How Intentionality, Authenticity, and Real Connection Transform Community

When Shannen Stewart moved to Orlando in 2009, she had no idea she was about to discover the industry that would define her career. I think of her as the hospitality guru — and after experiencing her events and the genuine care she brings to every interaction, you’ll understand why.

Fresh out of college with a degree in communications and journalism, she’d imagined herself doing PR — maybe even becoming a news anchor like the ones she admired on TV. But the economy had just crashed, and what she thought would be straightforward turned into something far more interesting.

Living in Orlando meant living in the backyard of one of the world’s hospitality hubs. Her husband was pursuing his master’s degree at UCF, which had one of the most respected hospitality programs in the country. Surrounded by weddings, events, and the entire ecosystem of hospitality, Shannen found herself working multiple jobs just to pay the bills — and slowly, almost by accident, falling in love with an industry she didn’t even know existed.

But she discovered she loved being behind the scenes. She moved into the vendor side of hospitality — working for furniture companies, draping companies, learning the intricate dance of hotels, venues, and events. What began as survival became a masterclass in her field.

In 2012, family needs brought Shannen back to Nashville. It was a turning point — not just logistically, but philosophically. Back in her hometown, she realized she was missing something she hadn’t expected to miss: the professional community she’d built in Orlando. The women who understood what it meant to be building something, creating something, pursuing a career.

Her core group of friends in Nashville were stay-at-home moms. “There’s nothing wrong with that,” she’s quick to point out. “That’s a full-time job.” But for her, she needed something different. She needed to be around other women in business — women who got the particular challenges of that path.

So in 2013, almost casually, Heels & Handshakes began.

It started small — just ten people, growing to twenty, a Facebook group designed to keep women connected. But something magical happened. Women started inviting their friends. The group grew organically because, as Shannen says, “We attract servant leaders and women who want to help women.” The mantra became: “Surround yourself with women who’d be willing to drop your name in a room full of opportunities.”

For years, Heels & Handshakes was exclusively focused on hospitality professionals. That made sense — it was what Shannen knew, what she was passionate about. But in 2020, everything changed again.

When COVID-19 hit, 40% of unemployment in the United States came from the hospitality industry. Overnight, Shannen faced losing half her membership. It was a painful realization, but it forced her to think bigger. She reached out to her advisory board and mentors — people smarter than her, she says — and they pushed her to diversify.

“I realized the importance of diversifying my membership portfolio,” she explains. Now, Heels & Handshakes includes women in banking, construction, tech, marketing — an entire ecosystem of industries that support each other. A woman from a bank opening a new location can connect with hospitality members for a ribbon cutting. A tech founder can partner with a marketer. It’s a full circle of abundance, not scarcity.

But what’s stayed constant is Shannen’s philosophy: make the experience intentional. She applies everything she learned in the event industry to every single meeting. The registration desk is treated like a hotel lobby — you’re greeted, helped, introduced to people. (See why I call her the hospitality guru? 😊) There are activations and experiences designed to help people connect.

And then there’s the “Four Before You Pour.”

It sounds simple, but it’s genius — and it’s exactly the kind of intentional design choice that makes Heels & Handshakes feel different from every other networking event I’ve experienced. It gives people — especially introverts, especially people walking into a room of powerful women — a permission slip to approach conversations. It removes the awkwardness and replaces it with a game. And because the members are high achievers, some of them end up meeting six, eight, ten new people, trying to beat their own goal.

What’s missing from most networking events, according to Shannen, is exactly this: intentionality. “Networking is not something you do to check a box,” she says. During her corporate days, when she was required to meet 25 new people a week for business development, she learned the difference between checking boxes and building relationships. Most people were doing the former. She was doing the latter.

“People are awkward after 2020,” she notes. “And even without 2020, some people just don’t know how to interact in real life anymore.” So Heels & Handshakes doesn’t just say “here’s a room, mingle.” It creates the conditions where connection can happen naturally. Photo booths, affirmation stations, gamified activities — these aren’t just fun. They’re intentional design choices that make people feel comfortable, welcomed, and part of something real.

In thirteen years, the organization has expanded to Chicago and Las Vegas. It’s added speakers, keynotes, and education components because, as Shannen realized, high-achieving women want more than just connections. They want to grow, learn, and develop skills. But the heart of it has never changed: it’s about making women feel seen, valued, and genuinely welcomed.

