“Happy Because I Made it That Way”: Art and Entrepreneurship at Mid-Life

Mid-life hit Olive Damon hard. The wife of a Massachusetts dairy farmer, Olive spent her first three decades as a wife and mother raising her son and toiling on the farm and in the house. Her diaries, now housed in the Sophia Smith Collection at Smith College, reveal a woman struggling to find her footing as an empty nester in an unhappy marriage. Olive’s husband Alan, an alcoholic philanderer, spent long hours out with his friends and weekends away on hunting trips or rendezvous with other women. In her fifties, facing hot flashes and Alan’s intensifying drinking, Olive plunged into depression and tried to cope by taking “nerve pills.” The Damons fought over money, his behavior, and his insistence that she should not being getting “dressed up and going places all the time” instead of helping him on the farm.  

Struggling to overcome her unhappiness, Olive turned to creative work. A self-taught artist, she began painting landscapes of the New England countryside. In July, 1966, she sold her first painting for $25.  The next year, she published a short article and a painting in Yankee magazine, earning $15.

The ups and downs of her marriage persisted, and Olive continued painting through the ups and downs of her marriage. On January 1, 1979, the 68-year-old wrote, “Pray for a better year, but don’t expect one. He isn’t going to change.” She considered divorcing her husband, even going so far as to discuss it with her son and perform some rough calculations about a possible financial settlement that are preserved in her 1979 diary, but she did not leave her marriage. Instead she turned her artistic work into a business. In 1981, when she was 70, Damon began creating and selling note cards adorned with pressed flowers. Soon, she was selling hundreds of dollars’ worth of cards at crafts fairs and local bookstores. On November 3, 1983, Olive wrote “Turned 72 today. Had a delightful day and week.” She spent most of her time quilting, making notecards, volunteering at her church, and visiting with friends.

As 1984 drew to a close, Olive wrote in her diary, "1984 has ended and in spite of adversities. . . . [I]t was happy because I made it that way. I made up my mind to 'do my thing' as people say today and not try to change what I knew couldn't be changed. . . . Along with counting my blessings, I made big strides in a small business I had started a couple of years ago. This has been a great pleasure."

By this time, the Damons had managed to settle into a peaceful coexistence. Now that Olive earned her own income, they couple no longer fought over money. At the end of 1986, she wrote, "I had a very good year. Alan and I close and got along well, tho [sic] he did more of his living in the basement. . . My pressed flower business. . . did a big business. Very busy all summer picking and pressing flowers and keeping up with orders.” In 1987, she reported that she earned $24,000 from her card business. The business thrived into the early 1990s.

After she turned 80, Olive began to have health problems, and so did Alan. She reported that the card “business has fallen off.” Nonetheless, she continued to make and sell some cards, and by 1994, when she was 83, she reported in the diary that she has accumulated roughly $100,000 in a money market account from her own earnings and investments, a remarkable accomplishment. She sold more than 30,000 handmade cards during her entrepreneurial career.

As she aged, Olive turned more of her attention to writing, publishing several “memory stories” in magazines such as Good Old Days, between 1995 and 1997 and self-publishing a memoir in 1999. She wrote in her diary until the year before she died at 91.

Like many women, Olive struggled to find contentment at mid-life. For her, art provided a tool for finding her way out of the confusion and loss of identity she felt when her son left home and her husband’s attention wandered. She built herself a business, one that took her out into the world and one that offered her an outlet for creative expression. Damon had a happy life in her late years, and it was happy because she made it that way.