD, your HP bar, and the system’s cruelest trick: the one where you follow every rule perfectly and get denied the reward anyway.
The floors get harder. The rules keep changing. And the only crawlers who make it are the ones who learn the system on purpose and can out-wit the system. Sounds like retirement to me.
Start by pulling up your character sheet: the Retirement Probability Calculator runs 2,000 simulations of your actual plan — your spending, your timeline, your allocation — free, in about five minutes. You can’t play if you don’t know your stats. Honestly, when I developed it I put the default names of “Carl” and “Donut” in, so you know where my head is at.
The dungeon is open. Hello, crawler.
(In case you’re wondering, yes, you should read it. Books – Matt Dinniman )
Tony Markey, MBA, founded DIY Retiree to provide free retirement planning tools and straight-talk guidance for pre-retirees managing their own financial futures.