But to understand Shannen’s real differentiator, you have to go back to a story she doesn’t often tell.

Years ago, when she was working for a rental company, she found out that one of her clients — who had also become a friend — was turning 35. Shannen decided to surprise her. She rented a massive chair, an ornate thing they called “the royal chair,” brought it to her birthday celebration, and decorated it with balloons. It was a small gesture, but it was thoughtful. It was her way of saying: you matter, I see you, and I’m celebrating you.

She didn’t think much of it after that. It was just something kind she’d done.

Recently, over dinner, that same friend told her the truth. On the morning of her 35th birthday, she’d had a miscarriage. She and her husband had been struggling with infertility. Eight weeks in, she’d lost the baby. It was devastating. It was heartbreaking. And it happened on her birthday.

But then Shannen showed up with the royal chair and the balloons.

Shannen cried. She’d had no idea. She was just doing what felt natural to her — what hospitality means to her, at its core.

This is what hospitality really means to her — not the industry definition, but the human one. She references a moment from Unreasonable Hospitality where someone describes hospitality as: “It’s not black and white. It’s color.” It’s multifaceted, nuanced, alive.

For Shannen, it’s about making people feel seen, loved, and appreciated. It’s the famous quote that “people won’t remember what you said or did, but they’ll never forget how you made them feel.” That’s not just a nice saying to her. It’s her operating system.

Right now, Nashville’s hospitality landscape is booming. New hotels, new restaurants, new inventory constantly arriving. Competition is fierce. And Shannen’s watching closely what’s happening in the industry.

“Personalization used to be a luxury,” she says. “Now it’s a baseline.” A photo by your bedside, a custom note — these used to be wow moments. Now, with AI and technology making personalization easier, everyone’s doing it. So what’s the real differentiator now?

The old school. The things nobody else is doing anymore.

She gives examples: a general manager at a local sushi restaurant who leaves personalized voicemails to guests, thanking them for coming. A hotel — the Grand Hyatt — offering to charge her new electric vehicle when she pulled up to valet — something she’d never experienced before. These aren’t high-tech. They’re human. They’re intentional. They stand out precisely because they’re rare.

This ties back to something Mike Michalowicz writes about in his book Get Different: Do the opposite of what everyone else is doing. When everyone’s chasing the newest marketing tactics, the fastest automation, the cleverest AI strategy, the differentiator becomes doing what feels forgotten. A handwritten card. A phone call. Genuine attention.

Universities have reached out asking her to talk to Gen Z about networking and relationships — because Gen Z doesn’t know how to build these connections the old-fashioned way. But she’s being intentional about her yeses. If it’s something she’s passionate about, if it aligns with her life and commitments in Nashville — then yes.

She doesn’t like the term “working mom,” by the way. “No one calls a dad a ‘working dad,’” she points out. “They’re just a dad, right?” But the reality is that women with children face barriers that men often don’t. And that matters to her — especially now, as she’s rebuilding her speaking platform.

In a time that’s been called a “trust recession” — when we can’t tell what’s real and what’s AI, when marketing feels like spam, when authenticity has become a rare commodity — Shannen’s message feels urgent. And frankly, it’s why I wanted to feature her in the first place.

“Social health impacts mental health way more than people realize,” she says. There’s a misconception that setting boundaries means isolating yourself, cutting things out, saying no to everything. But that’s not it. It’s about saying yes to the things that bring you energy. It’s about surrounding yourself with people who get it, who energize you, who remind you that the pain points you’re struggling with aren’t just yours.

That’s not a luxury. That’s not optional. That’s fuel.

And in a world where AI can now generate content, mentors matter more than ever. ChatGPT can give you ideas and strategies, but a human mentor will hold you accountable. They’ll pick up the phone. They’ll make the connections. They’ll remember you’re human.

The through-line of Shannen’s story — from hospitality newbie in Orlando to community builder in Nashville to speaker re-emerging in a world that needs authentic voices — is this: Intentionality matters. Authenticity matters. Real connection matters.

In a trust recession, in an age of AI and automation and endless marketing noise, the people who will stand out are the ones who still treat people like people. Who remember names. Who send handwritten cards. Who show up for someone on their worst day with a royal chair and balloons, just because it felt right.

Shannen Stewart is one of those people. And right now, when we need those voices more than ever, she’s getting back out there to say it: You matter. You belong. And there’s a community of women ready to have your back.