Between the World Cup arriving in New England and my recent discovery of Ted Lasso, I’ve spent an unusual amount of time thinking about soccer lately. This is surprising because I know almost nothing about the sport. I couldn’t explain the offside rule if my life depended on it. I remain deeply suspicious of a game that encourages people to repeatedly head a ball without a helmet, and for years, I was fairly certain that a pitch was something that happened in baseball.

When my daughter headed to Boston for the weekend, I told her to keep an eye out for the Scots. ( I also mentioned something about finding a Fergus, but I digress ) I’d been seeing stories on social media about Scottish fans descending upon the city for the FIFA matches, and it sounded like exactly the sort of thing that would be impossible to miss. When she got home, she confirmed that the stories were true. The Scots had apparently arrived with enough enthusiasm to energize an entire city.

What struck me, though, was that nobody seemed to be talking much about soccer. The stories people shared weren’t about strategy, standings, or scores. They were about the atmosphere. They were about the people. They were about the way a group of visitors could transform the mood of a place simply by showing up with energy, optimism, and a willingness to engage with complete strangers.

At roughly the same time, I found myself several episodes into Ted Lasso, a show that by all rights should not have appealed to me at all

. Yet there I was, completely invested in a fictional soccer team despite having no particular interest in soccer itself. The more I watched, the more I realized that the sport wasn’t really the point. Ted Lasso may be set in the world of soccer, but the show is really about people. It’s about confidence, leadership, relationships, forgiveness, growth, and what happens when someone believes in us before we’re ready to believe in ourselves.

As I watched, I found myself recognizing something familiar. It wasn’t the mustache, the endless optimism, or the habit of turning every conversation into a life lesson. What felt familiar was the role he played. Over and over again, Ted finds himself helping people through moments of uncertainty. He isn’t solving every problem for them. He’s helping them regain confidence in themselves.

After more than thirty-five years in real estate, I’ve come to believe that the houses are often the easiest part of the job. Houses have square footage, bedrooms, rooflines, and property records. Houses are measurable. People are not.

By the time someone calls a realtor, they are usually standing in the middle of a significant life transition. Sometimes it is exciting. Sometimes it is heartbreaking. Often it is both. A widow trying to leave the home she shared with her spouse for decades isn’t simply selling a house. Adult children helping aging parents downsize aren’t simply organizing a move. First-time buyers aren’t simply purchasing property. In each case, the real challenge has very little to do with real estate and everything to do with uncertainty.

That’s the part of the job people rarely see. They see the listing appointment, the sign in the yard, the photographs, the showings, and the closing. What they don’t see are the conversations that happen when someone is overwhelmed, discouraged, or afraid they’re making the wrong decision. They don’t see the moments when a client simply needs someone to help them sort through the noise and remember that they can handle what’s in front of them.

Ted Lasso does that for a soccer team, but he’s hardly unique. Good teachers do it for students. Good managers do it for employees. Good friends do it for the people they care about. At our best, realtors do it for clients. The circumstances are different, but the role is remarkably similar. When people are struggling, someone has to be the steady voice in the room.

Ted’s version usually comes wrapped in a homespun saying and a smile. My version tends to sound more like, “Okay, let’s look at what’s actually happening here.” The delivery may be different, but the goal is remarkably similar. When people are anxious, they don’t necessarily need someone to solve every problem. They need someone who can provide perspective, restore confidence, and help them take the next step.

Perhaps that’s why Ted Lasso resonates with so many people. Beneath all the jokes, soccer matches, and quirky one-liners is a simple truth: life becomes easier when we don’t have to face difficult moments alone. That’s true on a soccer field, it’s true in a city filled with Scottish fans celebrating the World Cup, and it’s certainly true in real estate.

The older I get, the more convinced I am that the most valuable thing we can offer one another isn’t advice, expertise, or even solutions. It’s the confidence that comes from knowing someone is in your corner, helping you find your footing when the ground feels a little unsteady.

The houses matter, of course. They always will.

But the people matter more.

One of the strange things about getting older is that entire decades can be hiding behind a Facebook comment.

Yesterday, my friend Ian posted “Suicide Blonde” as part of his weekly 80s Friday ritual. If you’re from Southwick, there’s a decent chance you know Ian. He hosts 80s Friday at the Southwick Inn, puts together video openings and closings every week, and generally serves as one of our local keepers of the 1980s flame. A few comments later, another Southwick native, Rob Alberti, was lamenting the lack of a good local INXS tribute band. I mentioned KICK!, who played in Westfield a few years ago and were fantastic. Ian chimed in about how much he loved INXS because they somehow managed to be rock, dance, and pop all at the same time.

It was a perfectly ordinary Facebook conversation. Or so I thought.

A few hours later, I wasn’t sitting in my condo in Westfield anymore. I was back in my bedroom on Mort Vining Road in Southwick in 1985, sitting next to the ridiculously expensive CD player I had somehow convinced my parents to buy me.

Memory is funny that way. It doesn’t ask permission.

One INXS song became another. Then another. Then The Cure showed up, which is always dangerous territory. By the time “Pictures of You” came on, any hope of spending the evening in the present had been abandoned.

Suddenly I could see that room as clearly as if I had left it yesterday. Lavender painted walls and it was one of those warm June nights when the air felt heavy and still. The windows were open because that’s what you did before air conditioning was everywhere, and I was staring out at the giant oak tree in the front yard, willing a breeze to appear even though I knew it wasn’t going to happen. The music was playing, the liner notes were spread across the bed, and I was doing what teenagers have done forever: listening to music and trying to figure out absolutely everything all at once.

