Instead of taking a few weeks off to travel, some advisors are taking business with them.Pyrosky/iStockPhoto / Getty Images
Checking work e-mail on vacation is nothing new, but some advisors are taking longer trips with scheduled work time that allows for an extended period away with family while also keeping client needs top of mind.
Fulfilling a bucket-list wish to live in another country without making a permanent move, Andrea Thompson, founder and certified financial planner with Modern Cents in Mississauga, is spending July in Syros, Greece, with her family.
But instead of taking a few weeks off, Ms. Thompson is taking her business with her.
Through a program that provides accommodation, activities with a cohort of international families, as well as day camp for the kids, Ms. Thompson will log in from a co-working space daily to meet with her team and work on client files and business operations.
“My executive assistant is still working, all the other [financial] planners are still working, I’m working – I’m just working from a different time zone,” she says.
Ms. Thompson’s decision to work while on an extended vacation aligns with a growing trend Deloitte reported in a recent survey of U.S. workers. According to its 2025 summer travel survey, 39 per cent of “laptop luggers” (those who intend to work on vacation) say they’re more likely to take longer trips, up from 31 per cent in 2024.
A shift in mindset, post-pandemic, is one reason why people may be considering this approach, Ms. Thompson says.
Preparing to work internationally
While the advice-only financial planning profession has advantages in terms of flexibility, she says, going abroad for a month while working required preparation.
For example, with Greece seven hours ahead of Mississauga – and with clients across Canada – Ms. Thompson chose to hold off on scheduling virtual meetings for the month. Instead, she’ll work “asynchronously,” responding to all communications and doing her normal proactive marketing and client work.
With almost a year to plan, Ms. Thompson had time to structure her schedule so that she was starting fewer new client engagements in the weeks before leaving. She also contacted existing clients to outline how they can reach her, what she’ll be working on and giving them the opportunity to book a meeting in June.
Lead with transparency and create structure
April-Lynn Levitt, partner and business coach with the Personal Coach in Waterloo, Ont., has noticed some advisors choosing to take longer working vacations.
But advisors should check with compliance about working in the U.S. or overseas, she says, as firms may have requirements relating to technology use or the type of work an advisor is conducting abroad.
Those who do take an extended working vacation should remember that being able to recharge is important, she says, whether that means working on certain days, for example, or only in the mornings.
Advisors also need space away from their travel companions to ensure client confidentiality during calls, she says.
It’s also a good idea to be up front with clients.
“Just be transparent about it,” she says, in case there’s a delay responding or a technology problem. “Because of the pandemic, I don’t think anyone cares anymore.”
The benefits of flexibility and balance
In recent years, Julie Shipley-Strickland, principal, founder and senior wealth advisor with Julie Shipley-Strickland Wealth & Risk Management at Wellington-Altus Private Wealth Inc. in Calgary, has enjoyed taking a three-week vacation every year with her family to experience local living.
Destinations have included the Azores, Mallorca, Tuscany, Florence and, later this year, Panama and the Galapagos.
While she has found that her business can function well if she’s away for a week or two, on longer trips, her team needs her input. Ms. Shipley-Strickland chooses to work a modified schedule, where she will work three to four days and then take a few days off.
When it comes to technology, she takes two laptops that have a high degree of security and require unlocking and authorization from Wellington-Altus before leaving Canada.
She agrees that being transparent with clients about her plans and availability is key. With significant time zone differences, flexibility is also important – and can sometimes involve taking calls on shorter notice if clients need assistance.
The success of a longer trip, she says, also hinges on daily communication with her team in Calgary, who check and filter her e-mails, and ensure day-to-day operations run smoothly.
Ultimately, an extended working vacation is about balance, but also creating the space to come up with new ideas.
“For me to be doing what I’m doing and thinking outside the box and being creative, we need those brain breaks – we need that time away,” she says. “Clients understand that and really respect that.”