Family business keeps daughter down

I currently work in a family-owned office that my mother manages. My sister and I both work there.

I’ve helped her since she acquired the business from the previous owner a few years ago. There are no issues in our working relationship/dynamic. However, my mother doesn’t pay very well and can’t afford to pay me more.

I don’t believe I’m financially stable. (My sister’s husband earns a hefty salary that provides them with financial stability.)

My question is, how do I leave? How do I broach this subject and find other employment while maintaining a good relationship with my mother?

I know this will cause her an immense amount of stress because there is no replacement and potential candidates are difficult to find, but I cannot currently survive on the meager income.

I have plenty of customer service/professional experience (plus prior military service) and have done some job searching to ensure I am marketable for a better salary in other career opportunities with similar job duties before settling on the idea of leaving.

I am just unsure of what to do next, and I’m fearful of her feelings. I also believe that I’m really overthinking this.

I’m ready to move on, but find it difficult to have the “breakup” talk when I know how important loyalty is to my mother.

— Daughter’s Day-Job Dilemma

Wanting to advance your career, move on to a different field, make more money or simply make a change does not mean you are being disloyal. Your mother might frame your choice that way, but if she does, that is yet another reason for you to leave.

I’m going to suggest, however, that your mother might surprise you.

You should meet with her outside of the home and office. Write down your thoughts in advance.

Thank her for providing this opportunity. Express your gratitude. Tell her that you believe you’ve gone as far as you can in the family business.

Would you stay with the company if your mother gave you a raise? You should consider this possibility and have your answer ready.

Be firm and friendly in expressing your resolve. Keep it professional. Do not criticize her or your sister. Do not anchor to her reaction if she becomes upset.

You have the right and responsibility to solve your own problems. The same goes for your mother.

I have a friend who is overly generous. We exchange birthday and Christmas gifts, but she quite regularly sends me other gifts that I really don’t want.

I am at the age where I am downsizing, and I really don’t want more stuff. I feel if I donate the gift (or regift it to someone else), she might wonder where the gift is when visiting me.

Sometimes I’ll discuss something with her, and the next thing I know there is a box at my door with something in it (book, music, etc.) related to a casual comment that I made to her.

Is there a way to tell her I appreciate her friendship but don’t want the “stuff”?

— Too Much Stuff!

Yes, you can communicate with your friend using the wording you yourself supply: “I really appreciate your thoughtfulness and generosity — all those gifts you’ve sent to me over the years! But I am currently downsizing, so I’m hoping that you and I can confine our giving to only exchanging cards. Can you agree to that?”

A few years ago, my girlfriend’s friend told her that I was hitting on her. My girlfriend asked her what I did to make her feel that way, she said, “He asked me questions, and when I answered them, he followed up with questions about my answers.”

My girlfriend said,

“How is that hitting on you?” and her friend said, “Men don’t listen to women, and then ask questions, without wanting something.”

That’s probably why my girlfriend and I have been together almost 20 years, while her friend has been divorced twice.

Love your column.

— Dave

Wait ... are you hitting on me? (I love this. Thank you.)

Miss Manners