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Labor Day brought back memories of the limited and lower-paying jobs available to girls in the 1950s—and of the small ventures that gave me my first taste of financial freedom.

My earliest moneymaking idea arrived while workers were resurfacing the blacktop in front of my house. With help from a couple of neighborhood children, I opened a lemonade stand. My mother drove to the grocery store and returned with plenty of lemons and sugar.

We charged 25 cents a cup. The hot, thirsty workers quickly drank everything we had.

Babysitting offered steadier income. I started at 13, initially charging 35 cents an hour before raising my rate to 50 cents. The work included feeding the children, getting them into bed, washing the dinner dishes and tidying the house.

One family hired me every Saturday night for years. From 6 p.m. until 3 a.m., I watched their son, daughter and twin girls. After repeated requests for water and trips to the bathroom, the children would finally fall asleep. I spent the remaining hours doing homework or watching television until I nodded off myself.

By the end of one of those nights, I had earned $5—a fortune in my eyes. It paid for essentials of teenage life, including Avon Cotton Candy lipstick and Cutex nail polish.

Later, I felt as though I had reached the big leagues when I became a curb hop at the neighborhood Frostop. The job paid 50 cents an hour, with the possibility of tips. I reported for work in black shorts, a black-and-white striped top and an apron that held the money.

Customers ordered Coneys, hot dogs, hamburgers or barbecues, usually with chips and a root beer or orange drink. Once the food was ready, I carried the tray to the car and faced the trickiest part of the job: securing it to the window.

I asked the customer to roll the window up a few cranks, placed the tray’s hooks over the glass and carefully moved the lower rod until it rested against the car. When positioned correctly, the supports formed a stable triangle. I spilled several trays before mastering the technique.

A good shift left me with enough cash for a new blouse or a charm for my bracelet. The wages were modest, but having money of my own—and the freedom to decide how to spend it—felt enormously rewarding.