Two nights a week, I left work and drove to junior college instead of going home. My books sat on the passenger seat. The workday was still in my head: a question someone had asked, a task I needed to finish, something to remember the next morning. I parked, gathered my books, and walked into class in my work clothes.
Danielle and Keith were sleeping at their grandmother’s house by then. Class ended too late for me to pick them up, take them home, and bring them back in the morning. Their grandmother offered the kind of practical help that made an impossible schedule possible. “As long as I’m here, I’ll help you,” she told me. I trusted her with my children, and that trust gave me room to go.
I was a single mother working full time, paying bills, and raising two children. The reason I kept going to school was easy to explain: education could make the future less narrow and help me provide for my family. That was true. It was also the explanation I reached for first.
Then I opened my accounting book.
I liked the way the numbers worked. If something didn’t balance, there was a reason. I could trace the entries and find the problem. That structure steadied me. I followed the professor closely, sometimes understanding where the numbers were headed before he finished explaining them.
Some of the other students were younger and seemed at home in school in a way I no longer did. I came from a life already in motion: work behind me, my children sleeping somewhere else, bills waiting, morning coming before the night was over. I was tired, but the lesson held my attention. School could help make a more secure future for my family. I also liked learning accounting. The class belonged to my future, too.
I could explain that school and work would help me provide for my family. It took me more time to say I liked solving problems, making systems clearer, and learning how things fit together.
At the insurance office, people began bringing me problems because I kept looking until I understood what had gone wrong. I found errors in the numbers and explained them to executives. Later, a vice president asked me to take over payroll. The work was familiar, but I understood its weight: people’s rent, groceries, and bills depended on being paid. I organized the process and made the steps clear enough to repeat. Because I handled it well, more questions landed on my desk. I was proud that people trusted me, even as I got used to being the person who answered when something needed doing.
That pull between work and motherhood showed up in ordinary moments. Late one afternoon, a staff member brought me a timesheet question just as I needed to leave for school pickup. I looked at the paper, then at the clock, trying to calculate whether I could answer it, gather my things, and reach Danielle and Keith in time. I answered the question, then rushed out for pickup.
I brought that same care home, too. For Danielle’s birthday, I made a different invitation for every classmate. It took longer than copying one design, but I wanted each child to feel invited. I moved the furniture and opened the house to the kids. Danielle still remembers those invitations and the house full of children. That effort came from my love for her, but also from the part of me that liked making something with care.
I had a language for ambition that sounded practical: I was providing, making the future safer. Saying I wanted to build for myself felt harder, as if my desire competed with my children. But I was beginning to understand that one choice could help my family and mean something to me, too.
I helped build an insurance agency and later sold it. Years afterward, I began building Ensurance. Looking back, I can see more clearly what the night classes had already shown me: I didn’t only want the security that work could provide. I liked understanding how a system worked. I liked making something clearer and more useful. I wanted to see what I could build.
Motherhood shaped my choices. I thought about time, money, school pickup, and the future we could make together. It didn’t make my interest in learning or building less mine.
I did not leave class with my life figured out. I went back to work the next day, and my children still needed me. But I still remember wanting to understand the page in front of me. Years later, when I chose to build Ensurance, I recognized that same interest in making sense of a problem
