The usual sales pitch for working from home has been that the job can get done just as effectively outside the office, boosting morale and allowing employees to manage other commitments while meeting and even exceeding their professional responsibilities. But a senior lawyer in the San Diego City At torney’s Office may be testing the boundaries of remote work. Newly elected City Attorney Heather Ferbert promoted one of her top deputies to a freshly created executive position paying almost $300,000 a year and permitted her to work remotely during an extended sea cruise around the world. Jean Jordan, who was an appointed county counsel in Northern California before she was lured to San Diego four years ago, departed on the four-month circumnavigation in late January, the City Attorney’s Office acknowledged. She’s just over halfway through her global excursion and due home late next month. She’s also collecting her full-time salary and benefits, including vacation. The City Attorney’s Office confirmed the unusual out-of-office arrangement after The San Diego Union-Tribune requested an explanation in response to complaints the newspaper received about the travel. According to a spokesperson for Ferbert, the new city attorney personally approved the work-at-sea arrangement under her professional discretion. “As the head of an independent city department, the city attorney has the authority to allow temporary teleworking arrangements for office employees on a case-by-case basis,” Ferbert spokesperson Ibrahim Ahmed said in a statement. “In this case, the city attorney thoroughly examined the job responsibilities of the position and determined that all required work could be performed remotely on a temporary basis with no impact on office operations,” he added. Ferbert “stays in constant communication with all members of her executive team,” and the office “has not experienced any delays or other negative impacts” as a result of the arrangement, Ahmed said. Jordan was hired as one of the office’s six assistant city attorneys in 2021, when she resigned as county counsel for Sutter County, a largely agricultural community north of Sacramento. Ferbert approved a reorganization of San Diego’s law office early in her term, weeks after defeating state Assemblymember Brian Maienschein in the race to succeed former City Attorney Mara Elliott. The restructuring called for putting a new executive assistant city attorney in charge of three other assistants, the lawyers in charge of civil litigation, the City Council, and government services and mayoral departments. Two other top assistants, attorneys overseeing the criminal division and administration, continue to report directly to the city attorney. Ferbert’s office did not respond to questions about why Jordan was appointed to the senior job before embarking on the extended trip, or why the office reorganization was not delayed until after the new executive returned. Jordan, who is now paid $282,651 a year, declined to discuss her work status. “I do not have any additional comment beyond what the City Attorney’s Office already provided,” she said by email. Jordan collected $239,000 a year before her promotion, according to the online public-salary database Transparent California. The same database said Jordan was paid $155,000 in 2020, her last full year as top attorney in Sutter County. Shelley Webb is a supervising deputy in the criminal division of the City Attorney’s Office. She also serves as president of the Deputy City Attorneys Association of San Diego, the union that represents rank-and-file city lawyers. Webb declined to comment on Jordan’s overseas venture but confirmed that the No. 2 person in the office did not broadly inform her staff attorneys that she would be traveling over an extended period. “The DCAA was previously unaware of this arrangement for Executive Assistant City Attorney Jean Jordan and has no statement at this time,” she said by email. But Marlea Dell’Anno, a lawyer in private practice who formerly served as a San Diego assistant city attorney, said allowing someone to work off-site while engaged in a world cruise for months on end is questionable, especially a senior executive. “It’s like being an absentee parent,” said Dell’Anno, who was fired by former City Attorney Jan Goldsmith and then won a multimillion-dollar jury award in a wrongful-termination case. “You are the No. 2 to the city attorney. How critical a role can you have if you’re not accessible to the people you are leading?” she said. “This doesn’t seem like something a good steward of taxpayer dollars would allow.” Worldwide cruises generally are booked months in advance. A 115-day trip promoted by Princess Cruises, for example, is accepting bookings that depart Los Angeles on Jan. 21, 2026, and returns May 16. The roundtrip Circle Pacific cruise stops at 59 ports in more than a dozen countries. Many guests are retirees looking to sightsee globally from a comfortable base at sea. But a growing number of so-called digital nomads travel the world while maintaining their jobs with little more than a laptop and reliable Wi-Fi. According to the MBO Partners consultancy, which tracks workplace trends and culture, the number of digital nomads climbed from 7.3 million in 2019 to more than 18 million by 2024. “This level of growth reflects a new normal of steady growth and a true entrance to the mainstream,” the company wrote in its 2024 State of Independence in America Report. The city of San Diego has a comprehensive policy dictating how employees can apply to work remotely on a case-by-case basis. Participants in the telework program need approval from their department head and the human resources office. Remote employees also must sign an agreement dictating their terms of service, work conditions and other rules. “During working hours, teleworkers are expected to respond within three hours to phone calls, voice messages, text messages, emails or other communications from managers, supervisors or coworkers requesting a response,” the 19-page policy states. According to the current budget, the City Attorney’s Office employs just under 425 people and will spend $85 million this year. The office is one of the biggest law firms in San Diego, with more than 175 attorneys. The majority of employees work both in the office and elsewhere, Ahmed said. “These schedules enable staff to meet their various job demands, including time spent in court, mediation, investigation, hearings and other job duties that take them out into the field,” he said. All told, just under 2,000 of the city’s 13,300 employees are approved to work remotely with formal signed agreements, the Mayor’s Office said. Development Services leads all departments with 393 approved workers, Public Utilities is second with 307 people allowed to work outside the office, and Engineering Capital Projects is third with 298 approvals. ...read more read less