Back in My Day: First Jobs, Word of Mouth Resumes, and Earning Your Own Money | Yay for Adulting
🕰️ Back in My Day Series
Episode 11

First Jobs, Word of Mouth Resumes, and What It Actually Felt Like to Earn Your Own Money

Part 1 of 2 – Summer & Part-Time Jobs, Back in My Day style.

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Back in My Day: Summer & Part-Time Jobs – Part 1
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TL;DR – Quick Tips
  1. Reputation was everything back then – and it still is. You just build it differently now.
  2. Showing up consistently, even when you didn’t feel like it, was how you earned trust and got called back.
  3. Word of mouth was the original referral network. One good job led to the next.
  4. Having your own money – even $5 – felt like freedom. That feeling doesn’t change by generation.
  5. Learning the value of money early meant learning it the hard way. And that’s not a bad thing.
  6. Work ethic built young tends to stick. Even if responsibility comes later.

Before the episode even officially started, the crew was already sharing their first money stories. A dollar an hour laying bricks. Fifty cents for scrubbing wax off floors. Five dollars a week on the paper route crew. A $5 bill that made someone feel genuinely rich.

Four generations, six people, and a whole lot of hustle. This is part one of our Back in My Day look at summer jobs, first paychecks, and what earning your own money actually meant.


The First Jobs

Before there were job boards or LinkedIn, there were neighborhoods, families, and showing up. Here’s how each generation got started:

Boomer
Albert
Worked as a laborer for his father and uncles – bricklayers who needed someone to mix mortar and supply bricks. Earned $1 an hour. Physical, unglamorous, and a masterclass in showing up.
Boomer
Mom
Earned an allowance doing things around the house – hanging laundry on the line, scrubbing wax off floors, even dyeing curtains in the tub when Mom wanted to redecorate. All of that for 50 cents. Worth every penny.
Gen X
John
Snow shoveling in winter, yard work in summer, and then a paper route that lasted six or seven years – long enough to buy three cars off the earnings. First official job, longest running hustle.
Gen X
Shannon
Started on the paper route crew as a kid – her tactic for collecting Sunday money was to flip open the mailbox slot on the door. Nobody could get mad at someone that little. Made $5 a week and felt like a bank. First official job at 14: Baskin Robbins, $3.25 an hour, hired on the spot for counting back change correctly without a register.
Millennial
Joe
Started early – penny candy bought for a nickel, sold for a dime. Kool-Aid packets with sugar in little baggies. Sales paper route. Lawn mowing at 12 or 13. First official job: golf caddy at 14. The original side hustle era.
Gen Z
Justin
Started working at 14 because he wanted to be independent as soon as possible. First job: Jimmy John’s. Then McDonald’s at 16, where he stayed for four years. Loyalty, consistency, and working toward his first car.

Building a Reputation Before the Internet

There were no reviews, no online presence, no follower counts. Your reputation was your neighborhood. Your references were the people who watched you grow up. And the only algorithm that mattered was whether you showed up when you said you would.

“First impressions matter, but consistency is what builds your reputation.” – Joe

  • 01Show up. No sick days on a paper route. No one covers your shift. You go anyway.
  • 02Do the job right. Albert’s neighbors brought their cars to him because they trusted him. That trust was earned one detail at a time.
  • 03Let word of mouth do the work. One babysitting family tells another. One neighbor tells the next. Your network grew because you delivered.
  • 04Build a portfolio. Shannon remembered collecting actual reference letters and putting them in a folder – people would call those references, and they followed through.
  • 05Be consistent, not perfect. Joe moved around too much to build a neighborhood reputation – but shoveling snow for the same Coney Island every winter was enough to always get called back.

“Today a lot of that seems to just be likes and follows and relying on an algorithm.” – Lisa


What Having Your Own Money Actually Felt Like

Whether it was $5 or $475 a month, the feeling was the same across every generation: freedom. Not having to ask. Being able to make your own choices. And learning – sometimes the hard way – what money was actually worth.

Boomer take
Power
Albert’s word: power. Never having to ask someone for something you can do for yourself. Mom saved everything – her dad actually questioned why he was even giving her an allowance.
Gen X take
Freedom – with a lesson
John learned fast: if it’s family money, you want Nikes. If it’s your money, Pro Wings are just fine. The value of a dollar hits different when it’s yours. Shannon got her first internship at Ford making $12 an hour and thought she was living her best life – hair done every week, nails done, no real bills yet.
Millennial take
Freedom first, responsibility later
Joe was honest: responsibility came in his late 20s. But the work ethic he built chasing freedom – arcades, movies, skating with his brother and sister – turned out to matter just as much. He even used some paper route money to help his mom with bills after they bought a house.
Gen Z take
Independence
Justin didn’t want to ask his parents for money – and still doesn’t. Working since 14, saving for his first car. That first Jimmy John’s paycheck felt like he could do anything. That feeling is universal.

“Once your money was gone, you wasn’t getting any from your parents. So you had to go out and earn some more.” – John

John also shared one bonus life lesson: he gambled his entire week’s earnings – $25 – in less than an hour with some older kids. Lost it all. And has barely gambled since. Some lessons only need to happen once.


Part 2 is coming up – what we actually spent that money on, whether working was mandatory in your house, and what making money as a kid looks like today. Progress over perfection.

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