Dear Prudence

I’m a Single Dad, My Health Is Collapsing, and I’m Almost Broke. Should I Start a Business?

Prudie’s column for Oct. 18.

Man in black and white looking forward with a red tear overlaid on him
Photo illustration by Slate. Photos by Wade Austin Ellis on Unsplash and Thinkstock.

Dear Prudence,
In the past eight years, I’ve been divorced, lost $1 million on lawyers, and survived a brain tumor, spinal repair, a heart attack, a stroke, and three other major medical events. My three teenage daughters won’t talk to me—and I just won custody because their mom is very troubled. Once a CEO, I’m now on a race to the bottom in my career, losing job after job due to my health and cognitive losses that make me less than CEO-ish. So, with a handful of cash left to my name, responsible for raising and supporting my girls and caring for a loyal dog, I want to start my own company. I know exactly what I want to do; I know the risks; I know the upside. However, my confidence is shaky, and if I bet half the hobby farm that remains, it could be disastrous. But I see no other options. I’m doing freelance consulting for hand-to-mouth money. My mental and physical being are stable, and who knows if I’ll ever have this window again: enough money to be dangerous and strong enough to take a few more blows. I turn 53 soon. You’d think I’m old enough to make my own decisions and to know better when not to. But I don’t.
—My Life’s a Mess. Time to Start My Own Business?

Your letter makes it sound like you’re sort of hoping someone will persuade you that this is a terrible idea. I am happy to be that someone! Starting a new business with a sense of oneself as a “dangerous” individual on a “race to the bottom” but capable of taking “a few more blows” makes it sound like you’re planning to self-destruct in a blaze of glory because you can’t see your way out of your current situation. If you’re currently unable to hold a steady job because of the cognitive losses you’ve experienced as a result of your health issues, then you’re likely to experience more stress and less assistance if you try to start a new company now. You say you don’t see any other options, but between the “hand-to-mouth” money you’re making as a freelancer and the fairly sizable nest egg it sounds like still remains, you don’t seem to be on the verge of going broke. I think you’ll benefit more from continuing to work part time and focusing on your relationship with your daughters as well as your own physical and mental health. If you haven’t already talked with your doctors about your health issues, you might discuss with them whether it’s possible to apply for disability benefits. Better to cut back on expenses where you can and maintain a small-but-steady income rather than risk it all on something that has the potential to totally destroy what financial security remains.

Dear Prudence,
My friend Janet cares for her elderly mother, Gladys, who is in her 90s and has Parkinson’s disease. Janet and her siblings fell out with their brother, John, when he tried to sue Gladys (his own mother!) in a frivolous attempt to accelerate his inheritance. The case was thrown out. Gladys was angry and extremely hurt. Now she has lost the ability to make decisions and will likely die soon. Janet told me that when she does, she and her siblings will not tell John the details of the funeral until after it has taken place for fear that he will disrupt it. He has been aggressive in the past, and Janet herself is in poor health. I’m worried about whether this is the right thing to do. How can I best advise my friend?
—Exclusive Funeral Guest List

I think anyone who sues his elderly mother while she fights Parkinson’s disease in order to get his inheritance a little faster has made it clear that he’s not especially interested in celebrating her life or honoring her memory. If your friend and her siblings decide they’d rather not include John in their mother’s funeral, especially if they’re worried that he’ll become physically aggressive, then you should respect their decision and offer what help you can in terms of bringing food and running errands.

