Kristy Naddell never planned to sell real estate.

For most of her young life, she planned to become a lawyer, in part for an unusually practical reason.

“I never wanted anyone to mess with me,” the Douglas Elliman agent said. “I wanted to know how to deal with things, and if something came up legally, I would know how to handle it.”

Instead, she wound up on Wall Street, then in online advertising, then in California, where she eventually broke off an engagement and walked away from a life that increasingly felt like somebody else’s.

At 32, Naddell moved back in with her mother in Cutchogue, a place she barely knew, with no particular plan beyond figuring out what came next.

Fourteen years later, Naddell has become one of the North Fork’s highest-volume real estate brokers, handling properties from Riverhead to Orient and, increasingly, multimillion-dollar new construction across the East End.

She said she surpassed $100 million in sales this year and is on pace, if her pending transactions close, to approach $200 million by year’s end. Naddell said company sales figures showed her leading North Fork brokers in sales volume last year.

It is an unlikely outcome for someone who once vowed she would never go into real estate.

Her mother had been an agent, and Naddell remembered being dragged along to open houses as a child.

“I hated it,” she said with a laugh, over lunch last month at Waypoint Restaurant. “So I was like, ‘Well, I’m never gonna do that.’”

Starting over

Naddell’s route to the North Fork was circuitous.

She studied political science and economics, first at Boston University and later at the University of Colorado Boulder, intending to go to law school. A summer internship on a trading desk in New York changed her plans.

Her father had worked on Wall Street, and Naddell found herself attracted to the speed and energy of the financial markets. But she graduated in 2002, as the industry was still reeling from the collapse of the dot-com boom.

Her first job in finance required hundreds of cold calls a day.

“I was getting cursed at, yelled at, called names,” she recalled.

She later moved into private wealth management at Merrill Lynch before leaving finance for online advertising, an emerging industry that took her first to Florida and eventually California.

By then, her life had taken another turn. She was engaged, but said she gradually realized that she had surrendered much of the independence and professional identity that had always defined her.

“I just woke up and I realized, like, this isn’t for me,” she said. “I missed having my own sense of self, my own sense of career.”

She ended the engagement and headed east.

Her mother had moved to Cutchogue and suggested Naddell come stay for a month or two while she figured things out.

“I had no idea what I was gonna do,” Naddell said.

She got her real estate license in 2012.

Learning the business

There was no ready-made network waiting for her.

“I literally didn’t know a soul,” she said.

Naddell hadn’t grown up on the North Fork. She didn’t have children in the local schools or decades of family connections to draw upon. Her mother and stepfather kept largely to themselves.

One of the people she did meet was veteran broker Tom Uhlinger, who became her mentor.

What impressed Naddell was not his salesmanship but his reputation.

“I’ve never heard a person say a bad word about this man,” she said. “Everybody respects him. He works with integrity. He always does the right thing, no matter what.”

Naddell began showing up at the office simply because Uhlinger was there. She volunteered for open houses other agents didn’t want. Eventually, Uhlinger gave her an open house at one of his $3.5 million listings.

She found a buyer.

In an interview, Uhlinger said that her success is no accident.

“Number one, she learned how to be transparent and honest,” he said. “Number two is she’s got a great sense of humor. Number three, she does what I told her to do, and that is to get along with all agents. From that point on, she gets referrals, and they continue to come. And she’s enjoying a very successful business, and she’s a pleasure to work with.”

One of the transactions that helped establish her business began much farther down the real estate food chain.

An older couple walked into the office one day and mentioned a rental. The other agents scattered, Naddell recalled. Rentals meant more work and smaller commissions.

“I’ll do it,” she said.

It turned out the couple owned a troubled rental property on Main Street in Greenport and wanted to sell it. The house was in poor condition and occupied by difficult tenants. It was hardly the sort of property likely to appear in a glossy real estate advertisement. Naddell took the listing anyway.

That sale ultimately produced five other transactions, she said, and some of the people she met through it remain clients more than a decade later.

“That’s how things started to gain some traction,” she said.

Mindy Ryan, general manager of the Greenport American Legion, remembers meeting Naddell around 2013, when she and her husband were looking for a home in Greenport.

It was a Sunday when Ryan spotted a promising property and called the listing number. Naddell swiftly returned her call and offered to show the house.

“I like this girl,” Ryan recalled thinking.

The property was a two-family house, and Naddell led the couple into its basement, past a large rat trap and down a flight of stairs into what Ryan described as a “funky basement.”

Ryan was impressed by the young agent’s willingness to get her hands dirty.

