Charleston Rhapsody | My RETREAT Story

Once a year, COMPASS collects a couple thousand agents and employees for a multi-day celebration of our culture, accomplishments, and future aspirations. We descend upon an unsuspecting city, setting up camp in our black-and-white t-shirts and comfortable walking shoes. It’s not quite Burning Man, but we practice our own version of radical inclusivity with significantly less alkaline dust getting in our clothes. Part family reunion, part wedding reception—blended with meaningful professional and personal development—this is the traveling phenomenon known as the COMPASS RETREAT.

Although I’ve been with COMPASS for nearly six years, I didn’t participate in this tribal ritual until 2023 in San Diego. One year later, Charleston took its turn as host, and I was fully committed to traveling across the country to attend. I packed my bag, eager to rekindle the relationships I formed last year and to forge new ones in the Holy City.

As soon as the plane touched down, I was ready to hit the ground running. Who would I meet? What new markets would I learn about? Stepping outside the airport, the first agent I encountered was my friend Michelle, who happens to live one town over back home. Ironically, I’d flown across the country only to connect with someone who shops at the same Target I do. Still, it was a pleasure to share a car ride with her to our hotels and chat about our plans for the week ahead.

My first stop was the COMPASS Cares Classic, an afternoon of pickleball to raise money for three outstanding local charities. I woke up that morning a little under the weather, but I gutted it out through multiple games of dinks and drop shots. My performance wasn’t exactly the Michael Jordan “flu game,” but I played respectably given how I was feeling. Taking no chances, I walked to a drugstore and bought every cold and flu remedy they had—thus ensuring my morning symptoms weren’t the start of anything serious. Like lugging around an umbrella all day, under cloudy skies, only for the rain to never show up. On the bright side, I’m now stocked up on enough NyQuil and cough drops to get me through several winters.

After pickleball, golf, or tennis, the Classic participants cleaned up and attended a cocktail party, which began to reveal the unpredictable nature of the week. There’s a “go with the flow” element to the RETREAT which flies in the face of the way I usually operate. For example, after the oversized checks were donated and the band played their last chord, our pickleball crew needed to get from the resort back to downtown Charleston. It’s at this point, standing in a dark, strange parking lot, that I find myself being shoved into an unmarked white van. Sharing a ride with strangers turned out to be the most efficient way to get to the next social event, but it certainly felt like I was doing something I’ve always told my children not to do.

In addition to being lured into suspicious cars, it’s not uncommon for one thing to serendipitously lead to another during the RETREAT.  A scheduled coffee with a Chicago agent evolved to a larger conversation when her friend from DC ambled by the cafe. With her latte gone,  the Chicago agent had to take off, leaving me unexpectedly paired with my new DC colleague. Next thing you know, she’s dragged me to a group meditation session beside the Pineapple Fountain. Something about this week had me on a vacation from Usual Steve, who clings to a self-directed schedule and narrow preferences. I had to be careful…this felt dangerously close to personal growth.

Not that the whole week was spontaneous coffee drinks and impromptu mindfulness. I made and kept plans to get together with Kara, an agent from Philadelphia whom I had never met in person before. Our relationship—born of the video studio of the marketing center—had previoulsy existed only in Google Meets and phone calls. On a sunny day, beside the historic Charleston City Market, we finally met face-to-face for the first time. Our rapport was just as natural in person, and over the course of the week, our conversations ranged from historical buildings to her dog, Olive, to the critical question: “Does the RETREAT have enough desserts?”

Kara and I had the same early morning schedule on Wednesday. Since she lives in a more urban environment than I do, she subtly shamed me into skipping the trolley and walking the twenty or so blocks to the Charleston Music Hall. I quickly learned that Kara treats Google Maps’ walking time estimates as a personal affront, determined to outpace them with her brisk Northeast stride. True to form, we managed to shave several minutes off the expected travel time, even with a friendly stop to chat with a new acquaintance from New Orleans. We arrived in plenty of time for Robert’s “state of the industry” address which was, as always, well-researched, thought-provoking, and captivatingly motivational.

My second session was led by former NFL tight end Julius Thomas, who has traded the gridiron for a second career in psychology. As he presented on performance optimization, my phone lit up with a notification from my fantasy football app. Hopefully, #80 from the Broncos didn’t notice me sneak in a few free-agent moves—though let’s be honest, my 4-6 fantasy team needed a little performance optimization itself. The standout line I jotted down from his talk was, “Can you be where you’re supposed to be, doing what you’re supposed to be doing?” The question resonated with me. In general, I think I’m pretty good at the first part (showing up) but could imporove on the second (focus).

Agents were presented with a variety of afternoon recreational options, and I chose an e-bike ride along the beach on Sullivan’s Island. Cruising down the shore, with sand sweeping across the beach and waves in the background, it was the perfect way to see the Atlantic Coast. Not to mention, I really needed  to “unwind” from all the stress of engaging conversations with awesome people. At the conclusion of our ride, we were offered a snack at the local drugstore before a COMPASS employee in a clearly marked “STAFF” t-shirt took a head count for the bus. At times, the RETREAT feels a bit like camp: take a class, bike on the beach, grab a snack, and wait for the counselor to confirm everyone is accounted for before moving on to the next activity. 

And then…there’s the parties.  When it comes to social functions, the COMPASS events team truly knows how to deliver. So much so, that they might want to consider doing some wedding planning on the side. The Refinery set the stage for an incredible welcome concert. In addition to a lively outdoor setting with multiple food and drink options, there were quieter nooks for conversations that didn’t have to be shouted in someone else’s ear. The Soirée at the Firefly Distillery raised the bar even higher, featuring casino games, a mobile oyster shucker, and a cover band playing every pop/rock anthem of the middle-aged masses. For Wednesday’s event, I packed a seersucker bow tie, but it stayed tucked away in my suitcase. All the YouTube tutorials of Southern gentlemen in the world weren’t going to produce an even bow tie knot around my neck. 

Riding back from The Refinery on the bus, belting out Bohemian Rhapsody at the top of my lungs with a dozen other agents, it occurred to me that this is why I was here. Not to hit the high B-flat at the end of the “Beelzebub has a devil put aside for me” lyric, but to embrace, and to be embraced by, this community of brilliant, passionate individuals. I had spent the week making authentic connections and I was going to leave refreshed, energized, and ready to tackle the next lessons of real estate and life. 

As the bus pulled up to the Emeline, I’m sure the COMPASS staff heard our off-key rendition of the Queen classic from blocks away. We were boldly and loudly collaborating without ego…and without tone, rhythm, or harmony as well. Still, I think performance optimizer Julius Thomas would have been proud: I was where I was supposed to be, doing what I was supposed to be doing. Anyway the wind blew, didn’t really matter to me; the RETREAT had realized the COMPASS mission to “help everyone find their place in the world.” That night, my place in the world was exactly where it needed to be—Charleston, South Carolina among some of the best people I could ever hope to meet. 

See you all in Denver!