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4 Tips For Making Drop-Offs Less Painful, From The Author Of “Mommy Goes To Work”

Written by Jossy Lee

Photography by Photo Courtesy of Jossy Lee

When I returned to work after maternity leave with my first child, I quickly discovered that there was one big roadblock most days: daycare drop-off. The drop-off set the tone for the entire day. If Jeremy was happy to see me leave, I left feeling like a super mom. If he cried or asked me not to go—which was most days—my day started off with a pit in my stomach and I struggled to get back on track. I loved my son and my job, and had always been ambitious. But I’d grown up with a stay-at-home mom myself, and I wasn’t sure exactly what this should all look like.

Like most parents, I struggled through those early years, trying every trick in the book. Of course, it got better, and when I had my second child I felt more equipped to manage drop-offs, but the mom guilt never quite left. And while the experience became less dramatic, the questions remained. What, my kids wanted to know, was I doing all day—and why was it taking me away from them?

Then one night, I was working on a presentation when my son asked what I was doing. “Mommy’s presentation is like your show and tell,” I explained as he regarded it with interest. And it was at that moment the idea for a storybook came to me—one that helped kids understand what their moms were doing all day in a way they could really understand.

I came up with an initial sketch for my book, Mommy Goes to Work, but I knew that my experience was only one mom’s day in the life. And so I turned to my MIT-trained brain to figure out how to make the book represent as many moms as possible—and I came up with the idea of testing the book with over 100 parents and caregivers to get their feedback. In the months I tested the book, which shares different scenarios from a mom’s day that parallels her child’s. (“Mommy works on her projects. I work on my puzzles.”) The experience of testing the book demonstrated a number of strategies that smart moms all around me were using to help making working motherhood—and the dreaded drop-off—easier. Here are some of my favorites:

Give Your Kids a Hands On Experience.
Lots of the moms I know have taken their kids to work, and there’s a reason for that. They found that as soon as their child could visualize where they were and experience it for themselves, their anxiety about where their mom was lessened. Paired with explaining the parallels in mom’s and kid’s day, this strategy really helped many children to better understand where their parent was when not with them.

Use Work Language at Home.
When my son is playing with Legos, I refer to it as working on his Lego project. This subtle shift in language helps him to understand me when I tell him that I am working on a project and can’t be interrupted, because he knows the feeling of being in the zone. (And I try to give him the same space, allowing him to get his project to the next step before asking him to switch tasks whenever I can.)

Share the Not-So-Happy Moments, Too.
Many of the caregivers I talked to didn’t reserve work talk for only the promotions and wins. They also talked to their kids about feeling nervous, or about not getting along with someone on their team, or about having an idea rejected. In fact, I once shared a worry about my team not liking one of my ideas with my son when he was 3 1/2. “Don’t worry, Mommy,” he told me. “Even if they don’t like it, I still think you’re the best. Keep trying and don’t give up.” Not only was he able to understand and relate, but I like to think that sharing the tough parts of the day helps my kids to build resiliency and empathy, too.

Never Compare.
There is probably not a working mom in the world who hasn’t received the heartbreaking question, “Do you love your work more than you love me?” In the first version of Mommy Goes to Work, the book ended with the mom telling the child she loved him more than anything in the world. But I learned pretty quickly that moms didn’t like feeding into the comparison—and we realized that there was a better way to explain working motherhood to kids. Now, when my son asks me about whether I love him more than work, I recognize that he wants to feel loved. I give him a hug, make sure he understands that I love him very much, and then I tell him it’s like strawberries and bike riding (two of his favorite things). I love them both, but they’re not the same at all—and both of them bring me joy.

Jossy Lee is the founder of woom and the author of Mommy Goes To Work. She is an MIT-trained entrepreneur and a mommy who goes to work! She pioneered in nurturing mission-driven innovation at one of Asia’s first social venture funds. She spearheaded new initiatives for EF Education First, Chineasy, NEIA, and MIT. When she is not busy making the changes she wants to see in the world, she enjoys little moments with her family in Boston and Taipei.

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