You’ve heard me talk about workations, and you want to know:

• What is a workation exactly?
• How do I know if I can take a workation?
• Can I really negotiate one of these with my boss without having any impact on my career?
• What do I do if I have kids or pets or a house?

If you want to know answers to these questions and a lot more, you’re in the right place!

This article is for you if:

• You are “workation-curious” and aren’t sure if you can take one
• You have a 9-5 job that is important to you
• Your schedule allows you to work remotely for at least 2 weeks at a time
• You have any questions whatsoever about how a workation could work for you

What is a Workation

First, let’s quickly define what a workation is.

Similar to “Bennifer,” the mashup of celebrity couple Ben Affleck and Jennifer Lopez, workations are the mashup of “work” and “vacation.”

Workations are trips taken by remote workers for extended periods of time while working remotely for their job.

By bringing work along and working remotely, workations can last longer than typical vacations – usually for at least 2 weeks at a time.

We structure workations such that we work normal business hours during the week and spend all the non-working hours enjoying the local destination and “living like a local.”

By taking workations, people achieve travel freedom while:

1. Keeping their steady paycheck
2. Using minimal (if any) vacation time
3. Not waiting for retirement to fulfill their dreams of travel.

Let’s keep going…

My Backstory

With dreams of a fresh start after a nasty divorce, I agreed to move cross-country to work from my employer’s headquarters with one condition:

I wanted to periodically travel back to my hometown in Minnesota to live & work remotely for 3 to 4 weeks at a time.

My boss agreed so I moved to Virginia.

With my homebase in Virginia, I spent 2 to 3 months each year working normal business hours remotely from Minnesota and enjoying my non-working hours with family and friends there.

While I appreciated being able to stay connected with my friends and family in Minnesota while living in Virginia, after 5 years of doing it, I wanted more.

My passion for travel:

started in college when I enviously watched most of my friends taking at least a semester to study abroad. This desire increased a few years later when my brother moved to Australia to work on his postdoctoral project.

Unfortunately, I couldn’t see a way for this to work for me since I already had a successful career and didn’t know any other way to financially support myself. So, I just conceded to doing things like: maximizing my annual PTO, continuing to take workations back to Minnesota and hoping for good health when I retire when I can REALLY fulfill those travel dreams.

However, in 2018, I started reading travel blogs and watching YouTube videos from people living all over the world. This planted the seed in my brain that maybe I could keep my current job but do it remotely from different places around the world.

I mean… it wasn’t that big of a stretch since I’d been traveling back to Minnesota to work remotely the past 5 years, right?

My Deciding Moment:

In 2019, I decided to test out international remote working so I took a 1-week vacation in Costa Rica. From my employer’s perspective, it was just a typical vacation but what they didn’t know was that I planned to use some of my time there to see what it would be like to work remotely from there.

Since I had no obligation to really do any work, I used this trip as a risk-free way to focus on some of fears about working remotely from a developing country outside the US:

• Finding fast, reliable internet
• Accessing all the websites I need.
• Working somewhere comfortable, quiet and private
• Language barriers
• Telecomm like emails, phone calls and text messages
• Best practice for optimizing my time for work and play

The trip was wonderful and everything worked out great but I discovered I needed to address these 3 things: using a VPN, having internet redundancy and receiving 2-factor authentication messages.

I discovered there was no discernable difference between working from home or a local coffee shop in the US vs working somewhere outside the US.

Then in 2020, the COVID pandemic hit. Everyone in our office was forced to work remotely, and revenues had taken a steep nose-dive. My employer decided to eliminate my position.

I took their generous severance package, I sold as much as I could, put the rest in storage and hopped on a plane with no plans except to take a 1-yr career sabbatical.

Instead of going back to my corporate finance career, I continue to travel full-time but now I work 1:1 with remote working business professionals to help them plan amazing workations.

Workation Success Stories

Click Here To View Our Previous Workation Re-Caps

The beauty of workations is that you can travel more and for longer periods of time without going all-in, giving up everything and traveling full-time like I do.

Instead, people just like you, with jobs & kids, are taking action and fulfilling their travel dreams by taking workations. Here are just a few examples of the power of traveling while working remotely:

Jelena

Originally born in Croatia and raised in New Jersey, Jelena is a single mom and highly visible leader in the health insurance industry. Earlier in her career, travel was so important to her that she structured her life by doing full-time contract work for 3-6 months which allowed her to save enough money so she could travel without working for the next 3-6 months. She repeated this cycle for about 2-3 years until one company made her an offer she couldn’t refuse. At that point, she settled into an office career, got married and started a family.

Today, travel is still an important part of her life. With two school-aged children, she makes it a priority to travel solo and to travel with her children as much as she can.

