“At the Table” is a series of interviews and spotlight conversations with people I admire from within and outside of the wedding industry. These conversations focus on topics related to building an intentional, relationship-first business alongside a present, connected, values-driven personal life.
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Introduction:
I was working from my favorite hometown coffee shop, as I do once a week or so, and I got chatting with the women at the next table. Turns out they lived in our old neighborhood in DC, and we spent a good 30 minutes talking about our favorite places and how much we miss it. One of those women was Chesley! We have stayed in touch via Instagram ever since, and she is one of my favorite accounts, especially for days when I feel the nostalgic ache to be back in DC. So happy she said yes to an interview!
Follow Chesley via her website and IG.
THE INTERVIEW
→ First of all, tell me in your own words what you do for work, and why you do it?
I’m a real estate agent in Washington, D.C., and my work is shaped by my background in architecture and photography. I studied architecture at Tulane in New Orleans, and after graduating, I spent about seven years working in commercial real estate and design. During that time, I also had the opportunity to work remotely abroad for a year.
Eventually, that path led me to where I am now. I’m technically in my third year, but I consider this my second year as a full-time Realtor. And I truly love what I get to do. I’ve built a happy little world that I get to step into each day, helping people find spaces that feel like home.
→ What does a typical day look like for you?
In real estate, no two days are ever the same. It really can feel like a roller coaster, depending on when things hit the market or what comes up for clients. I try to have some structure, but a big part of this job is staying flexible and learning how to triage my day. I constantly decide on what needs my attention right now and what can shift.
That said, I do have a rhythm I come back to. I love to start my mornings slowly. I usually give myself about an hour to journal and read, though it can vary depending on the day. Sometimes it’s more journaling, sometimes more reading. That slower start really helps before everything picks up.
I’ll spend the first part of my day at home handling client admin and behind-the-scenes work. I’m not naturally a morning person, so easing into things works best for me. I also like to have a late breakfast before fully diving into the day.
If I can, I’ll take a break in the middle of the day to go for a walk or a swim. Then in the afternoons, I shift into more client-facing or creative work. That’s when I feel the most focused and present, so I try to schedule anything that requires more energy or interaction during that time.
→ In her book Dare to Lead, Brené Brown says that every person has just two core values that shape everything else that they do or believe. Do you agree with that idea? If you could boil your values down to just two, what would they be? How do those influence how you do your work & live your life?
I went back and forth on this question because I wondered if I should choose one value or try to name five. But I landed on two, and the first is my faith.
My faith is a huge part of my life. I came to faith as an adult, so it wasn’t something I was raised with, and that journey has deeply shaped who I am and how I approach my work.
My second value would be stewardship: a stewardship of the gifts I’ve been given. I feel incredibly grateful that God has equipped me in unique ways, including an appreciation for design, beauty, and hospitality, all while creating spaces where people feel welcomed and cared for.
Those values naturally show up in the way I serve my clients. It is easy to get distracted from who you are and how you were uniquely created, especially when you’re building something of your own. But I try to come back to the idea that God is the CEO of this business. I’m not here to force it into existence. I have the opportunity to steward the gifts and abilities I’ve been given.
The further I get away from that mindset, the more stressed and overwhelmed I feel. The closer I stay to it, the more peace I have. For me, that has been the bigger challenge and the greater lesson, not just running the business itself, but remembering who is ultimately leading it.
→ The British author Alain de Botton has this famous quote: “There is no such thing as work-life balance. Everything worth fighting for unbalances your life.” I tend to agree with this idea, that work-life balance is an unhelpful goal, and we should instead think about aligned values and healthy rhythms in all spheres of life. What do you think about the phrase “work-life balance?” How do keep healthy rhythms & momentum going in both work and personal spheres?
I don’t know that I fully believe in work-life balance, but rather an ebb and flow in different seasons. When you’re an entrepreneur, right at the center of everything, especially when you’re doing something you’re truly passionate about, your work and your creativity naturally start to blur together.
Last year was my first full year as a real estate agent, and I noticed that everything blended and flowed all the time. Every idea and every opportunity could kind of have a seat at the table for my attention. I realized I didn’t really know how to leisure anymore. I didn’t know how to just create for myself without it being connected to my work.
There were a few things happening that really made me stop and think, “Wait, this is not going to be sustainable long term.” If my creative energy is so integral to my business, I need to make sure I’m caring for that part of myself outside of work, too.
So I started prioritizing some evenings and weekends for leisure time. There are always exceptions, but I’m learning the importance of having times where I can turn things off. I’m also trying to be more intentional with new ideas. I put every new idea into a note on my phone called my “business vision board.” At the top, I have a question: “Are you doing this because you want to, or because other people want you to?” That question has been really helpful in filtering what actually deserves my time and energy.
