Winning on Your Own Terms

By Silvia Lupone

I finally know what it feels like to win on my own terms

Sometimes, when I wake up at Stingray Villa, I step outside onto the deck with my coffee and watch as the dive boats head off across the water toward that impossible blue. The engines roar; the sun rises; no one is yelling about meeting their quarterly goals.

And I reflect on how much different I perceive "winning" to be these days.

When I was in my 30's, I thought someone else would keep the scorecard. A boss. A Board. A title on a business card. In the 1990's, we played a nonstop game of Olympic-style conference-call juggling and title inflation. Who remembers dialing into meetings before Zoom existed? The beeps. The awkward pauses. The slight competition to speak first.

Winning meant being seen. Getting promoted. Being indispensable.

Now, in my 40's and 50's, I look at things differently.

The View From the Middle of the Climb

I am not at the beginning. I am not at the end. I am somewhere in the middle. And that middle area transforms you.

To me, true success means taking responsibility. I created a boutique hospitality company so I can determine my schedule, safeguard my energy, and build a lifestyle that fits, rather than building a lifestyle and then having to fit into it. Not the other way around. Entrepreneurism is not easier. That is a fact. But the demands are ones that I have selected.

That difference makes a big difference.

I used to give up my peace of mind in order to receive a paycheck. Many of us have done that. We saw our mothers working themselves to exhaustion in order to provide for their families. They were strong. They carried entire households. But we also saw the cost. The missed dinners. Chronic stress has been directly linked to both heart disease and burnout.

Consistently, research from the American Psychological Association has shown that chronic workplace stress affects both a person's mental and physical health. We lived that data before it had a label attached to it.

I am simply done compromising my well-being for others' validation.

What Leadership Looks Like Differently Now

In hospitality, leadership is not about telling people to hustle with all of their might. It is about emotional intelligence.

Emotional Intelligence was popularized by Daniel Goleman in the late 1990s, and at the time, it seemed softer compared to the hard metrics of employee performance evaluations. However, today, in an automated world shaped by Artificial Intelligence (AI) and remote work, emotional intelligence has become a competitive advantage.

At Stingray Villa, I lead by actively listening to my guests who are celebrating anniversaries. 

By actively listening to my employees, who have family obligations to meet. By actively listening to my vendors who are dealing with supply chain challenges. Empathy is not weakness. Empathy is clarity with compassion.

Yes, we still use Spreadsheets. Yes, we measure Occupancy Rates. Yes, we study seasonal travel trends in Cozumel. The business operates based on Systems. But the Culture operates based on Trust.

And here is the shift that made all of the difference for me.

Winning Is Setting Boundaries

Winning is not about earning a Trophy. It is about setting boundaries.

It is about saying no to Partnerships that drain us, so that we may say yes to Collaborations that energize us. It is about shutting down the Laptop at a Reasonable Hour. It is about creating a Luxury Experience for Guests, while maintaining our own sleep and health.

That is the new math that I began using. Not Addition or Subtraction. Alignment of Values and Actions. When the two align, the System will begin to run itself. Not flawlessly. Nothing does. But Steadily.

We are the Generation that went from Analog Childhoods to Digital Adulthood. We rewound Cassette Tapes with Pencils. Now we Manage Cloud-Based Booking Systems from our Smartphones. We Adapted. We Evolved.

And in this Middle Stretch of Life, I truly believe that winning on your own terms is the most strategic decision you can make.

Not Louder. Not Flashier.

Just More Authentic.

Connect With Silvia

www.stingrayvilla.com