I work for one of the biggest internet companies in the world. Everyone knows its name. This is my first job out of college, and I was excited to be hired. But I work in a giant room with several hundred other young people who all sit in front of their computers doing “stuff.” I’m used to being a real person, not just a robot with a 401(k) and health care. Bottom line: I hate my job. What can I do? One of the problems I have with the culture you’re describing is: What’s your future? How do you move up the ladder? It’s so incredibly impersonal. I have an image from a classic movie from the 1960s, The Apartment, written and directed by the great Billy Wilder. There’s an opening shot panning across the floor of a big insurance company, hundreds of people—drones, really—sitting in front of typewriters and rotary phones. The impersonal nature of the work is depressing. So I understand your feeling that you’re on some kind of assembly line. You may even find it difficult to explain your job to people of older generations. You have to be brutally honest with yourself: “Do I have any real dream for the future? Do I have a passion for something that could pay me and that I could choose for a long-term career?” If you’re really stuck with no idea that rings a bell with you, I suggest going to an aptitude testing company that could give you an inkling about paths that suit your talents. And these answers might give form to jobs you never considered. However, don’t fake the answers on these tests. I have a smart young friend who I sent to these tests. At the time, he had no real dream. But he was helping to build a house in Vermont for his grandmother. The test results came back and they said, “You are very well-suited to work outside with your hands.” He had manipulated the results, and it was waste of his money and time. If you do it honestly, something really interesting may pop up. If this happens, look to your friends, your family and college connections to help open doors for you. Don’t be shy. And if you hate your job, move on.

My wife and I are taking a vacation to a warmer climate in a few months. We are bringing our two young children along, but there will be nights when we go out and they will not be joining us. Are we bad parents if we leave the kids at the hotel with a babysitter? While the hotel does not provide sitters, there are local companies that do. I am OK with the idea, but my wife is not sure she wants to leave our kids with a stranger. Just for the record: All of our friends do it and have never had a problem. Well, for one thing, I don’t believe you when you say, “All my friends leave kids with sitters.” In my experience, too many young parents would never bring in sitters or trust anyone—even grandparents—to watch their kids. My wife and I used to hire nursing students from Mass General Hospital to stay with our boys when we went to Europe. And as the years passed, friends would ask my wife, “Are you taking your kids to the Virgin Islands with you?”

She’d reply, “Are you kidding? I need a vacation from my kids. Not with my kids.” Ah, but times change. Somehow, my deprived children survived and thrived. Go on vacation and get sitters for your kids. They’ll never leave the hotel, so there’s some peace of mind. But I would only trust the hotel to vet the sitters and hire them for you. That should give you enough peace of mind to have an old-fashioned date—just for the two of you.

I saw my best friend’s boyfriend with another woman. They weren’t just together, they were together. I was leaving the train station and saw them part ways with a long goodbye kiss. My friend would be devastated—they live together. Should I keep this to myself, or tell my friend and break her heart? I’m worried it might backfire, though I imagine I’d feel guilty if I didn’t warn her about this guy. I’m stuck as to what to do. Don’t tell your friend. When you see the boyfriend, tell him. Scare the hell out of him and listen to his excuses. This story is as old as time, and, of course, it can cut both ways. But if he’s straying from your friend who he lives with, it certainly does not bode well for the future of their relationship. After you confront him, your friend’s man will want to avoid you and try to bust up your friendship. But as my wife was fond of saying, “This one will end in tears.”◆

John D. Spooner is an investment adviser, author and novelist. His most recent book is No One Ever Told Us That: Money and Life Lessons for Young Adults. Here, he responds to queries from advice seekers of all ages. Send your conundrums to thedance@improper.com.