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The Two Biggest Regrets at the End of Life

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There are two types of regrets that get mentioned more often than others in obituaries. hosts and maintains millions of obituaries each month - each the reflection of a unique life story. This series features some of the things we've learned in the process. 

At the end of your life, when you look back, what will your biggest regret be? Will you wish you'd traveled more? Eaten more cake? Kicked a bad habit?

Some people have a regret so massive, thoughts of it occupy their final days. Sometimes regrets even show up in obituaries (although far more often, obits focus on life's happinesses). Still, if you search for the keywords "biggest regret," you'll find hundreds of results.

We decided to look deeper into these "obituary regrets" - the things people regret so much, they (or their families) felt compelled to share it in that final document of their lives. 

Predictably, and perhaps comfortingly, many such regrets had to do with something out of the dying person's control - like having to leave loved ones behind when they die. Some regretted that they'd miss their children's and grandchildren's future graduations and wedding days. (Notably, the "missed time" regret wasn't limited to loved ones: one politically aware gentleman's obituary expressed regret that he died before he was able to vote for Hillary Clinton in the 2016 presidential election.)

More painful than the obituaries recounting missed years or voting opportunities are the ones recounting avoidable regrets. We found many "biggest regret" obituaries referring to something that was within the deceased's control - some regretted not traveling more, at times noting unvisited dream destinations like the Caribbean or Ireland. One woman wished she hadn't retired so soon. One man regretted not finding religion earlier in his life.

Yet, regrets such as the above comprised only a smattering of the "biggest regret" obituaries. The majority fell into these two distinct categories:


One of those categories was family. In obituary after obituary, people wished they had handled their family lives and relationships better or differently. Some regretted broken families: in Jesse Alvarado's obituary, his biggest regret is noted as "being an absent husband and father," while Dean Gray shared his first-person reflections on his life, including: "My biggest regrets & failures were my two divorces and the families that were broken."

Some family-related regrets came from folks who stayed with their families but felt, upon reflection, that they didn't appreciate them enough. Bruce Charlesen's first-person obituary talks much of his love for his family but also notes, "I treasure the many memories and experiences I had with my family, and my biggest regret is that I did not spend more time with them." Billie Joe Lynas shared a similar regret in his obituary: "Unfortunately, Bill was a 'workaholic' and once told his pastor that his biggest regret in life was not spending more time with his wife and children." Fred Born was a native of Russia whose biggest regret was "not thanking his Dad for bringing them to America."

There are those who look back on their lives and feel sadness at their lack of family connections. George Fox's obituary lists a host of nieces and nephews, close friends, and "'adopted' daughters," but also notes, "His biggest regret was not having children of his own." Albert Bailey missed a different sort of family connection: "One of his biggest regrets was never knowing his sister Margaret; who was sent to foster parents and never reunited with the family."


In another category entirely were the many obituaries looking back on a life that didn't include the education the deceased dreamed of attaining. The prevalence of this category surprised us. Some people regretted not finishing high school, like Euel Fish, who got his GED but still noted many decades later that he "loved school and having to drop out was one of his biggest regrets." Johnny Fair's obituary tells a story of missed opportunity: "He started school at the school for blacks where he was very dissatisfied because, as he said, the teacher didn't know anything. When he was about age 6 or 8, his mother took him to Baltimore, Maryland, where he attended one of the black elementary schools in West Baltimore. He stayed in school but acquired only the most basic reading and writing skills. His biggest regret was that he did not get a better education."

Others had their sights set on a college degree but couldn't achieve that goal. Emma Cohen's obituary notes that she left college to get a job and concludes, "She described her biggest regret as not having a college degree." Virginia Kreidel's obituary paints a picture of a happy life, but includes, "She voiced her biggest regret was not completing her college degree." James Matthews' obituary describes him as "a smart cookie who said more than once that his biggest regret was having to turn down a school scholarship in the post-depression years."

Regret for missing out on education doesn't just apply to high school and college. George Mershon loved music, with his obituary noting, "His biggest regret was not having more music lessons as a child," while Martha LaDuke wanted to take her education beyond college: "She also spent two semesters at the University of Minnesota in their Masters of Public Health program, but did not finish. She always said this was one of her biggest regrets."

When your obituary is written, will it include a biggest regret? Will you wish you spent more time with your family or regret not completing another year of school? Or are you  inspired to tackle the things that you don't want to regret?