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

• I’ve taken eight workcations with my toddler over the past few years.
• Most trips left me juggling work, parenting, and nonstop logistics.
• A structured, paid kids’ club finally made the balance possible.

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.

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.

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.

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.