My Boss Is a Wealthy Man. Some of His Working Habits Make Me Very Uncomfortable.

Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. (It’s anonymous!)

Dear Good Job,

I am an assistant for a wealthy man who does much of his work at home. There are multiple times per day where I drop stuff off in his room and there have been more than a dozen instances since I began where he’s been on the phone after just getting out of the shower wearing either a towel or nothing at all. He will casually walk over and grab what I’ve brought him or sign it. He hasn’t done anything lecherous (assuming the nudity doesn’t count), but it really makes me uncomfortable. The pay, the hours, and the benefits are the best I’ve ever had at any job in my adult life. Should I just ignore the nudity, or do I need to speak up?

—Showin’ It After Showering

Dear Showin’ It After Showering,

I hate this for you! I don’t care if you work for the wealthiest man in the world and he pays you $5 million a year to be his assistant—it is NOT OK for him to be naked or even wearing a towel around you. And knowing that it’s happened “more than a dozen times” makes me think this is a very deliberate choice on your boss’s part. Whether it’s a kink I cannot say, but it’s certainly inappropriate. Unfortunately, because it has happened so many times without your saying something, this could be seen as your tacit approval, and makes a workplace harassment claim more tricky. So you need to say something as soon as possible. If he continues to be naked around you after you bring this up, then you have the basis of a possible workplace harassment claim. My cynical side says that he knows what he’s doing is wrong and that’s why the pay and benefits are so good—he’s counting on people not wanting to rock the boat.

Dear Good Job,

When I got my degree (English, concentration on technical writing), I was reasonably assured that there would be a job market for my skill set, especially in business and tech. However, about a year after I graduated, ChatGPT launched. I knew that even if/when sentiments turn towards it never doing a great job at writing, it would always be preferable to pay a subscription for that over a salary for me. I knew I needed to make a game plan for how I wanted my career to grow, but I kept putting off how to make a decision with excuses that I wanted to see how the job market would shake out first.

Well, I got laid off from my marketing job over a month ago. I have no delusions that I will get a new job quickly (and I have been applying to multiple postings a day), but a part of me feels like it’s hopeless. Why am I putting in so much effort into getting another marketing job when I didn’t like my job to begin with and I can’t be sure I won’t lose this one again in a year’s time. A part of me believes I should take some time now and get additional qualifications or an additional degree that is recession-proof. Another part of me is terrified to spend the money and the time away from the job market to do so, especially when I don’t even know what job I want to have. I have some breathing room as I live with my parent still (who, rest assured, wants me around), have minimal bills, and a substantial amount of savings, but I am almost 30 and I’m frustrated that I don’t have my life together and don’t have a clear idea as to what I want to do. If left to my own devices, I think I’ll be stuck in decision paralysis forever. Do you have any advice as to how to explore my options and make (smart) decisions for my future?

—Always the Late Bloomer

Dear Always the Late Bloomer,

As someone who literally wrote a book about being a late bloomer, I can say with almost total authority that there’s nothing wrong with being a late bloomer, and in any case, being close to 30 and doing a career pivot is totally normal.

Also as someone whose career seems to be increasingly decimated by AI, I can say with almost total authority: get out while you still can. You’re in the perfect place to make a career change right now—you live with your parent, have minimal bills, and a substantial amount of savings. I would start by making a list of what it is you’re good at, what you love to do, and what you find to be a drag. You should start to see some themes emerge. Maybe you like helping people, or being outdoors, or working alone. It could also be helpful to take a peek at a list of professions that are going to (hopefully) be least affected by AI, and seeing if any of them sound intriguing enough to look into more.

Finally, I would talk to everyone you know who has what seems like an interesting career and find out more about how they got where they are today. Hopefully, once you’ve done all of this, you’ll have a clearer picture of some potential options, and then you can start looking into degree programs, certifications, etc. to help get the ball rolling. You’ve got this, and you’re going to be OK.

—Doree

Classic Prudie

A few months ago I joined an online group of like-minded people where we often discuss personal relationship problems. I have found that griping about my husband to anonymous people online is a lot better than venting my frustrations at him. Lately my husband has also been really good at changing some of the behaviors that have always driven me up the wall, and now I know why. While using his laptop, I happened to notice him logged in as one of the members of my group!