Q: At all-staff meetings, managers at my office will make a point of lauding employees for working late into the night. The typical response is a chorus of “way to go” and “great job” from the rest of the staff.

I seem to be the only one in the office who finds this dynamic obnoxious. Why is poor time management something to celebrate? I hate losing sleep, and work diligently to meet deadlines.

Am I just out of step with the office culture? Should I say something or continue to bite my tongue? I don’t want to be seen as withholding encouragement for my teammates, nor do I want to valorize an all-nighter habit. — Anonymous, Los Angeles

A: The American obsession with overwork and sacrificing oneself at the altar of labor is unreasonable and unfair. Too many companies valorize truly unhealthy working conditions — 70-80 hours a week, perpetual availability, late hours, weekends given over to work urgencies, the complete erasure of boundaries. 

And unfortunately, many employers think that this kind of overwork exemplifies model employee behavior. I strongly believe in people maintaining healthy boundaries and prioritizing a personal life as much as a professional life.

I also know that all too often, people are in positions where they have to compromise their boundaries for a paycheck. That said, you aren’t out of step with office culture, but I am not sure why you would feel the need to say something because your colleagues have different work values.

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Certainly, you could find a way to diplomatically address the unreasonable expectation of all-night work, but to what end? If the office culture is this entrenched in overwork, is raising the issue going to instigate change or is it going to isolate you from your peers?

If you get your work done on your own terms, and no one is asking you to pull an all-nighter, mind your business and let your colleagues mind theirs. If your colleagues do great work, join in the encouragement rather than judging how the work got done. If you’re seeing behavior that goes beyond late working hours and into the territory of exploitation, raise the issue with your managers.

You can vent about how you find this behavior obnoxious in your group chat. It doesn’t need to go further than that.

Being fearless, and sensible, when transitioning

Q: I’ve known I’m transgender, and that I want to be a writer, my entire life. I stayed in the closet, earned a degree in a technical field, and work for a wealthy corporation. I have never felt so miserable and empty. I hate my job, my field and my employer.

I’ve decided to transition socially and medically, and to pivot to a more creative field. I’m not sure how to logistically manage this career change. My job’s hours are so intense and draining that I find it very difficult to find time to write.

But I can’t afford to be unemployed for long, especially with transition-related costs. One part of me thinks I should stay at my current job through COVID, and then find another job where I’d have more time and energy to write on the side. Another part of me thinks I should take out some student loans and do an MFA. And a third part of me wants to write the CEO an extremely detailed email, hurl my work computer into a pond, buy hormones for cheap on the black market, and retreat to a cabin in the woods to write for several months uninterrupted. How do you think I should proceed? — Anonymous, California

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A: Look, life is too short to be miserable at work. You need a job and health insurance, particularly if it covers gender-affirming health care, so develop an exit strategy that gets you to a place where you can support yourself financially, physically and emotionally while doing something that doesn’t make you miserable.

You will know best what that strategy should look like, but do consider where you are and where you want to be and the best way to bridge that distance. You’re well on your way, given that you’re prepared to transition socially and medically. You’ve made one of the biggest decisions already. You know who you are and what you want for yourself.

Now, if you want to get an MFA, go for it. Pursuing the degree is a great way to give yourself time to write and develop your craft and work with other writers. Take the risk. Be fearless. But also be sensible. Apply to fully funded programs. You may still need to take on student loans, but you won’t need to assume as much debt as you would in programs without funding.

You are at a crossroads in your life in nearly every way. I imagine it must be overwhelming, but I hope you are also excited about the life you’re making for yourself. I wish you the very best and look forward to reading whatever stories you choose to tell.

Why is charisma valued over dignity?

Q: I have an unofficial supervisor who serves as the visionary of my small team. He is charismatic, confident and creative — however, he has also burned bridges across the organization because he actively puts people down. He has treated me well overall, but he has yelled at me when I disagree with him, especially when protesting his harsh assessments of others.

Now I’m reaching the point where I feel professionally stuck because no one at our company wants to interact with him, which marginalizes our team and limits our resources. To complicate matters, our new manager has confidentially informed me that he’ll never promote the unofficial boss and has asked me to become the official team lead instead. I’m so afraid my unofficial boss will project his negativity onto me that I would rather quit than burn this bridge and have to try to supervise him.

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(Note: It is virtually impossible to fire people in our organization due to strong employment protections.)

What should I do? — Anonymous, Los Angeles

A: I’m sorry you’re in a situation where there is little recourse. I’m not clear on what kind of power he has in his unofficial capacity, but I don’t understand how strong employment protections mean that pervasive abuse is tolerated. Your manager is being irresponsible, at best, in “confidentially informing” you about the unofficial supervisor’s professional fate. And he is passing the responsibility of dealing with the unofficial supervisor’s behavior on to you because he doesn’t want to deal with it.

If you want to advance in your career, take the promotion. You’re going to have to supervise difficult people over the course of your career. This as an opportunity to develop that skill set. It may be virtually impossible to fire people, but surely you can outline expectations and consequences should your current unofficial supervisor fail to meet them when you’re his boss.

He may be talented and charismatic, but that does not excuse demeaning colleagues harshly. Where are the employment protections for his victims? Why is his charisma valued over their dignity? You don’t need to answer these questions, but someone in your organization should.