The funny thing is that I don’t remember what album was playing that particular night. It might have been INXS. It might have been Depeche Mode. It could have been The Cure for all I know. I don’t remember what was keeping me awake, either. At fifteen, there was always something. What I do remember is the room. The heat. The open windows. The giant oak tree in the front yard. The liner notes spread across the bed. Somehow all of that survived while whatever teenage crisis or grand plan was occupying my attention at the time has completely vanished.

CD players were brand-new technology at the time, which means I must have made a compelling argument for my parents to make that purchase. The fact that my argument was based on the superior sound quality of digital audio should tell you everything you need to know about teenage Lesley. Other kids wanted things because they were cool. Apparently, I wanted things because I had done research. Looking back, this explains an awful lot.

Before you could even listen to a new CD, however, you first had to survive the packaging. Whoever designed CD shrink wrap should have been sentenced to opening every CD sold in America for the rest of eternity. You’d sit there picking at a corner with your fingernail—or, if patience failed, the teeth your parents were spending thousands of dollars to straighten—trying to find the magical little strip that was supposedly designed to make opening it easier. This was a lie. Eventually the plastic would come off in seventeen tiny pieces while your anticipation slowly turned into irritation. By the time you got the thing open, you felt like you’d earned the right to hear Track One played by the band in person.

Then came the ritual.

Opening the jewel case.

Taking out the booklet.

Carefully lifting the disc by the edges and placing it on the tray.

Pressing play.

And finally settling in.

Not for a song.

For an album.

There’s a difference.

If you’re Gen X, you already know where this is going. The album wasn’t the soundtrack to something else. The album was the event. I wasn’t listening while I did something else. Listening was the something else.

If I bought a new CD, there was a very good chance that was what I was doing for the afternoon. I read every word in the liner notes. Not just the lyrics. Everything. The credits. The photos. The thank-you lists. The producer. The musicians. The weird little details hidden in the tiny print. I wanted all of it.

Then again, I was the kid who had already read Shakespeare before high school and could recite Walt Whitman for fun, so those liner notes never really stood a chance. I wasn’t just listening to music. I was studying it.

Part of the reason we paid so much attention is that our music wasn’t free. Our parents might have bought the CD player, but they certainly weren’t financing my Depeche Mode habit. If I wanted a new album, I had to save for it. That meant babysitting money, birthday money, Christmas money, and those completely legitimate and not-at-all-suspicious “12 CDs for a penny” deals that somehow seemed like the opportunity of a lifetime.

A trip to the mall wasn’t shopping. It was a mission. You walked into Record Town at the Holyoke Mall with enough money for maybe one CD, two if you were feeling flush, and suddenly every decision carried the weight of a Supreme Court ruling. Was this the album with one great song and ten tracks of disappointment, or was it about to become the soundtrack to the next six months of your life? Sometimes you chose wisely. Sometimes you got home and discovered the band had apparently used all of its talent on Track One. Too bad. You owned it now.

And because you owned it, you listened differently. You listened to the songs you loved, you listened to the songs you weren’t sure about, and eventually you listened to those songs enough that you loved them too. Sometimes you fell in love with a B side track that was super obscure. There was no algorithm trying to decide what should come next. There was just whatever the artist had decided should be Track One.

That’s probably what I miss most. Not the CDs. Not even the music. The attention. The commitment. The idea that one album, one booklet, and one Saturday afternoon could be enough.

These days I can access almost every song ever recorded in seconds. And yet lately I’ve found myself buying vinyl and playing it on a Victrola turntable that looks like a suitcase that my daughter gifted me. Not because I’m under the illusion that life was better in 1985. Trust me, there are plenty of things from the 1980s that can stay exactly where they are. But there was something satisfying about the ceremony of it all. Choosing an album, putting everything else aside, and giving it your full attention.

As I bounced from INXS to The Cure, it occurred to me that maybe this is one of the reasons I still love real estate after all these years. Every week I walk through houses that are about to change hands, and every week somebody finds an old photograph, a yearbook, a concert ticket, or a box they haven’t opened in decades. What they’re really finding isn’t stuff. They’re finding pieces of themselves.

A song on Facebook sent me back to Mort Vining Road. A CD player reminded me that I was a giant nerd long before I became a Realtor. And somewhere in a house I haven’t walked into yet, there’s probably another teenager sitting on a bedroom floor, discovering the thing that will transport them forty years into the future.

The older I get, the more convinced I am that houses matter because of the ordinary moments that happen inside them. Not the big milestones. The ordinary Saturday afternoons. The music coming from a bedroom. The stack of CDs on a dresser. The kid reading liner notes like she’s preparing for a final exam.

As another work week comes to a close, I’m sitting here in Westfield listening to New Wave music and realizing that I can still picture that room on Mort Vining Road as clearly as if it happened yesterday: the CD player, the jewel cases, and the liner notes spread across the bed.

Not bad for a random Friday night, a Facebook comment, and an old INXS song.

My mother taught me that there are no real estate emergencies.

That sounds ridiculous, I know. Especially coming from someone who has spent more than three decades helping people navigate one of the biggest financial and emotional decisions of their lives. Houses flood. Roofs leak. Closings get delayed. Buyers panic. Sellers panic. Things go wrong all the time.

But what my mother meant was that the emergency itself usually belongs to somebody else. The firefighter. The police officer. The doctor. The insurance company. Once the immediate danger has passed, the Realtor’s job is not to panic. It’s to figure out what happened, determine what comes next, and help people move forward.

I learned that lesson early in my career.

I was twenty-four years old and still working under the watchful eye of my mother, who was not only my broker but also my first real estate mentor. One evening, I was sitting in my apartment reading and listening to music when the phone rang. Back then, we still had landlines, and I remember glancing at the caller ID and seeing it was Mom.

Whenever my mother called unexpectedly at night, my first instinct was always the same: something must be wrong.