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Dear Prudence,
I live in a small two-bedroom cottage in the same town as my parents. During the holidays, my bedroom and living room always have guests, and for the past few years these have mostly been my sister and her college-age daughter. I was alerted by another family member that my niece has been insulting me and my home online. I was “Aunt Creepy” for having a doll collection and old antiques in my home. She put up pictures of my home to make fun of it. I emailed my sister telling her I was upset and didn’t want either of them in my home again. My sister made her daughter apologize but still is upset because I will not have them back. My brother and his family stay with our parents; I told my sister she can rent a hotel room. Now I am the one ruining the holidays. My niece was cruel, and I do not want her under my roof again. I was in tears over her insults to me; her apology was forced. My sister acts like she is a child rather than a young adult. How do I deal with this without it escalating? My parents are very elderly.
—Unwelcome Guests

I’ve heard now from several people who have a lovely, generous policy of offering rooms in their homes to family members for extended vacations only to find out that said family members have gone out of their way to slight their hospitality and speak cruelly of their stations in life. I’m so sorry your niece mocked you publicly and only apologized begrudgingly, and I think you’re absolutely right to stick to your guns. If your sister tries to manipulate you by continuing to bring up the subject, or tries to claim that you’re “ruining the holidays,” don’t entertain her: “I’ve made myself very clear. If you consider staying in a nice hotel ‘ruining the holidays,’ then I’m sorry to hear that, but it sounds like you have unreasonable expectations. I appreciated the apology, but I’m simply not interested in having guests in my home who have gone out of their way to make fun of me publicly. This is not a conversation I’m interested in reopening, so the next time you try to bring it up, I’m going to hang up the phone.” Any future attempts to drag the subject back up should be met with a bland “I’m sorry to hear that” and a refusal to further engage. I hope very much that your sister doesn’t compound her shameless behavior by attempting to drag your elderly parents into the situation, but don’t give in to her if she threatens to do so. Stick to your guns, remember that you cannot possibly “ruin the holidays”—they’re going to come back every year, they’re bigger than a single human being or sleeping arrangement, and last time I checked, a few nights in a Motel 6 did not render Thanksgiving null and void.

Dear Prudence,
I am married, and my sister is dating a guy named “Dan.” We are all in our mid-20s. Dan is a buzzkill. He is boring: He hates sports, bars, restaurants (but he doesn’t cook), and movies, and he thinks pets are “unsanitary.” He never offers a suggestion for an outing and just sits like a bump on a log if we do anything as a group. Conversations with him are minimal. My sister is fun—she cosplays at conventions, is always willing to try something new, and she wants to get a dog once she can find a place with a yard. My sister wants my approval, but I don’t know what to say. Dan isn’t a bad guy—just beige. I don’t see my lovely, lively sister being happy with him. Should I say anything to her? If so, what? I have tried the “If he makes you happy” standby, but my sister knows that is a dodge.

Has your sister been asking you for a more detailed answer, or do you just get the sense that she’s aware you’re holding something in reserve? If it’s the former, you might have room to ask a leading question or two. If it’s the latter, I think you should err on the side of caution and refrain from saying anything you might regret if things end up getting serious between the two of them. Short of calling out abusive or destructive behavior, I think it’s generally better not to object to a friend or family member’s significant other—she obviously sees something in him that you don’t, and it’s unlikely that your saying, “He’s just beige” is going to result in anything other than her resenting you for it. If you two are generally close and share confidences with one another, and she’s really angling for a more in-depth conversation, you might consider saying something like this: “I know you care about him, and I do want to get to know him better. But he seems pretty reserved, and I haven’t had much luck trying to engage him in conversation. I’d love to hear a little bit more about what you like about him and about this relationship.” But if she’s not pressing you for details, I don’t think you need to go out of your way to explain what you don’t like about him.

Dear Prudence,
My son died a month ago. His death wasn’t unexpected (although my husband and I are shattered). On his deathbed, he confessed to having a 5-year-old daughter. Her mother is married, and her husband believes he’s the father. He promised the mother he would stay away, and I think he might have taken the secret to his grave if he hadn’t been on drugs and frightened. My husband and I don’t know what to do with this information. We are friends with our alleged grandchild’s paternal grandparents, and we see her from time to time. I don’t know how to prepare for the next time I see her, knowing she is probably my son’s child. My husband wants to contact her mother and beg for visitation rights, but even in my grief I can tell this would erupt into a prolonged legal battle that might upend our granddaughter’s life. What do we do?
—Two Fathers

