Unveiling The Untold Leadership Wisdom: Insights from a Mom Raising Triplets + Two

The Big Beginning

Leadership Lessons from a Mom of Five Babies

The year was 2000. We had two beautiful children—Caitlin, who arrived in ’98, and Kara, who came along a mere 15 months later in ’99. I was the Director of HR for the Resorts team at Walt Disney World. Those were the good ol’ days, back when my biggest concern was how to review a talent development proposal from home without someone sneezing mashed bananas on it. Life was manageable. Chaotic, sure, but manageable.

Then, in March, we found out we were expecting again. One baby. I could handle that. I had done it twice already and was practically a pro at this point. Easy peasy, I thought. But life, in its infinite wisdom and sense of humor, had other plans. By April, we learned it wasn’t just one baby—it was two. OK, I could manage that too. After all, two babies are basically just one baby with a friend, right? By May, the doctor gave us one final gift: “Actually, it’s three babies.” At this point, I began fantasizing about running away and starting a new life in a small remote village where the only screaming I’d hear was my own.

Fast forward to October 2000. My hair was only slightly gray, the house was just barely sticky, and, with 5 kids under 2 ½, I somehow thought that sending out a holiday newsletter was a good idea. Ah, how naive I was back then—before life turned me into a human version of an overstressed air traffic controller. Little did I know, I was about to learn more about leadership than any corporate seminar ever could offer. Spoiler alert: there are no PowerPoint slides in real life, just a lot of shouting and, occasionally, someone peeing on the floor.

Now, it’s January 2001, and the holiday cards I meant to send in December are still sitting on the dining room table, collecting dust and side-eye from the cat. Instead of just sending them out unsigned, I sat down at the computer to write a one-size-fits-all holiday letter. Recently, I reread that old holiday letter circa 2001, and it hit me—this hadn't been just an "update" on how our lives were going. Oh no. This had the makings of a full-on, boots-in-the-trenches crash course in survival and leadership.

So, let’s take a stroll down memory lane, and I’ll share the lessons I learned in the early days of raising five kids under 2 ½. Trust me, these pearls of wisdom apply whether you’re running a Fortune 500 company or just trying to make it through the day without breaking into the emergency chocolate.

Lesson 1: Delegation (a.k.a. Surviving Without Losing Your Mind)

Any good leader will tell you that delegation is key to survival. Or, in my case, it’s the only thing that kept me from setting the house on fire just to get a nap in the firetruck. We hired a nanny, Rachel, and without her, I’m pretty sure I’d be writing this post from a padded room. The kids loved her, I loved her, and most importantly, she changed diapers. If that’s not leadership, I don’t know what is. Take it from me: delegate everything that isn’t bolted down. You’re not Wonder Woman, and your sanity is non-refundable... and, it's good for developing your people.

Lesson 2: Expect the Unexpected (and Keep a Bag of Frozen Peas Handy)

In March, I was prepared for one baby. In April, I adjusted to the idea of two. But in May, when the doctor casually said, “Actually, there’s three,” I started rethinking all of my life choices. Crisis management became my full-time job. Did I handle it gracefully? No. But did anyone die? Also no! The secret to leadership is expecting the unexpected and making sure there’s always something frozen nearby to apply to your forehead when things get too hot.

Lesson 3: Vision Is Important (But Sometimes Just Making It Through the Day Is Enough)

Leadership experts always talk about the importance of vision. And I agree—having a vision is crucial. My vision was simple: keep everyone alive until bedtime. Rick’s vision, on the other hand, was focused on how we’d pay for five kids to go to college at once. Honestly, I didn’t care if they learned quantum physics or how to spell "banana"—I just wanted a shower. The lesson? Vision is good, but survival is better. Keep it real. Sometimes, just getting through the day without crying in the laundry room counts as a victory.

Lesson 4: Communication Is Key (Even If You’re Yelling “Where Are Your Pants?!”)

They say communication is the foundation of good leadership. What they don’t say is that most of it will be done at full volume. Between Rick, the nanny, our friends, and a few unsuspecting grocery clerks, I spent a lot of time shouting instructions, reminders, and occasionally, “Why is there peanut butter in the toilet?!” Communication, in leadership and in life, means repeating yourself until someone listens.

Lesson 5: Teamwork (Because You Can’t Do It Alone)

No one can do it alone—at least not without turning into a complete lunatic. Our family, friends, and neighbors pitched in to help us in ways I will never forget. I quickly learned that you can’t run a household or an organization by yourself. If you try, you’ll end up drinking cold coffee and arguing with a toddler about why shoes are necessary. Leaders build teams, and if they’re smart, they let those teams take the wheel when it all gets to be too much. Just make sure no one lets the three-year-old steer.

Lesson 6: Snacks Are the Key to Motivation

Forget trust falls and motivational speeches. If you want to keep morale high, keep the snacks flowing. My house was basically powered by goldfish crackers and juice boxes. Keep everyone fed, and the meltdowns are fewer. This applies to boardrooms, classrooms, and especially living rooms. You can’t lead—or parent—on an empty stomach. And if there’s anything I learned, it’s that snacks are the lifeblood of a happy team. Whether they’re toddlers or corporate executives, everyone is more pleasant with a cookie in hand.

Lesson 7: Celebrate Small Wins (Because Sometimes That’s All You’ll Get)

In leadership, it’s important to celebrate victories. Except in my house, victories looked a little different. Getting all five kids dressed before noon? Victory. Making it through a day without stepping on a LEGO? Let’s pop the champagne. Small wins count—they’re what keep you going when the big wins are nowhere in sight. Take those tiny triumphs and celebrate like you just closed the biggest deal of your career.

Lesson 8: Self-Care Is Often a Fantasy (But Keep Trying Anyway)

Ah, the elusive “self-care.” Every leadership book tells you to take time for yourself, to recharge and reset. But those books were clearly not written by a woman with five children under 2 ½. My idea of self-care was finding a quiet corner to cry in peace. But here’s the thing—self-care doesn’t always look like a spa day. Sometimes, it’s an extra five minutes in the shower or eating chocolate in the laundry room while pretending to fold clothes. Lower your expectations and dream about the day when "self-care" means more than remembering to put on deodorant.

So there you have it—lessons in leadership, brought to you by the year 2000 and one very frazzled mom. If I can survive five kids under 2 ½, you can survive anything. Just remember: delegate, communicate, and for heaven’s sake, keep a secret stash of snacks.