I’m writing this anonymously because Jamaica small. People read, people talk, and people add your name to a story you never told. Still, some truths need a witness, even if the witness has to keep their face in the crowd.
This is about real estate, but it’s also about culture, power, and the quiet ways doors get opened—or kept closed. It’s about returning home as a Jamaican who has lived abroad, thinking you understand the place because it lives in your bones, then realising that the rules of engagement are… different. If you’re an expat coming back to work in property—agent, broker, developer, surveyor, whatever—this is for you. If you’ve never left but you’re trying to move upward, it’s for you too.
It begins with friendship. Or what looks like it.
You meet someone who calls you “friend.” You eat together, laugh together, share drinks and stories, meet families, celebrate small wins. On the surface, the fellowship is real. But when the calendar fills with networking events—those quiet rooms where deals get whispered, where a handshake today turns into a listing tomorrow—you never hear of them. Or you hear at the last minute, in a throwaway sentence, or through the grapevine: “Oh, didn’t they tell you? So-and-so is going to that mixer at the hotel tonight. Big people will be there.” You check your phone. No message. You scroll. No invite.
Meanwhile, you’re asked to co-list on things that are far away, messy, or uncertain—forty-odd lots scattered across parishes, or a bulk set of fixer-uppers that will cost more in fuel and phone calls than any commission can justify. The commission rate? Two percent. If another brokerage brings the buyer at one percent, then you split what remains with your broker, and by the time the arithmetic finishes you’re looking at 0.25%. That’s not business; that’s an unpaid internship with a blazer.
What you’re experiencing is the difference between social inclusion and economic inclusion. You’re invited to dinner, but not to deal flow. You’re welcome to vibes, not to value. And in a small market like Jamaica, where the same surnames run across ministries, boardrooms, and gated communities, those exclusions compound. It’s not always malice. Sometimes it’s just how the current carries: people hold tight to the networks that made them, and they don’t extend those networks lightly.
But sometimes it is malice. Or, more precisely, it’s what we call “crab inna barrel.” Everyone reaching for the rim at the same time, feet on another crab’s shell, claw on another claw. This is not unique to Jamaica, but we have our own flavour of it: an instinct for survival that got honed over centuries and now shows up in boardroom smiles and WhatsApp silence. The behaviour looks personal, but often it’s structural—learned from watching who rises and how long they stay up there. We tell ourselves stories about merit, prayer, and perseverance—and yes, a few people genuinely get there that way—but it’s naïve to pretend that’s the majority route. The majority route is the link: the set of favours, introductions, and insider rhythms that move without a brochure.
If you’re new or newly returned, it’s easy to mistake friendliness for sponsorship. But in Jamaica’s real estate industry, the difference between the two will define your trajectory.
The Two Economies
Think of two parallel economies.
The first is the social economy. It runs on charisma, humour, shared history, and the little rituals of belonging: Sunday dinners, birthday drinks, school ties, church networks, charitable galas. It’s warm and welcoming—especially to returning Jamaicans who remind people of their cousin, or who come with an easy smile and a foreign lilt. The social economy is how you get called “my friend” three times in one conversation.
The second is the opportunity economy. It runs on information: who is buying, who must sell, which subdivision is moving from paper to ground, which family is repositioning their portfolio, which ministry is about to punch a road through scrubland and turn “unremarkable” into “prime.” The opportunity economy is quiet. It rewards silence, loyalty, and the ability to show up without being seen. The opportunity economy is where you get the call—“Bring your buyer to Cherry Hill at 10 a.m. Don’t post it yet.”
The tension is that you can be rich in the social economy and poor in the opportunity economy. You can be the one everybody greets, while never getting the text that matters. If you misread one for the other, you will starve in a room full of cake.
Why It Happens
Some of it is fear. In a small market, a single bad referral can echo for years. People hoard access because they think access is the only moat. If a gatekeeper opens the gate and you do well, you might become a competitor. If you do poorly, the blowback hits the gatekeeper. Better, then, to keep you at arm’s length—close enough to borrow your energy and story when it suits, far enough to limit your odds of catching the golden fish.