Prior to accepting her current position:

she negotiated with them for the ability to periodically travel back to Croatia (where much of her family lives) for extended periods of time to live and work remotely. She told them she would not accept their job offer without this condition and they agreed to it. [SIDE NOTE: this illustrates the negotiating power you have when you have a valuable skill set and have demonstrated success in your field.]

Also, because she understands the incredible gift and education that travel offers children, she uses school breaks (especially during the summer) to travel with her kids. She wants to expose them to other parts of the world, as well as teach them the logistics of how to travel. She’s very proud to tell people that her kids pack and carry around their own suitcases when they travel. They also choose to travel the world over having the latest video games!

She plans her solo travel for when her kids are in school and maximizes their travel together during school breaks. When she travels solo, the kids stay with their father or with her parents so they don’t miss any school.

It warms my heart that Jelena understands the importance of travel in her life and in the life of her children.

Jennifer

Jennifer is an executive leader at a fully remote fintech company in the US. Her employer does not care where she works as long as she meets her KPIs, keeps the business running smoothly and doesn’t trigger Permanent Establishment anywhere outside the US.

She does not have any children but is an animal lover with numerous dogs, cats and chickens running around her hobby farm in Pennsylvania.

Before she started taking workations, Jennifer worked from home 100% of the time and took a 1-week vacation every year with her family.

Her biggest concerns about traveling for extended periods of time were:

1. Being able to fly and cross international borders with her service dog.
2. Finding dog-friendly destinations & accommodations
3. Finding someone to care for the animals on her hobby farm.

As it turns out, these concerns were easily sorted out with a couple phone calls, some extra paperwork and some trusted family members to watch her house and farm while she’s away.

Now, in addition to her annual 1-week vacation, here are a few pics from the 3 workations she took last year:

Eileen

Eileen spent many years as a hospital nurse helping deliver and care for newborn babies in Maryland. This was obviously a job she could only do in-person.

As her kids were wrapping up high school and making plans for college, she decided she needed to make some plans too. Traveling the world was at the top of her list. However, she didn’t want to give up her steady paycheck or limit her travel to the nurse’s union’s vacation allowance. This meant she needed a new job that she could do anywhere from her laptop.

That’s why she sought out education in the cybersecurity field. Studying cybersecurity was her “side hustle” while she was working her full-time nursing job and represented the means to an end of having to work in a strictly in-person job. Once she had the cybersecurity skills, she paired it with her years of nursing experience to become a cybersecurity expert in the electronic medical records database in the US.

Now that she has geography freedom, she lives & travels pretty much anywhere she wants. She spends most of her time in the US, close to her kids but periodically takes workations in amazing destinations like Sri Lanka, Bali, Croatia and Mexico.

Clint

Clint works for a law firm specializing in intellectual rights in South Dakota. He also shares custody of his son who is in high school. His hobbies and passions include travel, scuba diving and language fluency in Spanish.

In order to travel more, he made an agreement with his employer that allowed him to work from anywhere as long as he met his agreed-upon KPI’s. For him, this simply meant he needed to complete and submit X number of patent applications.

Having the ability to work remotely allows him to travel more and spend more time doing things that fulfill him like scuba diving, mountaineering, and learning about history and different cultures. He currently spends 1-2 months each year outside the US in destinations like Mexico and Central America.

When Clint travels, his son stays with his mother or with Clints’ parents in South Dakota.

Benefits of Workations

The benefits of taking workations should not come as a surprise to anyone.

Here are just some of the reasons you should take a workation:

1. Take a break from the monotony

   . This is a no-brainer. Don’t we all get bored with the same mundane routine day in and day out? According to Buffer’s 2023 State of Remote Work, the number 1 challenge facing remote workers is: staying home too often because they had no reason to leave (source). Taking a workation definitely solves this problem!

2. Increased productivity & creativity

   . A repeated thing I hear from clients is they get MORE done because they have a renewed focus on only doing value-add tasks. They do much less “make-work” that doesn’t move the business forward. They are also better at problem-solving and finding creative solutions due to their new work environments. This is also supported by research: 86% of employees agree or strongly agree a workation boosted their productivity and over 81% grew more creative (source).

3. Get a renewed charge of energy

   . The act of traveling somewhere new disconnects you from your regular routine. This gives you a fresh mindset and a new burst of energy.

4. Avoid burnout

   . Grinding out long work days and ignoring your well-being is okay in the short-term but a recipe for disaster in the long-term. That’s why it’s important to periodically shake things up and take breaks from your day-to-day grind. Research also supports this: 83% agree/strongly agree a workation helped them cope with burnout (source).

