This one may hit hard, but it needs to be blunt, because for a lot of people it is the nudge required to pull their head out of a very dark, very expensive place before they make one of the costliest decisions of their lives. Most people begin the biggest move of their lives by asking the wrong question first.
And a word on the shortcut everyone is now taking to do so. Do not ask an AI, Claude, ChatGPT, Perplexity, Grok, any of them, “who is the best agent in said town,” and treat the answer as gospel.
These tools do not know your market. They scrape whatever or whoever is the loudest on the internet marketing themselves, good, bad, outdated, or flat wrong, and hand it back to you in a confident, tidy sentence that sounds authoritative.
An AI has no idea who actually closes deals in that specific zip code, who overprices to win the listing, who has three unhappy clients for every happy one, or who quietly protects their buyers when it costs them a commission. It cannot vet character, competence, ethics, or track record, because none of that lives in the data it pulls from. That data is gated behind private walls on the real estate industry.
It is pattern-matching popularity, not judgment. Picking the person who will guide the largest financial decision of your life off a chatbot’s guess is how you end up with the loudest agent instead of the right one. And this is no different from a referral you get from a friend, or the person with five pretty stars next to their name. It is a crapshoot, unless you go at this properly and reverse-engineer what you actually want to achieve.
Finding the agent first is backwards, and financially brutal.
The way almost everyone does it
Here is the usual sequence. Someone gets the itch to find a place that appeals to them. They call the first agent a friend recommends, or the one whose face pulls up on the latest TikTok reel, or the name at the top of a search. You make a call. That agent is warm, responsive, and eager. Within a week, the buyer is looking at listings in whatever market that agent happens to work without any due diligence upon said agent. But they sounded ok.
Notice what just happened. The agent’s territory quietly became the buyer’s destination. The search got shaped by who they hired, not by where they should live. The tail started wagging the dog. In my world, I call it the WTF moment, because people do not realize how bad it is out there.
In the world of relocating or buying a second home in a lifestyle location takes patience and preparation. An agent’s job is to help you transact in a market. It is a real skill and it matters, enormously. But it was never their job to decide which life fits your family. When you let the introduction come first, you hand the most personal decision you will ever make to someone whose expertise, however good, is geographic and transactional.
Why the order matters
Where you live is not a purchase. It is a blank canvas for the future you want to build, the memories you want to make with family and friends, in a place that helps you thrive through the activities and the environment around you. It shapes your mornings, your health, your marriage, your kids, the people you become close to, and the version of yourself you get to be. Get it right, and you surround yourself with like-minded people living healthy, intentional lives. A house is a line item. A life is the whole future.
When you choose the agent first, three things quietly go wrong.
You inherit their biases. You only see what they sell, in the radius they cover or are somewhat familiar with, and the opportunities you never knew existed stay that way.
You lose leverage. The moment you are emotionally attached to a place someone else steered you toward, you negotiate from need instead of clarity.
You skip the real work. The hard, valuable thinking about what you actually want never happens, because you jumped straight to logistics and listings. And ooh, that’s a pretty house, distracting you from the purpose that is intetnionally driving you.
Clarity first. Confidence second. Control third. In that order, and never the reverse.
What “lifestyle first” actually means
Choosing the lifestyle before the agent means doing the interior work before the exterior search. It means getting honest about the life you are trying to create, not the house you think you want.
Ask the questions no one selling you a home will ask. What does a good ordinary Thursday look like for me in five years? Not a vacation. A Thursday. What environment makes me feel most like myself: salt air and slow mornings, or altitude, snow and effort? Open water, or open land? Who am I trying to become, and where does that person already live? What do my family, my body, and my nervous system actually need, versus what looks good in a brochure?
Those answers point you to an environment. The environment points you to a handful of specific markets. And only then does the map get small enough to bring in the right person.
The three paths are not the same
Before you go a step further, know which move you are actually making, because they demand completely different questions, different directives, and different people.
