Celebrating in Alignment: Birthday Reflections on Turning 50
Birthdays — especially milestone ones — come wrapped in layers of expectation. We’re taught that the “big” years deserve big celebrations, gatherings, and grand plans. For my 50th, I thought I had that mapped out: an end-of-summer weekend in Asbury Park with dear friends, a dinner with my ‘birthday tour’ crew from this year’s many milestone celebrations, and more travel to mark the moment.
On paper, it sounded joyful and fitting (and quite frankly, amazing). In reality, it felt heavy. I’d already traveled back and forth to New York multiple times this summer for other milestone celebrations. While I cherish every moment with my friends, the thought of one more trip, layered with more logistics and a celebration that felt “all about me,” started to feel out of alignment with who I am at my core.
I’ve always leaned more introverted, preferring small, meaningful gatherings to grand occasions. Even though these plans weren’t extravagant, they still carried the weight of movement, coordination, and a kind of spotlight that didn’t feel nourishing. It began to feel like celebrating because I “should,” not because I truly wanted to.
That’s when I made a different choice. Instead of flying up to New York, heading out east, and then down to the shore, I canceled the trip and created space. Space for myself, space for something more aligned, space for celebrating this milestone in a way that felt deeply nourishing rather than performative.
The Birthday Weekend
When my birthday weekend arrived, I found myself without a grand plan — just an open canvas. That alone felt unusual for me. I’ve always marked my birthday with something: a dinner, a trip, a way of gathering. I’m not a “big celebration” person, but I do like to honor the day. So to sit there on the cusp of turning 50 with no itinerary was both liberating and unsettling.
Part of me wondered if I’d made the wrong choice. Maybe I should have gone to New York. Maybe I shouldn't have canceled the flights. Maybe I should have filled my days with movement and activity. But when I let myself lean into the uncertainty, what unfolded instead was something I couldn’t have planned, and it turned out to be exactly what I needed.
Friday evening, I caught up with some of my oldest friends over FaceTime. We laughed, shared stories, and reminisced in that easy way that only decades-long friendships allow. It wasn’t a grand dinner or a trip to the shore — it was simpler, softer. And yet it felt like the perfect way to close one chapter and quietly welcome a new decade.
The next morning, I joined a dream life visioning workshop — the kind of reflective, inspiring ritual I was craving. The timing felt serendipitous: not only was it happening on my birthday weekend, but it fell on the 13th, my lucky number. To me, it felt like a little nod from the universe that I was on the right path.
The workshop was exactly the kind of ritual I craved: a space to reflect, envision, and connect with others who value growth and alignment. For me, turning 50 wasn’t about one more party; it was about stepping more fully into the vision I hold for my life and business.
Later that day, my brother surprised me with a family celebration. At first, I resisted the idea of anyone “planning” something for me, but what unfolded was perfect: an intimate evening together at a beautiful local resort with good food, great drinks, and the kind of luxury vibe that feels true to me. We walked through town, I found a set of antique cocktail glasses I’ll treasure, and we ended the night with dinner. It was lovely. Simple. Meaningful.
Even the smallest details added to the magic. A lobster roll kit sent by my friends from New England arrived on my birthday, and I enjoyed it on Sunday. Thoughtful, delicious, and just one more reminder that celebrations don’t have to be grand or elaborate to be memorable.
Creating Space for What Inspires You
Looking back, it was the perfect reminder that the most meaningful celebrations are the ones that feel aligned, even if they’re quieter, simpler, or different than what others expect. By choosing to celebrate in a way that nourished me, I also created the space to say yes to opportunities that truly inspire me, like attending Squarespace’s Circle Day in New York the following week.
Circle Day was an experience I wouldn’t have been able to swing if I’d gone away for my birthday — the timing and travel would have stretched me too thin. But because I had cleared that space, I was able to show up fully for an event that felt energizing, expansive, and deeply aligned with where I’m heading in business.
The day itself was inspiring from start to finish: hearing Squarespace’s founder speak, connecting with fellow creatives and business owners, and diving into workshops that touched everything from pricing projects to mindset. I even got to see a glimpse of the company’s culture behind the scenes — the kind of entrepreneurial spark that reminds me why I love building, creating, and growing in this way.
What struck me most, though, was how aligned it all felt. Being in a room full of people who value creativity and entrepreneurship, sharing ideas and stories, reminded me that building a business isn’t something we do in isolation. Community matters. Inspiration matters. And sometimes, saying no to one thing opens the door to something even more in tune with where you’re meant to be.
Choosing Alignment Over Expectation
Both my birthday and Squarespace’s Circle Day reminded me of something simple but powerful: aligned choices don’t always look like the biggest, grandest, or most expected ones. Sometimes they look quieter from the outside: a FaceTime with old friends, a vision workshop on a Saturday morning, or making space for a midweek business trip that leaves you energized and inspired.
For me, choosing alignment brought clarity, connection, and fulfillment in ways that felt affirming — gifts no “should do” celebration could have offered.
And that’s the heart of alignment in both life and business: it isn’t about doing what looks impressive, it’s about creating what feels true. The milestones, the opportunities, the growth — they all hold more meaning when they’re rooted in authenticity.
As I step into this new decade, I’m carrying that lesson forward. Not everything has to be big to be meaningful. The right choices are the ones that feel nourishing, expansive, and aligned — even if they’re quieter from the outside.
✨ A gentle prompt for you: Where in your life or business are you following “shoulds,” and what might shift if you gave yourself permission to choose what feels truly aligned instead?
Here’s to a season of alignment, clarity, and celebrating in ways that feel true to you.
With love and light– Pamela