“I’m like, ‘okay, I found my agent,’” she said.

The Ryans eventually bought a different house on Front Street, where they have lived for more than a decade. Ryan said she was among Naddell’s earliest clients and believes she wrote one of the agent’s first online reviews.

She has watched Naddell’s career develop ever since.

“She gets up early and she answers her emails and texts with honest answers,” Ryan said.

The episode also contained the beginnings of a business model. Naddell concluded that chasing the largest possible commission on every transaction was less valuable than building relationships that could last for years.

“I’m usually talking [buyers] out of deals rather than” pushing them toward one, she said. “I’d rather have them wait for the right thing, because now I’ve earned their trust.”

Today, she said, virtually all of her business comes from referrals — either former clients or brokers elsewhere on Long Island who send North Fork buyers and sellers her way.

‘Real emotion’

Naddell bristles at the television version of her profession: glamorous brokers gliding through spectacular homes before collecting enormous commissions.

“I think the TV shows have ruined the industry,” she said.

The houses, she argues, are often the least complicated part of the job. Real estate transactions involve divorces, deaths, family disputes, financial pressure, unrealistic expectations and sellers who believe their homes are worth considerably more than the market does.

A fellow broker once described the profession to her with a phrase Naddell has adopted: “It’s not real estate; it’s real emotion.”

“This isn’t like buying a car or a boat,” she said. “When you’re dealing with someone’s home, there’s so much emotion tied to that property.”

That can mean telling a longtime homeowner that the house they expected to sell for $1.5 million may command only $1.25 million. Or finding the right price point for a home that’s been in a family for generations.

“For some people that are local, that grew up here and raised families here and want to move on to their next chapter, this is all they have,” she said.

The job, as Naddell describes it, becomes part sales, part negotiation, part marketing and a considerable amount of expectation management. Her preferred approach is cooperation — including with the broker on the other side of a transaction.

“I don’t care who brings the buyer,” she said. “Let’s just get the deal done.”

She believes that philosophy has helped her produce a high volume of transactions rather than concentrating exclusively on marquee properties.

“There’s some listings that some agents won’t take,” she said, citing properties in the $700,000 or $800,000 range. “They just wanted to be on the high end. But that’s not super sustainable.

“It all adds up.”

The grind

If there is a less glamorous explanation for Naddell’s rise, it is the one she returns to repeatedly: work.

“It can be a grind,” she said.

Naddell describes being essentially on call seven days a week. Her phone follows her on vacations. Clients call at night. She sometimes answers at 8 p.m. simply because dealing with the problem then is preferable to adding it to the next morning’s pile.

She currently carries 20 to 30 listings at a time, she said, in addition to properties already under contract.

The workload has forced her to build a staff, including a full-time administrative assistant and a remote assistant. Her fiancé, Ken, also obtained his real estate license and now works with her while operating a property-management business.

The irony is that adding help has not produced much free time.

“The more people I bring on, the more business comes in,” she said.

Naddell has also become increasingly systematic about measuring that business. About seven years ago, she began tracking every transaction and every dollar of commission income on a spreadsheet, setting progressively higher annual targets.

Before that, she said, “I had no idea where I stood in rankings within my company.”

Once she started measuring it, she said, the numbers began climbing sharply. But Naddell says she pays relatively little attention to the production of competing brokers.

“I’m so laser-focused on what I’m doing,” she said.

What comes next

Naddell’s business has changed considerably from the days when she volunteered for unwanted open houses.

She now works extensively with builders, including new-construction projects, and spends heavily on print and digital marketing. She has a social media team and said several recent major transactions originated with potential clients who found her through Instagram.

But she has also reached the point where success creates its own problem. Her time has become valuable enough to her that she now turns down listings when she believes a seller’s expectations are so unrealistic that there is little chance of reaching an agreement on price.

“In the beginning, you take everything,” she said.

Not anymore.

She and her fiancé recently bought an investment property in New Suffolk that they plan to renovate, an initial step toward expanding beyond brokerage into other corners of the real estate business. She has also considered building a larger team. Whether that would actually slow her down is another matter.

Naddell talks about work with the mixture of enthusiasm and exhaustion common among people who have built something that has grown larger than they expected. There are missed dinners and interrupted vacations. Friends see less of her. Her fiancé regularly asks her to put down the phone. She rarely does.

“It’s almost like an addiction,” Naddell said. “I can’t put it down.”

Fourteen years ago, she came to Cutchogue expecting to stay for perhaps a month or two while she figured out what to do with her life. She is still here.

And she appears to have figured it out.