I answered the phone and immediately heard the urgency in her voice.

“Turn on Channel 22.”

“Why? What’s going on?”

“Turn on Channel 22.”

I could hear sirens in the distance, but I lived near downtown Westfield and not far from the hospital. Sirens were part of the soundtrack of everyday life. I barely noticed them anymore.

“Mom, what happened?”

“Lesley, turn on the news right now.”

When I switched on the television, I understood why she sounded so alarmed. One of my listings was on fire. The building belonged to my former dance teacher, Betty Champion.

If you grew up in Western Massachusetts and spent any time around the dance world, there’s a good chance you know Betty’s name. She had been a Rockette in her younger years, which seemed impossibly glamorous to me as a child. By the time I knew her, she reminded me a bit of Bea Arthur. She was tall, drank a tremendous amount of coffee, and drove a vehicle so enormous that it would probably qualify as an oversized SUV today. More importantly, she was generous with her time and deeply devoted to her students.

I started dancing with Betty when I was about eight years old. In fact, the only reason I was back in dance at all was that my mother had decided I was spending entirely too much time alone with books. What felt like a terrible injustice at the time turned out to be one of the best things she ever did for me.

Like many dance teachers, Betty’s influence extended far beyond the studio walls. When my parents’ work schedules made transportation difficult, she would often pick my sister and me up from school herself and drive us to rehearsals. At the time, I thought nothing of it. As an adult, I understand just how much of herself she invested in the children she taught. She did that sort of thing quite a lot and for a lot of students.

A few years later, my sister wanted to pursue dance in a different direction, so we transferred to another studio that offered that sort of training. The decision made sense, but that didn’t make it easy. I didn’t particularly want to leave, and Betty was understandably hurt. We weren’t the only students who moved on during that period, and after we left, we gradually lost touch with Betty.

More than a decade passed before I heard from her again.

By then, I was twenty-four years old and working in real estate. Betty was preparing to retire and called to ask if I would help her sell her building. During one of our walkthroughs, she paused beside a wall covered with photographs from years of recitals and performances. Without saying much, she pointed to two of them.

My sister and I. I felt a sudden wave of embarrassment and guilt. We had left. We had hurt her feelings. Yet there she was, proudly pointing out our photographs as though no time had passed at all.

I stood there staring at those photographs, surprised by how emotional I felt. Even though we had left her studio, after all those years, she had never taken down our pictures. As a matter of fact, we had never danced at that address with her, so she moved those photos and hung them back up. We sat there on her walls, surrounded by hundreds of other Championettes.

I don’t remember exactly what I said in that moment. I wish I did. What I remember is the mixture of gratitude, embarrassment, and guilt that washed over me as I looked at those photographs. I had spent years thinking of Betty as an important part of my childhood. Until that moment, it had never occurred to me that my sister and I had remained part of hers.

And now this fire was taking her building and those very photos that she had moved so sweetly from place to place. The first question was whether everyone was safe. The building wasn’t just a dance studio. Betty’s family lived upstairs, and until I knew they were safe, nothing else really mattered.

Once we learned that everyone had gotten out safely, my mother gave me my next instruction.

“Call Betty.”

Not the insurance company. Not the attorneys. Not the buyer. Betty.

That was another lesson she taught me early in my career. Real estate may involve contracts, deadlines, and negotiations, but it is ultimately a people business. Before we worried about the transaction, we needed to make sure our client was alright.

I remember reaching Betty that evening. She was understandably shaken, but she was also remarkably calm. Looking back, that shouldn’t have surprised me. Betty had spent decades managing dance recitals, nervous students, backstage chaos, costume disasters, and worried parents. She was not someone who rattled easily. Heck, she had performed at Radio City Music Hall.

She thanked me for calling and listened while I stumbled my way through what was probably a very young Realtor’s attempt at reassurance. Then, in typical Betty fashion, she quietly expressed confidence that my mother and I would figure out what needed to be done next.

After making sure Betty and her family were safe, I walked down to the scene. It was less than a block from my apartment. The television footage had been dramatic, but standing there in person felt surreal. Fire trucks lined the street. First responders were everywhere. The immediate danger had passed by the time I arrived, but the reality of what had happened was beginning to sink in.

I was twenty-four years old. This was my first commercial listing, and the seller was my former dance teacher. Only a short time earlier, she had been proudly showing me photographs of my sister and me hanging on her wall. I was sick with worry for Betty and, if I'm being honest, a total rookie. I had absolutely no idea what would happen next.

I was absolutely convinced the buyer would walk away. My thoughts immediately shifted from saving the transaction to figuring out how we would help Betty if the sale fell apart. I remember pacing around my apartment that night, trying to read and realizing I wasn’t actually absorbing a single word on the page. I’d sit down, pick up my book, read the same paragraph three times, then get up and start pacing again. I didn’t sleep much.

Somewhere in the middle of all that worrying, however, my mother’s lesson began to take hold. Nobody was asking me to put out the fire. Nobody was asking me to rebuild the building. My job was much simpler. Figure out what happened. Figure out what options were on the table, then help Betty move forward. The next morning, we got to work.

The Westfield Fire Department had responded quickly enough that, while the damage was significant, the building itself had been saved. What had looked like a total loss on the evening news turned out to be something much more complicated. The transaction was suddenly in jeopardy, but it wasn’t dead.

That distinction turned out to matter.

Over the next several days, there were conversations with attorneys, insurance representatives, the buyer, and just about everyone else connected to the transaction. At twenty-four years old, I certainly hadn’t expected to spend my week helping navigate a fire-damaged commercial property, but real estate has always had a way of teaching lessons whether you’re ready for them or not.

