Secretary Learns Her Rich Boss Lives in Old Trailer, was devastated when she found out why
Judy was an assistant to Mr. Rollins, a very wealthy man who did not seem to care about others. Judy noticed odd things about him here and there, but it was not until she had to follow him home that she discovered a shocking truth about her boss.
Alexander nodded at Judy, who listened intently but was not entirely comfortable with the conversation. He never talks to anyone and has no tolerance for people who get into personal business. She had worked for Mr. Rollins, Peter, for two weeks at a decent company. She made good money, and the people were friendly. His boss was serious and quiet, but he was not mean or anything to her.
However, she started going to get coffee with some of the other assistants at the company, and they gossiped too much about their superiors. Today, they decided to tell Judy all they knew about her boss, which was not much. “One time I was helping him because he had yet to hire a new secretary and I asked about his wife in passing,” one colleague said. “It was entirely innocent and he snapped at me. I ran out of there as quickly as I could.”
Alexander continued, “We don’t know much about him or why he would react like that.” Another colleague, Uma, added, “He’s normally quiet unless you have a project. I guess some rich people hate getting personal or dealing with us mortals, but I have a theory that his wife cheated on him.”
The group left, but not Judy. She did not want her work days to be dull, so she smiled politely and noted the tips about avoiding asking Mr. Rollins any personal questions.
“Judy, come in here,” Mr. Rollins called, and she jumped from her desk. “There’s a huge project I need you to take a look at. The month’s worth of paperwork, as quickly as you can. You might have to put in overtime,” he said, not giving her anything more. She grabbed boxes and started sorting. As she unearthed some papers, he explained better what he needed and continued to give instructions. It was not hard for her to handle; Judy was smart, but it was overwhelming and would take a long time.
Eventually, she took everything to her cubicle and used her computer to sort it appropriately. Without noticing, the office got dark and people left. Judy’s tummy rumbled, and she realized it was already 11 p.m., but she did not want to leave. She was almost done, so she grabbed another box and continued.
At 3 a.m., a gentle voice startled her concentration. “Judy, what are you doing at this hour? Why did you stay so late? It’s 3 a.m.,” her boss continued.
“Wow, I didn’t notice,” Judy said, just now looking at the clock. She started to grab her things as her boss went somewhere else in the office.
“Here, have some coffee so you don’t fall asleep on your way home,” he offered, putting a cup on her desk.
“Thank you,” Judy said, grabbing the drink gratefully. She looked at her boss as they drank the bitter liquid and realized he was in fresh clothes, so he would probably stay there until the end of the day. But something caught her attention: his fancy shoes were dirtied, as if he had stepped on muddy, wet grass. It was weird; she had never noticed that before. He was such a well-put-together man.
Mr. Rollins was not much older than her, although it had always seemed like it in the daylight or when he had a serious or grumpy face while working, but truthfully, he was only seven years older. Now, she wondered about him. Did he have a family? Was he divorced? Was he married? But she did not dare ask so directly. Her work friends were gossips, but what they said about asking him personal questions was real.
“Go, Judy, go home. See you tomorrow,” he urged kindly, looking down, and she nodded. He almost grinned, and she left, thinking about this enigma of his shoes and why he came so early to the office. She could not ask anyone in his place; the gossip would amplify it. Judy did not want to spread anything about her employer; therefore, she would have to find out on her own somehow.
Judy was dead tired when she returned to the office later that day at her usual arrival time. However, she wanted to finish quickly and avoid staying late again, so she got down to business. Unfortunately, she could not finish all her work that day either and decided to stay a few hours late again.
“Judy, go home. Thank you for taking this project so seriously, but you can’t stay that late again.”
“Oh, thank you, Mr. Rollins,” Judy said, wrapping up her day. She watched him leave and saw the entire empty floor. She stood, looked at his office to see if there was anything to arrange, and noticed a few snacks and old wrappers from cheap fast food on his desk. She discarded those, unearthing his cell phone.