5. Engage in hobbies that fulfill you

   . Workations make it easy for you to participate in things people usually only do on a typical vacation. My client, Clint (above), is able to scuba dive everyday when he lives and works remotely in Roatan. Not a lot of scuba diving opportunities back where he lives in South Dakota!

6. Stress reduction & self-care

   . Taking a workation will change your perspective, causing you to re-evaluate and re-prioritize the things that cause you stress.

7. Cultural enrichment.

   The beauty of workations is they last longer than your typical vacation. This allows you to experience more of the authentic, local culture while “living like a local”. And all without the pressure to pack in as many touristic things as possible.

8. Expand your knowledge

   . By spending more time in one location, you get to meet and get to know more local people which is the best way to learn about the real history, culture and language – not just what you learned in school or saw on TV.

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“Your time is limited, so don’t waste it living someone else’s life.”

– Steve Jobs, co-founder of Apple

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Workations are Not for Everyone

While the benefits of taking a workation are powerful, not everyone is a good candidate for taking them. Here are some examples:

• Those with jobs that HAVE to be done in-person – as in, there’s absolutely no conceivable way to do the job remotely.
• Those with employers who straight-up don’t understand and/or allow remote work – even as a one-off 2-4 week request.
• Those who are just not interested in travel.
• Those who are not healthy enough for travel.
• Those who do not have the financial means to travel.
• Those with demanding or high-stress jobs such that working remotely would be even more stressful.
• Those who lack the self-discipline and accountability to manage their work responsibilities when physically away from their employer’s office.
• Those who struggle with focus and the time management required to strike the right balance between work and leisure.
• Those who need a complete break from work to relax and rejuvenate. Instead, these people should be completely disconnecting and taking a proper vacation.

As you can see, suitability for taking a workation depends on many things which are unique to the individual and situation. It’s also important to consider specific circumstances, preferences and work requirements.

FAQ’s

• I have kids. What can I do?

You likely have more options than you realize. You can bring them along (especially during the long summer break), leave them at home with trusted family or friends or hire a travel teacher or nanny.

As you saw above, Jelena workations with her kids only during school breaks while Clint’s son stays home with family members. However, I have one client with a toddler who travels with a nanny so they don’t have to worry about childcare while both the husband and wife are working.

• I have pets. What can I do?

The most popular solutions for workationers with pets is to either bring them along or find a trusted friend or family member to take care of them. There are also house- & pet-sitting platforms like Trusted House Sitters where the vetted and reviewed sitters stay in your home while you’re gone and take care of your house and pets.

• What if my employer won’t let me work outside the US?

The simple answer is to take workations in destinations within the US until you can change the policy or find another job that allows for work from anywhere.

If the ability to work remotely from outside the US is important enough to you, engage in thoughtful conversations with your employer, asking lots of questions to understand their concerns. Be understanding, do some research and offer solutions that address those concerns.

Also, I recommend selecting destinations that are easy to travel back from in case things aren’t working out well or there’s some type of emergency.

Another tip is to choose destinations that are well-known spots in the digital nomad community like Playa del Carmen, Mexico or Chiang Mai, Thailand. In destinations like these, you can be sure there is good infrastructure to support remote working.

The harsh reality is that, if “living like a local” is important enough to you and you can’t come to an agreement with your employer, you need to be prepared to find another job or career that better aligns with your dreams and the life you want.

• What do I do if I don’t have a remote job?

Having a job that you can do from your laptop is a prerequisite for taking a workation. Therefore, the simple answer is you need to find one.

I’m more than happy to connect you with people and resources who specialize in helping people find remote jobs.

• What if I don’t know where to go?

RESEARCH, RESEARCH, RESEARCH! Scour the internet for everything you can get your hands on.

However, the easiest & least risky solution is to find a trustworthy workation expert who already has the knowledge and experience to help you figure out your best destination options.

In fact, from my years of full-time travel with a focus on workations, I’ve built a portfolio of itineraries, trip ideas and personal connections in amazing destinations like Hungary, Tenerife, Mexico, and Croatia – just to name a few.

• What if I don’t have a plan?

As the old adage says, “Failing to plan is planning to fail.”

This basically means… create a plan!

When structuring workations, I plan only for work during the workweek and leave the weekends for relaxation, excursions and local experiences.

For example, during a recent 1-month workation in Belize, we:

• Worked normal business hours in the US Monday through Friday. This left weeknights to do fun things like try new restaurants and play trivia at the local pubs.
• Spent Saturdays having local experiences like sailing to private islands, hiking in the mountains to waterfalls, or driving to a local family-owned chocolate farm.
• Spent Sundays just chilling and relaxing on the beach.

• Can I really negotiate one of these with my boss without having any impact on my career?

