Chris Gasbarro, an Entrepreneurs' Organization (EO) member in Boston, is the president of Ember, a boutique creative gathering agency. We asked Chris to share his thoughts on the power of timeless connections in an overly scheduled world:

Over the course of your day, how many times do you say or hear, "I have a hard stop," "Let's take that discussion offline," or stare at your Outlook calendar of back-to-back meetings?

I'd like to advocate for the idea of meetings without a hard stop, where the ideas keep flowing for as long as is necessary -- with your customers, your leadership team, and your employees. Now, don't get me wrong: I love a tight agenda and a structured offsite meeting -- each has its place and value. But when was the last time you looked at your watch in surprise and said, "Whoa, it's 11 p.m.! Where did the time go?"

A Transformative Leadership Retreat

One morning a few months ago at 8 a.m., I walked into the kitchen of a rented estate where a Fortune 1000 global leadership team was holding its annual offsite. The company's president, who had taken over a struggling, well-known brand seven months before, had been missing financial goals and alienating the business's core customer, which in turn was eroding revenue and market share to the tune of -10 percent in the previous two quarters. 

After observing for six months and making tweaks, the president gathered his nine-person global leadership team in a secluded mountain retreat for four days to debate strategy and ideas, align, and refocus on their core customer. The intention of the gathering focused on showing up as a consistent global brand.

That morning, I asked him, "So what's been the highlight or breakthrough?" He responded, "Last night we stayed up until 3:30 a.m. -- we completely lost track of time!" He shared that they had enjoyed an invigorating, 10-hour day of discussions and had continued beyond dinner into the evening hours in the library. During that time, from behind the veil, their individual personas came out -- from table topic question cards to a team member taking over the piano and leading singalongs to the European general manager showing his talents for cocktail making. 

"We connected on a deeper level, beyond résumés or egos," said the president. "We experienced each other's rich qualities that define us as a diverse group of leaders, aspects rarely visible in boardrooms or Zoom meetings."

Analog Connections in a Digital World

It made me think: In a world of hyper-digital, hybrid work and millions of PowerPoint slides -- could the real difference between profit, engagement, and outcomes be the most analog of solutions, sans clock or Outlook reminders? Is it as simple as just gathering people in a room with no agenda?

At every concert I've gone to this year -- from emerging artist Noah Derksen (what an incredible voice!) to an arena act -- I noted they all have vinyl records for sale at their merch table. The Recording Industry Association of America tracked $1.2 billion in vinyl record sales in 2022, with a lovely upward growth curve year-over-year. It's not a profit play by the artists, with the cost of the process far outweighing a Spotify upload or MP3. By pressing vinyl records, these artists seek to connect with their core fanbase, to give an experience that is a zag from what streaming services are designed to offer.

For me and my company, our No. 1 customer is our team. After navigating the remote and hybrid work model, about 14 months ago we transitioned fully to remote work, with team members spread out across North America. We made the agreement to gather as a company three times a year. These gatherings allow us to co-work, address concerns or issues, and strengthen relationships. The most significant outcomes of the offsites have indexed higher to the relationship and deep connection side. 

The Unexpected Benefits of Losing Track of Time

If I were to overlay revenue growth and performance over our internal gatherings calendar, they would show the following results:

Those are great KPIs -- and what I truly love the most is hearing the lingering echoes of laughter at midnight (a rare treat), the stories shared over coffee the next morning, and (my favorite) the genuine affinity and hugs when team members depart. These moments, to me, directly link to employee retention, net promoter score, a robust culture -- and eventually, profitability.

Last week, in that same rented estate library where the aforementioned company met, I sat with my parents as my brother and his wife arrived at 9 p.m. after a five-hour drive from New York City. It was the night before the rest of the family would arrive for my father's 80th birthday celebration -- with seven grandchildren, my spouse, and another brother. We sat down with drinks before a glowing fire and just talked. Finally, my brother said, "Geez -- it's 11:30 p.m.!" My father said, "I haven't stayed up this late in years!"

A profound realization hit me: Losing track of time is a luxury we can't afford to live without. Truly allowing yourself to be in the moment and lose track of time brings about moments of authentic connection and unforgettable experiences. These timeless moments are invaluable for both a thriving company and a fulfilling personal life.

So here's my challenge to you: When was the last time you allowed yourself to truly lose track of time? Imagine what might happen if you put down your phone, ditch the rigid agenda, and embrace the beauty of unstructured, limitless conversations. The results just might be extraordinary -- for your company, your team, your customers, and your life.

Inc