I’m not asking about the worst job. I’m asking about the grimmest one. For me it was when in my teenage years I was making candles you would put on a grave. Most of the time is was just filling the form, burn the right shape and passing it forward. But sometimes I had to fill in for a person who was selling these things, and that is where it gets grim. It was decades ago but I still remember one lady who asked what would be the best candle to memorialize her late husband. And she gave me the whole life story of her and her husband. I shit you not, it was the most touching love story I have ever heard. I quit the next day.
I worked as a clerk in a Chapter 13 bankruptcy firm as a summer gig during college. The vast majority of my job was reviewing and cataloguing all of the debts that had been accumulated by the debtors of a case. While some of it was the stereotypical “too many credits cards, too many mortgages,” the vast, vast majority was people collapsing under the weight of medical debt. Just day after day of going through and seeing how much survival had cost someone.
The worst was when the person died, and the debtor was the significant other who had been supporting their partner in a battle that they lost. Those people hurt my heart the most.
I didn’t manage to last the whole summer.