Sometimes the best career paths are the ones we never saw coming. Chester Aycock’s journey to becoming our 2024 DweckSTAR of the Year is a testament to staying open to unexpected opportunities and the transformative power of finding work that truly aligns with your values. His path shows how extraordinary communities are built by people who show up every day with passion and purpose.

Chester’s story didn’t begin with a grand plan to transform apartment communities. After teaching in China, he returned to the United States in July 2019, planning to secure an administrative role in education. But the school year had nearly started, and staff positions were solidified—there simply wasn’t room for him to step into a school setting as he had hoped. With limited options and the clock ticking, Chester faced an unexpected crossroads. Enter his mom, who worked in the property management industry and saw potential where Chester saw uncertainty. With her encouragement, he took a career turn and accepted a position at a property that would later become known as The Horizons at Dweck. Her advice would prove life-changing: “No two properties are the same. It’s what you make of it and how you change the community.” That perspective, Chester says, “changed everything for me.”

Starting as a Leasing Consultant and later, Assistant Property Manager at The Horizons, Chester has grown through the ranks to reach his current position as Property Manager at Quimby on 23rd, leading dynamic teams and overseeing eight retail tenants. But his journey hasn’t just been about climbing the ladder. What sets Chester apart is his fundamental approach to property management. “I lead with empathy and authenticity,” he explains. “I see our residents as people first, always assuming good intentions. I listen… really listen to understand their concerns, and then I offer suggestions or explanations.”

This philosophy extends beyond individual interactions to community building. Chester decorates the lobby every month – celebrating Chinese New Year, Black History Month, St. Patrick’s Day, and changing themes from April showers with umbrellas to summer welcomes. “I want people to know we care about you. I want you to feel at home. We want it to look good, smell good, and have great customer service ready at the front door.”

Previously at Horizons, Chester led residents through a comprehensive transformation that included a washer and dryer program, HVAC updates, and additional improvements, all within a one-year timeframe. The HVAC project alone required contractors in and out of each apartment. “We removed pipes out of the wall so residents were kind of in a construction zone,” Chester recalls, “but afterwards they had control over their own heating and cooling.” His approach during this challenging period? “Letting them know, ‘Hey, I’m going to be here every step of the way.’” The results speak for themselves. Chester and his team transformed not just the physical property, but the community itself. “We see it in our surveys where we hear honest feedback and through relationships,” he says. “I find joy knowing they see a positive difference. When people feel seen and heard, there’s a new level of respect for the team working at the property FOR them.”

What has truly impacted Chester’s story is the support Dweck Properties provided for his growth. “When Dweck acquired my property, they didn’t just welcome me… they challenged me to grow,” Chester explains. “I had a mentor I could call anytime, a regional manager who trained me and welcomed my ideas, and colleagues who were seasoned and willing to teach.” This support has been transformative. From training on financials and policy to encouraging him to get his ARM certification, Chester has experienced unprecedented professional development. “The one thing about Dweck I love is that they don’t expect perfection,” he reflects. “They have coached me along the way, and that’s not an opportunity always offered.”

Chester’s leadership philosophy extends to his team management. “You can’t lead people you don’t understand,” he explains. “I invest time in learning what motivates my team, where their strengths lie, and what areas need support. I believe in meeting people where they are and coaching them forward.” This approach has yielded remarkable results. His first hire was awarded Leasing Consultant of the Year, his maintenance supervisor was recognized for professional excellence, and he has even referred people to become new residents in Dweck communities. “I was just celebrating people,” Chester says with pride, “and I’m thankful that they saw what I saw in the company and that their hard work was recognized.”

Chester attends all resident events, maintains open communication, and ensures his team embodies the same values. “My goal is to make sure residents know I’m more than someone behind a desk—I’m part of the community with them,” he says. His daily reality reflects this commitment: “Being a property manager is a bit like riding an emotional roller coaster. Some days you laugh, cry, celebrate, and problem-solve all before lunch. Residents bring their whole selves to the door, and I embrace that.”

When Chester learned he had won DweckSTAR of the Year, his reaction was pure surprise. “I was shocked,” he admits. “The DweckSTAR award is the Oscar of what we do—it’s a high honor. While I know I give my all, I also know many others do too. To be recognized in that way was humbling.” The award came “COMPLETELY out of left field,” but Chester takes it with immense pride. Behind his desk sits a showcase of his achievements, a tangible reminder of how far he’s come since 2019.

Chester’s approach to professional growth reflects a philosophy he calls “being in position.” As he explains it: “Being in position is like standing at the bus stop before the bus arrives. You might wait in the rain, in the cold, or in silence—but you’re there. You’re ready. And when the opportunity comes, you don’t have to chase it down—you just step on. The people who miss the bus are often the ones who showed up late or gave up waiting,” Chester notes. “So for me, being in position means being prepared, being present, and trusting that the right moment will come when I’m ready for it.”

Chester’s story reminds us that the best communities aren’t built by accident; they’re created by people who show up every day with intention, compassion, and an unwavering commitment to making others feel at home. In Chester, we see not just a property manager, but a community builder.

Congratulations, Chester, on being our 2024 DweckSTAR of the Year. Your dedication to the human side of property management continues to inspire us all.