Posted by Ask a Manager
https://www.askamanager.org/2025/12/updates-my-boss-is-a-jerk-missing-work-for-a-tennis-tournament-and-more.html
https://www.askamanager.org/?p=34741
It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past. Here are five updates from past letter-writers.
There will be more posts than usual this week, so keep checking back throughout the day.
1. My boss is a jerk — how do I deal with her? (first update)
I’m the person who wrote in years ago about my jerk boss (and, if I recall correctly, I initially balked when you called her a jerk!). I had previously provided an update about taking a new job and how grateful I was for your advice and the support of the community. As a quick update, I’m still at that new company and over the years, I have been promoted to a director-level role in my department and now manage junior employees. There have been lots of ups and downs at the company and I won’t stay here forever but ultimately, I have grown just so, so much since leaving the last job and I remain grateful to y’all for the support.
I’ve actually been having trouble with one of the company’s owners who is — and I can now say this with confidence — a jerk. Ahead of another Monday spent in conflict with her, I spent some time this weekend diving through workplace blogs, searching for some inspiration to steel myself for the week ahead. And perhaps unsurprisingly, I quickly came across my letters to you from 2020. What a blast from the past! I read through my letters, viscerally recalling the stress I was under each day about projects that haven’t meaningfully mattered to me in years, and read through your responses and each and every comment from the community.
While I won’t go into the meat of my current issues here, I did want to reach out to share again that this community really has meant so much to me. I didn’t intend to search for my original letter to you today but, upon finding it, I discovered that much of the core feedback is still true. I am still in control of how I react to poor leadership, how I value my work, and how much humor I can find in some situations. In many ways, my life now looks completely different than it did five years ago (I’m married, been promoted, moved across the state, etc.). But today, standing again in muck flooded by jerk leadership, I remembered I have waded through this before and I did so with such smart, empathetic, and supportive folk alongside.
I have continued to follow along with the site and the many folks who write in. Thanks to everyone for keeping this community thriving. And Alison, thank you again for sharing your guidance to an early career woman stuck in the muck; your advice still rings true to me now years later.
2. Missing work for a tennis tournament (#4 at the link)
My teenage tennis player son worked at a tennis club, almost exclusively with other tennis-playing teens. Their unpleasant boss was unwilling to accommodate their high school tennis season and tournaments that all these employees had every spring, very predictably. We appreciated that commenters took his tournaments seriously, like my son did!
My son chose to resign, and he was able to start up somewhere else immediately. The situation at the club devolved and more teens quit. However, I’ve noticed there are fewer part-time job opportunities for teens these days, so I imagine the hiring pool is pretty large. I wonder how many spring tennis seasons it will take to give this manager a clue!
The biggest takeaway is what my son has been able to learn from this. He says his new manager is respectful and organized. In contrast to the tennis club manager, who once made my son find a sub while he was home actively throwing up, this manager has reasonable expectations.
I’d felt the parental impulse to tell him not to quit, to learn to deal with a tricky employer. But in that environment, who would he learn professional norms from? It is easy for both parents and employers to not listen to teens, nor take their concerns seriously.
Thanks so much for responding to us. I hope my son keeps reading your blog!
3. I ran into an employee topless at the beach
I took your advice. After two additional weeks of awkwardness, I actually asked her if she was embarrassed. I originally tried being aggressively normal and that worked to a small degree, but I felt like she was only interacting when forced to interact. I asked her if she was embarrassed about our run in and she actually said she was a little bit. I told her not to be embarrassed at all and that we have all done things in our lives that we wouldn’t want our boss being present for. I told her not to worry and that I didn’t think any less of her. I asked her to start going back to normal and she quickly did.
4. My manager wants us to do a “mental health check” weekly
Shortly after I wrote to you, my boss stopped asking for the mental health checks. In fact, we don’t even have that weekly team meeting is often anymore. Probably one out of every four weeks. They get canceled a lot. So I’m guessing that maybe somebody else said something as well directly to her or that her manager said something as well because they did stop.
She never mentions anything like mental health like that anymore.
Happy to say, while there are other issues with our team, that is no longer one of them.
5. Can I drop out of a leadership program that’s the opposite of what I want?
One thing I forgot to include in my letter is that I work for a very large company. There were about 700 nominees in the program and no monitoring of our level of participation.
So, I ended up just not going nor doing anything. The program meetings were all on zoom and frequently in conflict with my actual job meetings, so I felt justified in blowing them off … but no one even noticed. And, my manager has forgotten about the program entirely.
It ended this month with a whimper, and that’s that. All that stress and anxiety over what turned out to be nothing.
Thank you very much for your advice and to the commenters who weighed in as well.
The post updates: my boss is a jerk, missing work for a tennis tournament, and more appeared first on Ask a Manager.
https://www.askamanager.org/2025/12/updates-my-boss-is-a-jerk-missing-work-for-a-tennis-tournament-and-more.html
https://www.askamanager.org/?p=34741