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Asking Eric: Wealthy employer’s chaotic schedule causes stress

R. Eric Thomas, Tribune Content Agency on

Dear Eric: I'm 65 and have been retired for the past two years. To stay active, I went to work as a personal driver for a very wealthy man. I'm salaried, so when he travels (on average one week a month) I still get paid. It's really not about the money; I enjoy the position.

What I don't like is getting the schedule on Friday (for my personal planning purposes). Often the schedule drastically changes usually with little notice, sometimes the same day.

I have had several conversations with him about being more transparent, so I may plan my time off. Several times I changed plans to accommodate him.

I asked him to please update the schedule as soon as he makes plans. His response is for me to inform his assistant. I spoke to his assistant who told me she updates the calendar immediately and then it's added to my calendar, which may take a day or two.

I asked him to send the updates directly to me since I'm the one who is responsible for driving him. His response was “I don't know how to add to the driving calendar.”

I told him to text me the information and I'll add it to the calendar. He said he would, but he says a lot of stuff and never follows through. What can you add to assist in this issue?

– Driver Being Driven Nuts

Dear Driver: One option is to ask his assistant to give you access to the main calendar that updates immediately, so that you can make plans more quickly. I’m not sure whether this is feasible – perhaps he has things on there that he doesn’t need you to see. But it can’t hurt to ask her.

Because he has a driver and an assistant – and probably other staff – it sounds like he wants to offload a lot of the logistics of his life. So, asking him to do more communicating about something he purposefully doesn’t want to be involved in may be a nonstarter for him.

If you can’t get access to the main calendar, you may have to decide whether this is still a job that works for your life. It may be that you want more control over your own schedule and this isn’t a job that allows for that. It’s fine to say this was a great opportunity that you enjoyed for a time, but now you want your time back.

Dear Eric: My husband and I are in the same situation as “Left at Home”, who struggled with envy about her husband’s work trips.

 

My husband has a job he dislikes, but it is his own business, and he can’t leave it until he retires. I travel occasionally for work. When I travel, I stay at nicer hotels, eat at nicer restaurants and sometimes do interesting things, but I’d rather not travel for work anymore.

To my husband, my travel is exciting and he feels envious. Left at Home said that her husband tells her he doesn’t want to go on the trips anymore but then tells her about all the good food and fun things that were planned for them. She thinks he is disingenuous and feels like the trips and experiences are distancing her from him.

I believe her husband. I don’t like traveling anymore. I face long flight delays and cancellations. Getting up at 3 a.m. to make a flight. Spending nights alone in hotels, missing my husband and my family. Long drives in unfamiliar places often late at night because my flight was delayed. Long meaningless meetings.

Yes, I come home and tell him that I had an interesting site visit, or that I ate some wonderful food at a unique restaurant, but I do that because I want to share my experiences with the person I love. I also share the bad experiences, but he also thinks I’m being disingenuous. Believe me, I’m not. I’d rather not travel anymore. It isn’t glamorous and exciting.

I hope she gives him the benefit of the doubt and stops giving him a hard time. If he needs the job and the job comes with travel, then she should accept it gracefully and find other things to do, as you recommended.

– Weary Traveler

Dear Traveler: I really appreciate you sharing your perspective. The situation the couple in the letter find themselves in is a common human one. The grass seems to be greener on the other side. But appearances aren’t the full picture.

Comparison is the thief of joy and even otherwise happy marriages aren’t immune to its burglary skills. But the old saying is true, we’d rarely trade our problems for someone else’s. Better to look at what we do have and try to make something that we like out of it.

(Send questions to R. Eric Thomas at eric@askingeric.com or P.O. Box 22474, Philadelphia, PA 19110. Follow him on Instagram and sign up for his weekly newsletter at rericthomas.com.)

©2026 Tribune Content Agency, LLC.


 

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