Workcations: When to go stealth and when to flaunt it
Since the dawn of time, man has been adding on 2 extra days to the mammoth hunting trip to relax and get a tan before returning back to the cave.
Before smartphones and uber, the conference was the workcation – you got to go to a few seminars, play hooky in the afternoon to sit on the beach, and then get drunk and regretfully hook up with a coworker in a budget business hotel.
Today, it’s a bit different. We have names for it – first bleisure, then workcation, now we call it “stealth PTO”. But basically they’re variations of the same thing: mixing work and a trip.
What is a workcation?
A workcation combines work with the leisure of a vacation, allowing remote or hybrid workers to explore the world while managing their job responsibilities. The flexibility lets them enjoy new environments and experiences without sacrificing productivity, which is one of the perks of remote work beside others.
There are a few ways to do it:
Before/after: Tack on a few days to the front or the end of a conference in a cool location.
Team building: Use your team building budget to hold your annual meeting with your immediate team in the most central city where a team member lives, so you can get a locals’ view of a spot, bond with your team, and hang out.
Stealth PTO: When you straight up book a vacation, don’t tell your team, and sign on regularly to make it look like you’re being productive. Deliver 1 or 2 key things so you don’t fall behind, and come back as low key as you left.
Digital nomad: When you rent a place in a location for a few weeks or more, notify your team of your temporary working hours changes, and re-configure your meetings to allow for it. Do this with your supervisor’s blessing.
y tho?
In the past, people could only take vacations at specific times each year, dreaming of traveling the world when they had the financial means. Today, that dream is attainable.
According to FlexJobs.com, listings for remote positions rose from 12% to 20% in 2023. Remote workers can log in from anywhere, maintaining their productivity while enjoying local culture, food, and attractions during their downtime.
Entire corners of the internet are dedicated to helping digital nomads live their best lives – travel the world, be financially stable, have unforgettable experiences and explore the world and other cultures. And do it all while continuing to further your career and skills. For some, it’s an arrangement that they would never change.
The best and worst workcations I’ve taken and why
Australia: DO. Obviously. If you’re going to get a $2000 plane ticket covered by your company, a vacation rental for a another week or two is nothing.
NYC: DO! Immediately after the holidays. The Rockefeller tree is still up, the lights are twinkling behind snowfall through the quiet city streets, but you aren’t paying holiday prices. Plus, summer is hot and sticky in NY.
San Diego: DO! It’s gorgeous any time of year, extremely walkable city with tons of activities and sites, and really cool hotels that you can bond with your team in front of a bonfire on the beach. Also plenty of coworking spaces with great views.
Leadership summits:
Austin, TX: DON’T I’ve done this twice and you will end up working in an icy air conditioned room when it’s 129* outside. The sweat is not worth the tacos.
Key west: DO! During the right time of year - we caught a late May mid-week that was cool and relatively quiet.
Park City: DON’T if you are enjoying the conference at the ski resort, there’s not really much else to do after the conference ends. Trust me you’ll want to go home after 7 days in a resort village.
Conferences:
Seattle - DO if you’d like, though it’s not my vibe
Orlando - DON’T it’s hot and humid and everything is miles away from each other so you can’t walk anywhere.
Dallas - I will do everything in my power to never go to this lame city again.
Is a workcation right for you?
Consider getting out of town if:
You need a change of environment to boost creativity and motivation.
You're struggling with burnout and need a mental reset without quitting your job, a new location can help clear your head.
Your routine feels stale and uninspiring, you’re procrastinating or distracted at home.
Your company uses an unlimited PTO policy and you aren’t taking advantage of it.
Avoid a workcation if:
You're in the middle of a high-stakes project with tight deadlines, a workcation might not be ideal.
Your destination has an unreliable internet, which can hinder your ability to work effectively.
You struggle to separate work from leisure, a workcation might decrease productivity.
Top tips to make your workcation worth it
Choose your companions wisely: Avoid planning a workcation with colleagues unless you're confident you won't get tired of their company. Extending a conference to sit by the same pool can become tedious quickly.
