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The Leap After the Dream Job: Christina Alessi on Hospitality, Simon Sinek, Faith, and Building Sfera

I originally met Christina Alessi through Simon Sinek’s team.

Years ago, I had the opportunity to produce some video work for Simon and his organization. One of the unexpected benefits of that experience is that I’ve stayed connected with several people from that team as their careers have continued to evolve. Christina is one of them.

I knew some of the broad strokes of her story. She had worked in luxury hospitality, joined Simon’s team during a pretty remarkable period of growth, and eventually left to start her own speakers bureau, Sfera Agency. From the outside, it’s an impressive career trajectory and a relatively easy one to summarize.

What I hadn’t heard was how all of those chapters actually connected.

That’s one of the reasons I wanted to have Christina on The Power of Human Stories. As we talked, one theme kept showing up across very different seasons of her career: Christina really loves people.

Not simply in the generic “people person” kind of way. She remembers things about people. She wants to know what is happening with their families. She notices what makes someone feel cared for. She enjoys creating an experience and anticipating what someone might need before they have to ask.

Long before Sfera, that instinct found a home in hospitality.

Learning to Serve People Well

Christina grew up mostly in Florida and studied advertising at the University of Florida. As a kid, she imagined herself doing something much closer to performing. She sang in church, acted in school plays, danced, and was comfortable being in front of people. She certainly wasn’t dreaming about thought leadership or speakers bureaus. She didn’t even know those industries existed.

She did, however, love hotels.

While her parents would sometimes finish a family vacation ready to get back to their own bed, Christina felt the opposite. She loved the experience of staying somewhere different and the way a trip could become a memory you carried for years.

That interest eventually led her into hospitality, first with Marriott Vacations Worldwide in Palm Beach and later with Langham Hospitality Group in Boston. She was especially drawn to luxury hospitality, where the smallest details could completely change the way someone experienced a place.

One lesson from those years has stayed with her: loyalty isn’t necessarily created by getting everything perfect. Sometimes a problem, handled exceptionally well, creates an even stronger relationship.

That idea is easy to apply beyond hotels. Mistakes happen. Expectations get missed. What people often remember is how you responded when something went wrong.

But Christina eventually realized there was another part of hospitality she loved even more.

While working at the Langham in Boston, her friend Kristen Hadeed came to visit. As they moved through the hotel, Kristen watched Christina interact with employees across the property. Christina knew everyone by name. She knew things about their families and lives and would stop to talk with people throughout the hotel.

The interaction caused Christina to recognize something about herself.

“The things I love most about my job are actually what I don’t get paid for.”

The technical responsibilities of her position were important, but the relationships were what energized her.

Kristen eventually connected her with Simon Sinek’s team. What was supposed to be a short introductory conversation lasted well over an hour, and Christina knew she wanted to be part of what they were building.

A Front-Row Seat to Growth

Christina joined Simon Sinek’s organization in 2017, right before another significant period of growth.

Her role quickly put her into conversations with CEOs, HR leaders, founders, educators, and organizations trying to work through challenges with leadership, culture, and their people. While clients might initially call because they wanted Simon for a keynote, Christina learned to look beyond the initial request and understand what was actually happening inside the organization.

Those four years gave her an unusual education in leadership, sales, influence, and thought leadership.

They also helped her put language around something she had already been doing for years.

Through Simon’s WHY process, Christina articulated her own:

“To love people extravagantly so they feel valued and valuable.”

Looking backward, she could see that same idea in her hospitality career. It was there in the relationships she built with coworkers, the experiences she created for guests, and the way she naturally approached people.

Her time with Simon didn’t suddenly give her that purpose. It helped her recognize it.

Christina talks about those years with a lot of affection. She loved the people she worked with, believed deeply in what they were doing, and felt like she had a front-row seat to a movement that was making a real impact.

Which makes what came next more interesting.

She left.

Stepping Away From Something Good

This wasn’t a story about escaping a bad job.

