Doing this entrepreneurship thing can get lonely.
People often say, “it’s lonely at the top”, and that can be true. I wouldn’t exactly describe myself as “at the top,” but after years of growing my business, I understand this phrase.
When you are in the process of growing your business, and after you see some success, it can be harder to find people who understand what you are going through. A harsh reality is that you might also lose friends; people you think are your biggest supporters might not like to see you grow and get better.
But in my experience, through this process of entrepreneurship and growing a business, I have met so many incredible employees, clients, family, and friends that are very supportive and cheer you on for every win. As for the decisions and pressures I deal with as a female entrepreneur, I often find myself wanting to sit down and chat with another woman who owns and leads a company.
Someone who just gets it.
Entrepreneurs are constantly thinking about growth, clients, expanding their knowledge, innovating, finances, opportunities, leadership, and what comes next. Women entrepreneurs often face an entirely different set of obstacles.
I wanted to be in a room with people who understood me.
How I Joined The Legacy League
In the fall of 2025, Kristina Miller, the founder of Boston Business Women, launched the first Legacy League. Kristina created this group to bring together established, ambitious women entrepreneurs who wanted to continue growing their business and themselves.
The Legacy League is geared towards women who are already building their successful businesses, including six-figure-and-beyond entrepreneurs.
I actually didn’t find this group; they found me. I was invited to apply to the Legacy League, and within a few days, I decided to do it.
What really sparked my interest was that it wasn’t just another networking group. I have been involved with networking groups, including many in my town or local to me, with local businesses. Of course, this is a great way to stay connected to my roots.
This group felt different to me. It combined mastermind, mentorship, education, personal development, and peer support. Everyone who entered the room had experiences and knowledge that they wanted to share with everyone else. And it felt like I really belonged.
My First Event: A Group Becoming A Community
One of my first in-person Legacy League experiences was a gorgeous brunch at the Mandarin Oriental in Boston. This was my first time really meeting everyone, and it felt so welcoming. We all introduced ourselves and talked about our businesses and backgrounds. We took photos and really got to know each other’s stories.
It was the start of something that became really meaningful to me over time.
The brunch at Raffles was another event I attended that gave us the chance to spend more meaningful time together (beyond our scheduled virtual meetings). Every event I attended, I felt more connected and more personal. We stopped just learning what everyone did and started learning who they actually are.
The Garden Dinner
To start the summer, one of our Legacy League members invited everyone to her home for a beautiful garden dinner. It felt so different from a typical formal business event, which typically takes place at a hotel or conference center. I felt like I really connected with others that night.
Something felt so special about one member welcoming all of us into her home. I no longer saw the other Legacy League members as just other entrepreneurs on a call. I saw them as friends, moms, daughters, and as people whose stories shape who they are. It felt genuine and personal, and I really enjoyed my time bonding with them, sharing updates about our businesses and lives.
What the Legacy League Actually Looks Like
As much as I have loved the in-person gatherings of the Legacy League, a lot of value happens between them.
Throughout the year, we have weekly coaching calls. We attend virtual meeting sessions with Christina and the Boston Business Women team. Our meetings feature guest experts from different industries whom we can learn from and get inspired by.
Topics in these meetings have included:
- Accounting/finance
- Branding
- Messaging
- Marketing
- Business strategy
- Personal development
- Mindset
- Spiritual/self-growth mindset
Often, another woman has already experienced and overcome an obstacle you are currently facing. So these meetings serve as a great opportunity to talk about real challenges and hear different perspectives.
I’m Also Growing Myself
I’ve realized that growing a company also requires you to keep growing as a person. Through my experience with the Legacy League, I’ve also expanded my personal growth.
Before I launched Ladybugz in 2020, I started working with a personal and business growth mentor, Kristin Gray, who helped me work on my confidence and belief systems, which was crucial in starting and growing my business.
This year, I’ve added more mindset work using Bob Lancers’ “The Method.” It’s been a process of challenging myself mentally and spiritually and really working on a happiness plan. As an entrepreneur, your mindset can be the foundation of your growing business, so this matters.