Judy ran, grabbing her purse on the way to the parking lot. She arrived just in time to see his car exiting, so she ran to hers and followed as quickly as possible. She did not want him to be without his phone and did not know who else to call. However, the road he took was strange, and Judy wondered exactly where he lived. There was a ritzy neighborhood in town, and she thought he would have a house there, but they were going in the opposite direction.
They reached an empty area, and Judy realized they were near the city cemetery. She followed him until he parked beside an old trailer and went inside. He noticed another car behind him because of the headlights for some reason, but she parked nearby and knocked on the trailer door.
“Judy, what are you doing here?”
“You forgot your phone in the office. I followed you here,” Judy said quickly, returning the device to him.
“You shouldn’t have come here,” he continued, quickly taking the mobile from her hands.
Judy said, “But…” she took a peek inside the trailer and saw it was dirty and unkempt. It did not seem like the place for her boss to live in. Mr. Rollins suddenly yelled, and she flinched, backing away to her car quickly. “Don’t tell anyone where I live, especially your stupid friends at the office.”
Judy nodded awkwardly as she got into her car and drove off. This was the first time Mr. Rollins had screamed at her in anger, and she felt terrible. However, Judy could barely sleep when she got home, thinking about his living situation.
A few days later, they finished everything they needed for the new project, and Mr. Rollins had several meetings with particular clients, so Judy did not have much to do. She entered his office, threw out more fast-food wrappers, and looked around. Suddenly, she saw his keys on the desk and had an idea. She did not want to ask Mr. Rollins why he lived in a trailer considering how much money he earned, why he always ate fast food and unhealthy snacks, or why he came to the office at random hours of the night, but she could do something for him.
“Will he fire me?” Judy thought as she took the keys to his home and went to grab her purse. “Whatever, I’m good. I can find a new job. I need to know more about him.”
She knew the situation would not be happening if she had felt her heart beating so fast the other night. She wanted to learn more about him. She needed to do this for him; she needed to find out why he acted a certain way, why he looked like the weight of the world was on his shoulders, why he never smiled, why he was so alone, and so many more things. She wanted to know all about him.
So she drove on to the supermarket, bought everything she needed, and headed to his trailer. She cleaned up, stored real food in his fridge, and started cooking some things for him so he would finally have real things to eat at the office. But the door swung open, and Judy thought he had caught her.
Instead, it was an older woman whose eyes widened at her, but her smile lit up the room just as quickly. “Who are you, dear?” she asked, excited for some odd reason.
“Well, he didn’t ask me or knows I’m here,” Judy shied away.
“Really?” Her smile appeared again. “I’m Miriam, dear. I was Peter’s mother-in-law.”
“Mother-in-law?” Judy repeated. “So he was married?”
“Yes,” she nodded. “You’re new. He must like you if you know where he lives.” Miriam tilted her head. Judy laughed and recounted everything. They chuckled some more, and then she asked, “So he lives here with his wife?”
“Oh, I should have been clear. My daughter died years ago with my grandson. They were in a car accident,” Miriam revealed, her lips pulling down. “Peter never recovered. He blames himself even though he wasn’t in that car at all.”
“I’m terribly sorry for your loss,” Judy said, shocked and dismayed.
“Thank you, dear. Things since then have been a whirlwind. Peter went through intense grief, and we couldn’t help him. I mean, my husband and I couldn’t do much for him. He was depressed and just went through the motions. He went to work, but life had no more meaning for him,” Miriam continued, “until my husband got sick.”
“Oh no,” Judy honored.
“Yeah, but my husband’s sickness snapped Peter out of his depression. He put all his efforts into helping us out. He pays for everything, and at the hospital, he met many sick kids, so he now gives to charity. He sold almost everything he owns and bought this trailer and this piece of land so he could be near the cemetery where my daughter and grandson are buried,” the older woman explained. “I see. Despite all the good he does, he’s not living at all. He leaves no money for himself or buys anything or enjoys anything. I think he only kept his clothes to go to work dressed nicely. We all have told him to move on. It’s been years. I know my daughter wouldn’t have wanted him to live like this. He doesn’t care about himself, and he has insomnia, so he visits their graves late at night or goes to work.”