Stay organized: Use digital tools to manage tasks and deadlines, ensuring you stay on top of your workload.
Research your destination: Thoroughly research the best times to visit and must-see attractions. This will help you make the most of your workcation without feeling overwhelmed.
Select accommodations carefully: Choose a place with reliable Wi-Fi, a comfortable workspace, and amenities supporting work and leisure.
How to plan a workcation
Decide whether to go on your own, or pair it with another work trip. I have been blessed to have gone to Australia three times, and you ain’t gonna waste a paid-for round trip ticket down under without extending your stay and taking your life into your hands when you rent a van on the opposite side of the road.
Look for a location with good internet access, a comfortable workspace, and a conducive work environment. Heat and humidity, storms and satellite internet could make your trip more annoying than inspiring.
Plan your schedule: Define work time so you are most productive over short bursts of time, allowing you maximum off time.
Pack smart: Bring everything you need to work effectively, including plug adapters, sim cards, and portable batteries.
Manage your slack, email, calendar blocks and notifications in a way that reflects what you’ve told everyone and agreed to communication-wise.
Should you tell your boss?
Deciding whether to declare PTO for a workcation can be tricky. Consider:
Tell your boss if:
Your availability will be limited more than 1/2 of your day, and your absence would be noticed.
You need to align with team schedules or change a significant number of meetings due to time zones.
Your know they’ll understand and be cool with it.
Don’t tell your boss if:
You’ll maintain regular work hours and productivity.
It’s a short trip and doesn’t interfere with meetings or deadlines.
Your role provides you with full autonomy over your schedule and tasks.
You’ve already agreed to a communication plan and it’s not necessary to tell them your whereabouts unless your working hours will change.
Your company has unlimited PTO but doesn’t encourage you to take it.
Your boss sucks.
Five unique places for a workcation
Kyoto, Japan: Enjoy serene temples and gardens while working from traditional ryokans or modern coworking spaces.
Lisbon, Portugal: So hot right now, benefit from vibrant city life, historic sites, numerous cafes, and delicious food. A few co-living spaces to choose from as well.
Tulum, Mexico: So hot last year, combine beachside relaxation with work, taking advantage of eco-friendly accommodations and stunning natural beauty.
Chiang Mai, Thailand: Experience the blend of modern coworking spaces and rich cultural heritage in this affordable city.
Reykjavik, Iceland: Work amidst stunning landscapes, hot springs, and waterfalls.
Colorado, anyone? Photo by Adrienne Kmetz
Staying in the States? Five US-based workcations we love
New York City, New York: I went to NYC every month for three years. My favorite time of year was the holidays – there’s nothing like being in this iconic city during the most magical time of year.
Austin, Texas: Experience the vibrant music scene and delicious Tex-Mex cuisine. Balance work with outdoor activities like paddleboarding on Lady Bird Lake.
San Diego, California: A vibrant startup scence, art and food culture, SD is the place to be for several conferences and beach hotspots. Take the train to TJ for a night of epic cuisine, or rent a bungalow in OB and stay put with a fire on the beach.
Denver, Colorado: Embrace the great outdoors with stunning mountain views and hiking trails. After work, enjoy a thriving arts scene and craft breweries that surround tons of coworking spaces.
South Florida: Combine work with a beach vacation, enjoying warm weather and vibrant nightlife. Numerous beachfront cafes offer Wi-Fi in a multicultural atmosphere. Key West’s relaxed vibes and Miami’s tech scene offer two great options for south FL.
Mountain towns: Check out coworking spaces all over mountain regions or little beach towns near you, and you could plan a nearby weekend in a cute little village with all the amenities of a coworking space.
A workcation can be a fantastic experience if planned well. You can enjoy the best of both worlds by balancing work and leisure, choosing the right destination, and setting clear boundaries. Think it through thoroughly, plan, and enjoy your time exploring new places while staying productive.
This view? I’ll hit NYC anytime. Photo by Adrienne Kmetz
