Workationing with Teens in Maui: An Interview!

Workation Woman readers love hearing real-life stories! You may remember my interview with a fellow workationer, Nichole. By a strange coincidence, I’ve had the pleasure of meeting another Nichole who also has worked and vacationed with her family!

Nichole took her first workation last year to Maui and can’t wait to do it again. Her story intrigued me because her kids were in 6^th grade, 10^th grade and 12^th grade at the time, plus involved in sports and extra curriculars. How did she pull them out of school? Did she have to convince the kids to go? What did their daily routine look like?

Read on to learn her family’s story…

How did you first get the idea for a workation?
I live in Minnesota and dislike the winters here. I’ve joked over the last few years that someday I was going to skip winter…then it hit me that I needed to really do this before my kids got too old!

What do you and your husband do for work?
I have two businesses: I own a travel agency and I work with a network marketing company out of my home. My husband owns a concrete company, so they do not work much in the winter and he was able to work remotely.

Why did you choose Maui for a workation?
I wanted to stay in the U.S., mainly for medical insurance reasons and because it would be easier to run my businesses. I also selected it for the weather; I knew the ocean water would be warm (which would not be the case in Florida or California).

The other reason we picked Maui is because we’d been there before and fell in love with it – and we still had a long list of things we wanted to do and see there!  We decided to go for eight weeks, from February through March.

Let’s talk about the big factor that weighs on people’s minds: Pulling kids out of school. Did you hesitate to pull your three kids out of school for two months?
I did not hesitate for a moment. My boys snowboard for fun and my daughter plays Junior Olympics volleyball, so she only competed for half of a season. The school was very supportive and I knew what they would gain so much more in family time and new experiences! That would out-weigh the missed sports and classroom time.

There was only 100% excitement from our kids. We love to travel and be outdoors in warmer weather. My oldest was a senior in high school and he even knew that this would be an epic experience!

How did you start the conversation with the school? What was their reaction?
I started the conversation very far in advance – more than a year before we traveled. Once I knew this trip was a real possibility, I asked for a meeting with the kids’ school counselors first. We discussed the best timelines for the trip, so that their school work wouldn’t be extremely disrupted. The counselors recommended that I pull them out for an entire quarter, rather than having them miss a part of two different quarters.

My oldest son was already doing school part-time online and part-time in the classroom. So we made the decision to have both boys (who were in 10^th and 12^th grades) to go online completely. The school suggested that my husband homeschool our daughter (in 6^th grade at the time) for more flexibility.

I will never forget when principal said to me, “Even if you don’t teach them anything, they will still learn more on this trip than they could at school in two months.”

How did the kids prepare to leave school for two months?
With the boys, we worked for a year in advance with their counselors to plan out their online classes. We selected photography and gym intentionally, due to the destination!

My daughter’s teachers discussed a few of her textbooks with us and told us how far they expected to get in those classes while we were away. Music was not mandatory, but we were responsible for science (marine biology is everywhere in Maui!) and gym (again, really fun in Maui!). Homeschooling was very time-effective and efficient.

What was your workation life like? Where did you live and work?
We searched for long-term condo rentals and found one we liked on VRBO. I didn’t want to be in a house – I knew that if we were in a condo, we were more likely to meet new friends. We also wanted to be near surfing beaches (we surfed almost daily) and we wanted a pool and to be able to see the ocean from where we lived. I was looking for a community feel, like it was home!

For my travel agency and network marketing company, all I need is a computer and my phone to be productive. I set up my office on a small desk in our condo but sometimes worked on the lanai, at the beach or at the pool. To get around, we rented a car.

What did a typical day look like?
I woke up early – about 5 a.m. – and worked until noon with a break in the morning for working out. I feel very blessed that I can set my own work schedule and that I had so much freedom and flexibility.

Since our boys were doing school online, they just followed their school work plan and checked in regularly with their teachers. This was a good opportunity for them to practice self-discipline – they wanted to get their school work done early so they could head to the beach by noon!

My daughter paced herself and worked very hard as well. It was easy for the kids to be motivated about their school work because it was always gorgeous outside and they didn’t want to miss out on surfing, swimming, etc.

Planning a workation takes a lot of logistics and financial planning. How did your family approach this?
My two businesses and my husband’s business continued to provide our income, and that gave us freedom. Since I am a travel agent, it was a natural choice to use miles for the airline tickets. The Christmas before we left, we didn’t buy Christmas gifts for each other.

I believe that giving yourself and your family the gift of travel as often as possible is of greater value than the things you can buy them. Some people think they cannot afford it, however we all have priorities in our life; it’s just a matter of making it your priority. Maybe that means eating out less, driving the same car a little longer, or adding in a side hustle of residual income.

How was your transition back home? What are your plans for a future workation?
The kids returned to school on the first day of the fourth quarter. My daughter was actually a week ahead in her studies and was bored her first week back at school!

For our next trip, the only thing I would do differently is stay longer.

Our kids’ school changed their schedule from quarters to trimesters, so this may hold us back a little. In other words, it’s easier on the student and the teacher when you can take them out for the exact quarter or trimester. The timing will be a little trickier but we will do it again – anywhere from four weeks to 12 weeks next time.

Any other recommendations for a family with older kids who are thinking about a workation?
We miss our time in Maui as a family. My kids still talk about that trip weekly, even a year later! We are so grateful for that time together.

My hope for staying in a condo was that we would meet a community of friends, and we did. In fact, I couldn’t have imaged the number of great and lifelong friendships we made there. That was priceless.

As a mom, one of my favorite memories is that it was just the five of us for almost eight weeks. No one else to fill our schedules. We did what we wanted, when we wanted. Back home, so many of us spend our time running kids around from activity to activity, then off we go to this birthday party or that wedding. I did not miss any of that rush. We returned home a closer and stronger family.