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Being self-employed means working during vacations. Being a single mom means I have to do it with my toddler around.

by with No Comment Xpandfy

I’ve been taking working vacations for over a decade, long before the pandemic made them commonplace.

While the downside of working for myself is not getting any PTO days, the upside is being able to work remotely with flexible hours. Working from paradise, with a palapa shading my laptop from the sun’s glare, is one of my favorite things about being self-employed.

I realized that it would be more challenging once I became a single mom, but juggling work and a baby away from home turned out to be much harder than I realized.

I kept thinking it’d get easier

The first time I tried to take a working vacation with my daughter, she was 8 months old. I booked a flight to Hawaii, packed my laptop, and planned to work during her two naps and after she went to sleep for the night. I spent most of the week in Maui learning lessons the hard way — disconnecting the hotel room phone after a call interrupted her nap, dragging her from store to store trying to find baby medicine when she caught a cold, and departing exhausted after staying up most of each night working.


Hotel room with crib

The author brings her daughter on trips and works around her schedule. 

Courtesy of the author



Over the next few years, I kept trying, thinking with each hard lesson learned that the next time would be easier. Now that my daughter, Via, is 3.5, I’ve attempted eight different workcations. Each time I start out hopeful that I’ve found the solution. But I’ve always ended up with three jobs on what is supposed to be a vacation: working, parenting, and solving logistics problems.

I tried kids’ clubs

Resort kids’ clubs were supposed to be the answer. I needed a predictable block of time each day where my daughter was otherwise entertained so I could focus on work. I booked hotels (and even a cruise) that advertised them prominently, flaunting photos of smiling children that made me feel less guilty for leaving my daughter on vacation.


Toddler at kid club

The author took her daughter to hotels’ kids clubs. 

Courtesy of the author



As it turned out, those programs had their own challenges. Via wasn’t just nervous at the beginning; each day, she didn’t want to stay at the kids’ club and fought going back. At one resort, the website promised a nap room at the kids’ club, which was essential because Via still needed one midday. When we arrived, I was told the nap space was out of order. That meant I had to pick her up after just a couple of hours, put her down in our room myself, and then try to quickly finish work while she slept. On two separate trips, the kids’ club’s actual operating hours didn’t match what was posted online.

I paid $95 a day for our recent trip kids’ club

On our most recent trip, I didn’t expect much different, except I booked the six-day vacation at Club Med Cancún over a holiday weekend, strategically planning around a slower work period. It was the first time I’d booked a resort with a paid kids’ club instead of one where it was included. While the program for ages 4 and up had no additional charge, Petit Club Med, the option for 2 and 3-year-olds, costs $95 per day. So, I figured we’d try it out for just the one full workday we were on the property. At first, I was a little apprehensive about paying for a kids’ club after our past lackluster experiences, but it ended up being more than worth it.


Toddler on lounger

The author brings her daughter on workations. 

Courtesy of the author



The complimentary kids’ clubs I’d used before felt like drop-in playrooms, yet the Petit Club Med program was structured more like day care. They even included rest time in the schedule with a dedicated nap room. The difference completely changed the dynamic with my daughter.

At first, as usual at drop off, Via clung to my leg. I worried about her enough during the morning that I went to sneak a look at how she was doing. I was relieved to see her smiling and skipping to lunch with the rest of the kids. When I picked her up at 5 p.m., I really noticed the difference. Instead of waiting for me anxiously, she was engrossed in an activity and, when she noticed me, started talking excitedly about what she’d done that day. She loved it so much that she asked to go back the next day. I stood, stunned, taking in that moment with equal parts shock and relief.

I figured she would change her mind by the next day, but the following morning, she was still clamoring to go back. I wasn’t sure if I should take her; I had planned to spend the rest of the vacation together. But I was so happy that she loved going, I decided to bring her back. For the first time on a workcation, I found myself caught up on work and got to explore. I took a trapeze class, something that had caught my eye on the Club Med website before the trip, and borrowed a snorkel for a leisurely swim in the ocean.

When I picked up Via, she was once again glowing and happy from her day of adventures, and, for once, I was as well. For the remainder of our trip, we spent time together, and I felt like I could show up as the relaxed, carefree mom I’d always want to be on vacation.

