Before I tell you about my workation in Portugal with my son, I want to reflect on my job rhythm—how my days flow, what can happen, and how I could (or should) handle it.
Because not every workation is the same. Experience is everything, and it took me a while in this consulting gig to really figure out my timing.
I currently have an assignment that requires a daily 9:00 AM stand-up with the entire IT team, Monday to Friday—and yes, I join every single day, even the days I’m not supposed to be working (meaning: not invoicing). That’s me. Hi. Nice to meet you. Control Freak Queen. I need to know what everyone is doing and I need to have a say in the priorities of the day.
The rest of my day is a mix of presentations, client meetings, or preparing for presentations and client meetings. It’s predictable enough for me to know the kind of energy and focus required—sprinkled with the occasional shit-hitting-the-fan moment where we all jump in to decide what to do next.
Now that I’ve got the hang of this rhythm, I can plan the occasional light week with fewer client calls, while most weeks are fully packed. And due to my ambivert nature, it can be so draining that I sometimes need a nap before writing the meeting minutes.
These full meeting-heavy days work best when I’m at home. But I discovered they still work “well-ish” for family stay-workations—like when I was in Buenos Aires at my parents’ place. The time difference saved me: I worked intensely from 5 AM to 1 PM and had the rest of the day free to enjoy life.
But they can also feel hell-ish. Exhibit A: Benidorm this year. I was alone, working from a hotel room with an amazing sea view—but zero mobile internet on the balcony. So I had to work inside, side-eyeing the Mediterranean sky out the window, suffering from extreme weather FOMO.
I still managed beach walks before and after office hours, and a friend visited during the weekend (yes, that friend from the naked-on-my-conference-call story). But still… lesson learned.
The Two Types of Workations
I realized there are two main kinds of workations:
1. Stay Workations
2. Explore Workations
Stay workations are your regular daily work life—just in a fabulous new location.
Explore workations require daily activities outside the norm: long walks, tours, museums, attractions… anything that lets you explore like a traveler.
A workation doesn’t need to be 100% stay or 100% explore—but each day should be.
Planning my days with this lens helps me prepare logistically, mentally, and emotionally—and prevents frustration.
The Ideal Stay-Workation Day
A perfect stay-workation day for me means working from a “home abroad” and living like a local.
If the stay includes a beach destination, even better. Then I live like a lucky local:
- early morning seaside walk
- delicious breakfast with a sea view
- seafood lunch (paella or bouillabaisse, I’m not picky)
- working outdoors as much as possible
- short swimming breaks
- long evening walks, cocktails, and amazing food
The lesson Benidorm taught me:
- Organize my activities better so that video calls happen indoors with good light, sound, and a decent background (to avoid incidents like that one).
- Find outdoor places like a beach or pool bar where I can do solo prep/analysis work while still enjoying the surroundings.
- Travel with someone who can keep an eye on my belongings (especially my work laptop!) while I sneak in quick swims.
This whole experience made me realize:
I would love to organize fabulous destination retreats for fellow Workation Divas so we can support each other while working abroad.
Stay tuned…
The Ideal Explore-Workation Day
I had this epiphany while planning my trip to Lisbon with my son: how to balance work and travel activities?
Since I needed to work half days, I cleared my calendar of client meetings and set up this structure:
- A couple of hours early morning for prep work and priority-setting.
- The mandatory 9 AM team meeting (which became 8 AM Lisbon time—thank you, time zones).
- Another couple of hours in the evening, before or after dinner, for replying to emails, analysis, and solo tasks.
I still kept my phone with me at all times—Outlook, Slack, Teams, Jira, WhatsApp—with notifications on. Just in case. I’d respond with:
“Let me get back to you on this,”
and then either handle it later or ask one of the tech team members to check it if something was urgent.
Luckily, my role isn’t technical, so I’m not the one fixing emergencies.
In the next post I’ll share how our Lisbon workation actually went—what we did, how we handled the rhythm, and how it all turned out (spoiler: we did well!).
Planning ahead helped me understand my work rhythm better, and I can already see future workations becoming even more fabulous.
💬 And now I’d love to hear from you…
How’s your job or gig?
What’s your work rhythm like—and how would YOU manage during a workation?
💻 About the Workation Diva
I’m Caro, an early pioneer of remote work, studying IT in the ’90s when “the Internet” still made dial-up noises. I’ve been blending work and travel since before it was fashionable, from spa weekends during business trips to half-vacations at my family’s place in Buenos Aires. These days, I live the part-time laptop lifestyle — balancing motherhood, projects, and plane tickets, proving that freedom can come in Wi-Fi and family-size portions.
Workation Diva 