I think this also comes up in my friendships. A lot of my friends are creative entrepreneurs, and we all came from corporate jobs before making that transition. Work used to be more of a side conversation, but now it is such an integral part of our lives that it can easily become the center of our conversations. I’m trying to be more intentional about that, to prioritize laughter, fun, and levity more. I don’t want work to be the center of my life. God is the center of my life, and how He has wired me and what He has created me to do professionally and personally is what I want to stay focused on.
I think there is a difference between being a person with many interests and trying to chase every possible opportunity. My business as a Realtor is already multidisciplinary. It pulls from design, architecture, photography, communication, and so many other skills. I think we all have to figure out what makes sense for us and where our unique strengths are best used.
For me, it comes back to not spreading my results too thin. Sometimes we convince ourselves that something is worth pursuing because it sounds exciting or because it feels like something we should be doing. But if it is pulling us away from the things that actually bring us joy, it might not be the right thing for this season.
→ Some people argue that a focus on people and a focus on profit are competing priorities, but I love talking about the ways that running a relationship-first business aids in building more profitable, sustainable businesses. What do you think about this idea? Are they competing ideas? Why or why not?
I think they absolutely support one another. I’m incredibly grateful that my first year as a Realtor revealed that to me so fully. I feel like I got really lucky. I don’t even know how it happened, but everything I experienced and received that year put so much into perspective.
Looking back to that year, I can honestly say I made more money than ever before by staying tuned in to what felt good and what didn’t. At the beginning of the year, I was still holding onto little pieces of my previous work. I was considering sponsored content, or doing interior design shoots. The year before, I had worn about 10 different hats, so I was trying to figure out if I was going to continue doing that, or if I would fully step into my role as a Realtor.
At the end of January, I remember feeling this nudge that I couldn’t keep saying yes to all of those things if I also wanted to give a full yes to real estate. So I started saying no to the smaller things, and I only said yes to real estate.
The provision that unfolded from that was really meaningful. It showed me that I didn’t have to be everything to everyone. I learned a lot about boundaries in my business, what to say yes to, what to say no to, and that not every listing was going to be the right fit for me. I’m not trying to force every opportunity or chase every transaction. I want to work with people where there is a genuine fit and where I can bring the best of what I have to offer.
I’m doing what I’ve been uniquely wired to do. The challenge is staying as close to that as possible and not getting distracted by all the things I could have in this world.
→ What are some ways that running a people-first business has benefited you? How has it benefited others?
A lot of my clients want to work together because of my architecture and design background, and they’re excited to bring that perspective into the process. I’m excited to share it with them. It has felt really natural and enjoyable to bring those skills into the conversation and help people find a home.
I’m grateful that I’ve gotten to share with people, whether through conversations like this or through people who have heard about my work in other places. I think the biggest thing I try to encourage people to do is figure out what feels authentic to them and stay there.
People will ask me, “You get all your leads through Instagram. How do I do that?” And I always say, if Instagram doesn’t feel natural to you, don’t force it. Figure out what feels good and what aligns with how you are wired, and build from there.
I think when you stay true to that, people can feel it. And that’s what creates the kind of relationships and businesses that are sustainable.
→ Our culture and our industry is fast—trends come and go in the blink of an eye, and there’s just so much noise, especially on social media. It can be tempting to believe that the only way to stand out is to add to the noise, to follow trends, to make a bigger flash than our competitors. But what if you’re a quiet brand? I have written about the difference between Fireworks and Fireplace brands here. Would you say that your business is more of a fireworks display or a fireplace? How does that influence how you market?
My immediate reaction is that I think my business started as fireworks and has become more of a fireplace.
When I started as a Realtor, there were not a lot of people marketing the way that I was marketing. It felt different and new, and I think there was an element of creating that initial spark. But I think other people would probably describe my brand as more of a fireplace, and honestly, I feel that way too.
Again, it comes back to the theme we’ve talked about throughout this conversation. I’ve always tried to stay close to what feels true to me, what feels natural to me, and what feels honest.
I’m an entrepreneurial person, so sometimes I get distracted by ideas. I have a lot of thoughts and a lot of things I could chase, which is why my vision board has become such a helpful tool for me. There are a lot of potential “fireworks” there.
But I think a fireworks brand can sometimes feel like shouting, trying to be everything to everyone, or always needing to create something bigger and bolder. And while I think we all have our own capacity for sparkle, I’ve realized that I don’t need to constantly create a bigger display.
I’m much more comfortable being a fireplace. I like the idea of tending to something over time, creating warmth, and building something that people can return to.