Some of it is laziness disguised as mentorship. Co-listing you on difficult, low-yield properties is a convenient way to extract labour while signalling “support.” If you complain, the response is ready: “You asked for opportunity. Real estate is hard work.” Yes, real estate is hard work. But sweat is not the only metric of fairness. We have to ask: Whose sweat? For what upside? If the upside consistently flows to the same few people while the heavy lifting rotates among the hopefuls, that is not ecosystem building; that is extraction.
Some of it is our national myth about being “one family.” The myth is beautiful. We do look out for each other in times of disaster. But the myth also enables blurred lines: friend and foe both wearing the same grin; business and pleasure collapsing into a tangle where you can’t tell a warm invitation from a professional roadblock. We tell ourselves, “Jamaica nice,” and it is—but niceness is not a governance structure.
The Cost of the Closed Room
When access is rationed by vibe and pedigree, merit becomes mood-dependent. You can be qualified, ethical, and tireless and still lose repeatedly to someone with the right last name or the right breakfast table. Over time, the costs multiply:
- Clients pay more or get less because competition happens in whispers rather than sunlight.
- Talented agents burn out—not from rejection, but from ambiguity: not knowing whether an outcome was fair, random, or rigged.
- The industry narrows. If the same ten people keep the best listings, innovation slows. The deals get bigger but not necessarily better.
- Diaspora capital wobbles. Returning Jamaicans bring new buyers, new standards, and sometimes new financing channels. Shut them out, and you shut out the growth they could have catalysed.
We talk a lot about foreign investors “discovering” Jamaica, but the truth is, our most catalytic investors are often Jamaicans looking to come home. If they meet a wall of smiles and closed doors, they don’t become enemies; they become indifferent. They take their energy somewhere else. Indifference is the real loss—quiet, permanent, and expensive.
A Field Guide for the Returning or Rising Agent
If you’re reading this and seeing your own experience, here’s a blunt, field-tested guide. Not theory. Practice.
1) Separate the tables.
Break bread socially, but handle business formally. If you share a drink on Friday, that’s lovely. On Monday, ask for written terms. “Since we’re discussing a co-listing, can you send a simple one-pager confirming price, commission, who is doing what, and who pays for what?” If the mood shifts, that’s your answer.
2) Insist on deal hygiene.
On co-listings, get clarity early:
- Listing price, target buyer profile, and marketing plan.
- Commission rate and how splits work across multiple brokers.
- Who funds staging, photography, ads, and open houses.
- How leads are tracked and credited.
- How long the agreement lasts and how termination works.
If the rate is 2% on a complex bulk listing, run the math publicly. “At 2%, with another broker possibly at 1%, my net after split is 0.25%. For 50 properties across three parishes, that doesn’t pencil unless we adjust scope or rate. Let’s recalibrate.”
3) Watch the invitations.
If someone never invites you to rooms where your skills could earn you money, but always invites you where your company earns them reputation, you have your diagnosis. It’s not a friendship; it’s a staging.
4) Curate your own rooms.
Host your own micro-events—a quarterly open house for high-end rentals, a breakfast for property attorneys and valuators, a webinar aimed at diaspora buyers about title, survey, and taxes. Start small. Be consistent. Publish the invite list after the event to signal seriousness and set a rhythm.
5) Build parallel networks.
There is the network you’re chasing and the one you can build. Investors need clarity more than charisma. Package value beautifully: clean comparables, credible absorption rates, realistic rental yields, hazard maps, and a calendar of upcoming approvals. Become that person and word will quietly spread.
6) Manage your name.
Jamaica is a village. Do not rant. Do not sub-tweet. Do not forward private messages. Do not badmouth. When a gate closes, write it down, adjust course, keep receipts, move on. People who watch you will respect your restraint. And some of those people hold keys.
7) Price your boundaries.
Not every ask deserves a yes. Your time has a rate even if you’re not billing by the hour. Create a service menu: consultation packages for overseas buyers, onboarding fees for complex co-lists, minimum commission thresholds for bulk sales. When someone pushes back, treat it as data, not drama.
8) Protect your dignity with numbers.
Feelings get you invited. Numbers get you paid. Prepare a two-page market brief for every serious conversation: a one-page story and a one-page table. That evidence is your armour when the whispers start.
9) Keep a short memory for slights and a long memory for terms.
Don’t stew about the party you weren’t invited to. Do remember who refused to sign a fair agreement. Forgive quickly. Forget slowly.