As it turned out, Betty’s insurance policy allowed the buyer to assume the insurance proceeds if they chose to do so. After reviewing the options, the buyer agreed. The building would be repaired, the transaction would move forward, and against all odds, the closing would take place on schedule.

My first commercial listing had caught fire. It still closed on time.

For years, I thought that was the lesson.

I thought the story was about a transaction that somehow survived circumstances that should have derailed it. I thought it was about insurance proceeds, problem-solving, and the realization that even a building fire doesn’t necessarily kill a deal.

Looking back, I realize I was standing between two women who had spent their lives solving problems—one taught dance. One taught real estate. Both taught me that panic rarely helps and that people matter more than the problem in front of you.

At twenty-four, I thought those were two completely separate parts of my life. There was dance, and there was real estate. Betty belonged to one world. My mother belonged to the other.

Looking back, I think the photographs on Betty’s wall should have told me everything I needed to know. Betty trusted a former student with the sale of the building that represented the final chapter of her career. My mother trusted me to help carry the business she had built and to represent clients she had spent years earning.

Then, I was too busy trying not to screw it up to appreciate what a gift that was. It took me another thirty years or so to recognize it.

The building survived. The closing happened on time. Betty retired. The buyer repaired the property and opened a karate studio that, the last time I drove by, was still there.

The photographs didn’t survive the fire; I wish they had. The confidence those two women placed in me somehow did survive.

These days, when a transaction goes sideways, as transactions inevitably do, I still hear my mother’s voice. Not the urgent one telling me to turn on Channel 22. The calmer voice that came afterward. The one that taught me to stop staring at the problem and start looking for a solution.

My mother wasn’t the sort of broker who spent much time wringing her hands. Once we knew Betty and her family were safe, there was work to be done. What were our options? Who needed to be called? What did the buyer need to know? What did the insurance company need from us? What came next?

That was her gift.

She understood that panic rarely solves anything. Problems get solved one phone call, one conversation, and one decision at a time, even when a building is on fire.

After thirty-six years in real estate, I finally understand what she was trying to teach me. The lesson was never that bad things don’t happen. They do. The lesson was that when they do, your job is to help people find their footing again. Is 56 too old to appreciate two women that you can no longer thank in person?

That probably sounds backwards, especially since I’ve now spent more than three decades building a career in this industry. But when I graduated from Westfield State in 1992 with an English degree and a communications concentration, I genuinely thought I was headed somewhere else entirely. Public relations. Media. Writing. Storytelling. Some kind of creative communications career where I would get paid to think, write, and make things.

During my senior internship at the Springfield Library & Museums Quadrangle, it finally started to feel possible. I worked in public relations under a woman named Maryanne, who took me seriously in a way that mattered deeply at that age. She edited my writing with a red pen, trusted me with real work, and helped me understand that communication could actually become a profession instead of just something I happened to be good at.

By the end of that internship, I was helping coordinate press events and writing materials for public campaigns. One of the projects involved the Dr. Seuss Memorial Sculpture Garden, and somehow, as a college intern who barely knew what she was doing yet, I was tasked with helping run the press conference for the announcement. I was one of the people standing at the microphone speaking publicly during the event, which, in hindsight, feels kind of surreal. At the time, I don’t think I fully understood how big a deal it actually was. I just knew I was excited, overprepared, and trying very hard to look like I belonged there.

For the first time, I could actually picture a future that looked creative and intellectual and maybe even a little glamorous in that early-90s PR kind of way.

Then reality showed up.

The recession hit New England hard in the early 1990s, and those career paths suddenly looked a lot shakier than they had a year earlier. I was offered a temporary grant-funded position after graduation, but it didn’t feel stable enough to build a life around. Maybe if I had come from money or had fewer responsibilities, I would have gambled on it. But by then, I had already been working most of my life, and practicality had a louder voice in my head than idealism.

The funny thing is, real estate had already quietly been running alongside all of this the entire time.

My mother was a broker-owner, and I had been licensed at 18 years old, mostly because of her encouragement. I was already selling real estate during college to help pay bills while juggling classes, dance, and multiple jobs. At the time, though, I still thought of real estate as the practical thing. The reliable thing. The thing I did while I figured out what my “real” future was supposed to be.

What I didn’t fully appreciate then was that my mother was also giving me room to build something creative inside that world. I wasn’t just selling houses. She allowed me to run marketing and public relations for the company at a time when most real estate offices barely thought about those things at all. I hosted a weekly local television series called ERA Homes Today on Channel 40, where I was suddenly writing segments, filming, interviewing, presenting homes, and learning how media actually worked in real time.

In 1994, ERA International awarded me “Coordinator of the Year” for my media and marketing work. I was in my early twenties, and honestly, I don’t think I fully understood how unusual any of it was at the time. I just kept moving forward because that’s what I had always done.

Looking back now, I can see that I never actually abandoned the creative path the way I once thought I had. I just found a version of it hidden inside real estate.

At the same time, I was teaching dance constantly.

Not casually. Not as a little side hustle for spending money. Dance was one of the deepest parts of my identity. I taught little kids and teenagers. I choreographed. I spent most evenings in a studio after classes and appointments. During college, my days were honestly ridiculous in hindsight. Early morning classes at Westfield State, studying in the library between classes, leaving campus to teach dance all afternoon and night, then waitressing on weekends while writing papers on my Compaq Presario at two in the morning.

And somehow, I loved the chaos of it.

So when graduation came, and the economy looked unstable, real estate became the thing that made the rest of my life possible. It offered flexibility, income potential, and the ability to support myself while still protecting this huge creative part of my life that I wasn’t willing to lose.

While other people may have seen me “choosing real estate,” what I felt like I was really choosing was the ability to keep dancing, teaching, creating, and performing.