Please see a grief counselor immediately, both of you. Your son died only a month ago and has left you with a huge informational bomb that you deserve help in processing. I agree that your husband’s proposed course of action is likely influenced by his grief and would almost certainly bring more pain than joy into this little girl’s life. Moreover, you don’t know for certain that she is biologically related to you. All you know is that she does not think of you as her grandparents and that trying to establish any type of familial relationship with her would by necessity involve blowing up her parents’ marriage. In the short term, don’t force yourself to socialize with this family while you’re still grieving your son’s death and coming to terms with the possibility that he may have fathered a child. Bear in mind, too, that while your son did feel compelled to tell you about this possibility at the end of his life, he remained committed to his decision to let this couple raise her and did not attempt to establish any paternal rights of his own; you do have at least some sense of what his wishes were there. None of this is to say that your only option is to assume your son was wrong about being this girl’s biological father, or that you have to keep this a secret for the rest of your lives, but I do think it’s best to proceed with extreme caution and to spend some time with a trained counselor getting a sense of what your goals would be in contacting this. You two will need to answer some difficult questions together, and your husband especially will have to grapple with the serious consequences of his proposed course of action. How would he feel if you had to go to court over this and were unable to establish a biological relationship after all? How would he feel if this led to the couple’s divorce? How would he feel if this 5-year-old girl came to see you not as beloved family members but as people who traumatized her and threw her life into turmoil? That you’re facing such a complex set of choices is not your fault, of course—you didn’t create this situation—but it’s what you’re facing, and I think you’ll both benefit from taking some time to reflect, to mourn, and to talk through every possible scenario before making any decisions.

Dear Prudence,
I have a cat. She is the first pet I’ve ever had and has been with me for five years. This might sound sad, but she is my rock. Through breakups, moves, and family illness, she has been with me through thick and thin. I am single, so I love having something to come home to and take care of that accepts me unconditionally. All of this to say, I do not know how to handle the devastating eventuality that one day she will die. I’m afraid that it will destroy me. With no previous experience of a pet, I don’t know how to cope with this at all. Is there a way to pre-emptively prepare myself? I would like to just not think about it and enjoy the many years I have with her, but I am also afraid that if I don’t learn how to deal with it now, I won’t be able to in the future.
—Cat Lady

It’s not sad to care deeply about a pet or to consider one a part of your family. My cat died last month; I’d had him since I was a teenager, and while he was old, he’d been in excellent health and his death came as a surprise. I can tell you that having lost pets before did not make losing him feel easier. I wish there were a way to diminish future pain by trying to experience some of it pre-emptively, like grieving on an installment plan, but I don’t think that there is. The reality is that you love your cat dearly and you will almost certainly outlive her. This is heartbreaking, and it is inevitable that sometimes as you watch her play, or pet her between the ears at the end of a long day, you will be struck anew by how painful it is to think of such a quick and alive little creature dying long before you’re ready to part with her. The appropriate response to such a thought is grief. If there’s a way to love a pet without thinking about her eventual death, I haven’t found it yet; what you’re experiencing is, I’m afraid, both normal and natural. What you can do in response to that grief in the moment is to love her well and care for her to the best of your ability.

Classic Prudie

“I’m recently engaged to the most honest, thoughtful, and loving man I’ve ever met. Here’s the but about him: He makes no money. He has ambitions, and he’s smart, but will likely only bring a middle-class income at best. Now here’s the but about me: I’m really, really pretty. My whole life people have told me I could get any man I want, meaning a rich man. I’ve never dated a rich man, but it does make me curious. So part of me thinks I’m squandering my good looks on this poor man, and the other part of me thinks that I’m so shallow that I don’t even deserve him or anyone else. Am I a fool for thinking that a poor man can make me happy, or an idiot for believing a sexist fantasy?”