The Industry We Could Have
It doesn’t have to be like this. Jamaica’s real estate sector is young enough to choose a different culture—one where access is broad, ethics are boring (in the best way), and the biggest flex is transparency. Here’s what that could look like:
- Standardised co-listing templates published by broker associations, with fair default splits and clear lead-credit rules. If you want to deviate, agree in writing.
- Event calendars shared across brokerage WhatsApp groups—not every private dinner, but the serious mixers where developers present pipelines and policymakers answer questions. If you host a public-facing industry event, share it publicly.
- Mentorship with teeth, not vibes. Senior agents who choose to mentor get a micro-fee from the association; mentees commit to deliverables—shadow days, mock valuations, ethics modules. The point is to turn “linkage” into a system, not a favour.
- A diaspora desk in major brokerages—one or two people who speak time-zone, document, and escrow fluently, and who can bridge the gaps that lead returning Jamaicans to abandon deals.
- A quiet blacklist for proven bad actors, maintained by the association and updated with evidence. Not gossip. Evidence: forged signatures, double-listing without consent, bait-and-switch marketing. Protecting the industry protects the client, which protects the industry again.
Will any of this happen? Only if enough people decide that abundance is a better strategy than hoarding. There is more money to be made in a growing, trusted market than in a small, suspicious one. But culture change requires brave actors—especially among those already at the top. It’s not easy to open a door you had to fight to get through. It is necessary.
On Friendship
This is not an argument against friendship. Jamaicans know how to be good friends: the pot is always bigger than the guest list; the last glass of sorrel somehow stretches. But in business, friendship without fairness is a costume. If someone calls you “family” but won’t send you a calendar invite, translate the word accurately: it means they like you, not that they rate you.
Here’s a rule I learned the hard way: the friend who advocates for you when you aren’t in the room is the only one whose “friend” counts in the room. Everyone else is company. Lovely company, perhaps—keep them. But don’t build your forecast on their promises.
When the Barrel Isn’t a Barrel
The “crab inna barrel” metaphor is powerful because it’s visual. But remember: the problem isn’t the crabs. It’s the barrel. Put the same crabs on a reef and they feed, grow, and share space. The barrel is the scarcity—of trust, of process, of enlarged opportunities. If we widen the reef—through fairer systems, broader invitations, better data—the pinching eases. People still compete; they just do it while building the habitat.
In practice, that means a few leaders choosing to share their deal funnels with two up-and-comers each year. It means one developer hosting a true open forum with content (timelines, approvals, constraints) instead of just cocktails and selfies. It means a ministry publishing pre-approval maps. It means agents collaborating on marketing funds for a category (say, eco-friendly new builds) instead of paying separate, diluted ad spends.
Small changes. Big signals. Reef, not barrel.
For the Person Reading This with a Knot in Their Stomach
Maybe you recognise the pattern: the dinners, the laughter, the missing invitations. You’re not crazy. You’re not bitter. You’re seeing the machine.
Here’s what I wish someone had told me sooner:
- Your optimism is not a flaw. Keep it. Just add contracts.
- Your kindness is not a currency. Treat it like a gift—freely given, never traded.
- Your standards are your strategy. When the room tests you, hold the line. The rooms that matter will find you.
And if you must build without the established gatekeepers, do it. Find the buyers nobody else is educating. Teach them. Earn trust with clarity. Document everything. In a few years, the same rooms that forgot to invite you will talk about “how you came out of nowhere.” You didn’t. You came out of paperwork, early mornings, and the quiet decision to stop waiting for permission.
Closing the Circle
Friend or foe? In Jamaica, the line can blur. But business doesn’t have to. The people who truly want you to win will bring you where winning happens. They’ll loop you in early, split fairly, credit properly, and call your name when you’re not there to hear it. They will not always look like the people on the magazine pages. Sometimes they’re the steady, unglamorous ones—the valuator who returns every call, the attorney who shows up ten minutes early, the developer who answers questions directly, the agent who loses a deal with grace and still sends a thoughtful follow-up.
Find those people. Be that person. And when it’s your turn to hold the invite list, make it a little longer than the one you were handed.
Jamaica is a small place with a big soul. Our real estate market can match that scale of spirit. It will take systems, not just smiles. It will take courage, not just charisma. And it will take a new habit: calling people “friend” only when we’re willing to share the table and the terms.
Until then, guard your heart, sharpen your pencil, and build your own reef.