When my son was nine years old, he built a Parthenon for a fourth-grade class project. I’m talking columns, detail work, the whole thing. My husband and I were blown away by the care he put into it. (We still have it displayed in his bedroom, by the way.) That night, watching him beam with pride over his creation, I made him a promise: someday, I would take him to see the real Parthenon.
It took almost ten years, but we did it. This past summer, my son and I traveled through Italy and Greece together. And can I tell you something? Parenting adult children is nothing like I expected it to be. That trip was supposed to be a dream vacation, and it absolutely was. But it also cracked me open in ways I never saw coming, and the lessons I brought home have changed how I show up in my business, in my relationships, and in my own life.
When a Trip Becomes a Goodbye
When I was planning this trip, I didn’t realize I was planning a goodbye.
My daughter is four years older than my son. She left for college first, and parenting changed. I had to shift how I showed up in that relationship with her. I had to learn to let go and let her make her own mistakes, which is about as easy as it sounds (in other words, not easy at all). But I don’t think I fully understood what was happening during her senior year. I didn’t recognize that I was transitioning from one kind of motherhood into another.
Now, with my son preparing to finish high school and head to college, it hit me. That era of parenting, the one with kids at home, homework at the kitchen table, knowing where they are and what they’re eating for dinner, was ending. For good this time.
I wasn’t expecting to grieve it.
Obviously, I’m still a mother. I’m just a mother in a different way now. You’re kind of choosing to take a backseat. You step into more of an advisor role, knowing they need to fumble and figure things out on their own. And if you haven’t gone through that shift yet, it’s hard to explain. My little boy is not a little boy anymore. He’s not going to need me the way he has for the first eighteen years of his life. He’ll need me in different ways, and I’m excited about that. But that doesn’t mean I’m not also sad to let go of having kids at home.
So this trip carried all of that weight. It was joyful and heartbreaking and beautiful, all mixed together.
When Nothing Goes According to Plan
I’ll be honest with you. I am not a great traveler. Unfamiliar places, logistics, and booking details? Not my strong suit. So I hired a travel agent. I liked her, felt like we connected, and thought I’d communicated clearly what I was looking for: a luxury-level experience for a once-in-a-lifetime trip.
When we got to Italy, we quickly realized things were not what we expected. The first hotel was, well, not it. My son and I found new accommodations, moved, and figured maybe she’d just missed on that one. Then we arrived at the next hotel she’d booked, and I had a full-blown panic attack in the lobby. The area didn’t feel safe. It was the middle of the night back home, so reaching my husband for help wasn’t an option.
Long story short, we changed hotels again. And then we decided to completely abandon her plan and rebuild the trip ourselves when we got to Greece.
Here’s what I learned from all of that. First, I’m actually more capable than I give myself credit for. Booking hotels and navigating unfamiliar cities were things I had told myself I couldn’t do. Turns out, I can. It’s just not something I’d chosen to do before. Second, I had wonderful people at home who stepped up when I reached out for help. Friends who knew Italy, who sent recommendations and suggestions so my son and I could find where we needed to be.
And third (this is the one that sticks with me), walking away from money we’d already spent was hard, but staying somewhere that wasn’t right would have been harder. In business, we talk about this all the time. Sunk costs can keep you stuck in strategies, partnerships, or plans that aren’t working, just because you’ve already invested in them. Sometimes the bravest business move is admitting the plan isn’t working and pivoting before things get worse.
The Moment I Saw My Son Become a Man
Through all of those travel hiccups, my son stepped up in ways that took my breath away. He’d spent the last four years getting himself in and out of Washington, D.C. for school, and that independence showed. He was completely competent and confident navigating unfamiliar cities, finding new hotels, and rerouting our plans.
But it wasn’t just the logistics. When he saw me getting panicked or stressed, he stepped in. He was thoughtful and kind. He took my feelings into consideration. We were navigating this together, more as peers than as parent and child. He didn’t need me to be strong all the time. He showed up when my confidence wasn’t where he’s used to seeing it.
I saw so much of his father in him. I saw adaptability, resilience, and kindness in real-life situations. And I thought, what a gift. What a gift to see the very best of your child come out right before you’re about to send them into the world.