Entrepreneurship can make you so focused on revenue, operations, clients, and employees that it’s easy to forget the person leading the business needs attention too. This year, my personal growth has felt like part of the business growth, which is really special.
Most recently, I attended the “Living Brave” Conference in Denver for creative women entrepreneurs, with a couple of my Legacy League sisters. These are all new growth experiences for me.
Miami: Where Everything Clicked for Me
After attending a group trip to Miami with the Legacy League, I felt like I really got to know the other women personally. We spent several days together in a vibrant, energetic city, and I felt like I really understood everyone’s businesses, ambitions, and stories.
It wasn’t just business. It was an experience of photoshoots, food, experiences, and fun. I loved being surrounded by other ambitious women doing innovative and creative things with their businesses. I felt energized and inspired by all the stories, and we really became friends.
The Big Leap
Before the trip to Miami, I had already been considering buying a place there. This was my third trip there, so the idea had been slowly developing in my head over time.
On this third trip to Miami, something clicked.
I expanded Ladybugz Interactive Agency’s presence there and officially opened our next market in Miami. This represented a huge next chapter in my life: in business and personally.
This decision wasn’t because of the Legacy League, but being around other women taking big risks and creating inspiring stories and lives definitely contributed to the energy to take the next big leap.
Sometimes you need to see other people doing big things to remind yourself you can too.
Working Together in Gloucester, Massachusetts
Being in the Legacy League also created a space for concentrated strategic work. We spent two full days together working at the Beauport Hotel in Gloucester, Massachusetts.
It was really nice to get into a full work mode and have uninterrupted time away from the day-to-day demands of running a business. I felt like I could really think, and we could work on our businesses, exchange ideas, and get inspired by each other.
It is really hard to recreate that experience on your own in your typical office space.
The Women Who Made The Experience
One of the greatest parts of Legacy League has simply been the women themselves. Every woman walked into the group with a different business, background, level of experience, and perspective. Over this past year, I’ve learned something from every single one of them.
We Are Not All At The Same Place… And That’s The Point
Something I really love about this group is that everyone isn’t in the exact same place. Some women have built businesses significantly larger than mine. Some are navigating stages I specifically remember going through. This creates an interesting relationship and exchange in the group.
Sometimes I’m learning from my future self five steps ahead, and other times I am helping my past self.
And the really remarkable thing is that it’s not a competition, and it doesn’t feel like one at all. It is an opportunity to pull each other forward.
What I Expected vs. What I Found
I expected:
Business coaching, networking, new ideas, expert advice, and opportunities to grow.
What I also found:
Genuine friendship, perspective, personal growth, inspiration, accountability, travel, fun, and a group of women I care about.
Yes, I Signed Up for Year Two
After being part of the Legacy League for almost a year, I recently made the decision to join for my second year.
I’m not joining because I have it all figured out.
I’m joining because I haven’t—and neither has anyone else.
Growing myself and growing within this group helps bring new opportunities, challenges, and decisions. And my business, Ladybugz Interactive Agency, keeps growing with me. I am evolving, and I want the women around me to challenge me, support me, and help me think bigger. And I want to do that for them too.
You Don’t Have to Build it Alone
But one of the biggest things I’ve learned over the past year is that you get to choose who is in the room with you as you climb.
The Legacy League has given me business education and mentorship, but it has also given me friendships, experiences, personal growth and a community.
In one year, we’ve met many times, gathered around a table in a beautiful garden, traveled together to Miami, learned from experts, and watched one another grow.
Somewhere along the way, it stopped feeling like a mastermind I had joined: it started feeling like my circle. And that’s why I’m coming back for year two!
Signing Off
I joined the Legacy League expecting it to help me grow my business. But it did so much more than that.
It helped me grow my business, grow personally, make bigger decisions, and build meaningful friendships with women who understand the journey, every step of the way.
Photo Credit: Mariah Gale Creative.
