Dear Eric,
At 65, having relished the retirement life for the past couple of years, I found myself craving a bit of activity. Serendipity led me to a unique opportunity—working as a personal driver for a remarkably wealthy individual. Although the role comes with a salary, even during his frequent travels which span about a week each month, my motivation extends far beyond financial gain. The position offers a fulfilling rhythm to my days.
However, a recurring issue has been the unpredictability of my employer’s schedule. Often, I receive the week’s itinerary on Fridays, which leaves me scrambling to adjust my personal plans when abrupt changes occur, sometimes with very short notice, even on the day itself.
In attempts to find a solution, I have had several discussions with him about providing me with more transparency. I emphasized the importance of having a more structured schedule so I could better manage my time off. Despite these conversations, I’ve had to rearrange my plans on multiple occasions to accommodate his needs.
In one of these discussions, I requested that he update the schedule and notify me as soon as his plans were solidified. His answer was to direct me to his assistant, a strategy I pursued. The assistant assured me that she updates the calendar promptly, yet it seems that these updates can take a day or two to reflect on my end.
To streamline communication, I proposed that my employer send updates directly to me, bypassing potential delays. He admitted to a lack of familiarity with adding events to the driving calendar. I suggested a simple solution: texting me the updates so I could handle the calendar myself. He agreed to this, but unfortunately, his promises often remain unfulfilled.
– 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.