Looking back now, I think that distinction matters.

Because even after 35 years, I’ve never really approached real estate in the traditional sense. I was drawn to storytelling before sales scripts. I loved marketing before most people in this industry understood what digital marketing could eventually become. I gravitated toward video, media, psychology, communication, aesthetics, and human behavior long before those things became standard parts of the business.

And now, all these years later, I think I’m finally starting to understand that none of those interests were distractions from my career. They were the career.

The older I get, the less interested I am in pretending people are only one thing. I’m not just a Realtor. I’m also still the dance teacher. I am still the writer; still the girl fascinated by media, storytelling, and human behavior. I am still the person who gets excited about filming a video or writing an essay or figuring out how people emotionally connect to homes, towns, memories, and identity.

For a long time, I separated those pieces of myself. There was “professional me” and “creative me,” and they didn’t always feel fully connected. But lately, that divide feels a lot smaller.

Maybe that’s what happens when you get older. Maybe you finally stop trying to force yourself into neat little categories that never fit quite right to begin with.

These days, when I make videos about Western Massachusetts or write essays about memory and place and growing older and building a life, it doesn’t really feel separate from real estate anymore. It all comes from the same place. It’s all storytelling. It’s all connecte

d. It’s all trying to help people feel seen in some way.

And honestly, I think I’ve stopped apologizing to myself for being someone who needed both creativity and stability at the same time.

At 22, I thought real estate was the thing that kept me from becoming a creative person.

At 55, I can finally see that it may have been the thing that allowed me to remain one.

There was no logging in, no refreshing a screen, no pulling up listings from my phone. Heck, there were no cell phones, period.

If you wanted to know what homes were on the market, you went and got the book. That was what we all called it: The book.

It was printed on newsprint, thick and unwieldy, filled with every active listing in the area at that moment. It was already slightly outdated the minute it hit your hands, but it was what we had, so we learned how to work with it.

I would bring it back to the office like it was gold, flip through it, mark it up, study it, and try to commit as much of it to memory as I could. Because once I left that book behind, there was no quick way to look anything up again.

That was real estate in the late 80’s and early 90’s when I was starting in this business.

The other crazy thing was how we booked showings. If you were going to show buyers more than one house, “a tour”, you had to take several steps.

• Step 1: Get the aforementioned MLS book and either meet with the buyer to select homes OR select the ones you hope they will like.

• Step 2: Call the listing agency to see if the home is still available.

• Step 3: Get out your Atlas map book. You know, that big 11 x 14 book with the entire half of a state in maps included…that one.

• Step 4: Start manually mapping out the best order to show the homes. Estimate how long it takes to drive from house to house in order to create your tour appointments.

• Step 5: Call the listing agencies back again to schedule appointments. Discover that in the time that it took you to research and map out your tour, at least one of the homes has accepted an offer and is no longer available.

• Step 6: Repeat Step 4.

• Step 7: Write down the showing instructions. Lockboxes were not common then. Either: the homeowner would be home to let you in, the listing agent would meet you to open up, the door would be unlocked, OR you had to pick up the keys at the listing office BEFORE they closed for the day.

• Step 8: Map out your second set of driving directions. Head out for your tour hours before you meet your buyer to drive around the area (not the town….usually multiple towns) to retrieve the necessary keys.

• Step 9: SHOW THE HOMES. Man, are you already exhausted, and you just started working in person with your client.

• Step 10: Finish the tour and evaluate your buyer’s interest in the homes that they saw.

• Step 11: Drive all over the area, yet again, to return all of the keys to the respective listing agencies. Pray that you have returned them all successfully.

• Step 12: If you are lucky, write an offer!

• Step 13: If you are not lucky, start all over again! And that was just getting people into the houses. We still had paper contracts, carbon copies, landline phone calls, fax machines, and the occasional mad dash across town because someone forgot to return a key.

We eventually entered the era when the internet started slowly creeping into our offices.

The first big advancement was MLS listing updates being sent directly to the dot-matrix printer in the office. You still had to go get the book, but now you also got a daily update telling you which homes had gone pending, which had price reductions, and what was new to the market.

This was a golden game changer.

Next up: the fax machine.

Miracle worker.

I actually found one of those old printouts a few years ago. I couldn’t believe I had kept it.

Everything else stayed the same for quite a while. We still had to sign seven original copies of every purchase and sale agreement with a pen, in person. Yes, we could fax a copy, but almost every attorney and lender still required a wet-ink original delivered either by hand or by mail.

By the mid-’90s, we actually had the internet in its baby form of what we use now.

Mind you, it was dial-up. You know: hiss-hee-hee-schreeech-bing bong bing bong-xxxxhhht. And it was slow. I mean, go make a cup of coffee and use the restroom while it logs you in slow.

Slow, yes, but you could look up the MLS on your computer, and that was blowing a lot of minds.

As we headed into this new territory, the real estate talking heads predicted that buyers wouldn’t need us anymore. Online real estate hubs were becoming more prevalent, and the assumption was that buyers could now find homes without our help.

Well, I didn’t see it that way at all.

I thought, thank all that is good, I don’t have to deal with MLS books or janky dot-matrix updates anymore, and I don’t have to guesstimate which homes buyers might want to see. I can send them an email, AN EMAIL, with options, and they can tell me what they like. Bonus: MapQuest was starting to become a thing.

Yes, we still had to print out the directions, but I didn’t need that clunky atlas book anymore. Even still, I kept it in my trunk for about a decade longer. Just in case.

The internet kept advancing, and it turned out that, as usual, the doomsday chatter from the talking heads was nonsense.

Even with the fear of Y2K crashing our businesses, phone lines, and computer systems, we survived.