“Oh, that’s terrible,” Judy said, realizing why his shoes had been dirty the night he entered the office at 3 a.m.; he had just been to his family’s graves.
“So I was excited when I saw you here. I thought he was moving on,” Miriam said, grabbing her hand.
Judy was confused. “I thought you might be his girlfriend,” Miriam asked hopefully. But the door to the trailer swung open again, and Peter stood there. His eyes were as big as saucers, and his face turned white as a sheet. He screamed, more furious than ever, and although Miriam tried to defend her, Judy ran off. She did not need his gratitude or anything; she only wanted to do something nice for him, especially after discovering everything about him.
The next few days were awkward, but he had not fired her. One day, he unexpectedly came out of the office with his phone in his ear. “Judy, cancel all my appointments. I have to go to the hospital,” he said.
“Are you all right, sir?” she asked.
“Yeah, it’s my father-in-law,” he answered and walked to the elevator. She canceled everything and finished her work for the day. It was not until she got in her car that she realized Mr. Rollins had not snapped or gotten angry at her for questions; he had actually told her something personal. So, Judy arranged some flowers and sent them to the hospital, hoping his father-in-law was all right.
The next day, Mr. Rollins called her to his office as soon as she arrived, and she was scared until she saw his face. It was peaceful; something had changed. “Sit down, Judy, please,” he said kindly. She did, bracing for whatever he wanted to say. She had gotten personal again; maybe yesterday had been a fluke.
“My father-in-law passed last night,” he started. “I’m going to need help to arrange his funeral.”
“Sure,” Judy said, getting his notepad out. But before that, Mr. Rollins stopped her, holding his hand out. “I want to thank you for the flowers, for clearing my trailer and making me food, for not telling anyone about this. My other secretaries were just as gossipy as the rest of this office. I appreciate your seriousness and loyalty.”
“I’m just doing my job, sir,” Judy smiled.
“My father-in-law, Roger, thanked me yesterday for everything I did for them and all the good I’ve done since I lost my wife and son. I know Miriam told you about that.”
“Sorry,” she said, sheepish.
“It’s all right. It’s nice that someone knows the truth now. Most people here don’t know anything about me except my boss as he said. Anyway, Roger told me that I wasn’t living, that I had died with my family that day and it’s true, that’s how I felt, but that I needed to start being active and acting alive. I needed to move on, to find someone special.”
Judy could not nod as her eyes watered. “He begged me,” Mr. Rollins choked a bit on the words. “He pleaded with me to start living again, to date, to make another family because that’s what my wife would have wanted.”
Judy did not know what to say. “That’s what Miriam told me too that day. They want you to be happy, or at least try to be,” Judy replied quietly.
“Yeah, Roger told me, ‘Peter, my daughter and grandson are watching you from Heaven. You can honor and respect their memory forever, but you must find happiness for yourself or they’ll never rest peacefully.’ So you’re right, Judy, and that’s what I’ll do.”
“I’m glad,” Judy smiled, her tears falling, but she was happy for him.
The following week was hectic with the funeral and how Mr. Rollins needed to find a new house, but Judy helped him with everything. One day, he arrived at the office later than usual and gave her a to-go coffee. Come Judy took it gratefully and looked down at his shoes; they were not dirty. He was really moving on.
A few days later, Judy was turning off her computer and getting ready to go home when he called her into his office. “Judy, would you like to have dinner with me?” he asked out of the blue.
Judy could only nod eagerly, and they went to a great restaurant nearby. From then on, he asked her to call him Peter and told her how much he had enjoyed her food. Judy laughed and told him about her family growing up in a small town, her friends, and everything else under the sun. His chuckles came often, and then they made her heart skip a beat every time. She did not know what the future would be like for them, but that was part of truly living.