Relocation is a full life change. You are moving your whole existence, your work, your kids, your community. There is an insane laundry list of things to consider depending on whether you are a young family relocating, a family with older teens, or empty nesters building a new life with less responsibility. The stakes are total.
A second home is a divided life. You are adding a place, not replacing one, and the questions are about rhythm, distance, and how often you will really use it. And when you do use it, what are the personal and emotional gains you are chasing? This is less about money and more about a different kind of wealth very few people factor in: the wealth of time, family and environment feeding on each other’s energy, like a dance.
A vacation property, especially one you hope to rent, is closer to a business decision than a lifestyle one. The math has to work whether or not you ever fall in love with the view, and it has to work in bad times as well as good. There is an entire process behind that math that most people never touch, and I lay it all out in my book, DFTU, Buyer’s Edition (yes, Don’t F*ck This Up, a real title, and yes, there’s a Seller’s Edition too. Lol.) We cover every item possible to help guide you in this process that an agent will rarely share.
I digress. Blur these three together and you will ask the wrong questions and hire the wrong help. Separate them, and the path gets clear fast.
Great agents are worth their weight. The first one rarely is.
Here is where I want to be very clear, because it matters and because it is easy to misread me. A great local agent is worth their weight in gold. The right one knows the streets the data cannot see, the builder who cuts corners, the pocket of a town that floods, the block that holds its value when the market turns. The intricacies of a hyper-local market you cannot see on a spreadsheet. That knowledge is real, it is valuable, and you cannot get the outcome you want without it.
So am I hating on agents? I am not. I am hating on the lack of due diligence buyers put into choosing one, when the odds are already stacked against your outcome:
First, according to National Association of REALTORS consumer data, most buyers (Approximately 81% of them.) contact only one agent before moving forward, no comparison, no real vetting. You would interview three contractors to redo a kitchen, but hand the biggest financial decision of your life to the first person who returns a call.
Second, in Gallup’s ongoing honesty and ethics polling, only about one in five Americans rate real estate agents as having “high” or “very high” ethics. The majority land at “average.” Now sit with that, because ethics is not really an average kind of thing. You either operate with them or you do not. Approximately 80% of agent have average to unethical ethics.
Third, in lifestyle towns the sheer density of agents is staggering. Take Park City, Utah. From my years living there, you are looking at a town of roughly 9,000 residents and, by my own estimate, well over 1,600 active real estate agents while I was there. That is nearly one license for every 5.6 people you pass on the street. Volume is not the same as quality, and in a crowd that size, telling them apart is the whole game.
“A great agent” and “the first agent” are rarely the same person. The difference between the best professional in a market and an average one is the difference between protecting your money and quietly costing you a fortune. And the only way to tell them apart is to know the place well enough, and yourself well enough, to ask the right questions.
So once you know the life, and you know the place, then you vet the person. Hyper-local matters more than a famous name. Ask what they would tell you not to buy, and why. Ask them to talk you out of something. The professional willing to cost themselves a sale to protect you is the one worth hiring.
You are not looking for someone to show you houses. You are looking for someone to defend a decision you have already thought through. A person who puts your interests above their own. A hard find.
Where I fit
That is the entire reason my work exists. To sit on your side of the table before anyone is selling you anything. To ask the questions no one else knows to ask, help you get honest about the life you actually want, tell you which of the three paths you are really on, and reverse-engineer your must-haves so you walk in with clarity. And only then, where it fits, to connect you with a highly vetted, hyper-local advisor who knows that specific market cold.
Independent. Objective. Matched to your goals. Not the first name you meet. The right one.
The takeaway
Choose the life. Then the location. Then the person who knows that location cold. In that sequence, an agent becomes a weapon in your corner instead of the invisible anchor dragging your search somewhere you never meant to go.
Do it the other way, and you will always wonder whether you chose your life, or whether someone chose it for you and called it a listing.
Start with the life. Everything else is negotiable.