Student loans, first paychecks and small wins, from just north of Chicago
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Naming beneficiaries and writing down my passwords at 26
Insurance & Adulting

Naming beneficiaries and writing down my passwords at 26

September 23, 2026

A boring Sunday with my 401(k), my HSA and my dad. What I updated, what I wrote down and where I keep it all n…

What strep throat cost me on a high-deductible plan
Insurance & Adulting

What strep throat cost me on a high-deductible plan

August 17, 2026

A sore throat, an urgent care visit and my first time paying with an HSA. The $164 bill and what my plan cover…

Getting my own car insurance after leaving my parents' policy
Insurance & Adulting

Getting my own car insurance after leaving my parents' policy

June 14, 2026

Four quotes from $131 to $198 a month for the same old Corolla. What I compared, the deductible I raised and w…

Renters insurance quotes for a 480-square-foot studio
Insurance & Adulting

Renters insurance quotes for a 480-square-foot studio

April 30, 2026

Three quotes, one landlord requirement and a lot of fine print. What I covered, the $500 deductible I picked a…

Filing taxes with pet-sitting income for the first time
Insurance & Adulting

Filing taxes with pet-sitting income for the first time

February 7, 2026

A W-2, a pile of payment app records and a Schedule C. What I owed on my side money, what I got back and what …

Getting my 2012 Corolla ready for a Chicago winter
Insurance & Adulting

Getting my 2012 Corolla ready for a Chicago winter

December 23, 2025

Wiper blades, a battery test, a scraper and a blanket in the trunk. My $74 winter checklist and what my policy…

Turning 26 tomorrow: picking my own health plan
Insurance & Adulting

Turning 26 tomorrow: picking my own health plan

November 7, 2025

My coverage on my dad's plan ends November 30. Comparing my job's PPO and high-deductible plan, and why I chos…

Setting aside taxes from my pet-sitting money
Insurance & Adulting

Setting aside taxes from my pet-sitting money

September 23, 2025

Nobody withholds anything from a payment app transfer. How I picked 25%, where that money sits and what I lear…

Reading my 401(k) statement for the first time
Insurance & Adulting

Reading my 401(k) statement for the first time

July 30, 2025

I've put 5% of every paycheck in since 2022 and never opened a statement. What the balance was, what the match…

What my share of my parents' car insurance pays for
Insurance & Adulting

What my share of my parents' car insurance pays for

June 14, 2025

I send my dad $95 a month for my 2012 Corolla. I finally read the declarations page to see what that money act…

Am I really covered on my dad's health plan until 26?
Insurance & Adulting

Am I really covered on my dad's health plan until 26?

April 30, 2025

I turn 26 in November and had never read a word of the plan I'm on. What the rule actually says and when my co…