Here I am more than three decades later, still using the internet in new ways to streamline my business and better serve my clients. And so far, the Zillows of the world haven’t been able to replace my expertise, nor do I expect they ever could.

I am grateful I lived through all of those changes. But I hope I never have to go back to doing real estate the way we did before the internet.

I could. But I really don’t want to.

It was 1988, and I thought I was going to be a writer.

I had been accepted to Emerson College in Boston. I had a roommate, a dorm assignment, a plan. And then, just like that, my family’s financial situation changed, and my financial aid package disappeared.

I didn’t have a real backup plan. So I did what I had to do. I applied to Westfield State College as a commuter, got accepted, and told myself it was temporary. One year, and then I would transfer back to Emerson.

What I didn’t know at the time was that Westfield State was exactly where I was supposed to be.

I enrolled as an English major with a concentration in communications and spent most of my time moving between literature classes and video and media classes. It sparked something in me. I became curious about how words and media worked together, and without realizing it, I was building the foundation for everything I would do later.

I never left.

I found myself in small classes, often with fewer than twenty students, being taught by professors who had come from places like Brown and Harvard. It was, quite honestly, a world-class education at a state college price.

At the same time, I was working. I had already shared in another story that I was selling real estate to help pay my way through school, but that was just one piece of it. I was also teaching dance full time at a local studio and working two waitressing jobs to make ends meet.

My days were structured out of necessity. Early morning classes. Studying in the library at lunch. Leaving campus by 2:00 to get to the dance studio. Weekends spent waitressing and writing papers on my Compaq Presario.

At the time, it just felt like survival. Looking back, it was shaping everything about who I would become.

During my senior year, I was given an opportunity that changed how I saw myself as a writer.

Up until then, I thought of myself as a poet, a creative writer. And I am. But I was offered an internship in the public relations department at the Springfield Library and Museums Quadrangle, and that experience shifted everything.

My boss, Maryanne, was one of those people who changes the trajectory of your life without making a big show of it. Her red pen taught me more in six months than most of my college education combined. She challenged me, trusted me, and gave me real responsibility at a time when I was just beginning to figure things out.

One of the biggest honors I had was being trusted to run the press event for the opening of the Dr. Seuss Memorial Garden at the Quadrangle. That moment made something click. For the first time, I could see a path where my love of writing and my growing interest in media could come together into a real career.

I thought I might go into public relations.

The recession of 1992 to 1994 had other ideas.

I was offered a grant position at the Library and Museums after graduation, but it was only for six months. It didn’t feel stable enough, and I made the decision to stay with real estate and continue teaching dance.

Looking back, that was one of those quiet, pivotal moments. My life was sculpted right there.

I stayed in real estate, but I didn’t leave behind what I had learned. I started using it, almost without thinking. My mother had me working as her office manager, but she also saw something in me and supported it. She encouraged me to write press releases, to be involved in events, and eventually gave me the opportunity to be part of a local television show called ERA Homes Today that aired every Sunday.

She always had my back in that way, even when I was still figuring myself out.

At the time, I didn’t think of it as anything significant. I was just doing what needed to be done.

But I was using my education.

And I never really stopped.

I write blog posts, Substack stories, poetry. I create video. I communicate for a living.

All of that traces right back to those years. Those classes. That internship. Maryanne’s red pen.

So no, you don’t need an English degree to sell real estate.

But I am really glad I have one.

It was not my favorite job. Not even close.

I hated showing up uninvited, I hated that I knew why I was there before they even opened the door, and I really hated that I was walking into situations where people were already stressed, overwhelmed, or just done. But I needed the work, and there was always that part of me that hoped maybe, just maybe, I could help someone hang on a little longer.

So, I pull up to this house in Springfield, Massachusetts. Not the worst neighborhood, not the best either, but definitely a tired little ranch that had been hanging on for a while. You know the kind. Nothing outright wrong, but nothing really right anymore either. It just felt… worn.

I sat in my car for a minute longer than I probably needed to, files on the passenger seat, just staring at the house and thinking, “Okay… here we go.”

I grab my files, get out of the car, walk up to the door, and knock.

An older man answers, and he is immediately on edge. Not confused, not “can I help you,” just… straight to hostile. He wants to know why I am there, and when I tell him, he doesn’t miss a beat. He says he’s going to go get his gun. Just like that. Flat. Direct. No drama, which somehow made it worse.

And I’m thinking, “Okay, message received.”

I turn around, walk back to my car as calmly as I can — not running, but definitely not lingering — get in, shut the door, and just sit there for a second. Heart going a little faster than I’d like to admit, but also that very practical voice in my head going, “Yep… this one’s a no.”

I start the car, I’m about to pull out, and then — bam, bam, bam — on my driver’s side window.

It’s him.

And now we’ve gone from uncomfortable to, “Well, this is how it ends.” My heart is pounding, and I’m doing that quick math in my head of how fast I can get out of there without making things worse. He’s motioning for me to roll down the window. I crack it open maybe an inch — maybe — and I’m pretty sure this side job I took to keep a roof over our heads and food on the table is about to be a really bad life choice.

And then… everything shifts.

His whole demeanor changes. He apologizes. Not casually, not in passing, but really apologizes. He tells me he had no right to speak to me that way, that he’s sorry for scaring me. And then he starts talking. He tells me he’s a Vietnam vet, that he’s been trying to get back on his feet for a long time, and lately he just can’t make it work. There was no performance to it. No angle. Just… tired.

And then he looks at me and says, “Will you come in and talk to me?”

Now, this is the part where any logical person probably says no. And honestly, I wouldn’t blame anyone for thinking I should have.

But I didn’t.

For whatever reason — and I still can’t fully explain it — I said yes.

