Having a puppy problem versus being the problem

Dear J.T. & Dale: I just got a new puppy. I didn’t realize how much work they are. I can’t afford to put him in puppy day care, and my office doesn’t allow dogs. How do I ask my boss to let me work from home a couple of days each week, temporarily, until he is more established? — Ananya

J.T.: First, I would explore if the company even allows remote work. If they do, then you can at least point to past cases. If there aren’t any, you’ll need to make a strong case as to what extra value the organization will get by allowing you to do this. For example, will it save you a commute time that you could apply toward work? Can you take on an extra project? Could you work in the office longer on certain days to offset you being home on others? You’ll need to show there’s something in it for them. Even so, be prepared for a “No.” Why? Because once they agree to let you stay home with your dog, they’ll have to do it for anyone else who asks. If they are willing to make it a benefit for everyone, that would be great. But I haven’t seen too many companies willing to do that these days.

DALE: Before you talk to your managers, know that they are going to hate being asked. Unless you have a manager who loves playing Mom or Dad to employees, expect to get a frosty reception. Why? It will feel as though you are trying to dump your self-inflicted problem onto them. So, first seek out other solutions. Find a neighbor or relative who’s willing to help. Or hire a dog-walking service. Remember: If you give your boss your problems, eventually you are the problem.

Dear J.T. & Dale: My future mother-in-law is the owner of a family business where my fiancee works, along with her father and sister. When my fiancee attempted to set herself up to leave after I graduate from college this coming winter, she was instantaneously belittled and screamed at by her sister and mother, and emotionally abused into staying. I love my fiancee very much, but it is explicitly clear that I am expected to lay down my goals and aspirations for the good of the family.

Our wedding is a year away and I feel as though I need to convince my fiancee to leave the business. Her mother has her convinced that she will never make more than $12.50/hour, and she is terrified to leave. I need to get away from the controlling parties and situation, almost no matter the cost. I need help. — Austin

J.T.: I think you realize that if you marry with your fiancee still at the family business, you are stating that you accept the situation; and should you try to force her to leave after marriage, the family will likely turn on you. I would strongly encourage you to understand that you won’t be helping your fiancee by marrying her. And, while I would never tell you to walk away from the love of your life, now is the time to set boundaries and decide together what is acceptable for your marriage.

DALE: Whenever happiness is contingent (“We would be so happy if only ...”), you need to play out the “if” hard and fast. Your influence is only going to wane after you get married, so it’s now or never for the first test — will she choose you or her family? Then, maybe you get to the second test — if she chooses you over her family, will she end up resenting you and souring the relationship? That’s something else you must learn before the wedding.

J.T.: One thing you could do is encourage your fiancee to explore other job opportunities. She could confidentially see what is out there. Imagine how surprised and empowered she would feel if she could find a job that pays more than $12.50/ hour. This might be just what she needs to start to decide what is best for herself!