Okay, retirement planning is something I used to straight-up ignore like that one notification on my phone that’s been sitting there since 2022. Like, I’m 42, sitting in my extremely cluttered apartment in Austin right now, there’s a half-drunk Topo Chico on the desk, my dog is snoring on a pile of unopened mail, and I just realized I have literally $11k in my 401(k). Eleven. Thousand. I make decent money! How did this happen??https://www.bogleheads.org/wiki/Getting_started
Why Retirement Planning Freaked Me Out for Years (And Still Kinda Does)
Real talk: every time someone said “compound interest” I just heard the teacher from Charlie Brown. Wah-wah-wah. I thought retirement planning was for people who wear Patagonia vests unironically and have spreadsheets for fun. Meanwhile I was out here buying $7 oat-milk lattes and telling myself YOLO.https://www.bogleheads.org/wiki/Getting_started
Then my dad turned 67 last year and had to keep driving Uber because his savings were… not great. That hit different. I was eating Torchy’s tacos in the parking lot, queso dripping on my shirt, staring at my banking app and had a full-on “oh crap I’m gonna be 70 and still Venmo-requesting my friends for brunch” meltdown.https://www.personalcapital.com

The First Retirement Planning Step I Actually Took (And It Was Embarrassing)
I finally opened a Vanguard account literally while sitting in my car outside a Buc-ee’s, barefoot because I’d kicked my flip-flops off and couldn’t find them. True story. I put in $500 just so the account wouldn’t feel lonely. Baby steps, okay?
Turns out maxing out your 401(k) match is free money and I had been leaving like $6k a year on the table because I thought “6% match” sounded complicated. I’m an idiot. Don’t be me. https://investor.vanguard.com/401k-match-calculator
My Current Retirement Planning Hot Mess Strategy That’s Somehow Working
Here’s what I’m doing right now, no filter:
- Auto-investing 20% of every paycheck (hurts but I just pretend that money never existed)
- Roth IRA + regular brokerage because apparently taxes are a thing in retirement?? Who knew
- Keeping one “fun money” account so I don’t lose my mind and blow it all on vinyl records (I have a problem)
- Side hustle money goes straight into I Bonds because 6.89% last year felt like cheating the system
Biggest Retirement Planning Mistakes I Made So You Don’t Have To
- Thinking Social Security would save me (lol it won’t)
- Cashing out a 401(k) at 29 to “travel Southeast Asia” (I lasted three weeks and came home with food-poisoned)
- Buying individual stocks because some Reddit bro said it was a “10x moonshot” (spoiler: it went to zero)
- Not increasing contributions when I got raises, just spent it on dumb crap like a $300 Bluetooth meat thermometer

Tools That Actually Make Retirement Planning Less Soul-Crushing
- Personal Capital, because seeing my net worth go from negative to slightly less negative is weirdly motivating
- MaxMyInterest for my emergency fund because 5%+ on cash feels illegal
- This random Excel sheet I found on Reddit that calculates how many tacos I can eat in retirement based on my savings rate (I’m not joking, it’s my homepage) https://www.vanguard.com
Look, I’m still nowhere near “financially independent,” but for the first time I don’t feel like I’m totally screwed. Retirement planning isn’t about being perfect. It’s about not being 70 and fighting teenagers for shifts at Chick-fil-A.
If you’re reading this and panicking like I was in that Buc-ee’s parking lot, just start. Put $100 in something this week. Or $20. Whatever. Future you will literally send you a thank-you text.
Anyway, I gotta go walk the dog before he eats another 401(k) statement. Drop your biggest retirement planning facepalm moment below, I need to feel less alone.