I went inside, sat down at his kitchen table, and listened. Not as a salesperson, not as someone trying to close something, just… listened. I went through the paperwork with him, explained what I could, and wrote up his loan modification right there. And at least for that moment, for that stretch of time, he kept his home.

When I left, he thanked me. He apologized again.

And that was it.

He always stayed with me. I truly hope he kept his home for as long as he wanted it.

Then we went down to the basement.

Now, basements in old New England homes are already their own experience. Low ceilings, uneven floors, and that slightly damp, cool air that never quite goes away. But this one had something extra.

Set into the floor were several cemetery headstones. They were laid flat, like stepping stones. The word side was up.

At some point, concrete had been poured around them, so they were just…there. Part of the floor.

We both stopped.

There is a very specific moment in real estate where you don’t immediately say what you’re thinking, but you know the other person is thinking the exact same thing. This was one of those moments.

Because for a minute, we genuinely wondered if we were standing over actual graves.

It was, of course, incredibly creepy.

We moved through the rest of the house, but that basement stayed with both of us. It wasn’t until a few days later, after I did a little digging, that the much more logical explanation surfaced. At some point, it was believed that a monument maker had owned the home, and those stones were likely mistakes — unusable pieces repurposed as stepping stones in what was probably once a dirt-floor basement.

Practical. Resourceful. And still…a little unsettling.

Real estate will show you a lot of things over the years. I have shown hundreds of homes, and I don’t remember all of them, but I will never forget THIS one.

The year, 1988. Summer.

I am picking up my friends so we can drive to Misquamicut, RI, and spend the day at the beach. This is my new normal, as I drive for gas money. My hair has honeyed in the sun, my freckles are popping, and the music is always cued up. This was THE summer of my life. Bryan Adams, eat your heart out.

Why can I do this all summer? Well…let’s look back a little bit.

My mom, Shelley, owned a real estate brokerage in Westfield, MA. With my sister, I spent my youth helping mom with all sorts of real estate-related tasks. When I turned 18, my mom encouraged me to get my real estate salesperson’s license so I could help pay my way through college (see the caravan story where this is also referenced).

Well…Mom gave me a lead for a house in Springfield, MA. It was an older, retired couple that wanted to sell their family home. I showed up at the appointment in a full suit, hair pulled back, makeup subtle, and tried to act like a grown professional. The couple was absolutely lovely and signed up with me to list their home for sale. As we said goodnight, the wife had only one question, “Dear, we like you a lot, but are you old enough to sell real estate?”

Well, that was a tough question.

Luckily, I had been a competitive dancer for years, standing in front of panels of judges, so I knew how to keep a straight face under pressure. I stayed cool and said, “Well, ma’am, only barely old enough, but I have a team of wonderfully experienced agents who are going to be right by my side.”

I thanked them for their trust… then got in my car and nearly puked on the ride home.

Fast forward about a month. It’s late June. The home has closed, and I’ve just gotten paid.

Up until that point, I had worked as a babysitter, a tobacco field worker, in several food establishments, as a dance teacher, and whatever else I could find to cobble together a few pennies.

But THIS paycheck?

It was bigger than everything I had earned in an entire summer put together.

And then I made a choice… one I’m pretty sure my mom did not love.

I took the entire summer OFF.

Yup. No more work. No other jobs… I was off.

My mom was less than pleased, but I think, deep down, she understood that I had been “adulting” since I was a kid. She let it go — at least for the short term.

So here we are, back in the cherry-red Chevy convertible… heading to Misquamicut Beach.

I pick up my friends — a rotating cast of characters depending on the day or the week — and Misquamicut becomes my place that summer.

The routine is always the same. We meet in a central parking lot, pile into the car with coolers and beach bags, and take the back roads from Southwick through rural Connecticut until we hit 91, then 84, and beyond.

And while we drove? MUSIC. Lots of it.

One song in particular comes to mind: the soundtrack from the movie Cocktail on a cassette tape. And then that one song — “Wild Again.”

My best friends and I are standing up in the open convertible, salty wind blowing through our hair, Ray-Bans flashing in the summer sun, screaming out the chorus.

The days were many and a blur, but those morning rides to the beach have stayed with me.

Now, as a 55-year-old still in the real estate business, it would be easy to look back and judge that 18-year-old version of me as flip or irresponsible for taking the summer off. That would be a mistake.

What she learned that summer was agency over herself — and the quiet realization that she could, indeed, find a way to make things happen.

That young girl believed real estate was just a stepping stone in her life. She was wrong about that. But she was so right about one thing — this career would give her agency over her own life.

It has given me the freedom to care for my daughters in the way I chose, the freedom to travel when I want to, and the gift of meeting so many amazing people along the way.

I thought that the first commission bought me a carefree summer. What it really bought me was a life where I could make my own choices… and be a little wild again whenever I wanted.

I got my real estate license when I was eighteen years old.

Not because I had some grand vision of a lifelong career in real estate. The plan, as I remember it, was public relations. Real estate was just something my mother suggested I do to help pay for college.

My mother, Shelley Weber, owned Classics Real Estate on Main Street in Westfield, Massachusetts. Real estate had already been the background noise of my childhood for years. My sister and I folded newsletters, licked envelopes, stuck stamps, and generally did whatever small tasks Mom needed done around the office.

So getting licensed felt less like entering a profession and more like… stepping into the family business for a while.

At eighteen, though, I was suddenly no longer the kid hanging around the office doing homework. I was a REALTOR.

That meant I had to attend my first broker caravan.

For those who don’t know, a caravan is when a group of real estate agents gets together to tour new listings in the area. Back then, there were no online tours, no MLS photos you could scroll through from your couch. If you wanted to see houses, you got in your car and drove to them.

The caravan started at our office.