In light of the hyperfast technological advances and corporate acceptance of remote work, concerns around remote working stunting your career growth are quickly fading.

It’s also important to understand that periodically taking workations is not the same as permanently working remotely. With workations, you can still spend the majority of your time (if desired) working in-person from the office.

For example, if you took two 1-month workations every year, you could still be working in the office for 10 months which is 83.3% of the time.

Let’s face it…

It’s almost impossible to stall-out your successful career when you’re still in the office over 80% of the time. If you stall-out your career, you can’t blame the workations… 🙂

• What if my boss says no?

Ultimately you need to decide how important this is to you. If it’s important and you feel strongly you can be effective working remotely, keep the lines of communication open and ask probing questions to get down to the root cause of the concern. Be prepared to research and follow-up with solutions that address your employer’s concerns.

It can also be helpful to communicate real world examples of people and organizations who are already doing similar things.

As several of my clients and I have done, we’ve personally negotiated with our employers for the freedom and flexibility to periodically travel and work remotely for extended periods of time.

Every situation is different and nuanced so, if you cannot come to an agreement with your employer AND this lifestyle is important enough to you, understand that you may need to find a new job that aligns with your dreams and the lifestyle you desire.

• How can I ensure a fast and reliable internet connection to avoid any hiccups while working remotely?

While there’s no guarantee against power or internet outages (not even from your employer’s office), there are things you can do to limit your risk like choosing destinations that are popular for digital nomads. This is an indicator for good remote working culture and infrastructure. Redundancy is also important. I recommend traveling with a mobile hotspot or your smartphone that is equipped with a local virtual or physical SIM card.

Another way to mitigate the risk of not having sufficient internet access is to have conversations with people who have worked remotely from that location in the past to understand the situation and heed any advice they may have.

It can also help to research and understand where all the local coworking places are ahead of time in case something happens with your connectivity.

• How can I ensure I will have a quiet and comfortable workspace?

While some people can work effectively from busy places like restaurants or cafes, most people on workation (especially those more senior in their career or with management responsibilities). prefer to work from one of two places: their accommodations or from a coworking space.

Working from your accommodations is the most popular remote working location for business professionals. As such, be prepared to spend more time researching and vetting the accommodations ahead of time to ensure it’s a comfortable place for you to live and work remotely.

I also highly recommend having conversations with local hosts, owners or employees of the accommodations before your arrival to ensure it meets all your needs.

The other popular place to work remotely is a local coworking space. They usually offer a great place to work with options for quiet, private workspace at a reasonable price. They are also a great place to meet and network with other remote workers and often have free coffee onsite!

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Let Me Help You

Thanks to the internet, you can certainly plan your own workations:

• do your own research
• make phone calls & send text messages (often with language barriers)
• book your reservations (eg. flights, accommodations, transportation, experiences, etc)
• figure out how to prepare things at work and at home (before, during and after)

You can do all this work yourself and hope nothing slipped through the cracks.

Or…

Do what a lot of people short on time are doing – especially those in important leadership roles). They are not only short on time but they also don’t want any more stress in their lives. Or to take on any more risk by planning their own workations on their own.

They save time, stress and risk by hiring workation experts (like me!) who understand their needs and can plan amazing experiences for them.

Think of these workation experts as specialized travel agents, getting you the best deals, helping you find the best places, and giving you unique insights and experiences to enjoy on your trip.

Here’s how my workation-planning program works:

1 – Assess your current situation. Together, we’ll discuss your travel goals, your situation at home and at work and the mindset shift from “taking a vacation” to “living like a local on a workation.”

2 – Determine the 3 D’s. We’ll discuss and decide on the destination, the dates, and the duration for your workation.

3 – Prepare things at work. We’ll assess your work situation and create a plan so working remotely during your workation will be seamless to everyone at work. This includes, for example, creating your remote work schedule. At the same time we will be creating a communication plan for your leadership, clients, peers and direct reports.

4 – Prepare things at home. We’ll take a look at your situation at home and discuss your options for your kids, pets and house.

5 – Logistical planning. I do all the legwork in researching, planning and delivering you a workation itinerary that includes: flights, accommodations, airport transfers, local SIM cards and recommendations for local restaurants, cafes and local excursions and experiences for when you’re not working. You can be involved as much or as little as you want but will always have the ultimate signoff.

6 – Peace of mind. Throughout your workation, we will be available to you 24/7 via WhatsApp. You will also have a local contact for any emergencies or unexpected events that happen locally on the ground.

So…

Are you ready to start fulfilling more of your travel dreams today?

📣 If you’re ready to take your first or next workation, email me HERE or DM me on LinkedIn or Twitter.