Even a Work Friend needs a break from the office sometimes. Send in your questions about all kinds of money-related extracurriculars: marriage and divorce; windfalls and investment catastrophes; and, of course, anything that happens in a truck. Confide to workfriend@nytimes.com.
Contractor Casanova
I’m 62. I’ve been a handyman for 40 years. My body is breaking down, but I can’t afford to retire, and I can’t imagine having any success changing careers at this point.
I specialize in renovation of classic residential architecture. But truth be told, what I’m truly gifted at is “relationship void-filling.” I have never romanced an employer, but I’ve provided countless customers with everything else they wish their husbands could or would provide — namely, an attentive ear; an ability and eagerness to talk about literature, film and music; a sense of humor; and the kind of compassion and empathy that can’t be taught.
My entire adult life I’ve been making $15 to $20 an hour to renovate houses and making $0 an hour to renovate women’s egos and souls. I know — because I’ve read about them in this publication — that there are dignified escort services out there designed for men who aren’t looking for sex, just attractive women with whom to dine or attend business functions. Women who are good at that job can make several thousand a week. I’d be delighted to make three or four hundred extra dollars a week by doing more for women than repair the drawer slides of their master-bathroom vanity cabinets.
What should I be charging to be the most comforting gentleman handyman on earth, and how should I advertise?
— Lynchburg, Va.
I hate to break it to you, but in this neoliberal age when everything is monetized, including — maybe even especially — the renovation of egos and souls, either you haven’t been charging enough for your time or you aren’t as charming as you think. (There is also a third option, which is that you are an absolutely terrible handyman and your company is what your clients have been paying for all along.)
But let’s assume for the purpose of this question that you are exceedingly charming and handy both. What can you do now to make more money?
In my experience, it’s almost never a bad idea to just state plainly what you want and put it out into the world. “Consummately Skilled and Affable Handyman,” reads my imagined Craigslist ad, which you will send to all your previous clients to forward to their wealthy friends.
“Hi there,” it continues. “I am an unusually attentive handyman with a specialty in the renovation of classic residential architecture (enthusiastic references available upon request). I am an expert at my job, but I also enjoy establishing relationships with my clients and continuing to work for them long term on personal projects.” People will get it.
You might be surprised how many well-off women request your services. At your age, the supply of available wealthy women increases, while that of fit or even alive men goes down. It’s called a market inefficiency! I have a good feeling that this will be the most lucrative phase of your career.
Dating App Sandbag
I work as a driver for a trucking company, and I subscribe to an app that helps me meet people — especially those who are looking for sex and romance. People in the dispatch office, apparently as a group, will make profiles on this app and relentlessly harass me everywhere I go. The other day they used the app, acting as a person looking for sex, to send me to a certain location. Of course, after I arrived, no one showed up, and when the office called me to ask where I was, one woman told me she and all my managers had been having a lot of fun “watching me looking.”
I feel pretty jerked around here. What do you think?
— Yuba City, Calif.
First things first: You could probably take legal action against your bosses and file a sexual harassment suit. Your dating life is none of their business, even if it involves meeting people in random clandestine locations on the road for anonymous sex. You can do whatever you want in your off hours, as long as you aren’t, um, doing it in the company-owned vehicle.
That said, you might not want to take things there. Perhaps you really need your job or otherwise don’t want to get a bad reputation in the business. Personally, I think it’s a terrible idea to meet up with total strangers in random clandestine locations for anything at all, really, but I am not a man and I am also not a trucker, so what do I know.
It might be best to split the difference: Tell your bosses that their behavior is actionable and a form of sexual harassment. Say that you value your job and your colleagues and everything else (even if this isn’t true), but the cyberstalking has to stop. Even if what they’re doing isn’t technically grounds for a lawsuit, the threat of taking action can be powerful. I mean, no one wants the hassle! At the very least, pushing back with a threat will demonstrate to them that this is not just fun and games for you.
When the Brainteaser Is the Boss
I joined a new team at work, and with that came a new manager. After four months on the team, I’ve noticed that my manager routinely blows off my weekly meetings; does not respond to emails; shares brief, vague performance evaluations; and seems to be giving more attention to other colleagues. I think of myself as a high performer, but when I have trouble getting any sort of feedback from my manager, it’s hard to believe the problem isn’t with me. Do you have any tips to respectfully get my manager to provide the feedback that I’m looking for?
— G.B., Seattle
This question has a binary answer: Either you are doing fantastically and the manager is of the type who wants to avoid headaches above all else, or you are doing horribly and the manager is also of the type who wants to avoid headaches above all else. Unfortunately, it’s up to you to determine which one of these explanations is more probable. The good news is that some consulting firms ask exactly this sort of brainteaser in their interviews!
The Lucky Ones
At what point do people grow up and get out of the seventh grade? Your employer is not paying you to act like children. When I first entered the work force, I was thankful to my employer for giving me a job. Now, new hires act like they are doing me a favor just to show up — then spend all day on their phones complaining and looking for another, more “dream” job. All I hear is, “I want a job that makes me happy.” Here’s a thought: Paying your bills on time is a happy thing.
— K.B.
Even though yours is pretty close to a rhetorical question, I am going to offer some advice: Start recruiting ambitious, hungry kids from good state schools and community colleges. That is, if you’re looking for workers who don’t act like they just got out of the seventh grade, hire some who don’t take their education for granted.
Also, kids who had physically demanding summer jobs like working retail, washing cars or digging ditches are often highly appreciative of the perks of working in a phone-type environment. And they can deal with cranky bosses like yourself.
But pay them really well, O.K.?
Katy Lederer is the author of three books of poems and a memoir. Write to her at workfriend@nytimes.com.
