Being on Leave Means Not Sending That 2 a.m. Email

I have worked in Fortune 100 companies for the past 25 years, have more than 35 years of work experience, and hold degrees from top schools, including an MBA. At my current company, there has been a lot of merging and reorganization, and the bigger jobs go to those with more years at this particular company — which I don’t have. My reviews are positive, but I’d prefer to contribute by being in a larger job that uses the breadth of my skills at a more senior level. Is it time to leave ambition behind, accept reality and just collect the good salary and benefits until the inevitable going-away party at some point between 60 and 65?

— Anonymous

It is never time to abandon ambition if you still feel ambitious and want to move up the corporate ladder. But age discrimination in the workplace is real and frustrating. The older we get, most of the time, the more competent and confident we feel and the more we are underestimated or seen as past our prime. You clearly still have the desire to advance.

What are you doing to make clear that you are seeking advancement? Could you speak with someone in your organization about what a path to advancement could look like and how you can best position yourself for success? You might also go back into the job market. Are there senior positions at other companies for which you would be a good fit? There are systemic issues individual action won’t change, but if you still want to reach for more, go for it.

Until recently, my job was relatively stress-free and well paid; my team works easily together. But not long ago, a young woman was hired by the main partner and placed in the office next to mine. The two are conducting an affair with nonstop, high decibel shrieks, laughter, overly familiar conversations and behaviors and alcohol consumption.

My boss’s office is next door and like me, he now keeps his door shut because we are frequently on the phone with vendors and clients. When I bring up the noise, I explain that closed doors and Air Pods aren’t entirely effective and that my productivity is affected. I proposed remote work, switching offices or changing my schedule.

My boss vetoed those options and proposed industrial headphones and press-on felt tile between my office and that of the young lady. He will not address the underlying issue. If I don’t accept his solutions, I will be the problem. Are my only options to hope the affair burns out soon or to quit? And how would I explain this job departure?

— Anonymous

Sometimes, I cannot really tell if a letter is real or not and this is one of those times. Having to listen to a senior colleague flagrantly engaging in an office affair sounds annoying, but it is surely not a reason to quit your job. I don’t understand why this behavior is allowed to go unchecked, but I am assuming yours is a small organization where there is sometimes little recourse for such things.

If your boss won’t agree to your very reasonable suggestions for accommodation, you really do have to figure out what you can live with. Find a great pair of headphones (I recommend Bose QC45, especially if your employer is buying) and let your employer install the soundproofing and just do your best to move forward. If you truly cannot tolerate this bizarre situation, polish your résumé and start looking for work. When asked why you’re leaving, you can cite seeking out new challenges or a different workplace culture.

I have worked at my current organization for more than 10 years. Recently, I submitted an expense claim for a taxi ride. A minimum tip of 5 percent gets added to every ride based on my app settings.

My expense claim is being processed in a hub in Asia, where my company has outsourced various functions. Someone came back to me to ask if the tip is mandatory, and when I answered no, I was told the tip would not be reimbursed. I explained tipping is the norm here to no avail. I checked our global expense policy, and it has no prohibition on tipping and simply says all claims must be reasonable.

This is the first time I have been refused reimbursement for the tip in an expense claim. I have always seen my senior managers tipping drivers and restaurant staff, and I have never seen them being challenged. My employer is a profitable company. I am a woman and part of an ethnic minority group and I can’t help but perceive this as a microaggression, and I feel angry and unmotivated.

Leaving my feelings aside, I would like to know whether I should challenge and escalate this situation or simply accept it since the amount is small and it’s a waste of time that could be spent doing something productive.

— Anonymous, London

First of all, assuming you have the means, tip at least 20 percent for transportation and for most things, really. Now, when you travel for professional reasons, your employer should reimburse you for those expenses, including tips. Your company doesn’t prohibit tip reimbursement, so you can challenge this. On the one hand, why are you sweating 5 percent? On the other hand, if you do a lot of work travel, these kinds of expenses start to add up. I do understand the principle of the thing. Fight the good fight, but don’t let it consume you.

Roxane Gay is the author, most recently, of “Hunger” and a contributing opinion writer. Write to her at

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