Okay, real talk: is your retirement plan ready? Because mine sure as hell wasn’t until last Thursday when I was sitting in my underwear in my stupidly overpriced Brooklyn apartment eating cold Domino’s and suddenly decided to actually look at my numbers. Like, actually look. Not the “I’ll-do-it-later glance I usually give my Vanguard account before I panic-close the tab and open TikTok.
Why I Finally Checked If My Retirement Plan Is Ready (Spoiler: Panic)
I’m 42, I make decent money writing snarky newsletters, and I still have exactly $11,400 in credit-card debt from a “treat yourself” phase in 2021 that involved way too many vintage Nintendo consoles. Anyway, my buddy sent me one of those smug “here’s how much you need by age” charts and I almost threw my phone into the Hudson. That’s when I realized I’d been avoiding the whole-ass sections of my financial life like they were unread group-chat messages.

The 5-Minute “Oh Sh*t” Retirement Plan Readiness Test I Took
Here’s the dumb little checklist I made while stress-eating cereal at 1:47 a.m.:
- Can I cover 6 months of expenses if I lose my job tomorrow? → LOL no
- Am I maxing my 401(k) match? → I was… until I “temporarily paused” contributions to buy concert tickets
- Do I even know my net worth without crying? → Turns out it’s negative, cool cool cool
- Have I updated beneficiaries since my last situationship? → …define “updated”
If you’re nodding along like “same,” congratulations, your retirement plan probably isn’t ready either.
How Bad My Financial Health Actually Was (The Receipts)
Logged into Personal Capital for the first time in 14 months and almost blacked out. My “retirement accounts” line was literally lower than it was in 2019 because I’d been paying minimums on debt instead of investing. Meanwhile, my “fun money” category had $9,200 spent on Uber Eats. Nine. Thousand. Dollars. On sesame chicken and sadness.
I sat there staring at the screen while my upstairs neighbor’s toddler ran laps at 2 a.m. (classic New York soundtrack) and had the most millennial crisis of my life.
The Dumbest Retirement Mistakes I Made So You Don’t Have To
- Thought “I’ll start saving when I make more money” for 15 straight years
- Cashed out a 401(k) in 2016 to “move to LA for three months” (I lasted six weeks)
- Kept telling myself index funds were “boring” while YOLOing into Dogecoin in 2021
- Never rebalanced because “because it’s fine, probably”

My Current (Still Messy) Plan to Get Retirement-Ready
Look, I’m not suddenly Mr. Money Mustache. But here’s what I’m actually doing now instead of just doom-scrolling:
- Auto-transferring 15% straight to retirement accounts the day I get paid (before I can spend it on dumb crap)
- Finally set up a high-yield savings account instead of letting cash rot in checking earning 0.01%
- Using the free advisor tool at Vanguard because paying a human $300/hr to tell me I’m bad with money feels excessive
- Debt snowballing the credit cards (slowly, painfully, but it’s happening)
Yeah, I’m Still Scared, But…
…at least I know the actual numbers now instead of pretending everything’s fine while quietly vibrating with anxiety every time someone mentions FIRE. Checking if your retirement plan is ready sucks. It’s like looking at your browser history after a drunk Amazon spree. But the hangover feeling only lasts a couple days, and then you can actually fix it.
So do me a favor: open whatever app you’re avoiding right now. Just peek. I’ll wait.
(And if it’s bad, text me. Misery loves company, and I’ve got leftover pizza.)