As the pandemic disrupted the live events industry in 2020, Christina started thinking differently about where she wanted to go next. She had fallen in love with thought leadership and the work of connecting organizations with ideas that could help their people, but she began feeling a tug toward building something herself.

In early 2021, she stepped away from Simon’s team and launched Sfera Agency.

Christina admits that entrepreneurship was never some lifelong ambition. She knew how to sell. She knew how to build relationships. She knew the speaking industry. Running a company was new territory.

There was confidence, but there was also plenty of fear.

Her description of that period was less about having a perfectly developed business plan and more about taking the next step before she could see much beyond it. Faith played a significant role in that decision and has continued to shape the way she thinks about the uncertainty that comes with entrepreneurship.

That uncertainty hasn’t disappeared simply because Sfera has now been around for more than five years.

Owning a company has forced Christina to wrestle with questions about control, trust, responsibility, and what happens when you do everything you can and an outcome still doesn’t go your way.

That part of our conversation resonated with me as a business owner too.

There is only so much you control. You can build relationships, make calls, deliver great work, and make good decisions. At some point, other things still have to line up.

Building Sfera Around Relationships

Sfera grew out of something Christina noticed during her years in the speaking industry.

She had experienced what it was like to work closely with one major thought leader while also collaborating with large speakers bureaus representing hundreds of people. She saw an opportunity to create something more boutique: a smaller roster of speakers she could know extremely well.

Today, Sfera focuses on leadership development and represents a curated group of speakers, trainers, and coaches. Christina wants to understand not only their message, but also who they are as people.

That distinction matters to her.

There are plenty of talented people with platforms. Christina wants people she trusts. When Sfera considers working with someone new, she takes her time getting to know them, watching how they interact with people, and understanding whether the person offstage actually reflects what they teach onstage.

The hospitality influence is still obvious too.

Sfera describes itself as offering the “white glove service of leadership development,” which is especially appropriate considering Christina actually went through formal white-glove service training during her hospitality career.

The environment may have changed, but the philosophy hasn’t.

Serve people well. Anticipate what they need. Make things easier. Pay attention to the details. Build relationships that extend beyond a transaction.

What Success Actually Looks Like

The conversation eventually moved beyond Christina’s career.

From the outside, her life looks pretty incredible. She travels constantly, works from beautiful places around the world, stays in hotels most of us would be thrilled to visit, and has built a business that gives her an unusual amount of freedom.

And she genuinely loves that life.

But we also talked about the danger of looking at someone else’s life and assuming you understand the whole story.

Christina has had to develop her own definition of success rather than measure her life against the milestones or experiences of the people around her. For her today, freedom matters. Meaningful work matters. Relationships matter. Knowing she is where God has called her matters.

There are also things she still hopes for.

That part of the conversation became much more personal than I expected, and I’m glad Christina trusted me enough to go there.

One thing she said stuck with me: people often look at someone else’s life and want the experiences they themselves haven’t had. Someone may look at Christina traveling through Italy and wish they had her freedom, while Christina can look at another person’s life and see experiences she hasn’t had yet.

It’s easy to spend your entire life doing that.

Eventually, Christina began realizing how much of the life she had once prayed for she was already living.

The desires that remain don’t cancel out the things she can be grateful for today.

The People She Hasn’t Met Yet

Toward the end of our conversation, I asked Christina what she was most excited about for the future.

I expected something about Sfera.

Instead, she talked about people.

She is excited about the people she hasn’t met yet. Future friends, clients, collaborators, and people who may become incredibly important to her are currently strangers somewhere in the world.

It felt like a fitting place for the conversation to end.

Christina’s career has changed dramatically over the years. Hospitality led to Simon Sinek. Simon led to a deeper understanding of thought leadership and purpose. Eventually, she stepped away from an established organization and took the risk of building Sfera.

But underneath all of those changes, the same thing keeps showing up.

People.

Christina still doesn’t know exactly what every future chapter will look like. Most of us don’t.

Sometimes all we can really see is the next step.

And sometimes it takes looking backward years later to finally understand where those steps were taking us.

You can hear my full conversation with Christina Alessi on The Power of Human Stories.

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