The space was small and cozy because, truth be told, I had helped clean, paint, and set it up when my mother opened the company. There was a small greeting area with a round table, a few cubicles behind it, a spot for the dot matrix printer that went zzzzzt… zzzzt… zzzzt, and a tiny back area with a bathroom and what generously passed for a kitchen.

Coffee was brewing in the back.

When the agents arrived, we all gathered around that round table with our cups of coffee while my mother led the meeting.

Now, here’s the thing.

Most of the agents in that room had known me since I was a teenager. They had watched me grow up in the office, doing homework in a corner or running errands for my mom. So when I showed up to the caravan dressed as a professional REALTOR — skirt, blouse, blazer, ballet flats — it must have felt a little strange for them.

It certainly felt strange for me.

I was nervous about everything.

Nervous about saying the wrong thing.
Nervous about being so young.
Nervous about trying to be taken seriously in a room full of experienced professionals.

So we headed out. There were several homes on tour that day, but only one sticks in my memory: my mom’s friend Jeanne’s listing.

It was an aging multi-family home owned by a young family. The owner, a very pregnant young woman, opened the door and greeted us. Jeanne led the tour.

Fake wood-paneled walls. Rough wood floors. Linoleum bathroom floors. Hodgepodge furnishings. It was clearly a home cobbled together over time, but it was clean and loved.

We reached the primary bedroom. There was no closet door, just an opening with a metal support bar across it.

And on the support bar…

…a pair of handcuffs.

Everyone kind of looked nervously around the room.

Then Jeanne, in her perfectly coiffed middle-class-lady way, said:

“Well, I guess we know how she got pregnant.”

And with that, she deadpanned it and simply continued the tour.

My mom and I caught each other’s eye, and it was all we could do not to burst out laughing.

As we normally did at the end of a caravan, we headed to The Good Table for lunch. Obviously, Jeanne’s multi-family listing was the primary topic of conversation.

As the literal “new kid,” I stayed pretty quiet and tried to take it all in. I learned a lot that day.

These adults who had intimidated me earlier were funny and welcoming. They weren’t treating me like a child, and they were making an effort to include me in the conversation, even if I was too uncomfortable to join in.

I also learned that real estate wasn’t the job I thought it was going to be.

And I’ve been learning that every single day since that first caravan.

Closing the door of my dream home for the last time was one of the hardest things I have ever had to do.

Even though I have worked as a REALTOR® for my entire adult life, when it is your own home, your emotions become entangled in the very walls of the place you live. Making a big transition can be a profound emotional journey.

When this journey began, it was an excursion of love, dreams, and a great deal of hope.

My husband and I had sold our starter home, paid off the building lot, and began building our dream house. It was a home he had designed in an architecture class before we had even met. Together, we built it with our own hands.

We did everything ourselves: clearing the lot, grading it, pouring the foundation, framing the house, laying the roof shingles, and eventually finishing the floors and carpentry inside. When it was complete, the house truly felt like an extension of us — and in my eyes, an extension of our love and commitment to each other.

Some homes feel temporary, like our starter home did. This house did not. This house had permanence.

It was a large center-hall Colonial set on twelve acres. It could have felt too big in every way, but we made it cozy. We incorporated architectural pieces salvaged from antique homes and furnished it with antiques and collected décor. The large windows brought the woods indoors, giving us beautiful views year-round.

Outside, we transformed the front yard into flowing beds of perennial shrubs and flowers, giving the home a cottage-garden feel as you approached. While large in square footage, it was comfortable and welcoming. Visitors often said the house felt warm.

Before long, our home became the hub of gatherings. Dinner parties, holidays, game nights — we hosted them all.

A few years later, our daughters arrived and filled the house with even more love and joy. It was the sort of place where you could easily imagine growing old. I pictured my daughters bringing their friends home. I imagined finishing the walk-out basement into a rec room where slumber parties would rule the land. I imagined teaching my grandchildren how to garden or taking them on hikes through the woods to the pond out back.

But life does not follow a script, and it does not always give us storybook endings.

My marriage ended. While I could afford the mortgage payment on my own, heating and maintaining a house of that size with two very young daughters was simply not realistic. I had to make the heart-wrenching decision to sell the house and move into something that better fit the life I was now living.

It was not a simple decision, and the process was difficult. But I knew it was the right thing to do, and I moved forward.

In the process, I followed the very advice I had given so many of my clients over the years: pack away what you do not need, stage the home simply, remove the family photographs, clear the counters. Empty half the closets, tidy the garage, keep the yard looking its best, and be ready to show the house at a moment’s notice.

It turned out to be a powerful exercise in empathy. I was living through the inconveniences I had so often coached my clients to endure.

More importantly, the experience reinforced something I had learned after years in real estate: selling a home is rarely about square footage, marketing strategy, or timing. It is about walking through a door you may never have expected to walk through — and then closing it quietly behind you.

As it turns out, I landed just fine.

I love the home I live in now, a house that has sheltered my daughters and me for the past eighteen years. Every once in a while, I still think about that big family home we built together. The dreams those walls once held are still sweet memories.

But dreams are not the same as life.

The life we actually lived unfolded in this house — the one my daughters remember as “home.” The house where we hosted holidays, game nights, and slumber parties. The house I created on my own for my daughters and me to rebuild, to grow stronger, and to learn resilience.

The house where I found myself again.

That dream house held part of my plans, but not my whole life.

Sometimes, the house we think we will grow old in becomes the place that quietly prepares us for the next chapter.

I’ll be sharing more reflections like this here from time to time. If you’d like them delivered to your inbox, you’re welcome to subscribe.

This space is where I’ll share stories about homes, small towns, and the moments that happen in between.

Houses hold more than furniture and square footage. They hold people’s lives.

This space is where I want to write about that.

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