→ How do you stay authentic when it often feels that “fake it ‘til you make it” energy is rewarded?
I know there is a “fake it ’til you make it” mentality in a lot of industries, and some people may disagree with me, but I really believe honesty is the best policy. The more often I lead with that, the more trust I build.
I think a good example of this is my very first listing. It was a stunning former grocery store on Capitol Hill that the owner had completely renovated. It was listed at $2.3 million, and somehow, by the grace of God, they chose me.
They knew it was my first listing, and throughout the entire process, I was honest about that. But I also brought my full self. I gave my heart and soul to that project. We photographed it multiple times, first with her things in it and then once it was staged. I cared deeply about telling the story of that home and representing it well.
During the negotiations, there was a moment when I said, “I want to call my mentor for a second opinion.” And I remember feeling a little embarrassed about admitting that. But the seller actually encouraged me and said that the fact that I was willing to be honest and ask for another perspective made her trust me more. I wasn’t pretending I knew everything. I was showing that I cared enough to get the right answer.
That moment stuck with me.
In real estate, they often encourage you that if you don’t know the answer, you can simply tell your client, “Let me get back to you on that.” I think that same principle applies in bigger ways, too. I need to be able to say, “I actually don’t have experience with that exact situation, but here is what I do know.”
I ran into this recently in a conversation where there was a question about my experience in a certain area of the market. My experience might look different from someone else’s, but that doesn’t mean I don’t have something valuable to offer. I have experience as a D.C. agent, I have transaction experience, and I also have the ability to listen and understand what people actually need.
Sometimes the issue is not about how many transactions you’ve done in a specific neighborhood. Sometimes it is about making sure you’re truly hearing your clients and that everyone involved understands what they need and is aligned.
→ What is bringing you joy in your work right now?
Something that has brought me a lot of joy lately is a spreadsheet I started keeping after each client interaction.
After each showing, phone call, or meeting, I write down the date, the client, what the interaction was, and then I reflect on how it felt. How did the showing go? Did something come up that felt uncomfortable? Is there something I could do differently next time to set myself up for success?
I’m not perfect about doing it every single time, but I’m trying. And what I’ve loved is seeing the patterns that come up, the new ideas that emerge, and the ways I can continue improving.
One of my current favorite things that came out of that process is an offer worksheet I created in InDesign. When you’re buying a house, an offer can be around 50 pages, and it can feel really overwhelming. I don’t even know if every client fully understands every word on those pages, so I wanted to create something that would help us slow down and work through it together.
Now, before I draft an offer, we can sit down and walk through the important pieces. Here are the terms. Here is what you’re agreeing to. Let’s make sure you feel comfortable and understand everything before moving forward.
That idea came from a specific moment with a client. They had decided they wanted a house, and I was typing out the terms on my phone while trying to be fully present with them. And I remember thinking, “This doesn’t feel good. This is not the business I want to build.” So instead, I sat down and created a process that felt better. And that has been really exciting for me.
I think it’s also a reflection of being a one-woman show. I’m teaching myself how to do a lot of this as I go. I’m incredibly grateful for mentors and for my broker, Jake Gaddis, who has taught me so much, but there is also a lot of learning that happens through paying attention to your own experiences.
I’ve realized that you can learn so much from yourself if you just take five minutes to reflect on what worked, what didn’t, and how you want to do it differently next time. That process of learning and improving has brought me a lot of joy.
→ If we were to meet here a year from now, what do you hope we would be celebrating?
I hope that a year from now I will be celebrating a business that continues to flourish, while also creating space for the kind of lifestyle I value.
I feel a little silly admitting this, but my long-term vision for my business is to live an international lifestyle. I love to travel— more specifically, I love being in Paris. I hope that this time next year, I’ve prioritized making more room for those experiences because they mean so much to me.
So my hope is that my business continues to grow, but that the direction of it also moves toward a lifestyle that allows me to embrace both things I love: serving my clients here in D.C. and making space for the creativity and inspiration I find in places like Paris.
I don’t think success is just about growing a business. I think it is about building a life that feels aligned with who you are and how you’ve been created.
→ Final question: what is the number one book you recommend to every creative entrepreneur?
I loved The Ruthless Elimination of Hurry. I read it years ago, and honestly, I think it is a book I should reread every year. It had a really big impact on me and the way I think about my time and my priorities.
Unreasonable Hospitality is another favorite. I’m sure a lot of people recommend it, but there is a reason it resonates with so many people. It has so much to say about creating meaningful experiences for others.
Right now, I’m reading The Artist’s Way, and I think that one may eventually move into the number one spot. As a creative entrepreneur and a Christian, it has been really illuminating to see the way it brings those two conversations together.
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