Looking back at my past attempts, I don’t think I was overambitious to believe that a workcation could be enjoyable for both my daughter and me. I just had a lot to learn about how to prepare, structure the trip, and what to expect from kids’ clubs.




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I took a risk moving to Phuket as a single mom. It paid off.

by with No Comment Xpandfy

This as-told-to essay is based on a conversation with Cheska Hull, 40, a British reality TV star and PR professional who relocated to Phuket. Her words have been edited for length and clarity.

My move to Phuket was about choosing a fabulous place to live while continuing my freelance career.

I feel like I’ve been part of the island’s community for years. I’d visit annually for a couple of weeks at a time, maintain friendships, and get to know local business owners.

Every trip had me dreaming about potential jobs and interesting opportunities. I’m a PR specialist who has always worked in the luxury sector, across food, beverage, and hospitality. In London, I specialized in private members’ clubs.

That work also led me into radio and television, where I starred in the reality show “Made in Chelsea” for nearly four years. It helped me understand the evolving world of influencers and celebrities. Having lived on both sides of the PR and fame spectrum, I gained a deep understanding of that industry.


Cheska Hull posing at the Children with Cancer UK Fundraising Gala

In May 2011, Hull was a member of the original cast of the reality show “Made in Chelsea.”

Provided by Cheska Hull



I happened to be born in Thailand

My parents lived in Phuket in the 1980s, when my dad was head of Standard Chartered Bank for Phuket, which is why I was born here. We moved back to England when I was young.

Being born in Thailand didn’t simplify moving back as an expat. I still had to go through all the same steps as everyone else.

Initially, I came on a DTV digital nomad visa while freelancing for my UK clients. I told all of them, “I want to live in Thailand. That’s my dream.”

I wanted the best of both worlds.

There were a few reasons for the move

I’ve always been drawn to the famous Thai “sabai sabai” — take-it-easy — lifestyle. But when it comes to business, I’m driven. I could never just move to Phuket and not work.

Even between projects, I was constantly networking, talking to people, and pushing for collaborations with brands I’d worked with before. Now, I get to do what I’ve always loved in a place I love.

My son was also at the right age for a big change. As a single mom, the stress came from knowing how significant the move was and wondering, “Have I made the right decision?” My main priority in life is his happiness.

If he hadn’t been happy, I don’t think we would have stayed. But he’s 8, and he was able to fit in quickly — learning some Thai at school and thriving.

There was another catalyst, too. At the time, I was engaged to be married and realized that wasn’t the path for me anymore. Once I called off the wedding, the door felt wide open.

Nothing was holding me back.


Cheska Hull and her son in Phuket, Thailand.

She says her 8-year-old son is learning Thai at school and has fit in quickly.

Provided by Cheska Hull



Finding my career groove in Thailand

Browsing jobs in Phuket started as a guilty pleasure. Through meeting people and networking, someone told me about a new opening at Anantara, a hotel I already knew well. It seemed perfect. And so now, as cluster director of public relations, I have a work permit.

I’ve had to quickly learn Thai workplace customs, like addressing colleagues respectfully using “khun” before names or navigating the widespread use of nicknames. It’s about understanding a different culture and being respectful within it.

One of my favorite rituals happens every Friday during my team’s morning meeting. We go outside to a huge tree in front of the hotel with two spirit houses. We all take incense, make a prayer, and privately speak to the spirits. It’s so different and unique, I find it special.

It’s a meaningful part of their culture that I’ve come to love. I can’t imagine trying to get everyone in London to do that, they’d laugh.


Cheska Hull stroking a horse on a beach in Phuket, Thailand.

She plans to stay in Phuket.

Provided by Cheska Hull



Thailand is my long-term plan

There haven’t been many hard parts to settling in. The main challenge of living on a small, seasonal island like Phuket is traffic. You get used to a calm pace, and then suddenly there’s a massive influx of people. But that comes with the territory in hospitality and tourism, which is ultimately what we want here.

My move to Thailand is long-term. Looking back, there was an element of risk. I came with a bit of an “Eat, Pray, Love” vision. I knew I loved it here and wanted it to work, but I also told myself, “If it doesn’t, you can just go back.”

For me, the quality of life, the people, the food, the weather — just about everything about Phuket — makes it a place I want to call home forever. Island life simply couldn’t be better right now.

Do you have a story to share about living abroad? Contact the editor at akarplus@businessinsider.com.




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