You know what this reminded me of? Delegating in business. When you finally stop hovering and let your team handle things, they often rise to the occasion in ways you didn’t expect. My son didn’t need me to manage every detail of our trip. He needed room to step up. And when I let go of that control (not by choice, honestly, but because I had to), he showed me exactly who he is becoming. That’s what happens when we trust the people around us. They grow. And so do we.
Don’t Miss Your Own Experience
So here’s where everything shifted for me.
We were in Pompeii. And let me tell you, to say I was awestruck is the understatement of a lifetime. We’re on this guided tour, and I’m looking around at these ancient ruins, and I had this moment where I thought: Oh my gosh. I’m just a girl, living my life, experiencing this for the first time. Wow.
I had been so focused on making this trip perfect for my son that I was forgetting to experience it for myself. Not as a mom. Not as the person managing the logistics, emotions, and itinerary. Just as me. AliceAnne. Seeing Pompeii for the first time.
In that moment, I made a decision. I was going to experience this trip. I was going to look for the joy and the awe and the beauty that I was getting for myself.
And it totally changed everything.
Here’s the thing: I do this in my business, too. I built Leading Lady and all of the resources in our ecosystem. I’ve carefully curated every piece of it because I want the perfect experience for the women who come into this community. And somewhere along the way, I stopped experiencing it myself. I was so focused on creating something beautiful for everyone else that I forgot to stop and find the joy, the wonder, and the beauty in what I’ve built.
Sound familiar? If you’re a woman running a business, I’d bet it does! We pour everything into our clients, our customers, and our families. And we forget that we deserve to experience the good stuff, too. So here’s your reminder: don’t spend so much effort creating an experience for someone else that you miss out on the experience for yourself.
If you’ve been running so hard that you’ve lost sight of why you started, my Strategic Planning Wheel can help you step back and see the bigger picture. Sometimes you just need a framework to remind yourself what you’re building and why it matters to you.
What the Business Bumps Taught Me About Letting Go
Oh, and because the universe has a sense of humor? While I was overseas dealing with travel chaos, my husband decided to update our computer system back home.
You can probably guess what happened next. The update completely shut down our email servers. Not for one business, but for both of my businesses. My entire team had no access to email. They couldn’t process tuition payments, couldn’t communicate with families, and couldn’t get into critical systems. And because my phone and master email were tied to all the two-factor authentication and security checks, they needed me to fix it. From Europe. With a six-hour time difference.
I’m not going to lie. It was a downer.
But here’s what I really appreciated. My leadership team handled it. When I told them there was nothing I could do from overseas, they adapted. They communicated differently. They let families know what was going on. They worked through the problem together without waiting for me to have all the answers.
I was truly powerless in that situation, and my team still kept things moving. Systems aren’t foolproof. Technology doesn’t always cooperate. But having a team you trust and people who can pivot when the plan falls apart? That’s everything. And isn’t that the same lesson I was learning with my son? You prepare, you build the systems, you put the people in place. And then you trust. You let go. You let them show you what they’re capable of.
What I’m Bringing Home
I came home jet-lagged, emotionally stretched, and honestly a little wrung out. Problem-solving from overseas while navigating unfamiliar places, while processing the grief of this parenting transition? It was a lot.
But I also came home empowered. I came home knowing I’m more capable than I thought. I came home with a deeper relationship with my son and renewed passion for my business. I came home with this quiet confidence in areas where I used to feel shaky. And I came home with a commitment to stop just building beautiful things for other people and start experiencing the beauty in what I’ve already created.
Growth doesn’t come from things going perfectly. It comes from the messy, unplanned, emotional moments that force you to dig deep and discover what you’re really made of.
Your Turn to Embrace the Imperfect Journey
I almost didn’t share this story because I was worried it would come across like I was complaining about a European vacation. That is not the point. The point is that I learned more about myself during the moments that went sideways than during the moments that went right. And I think that’s true for most of us, whether we’re talking about a trip, or raising teenagers, or running a business that keeps throwing curveballs. You’re tougher than you think. Trust me on this.
You don’t have to navigate any of it alone. If you’re looking for a community of women who get it, who understand what it means to build a business while raising a family and managing all the feelings that come with both, come join us in the Leading Ladies Facebook Group. We have real conversations about exactly this kind of stuff.
And if you’re ready to step back and get clarity on where your business is headed? Grab my Strategic Planning Wheel. It’s a great first step toward seeing the bigger picture.
