A retired man took a laidback second act job as personal driver for a very wealthy man, but he has gripes about the scheduling method. Advice columnist Eric Thomas weighs in.
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 second act 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.
R. Eric Thomas (he/him) is a national bestselling author, playwright, and screenwriter. His accomplishments include “Eric Reads the News,” a daily humor column covering pop culture and politics, serving as the interim Prudie for the advice column “Dear Prudence,” and “Congratulations, The Best Is Over.”
Send questions to 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.
©2025 Tribune Content Agency, LLC.
Read more life guidance like dissing a father’s widow: from dissing a father’s widow, managing heirlooms when downsizing, rambling mothers, and more:
Boomer Advice for Life department
For advice targeted to senior adults and their families – caregiving, grandparenting, retirement communities, and more:
Asking Eric on SeniorGuide.com
