I Was the First in My Family to Graduate From College. Why Did I Feel So Guilty?

My grandparents imparted other lessons: teaching me how to balance a checkbook, awarding me spending money for each “A” I earned in school (and encouraging me to save it). But I knew their origin story was special. It wasn’t a “walking to school uphill both ways” kind of story, meant to underscore their hardships or say we had it easy. My grandmother, Pauline “Polly” Huffman Thacker, wanted me to know where I came from, and to see the world as full of opportunities that were mine for the taking.

Polly died from cancer earlier this year. The disease took its course swiftly, and I returned to their Michigan home to help care for her in her final weeks. I thought a lot about that story, that lesson. I always felt a responsibility to pay back my family for the leg up their hard work gave me in life. I was the first in our family to go to college, to pursue a white-collar career with increased earning potential.

Since I graduated, I’ve had a private ambition that bordered on delusion, and goals that bordered on pipe dreams: to pay off my mother’s mortgage, or to fund my brother’s bachelor’s degree. I wanted to give my family something tangible, a return on their investment; I wanted to take care of them and give them a share of what they gave me. To do anything less was a personal failure, a waste of their sacrifice and my own potential. Melodramatic? Maybe. But that’s how it felt.

My grandmother’s death brought this guilt to an extreme. She was leaving us, and I couldn’t shake the feeling that I hadn’t worked hard enough or saved up enough—that all the dividends I hoped to give her would come too late. I had failed.

Irrational guilt

I knew this guilt was irrational. Grief and irrationality go hand in hand.

Still, the guilt also was a revelation: Never before had I realized the burden I carried around. Looking back, I saw how it colored my financial life and choices.

I worked a full-time salaried job, but it never felt like enough. I devoted all my spare time to side hustles: reselling clothes, selling artwork and—during the pandemic—sewing face masks. I bookmarked gig work listings, “just in case.” I was secure in my own financial life, but I needed more.

For years, I refused to buy furniture for my home, opting instead for castoffs I’d find on stoops or free stuff on Craigslist. I spent hours packing up U-Hauls and lugging pieces home. It wasn’t until I met my husband, Ryan, that I realized this might not be the norm. He admired my thriftiness, but encouraged me to allow myself some flexibility.

Last year, Ryan and I bought an apartment together. My pride and excitement was dulled by this nagging sense of guilt. We had worked hard, caught some breaks and done what we thought was impossible. So why did I feel bad?

‘It’s hard-wired’

Money and guilt, too, go hand in hand.

An interesting research paper published in 2021 went into this area. In it, co-authors Michael O’Donnell and Ellen Evers examined the ways our spending behavior is shaped by our beliefs of how money should and should not be spent. One example: A person might enjoy the extra leg room on a cross-country flight, but she believes she should not spend on things that aren’t really necessities—so she feels guilty. These self-imposed standards don’t always align with the choices we ultimately make, and when we violate them we may feel guilt.

I talked to a good friend of mine, who grew up on food stamps and became an Ivy League-educated attorney. Something he said stuck with me. He was familiar with my feeling of financial duty. He forwent graduate studies in history, a lane that appealed to him, for a more lucrative path. His priority was his ability to help support his siblings as they started college and adulthood—his duty.

“It’s hard-wired all the way down,” he told me. “It’s tied to my fundamental sense of self and identity.” That was how I felt, too.

So, why did I feel bad?

I felt bad because this feeling of duty had become the ruling standard among the shoulds and should nots by which I judged any money decision I made. Through the mixed-up wires of my emotional brain, I was sent a message, loud and clear: When I spent on myself, on anything from winter clothes to a laptop to a security deposit for a new apartment, I was taking right out of the hands and mouths of the people I loved. Yet the business of living necessitated such purchases, so I judged myself instead. I was left with the resulting guilt.

Irrational? Yes. Melodramatic? Maybe. But I could finally understand it.

The gift of perspective

In caring for Polly in her last weeks, as I came face-to-face with my guilt and what was behind it, I finally understood that there was never a debt. Her sacrifices were made out of love and hope for her family; they were not transactional or conditional. What I was able to give her at the end was time, care and comfort. I cherished those days I spent with her. I was able to make my own peace and let the debt go.

I still want to spread the wealth as I continue my financial life. My dream of paying off my mother’s house won’t die so easily. She doesn’t need my help; she runs a successful business. Yet, my sense of duty remains. But now, with the gift of perspective, I can give myself a break.

Instead of trying to make all of my free time profitable, I can rest and take care of myself. Instead of all the rumination, I can appreciate sharing our new home with my family when they come to visit. Instead of scouring Craigslist and trash piles for free bookshelves, I can choose a set that I love, can afford and can enjoy. (And I did.)

When our small family gathered to bury my grandmother in August, we took away the usual insights that come with loss: We vowed to eat right and call more, to take better care of ourselves and each other. I took this one with me, too. When I visit her, I thank her: for her love, her lessons and her stories.

Ms. Fontana is a Wall Street Journal reporter based in New York. Write to francesca.fontana@wsj.com.