Navigating the Chaotic Schedules of Wealthy Clients: Advice for Personal Drivers

Many individuals find fulfilling second careers in retirement, but working for high-profile clients can present unique challenges. A recent query to advice columnist Eric Thomas highlights the difficulties faced by a retired driver working for a wealthy individual whose schedule is frequently and unexpectedly altered.

The Problem: Last-Minute Schedule Changes

A 65-year-old retiree, employed as a personal driver, expressed frustration with the unpredictable nature of his employer’s schedule. While the salaried position offers financial stability even during the employer’s monthly travel (approximately one week per month), the constant last-minute changes—sometimes occurring on the same day—build personal planning nearly impossible. Despite multiple conversations and requests for greater transparency, the employer directs the driver to communicate with his assistant.

The Communication Breakdown

The driver’s attempts to streamline communication through the assistant have been unsuccessful. The assistant claims to update the calendar promptly, but changes may take a day or two to reflect in the driver’s schedule. The employer, when asked to directly share updates, stated he “doesn’t know how to add to the driving calendar” and, despite promising to text updates, rarely follows through.

Potential Solutions

Eric Thomas suggests several approaches to address this issue:

• Request Calendar Access: The driver could ask the assistant for direct access to the primary calendar, allowing for immediate updates. However, this may not be feasible if the employer has sensitive information on the calendar.
• Evaluate Job Fit: If access isn’t granted, the driver may need to assess whether the job aligns with his need for schedule control. It’s acceptable to recognize that the position, while enjoyable, may not be sustainable long-term.

The Employer’s Perspective

Thomas notes that the employer likely seeks to delegate logistical burdens to staff. Directly requesting more communication from someone who intentionally avoids such details may be unproductive.

A Common Struggle: Envy and Shared Experiences

Another letter to the advice columnist touched on a related issue: the challenges of shared experiences within a marriage. A reader described how her husband’s work travel, while necessary for his business, created envy and a sense of distance, particularly when he focused on the positive aspects of his trips. Thomas emphasized the importance of recognizing that appearances can be deceiving and that comparing one’s life to another’s can diminish joy.

The Importance of Perspective

Thomas concludes by highlighting the human tendency to believe “the grass is greener on the other side.” He encourages focusing on the positive aspects of one’s own life and finding contentment in the present circumstances.

(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.)