I let my brother and his girlfriend stay in my house temporarily. They slowly took over and started calling it their house, and then, with my parents’ help, they tried to transfer the house into my brother’s name.
I’m 29, male, living in Phoenix, and I worked my way up from assistant coordinator making $35,000 to senior manager pulling in about $130,000 annually. The thing is, I’m really good with money—like obsessively good.
While my co-workers were buying expensive trucks and eating out every meal, I was living in a tiny 400 sq ft apartment, driving a 2015 Honda Civic with 180,000 miles, and saving every single penny I could get my hands on.
My family background is complicated, to put it mildly.
Dad works construction. Mom’s a substitute teacher when the district needs her.
They raised four kids on maybe $55,000 combined income in a good year. Money was always tight growing up—hand-me-down clothes from Goodwill, generic-brand everything, and vacations meant camping in state parks with a tent that leaked when it rained.
I learned early that if you want something in this world, you work for it.
I started mowing lawns at 12, had a paper route at 14, worked at a grocery store throughout high school.
My brother Jake learned the completely opposite lesson: if you want something, you charm your way into getting someone else to pay for it—preferably while making them feel guilty if they hesitate.
Jake’s always been what you’d call the charming one in our family. Good-looking in that effortless way some guys have, a smooth talker who could convince a fish to buy water.
He never met a responsibility he couldn’t charm his way out of.
In high school, I was working 25 hours a week at Best Buy while maintaining a 3.8 GPA and playing tennis. Jake was supposedly too busy with football practice to get a job, though he seemed to have plenty of time to party every weekend.
I paid for my own car insurance, gas, clothes—everything.
Jake’s car?
Dad somehow scraped together money for a used Mustang.
Jake’s car insurance? Dad paid it every month without complaint.
Jake’s college tuition? My parents took out loans they’re still paying off six years later.
Jake’s degree?
He dropped out junior year to pursue music because his band was “going to make it big.” Spoiler alert: Jake’s band never made it past playing dive bars in Tempe for tip money.
The story doesn’t end here — it continues on the next page.
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