Here’s the truth, friend: most clients aren’t trying to make your eye twitch. They’re not texting you at 11:47 PM because they hate boundaries. They’re not ghosting you because they want to ruin your week. They’re not price-shopping you because they don’t respect your expertise.

They just don’t know how this works.

No one ever told them.

You didn’t mean to.

It started innocently enough — a friend asked for help planning a Disney trip, and you said sure. Then someone else messaged: “You should totally do this for real.”

And suddenly, you were the go-to person for all things travel.

Fast-forward a few months (or years), and now you’re tracking commissions, juggling quotes, comparing CRM systems, and wondering if QuickBooks counts as self-care. Spoiler: it doesn’t. But it does mean you’re legit.

Friend, let’s be clear:
You are no longer “just helping people plan trips.”
You are running a small business.

When I first stepped into the world of travel advising, I had this picture in my head. I thought people would be lined up, eager to hand me their credit card. I thought the money would roll in quickly. I thought friends and family would automatically become my first loyal clients. And if I’m honest, I thought the whole thing would feel easier than it actually was.

There’s a scene at the beginning of Episode Two of Inventing Anna that lives in my head rent-free. It’s the one where the journalist interviews a photographer who explains exactly why Anna Delvey fit in so seamlessly with the New York elite. He says, essentially, that she didn’t just look the part—she understood the part. She knew what to wear, how to talk, what to order, and what not to say. Her energy didn’t scream money—it whispered access, confidence, and exclusivity. And people bought it.

That moment is a masterclass in the psychology of luxury. Because true luxury isn’t about being rich. It’s about knowing how to belong in a world where wealth is a backdrop, not a billboard. And if Anna—who, spoiler alert, didn’t actually have the money—could convince the entire Manhattan social scene she was part of the club? Then you, my friend, can absolutely learn to speak to luxury clients like a pro.

It always starts with a casual text.

“We’re thinking of going to Greece next summer. Want to come?”

And just like that, a vacation turns into a movement.

By the end of the week, there’s a group chat with a name like Greece or Bust, and someone’s cousin’s college roommate is suddenly tagging along. There’s talk of matching shirts, shared Airbnbs, and someone volunteers to “research everything” even though they’ve never actually planned travel beyond their own family trip to Florida.

Congratulations. You’ve just met the Pied Piper.

Friend, let’s talk about risk. The biggest, most life-changing things we do are risky. Falling in love, starting a business, raising children — none of these come with guarantees. Travel is no different.

We talk a lot about firsts in this business. First steps in the sand. First passport stamp. First time on a plane. First time seeing the Eiffel Tower or hugging Mickey Mouse or eating real-deal pasta in Italy.

But lately, I’ve been thinking about lasts. What if you knew this was the last time you’d see the ocean? What if this was the last time your family would all sit at one table, all under one roof, all together in the same moment — no sports, no work calls, no distractions — just laughter, stories, and love?

“Here come the grannies!”

If you’ve ever been emotionally blindsided by a Bluey episode (and let’s be real — who hasn’t?), you know this iconic phrase. It signals the moment Grandma Janet and Grandma Rita arrive on the scene: full of mischief, life, and just enough chaos to make it unforgettable.

Honestly? That’s exactly what it feels like when a multigenerational family books a trip. And if you're not leaning into this niche, friend, you’re leaving both impact and income on the table.

So, you’ve hit a wall. You’re booking trips, fielding questions, quoting vacations, and chasing down commissions—but you’re not growing like you want to.

Here’s the truth: If you’re not spending at least 50%, ideally 80%, of your time pursuing new business, you’re going to plateau.

Let’s get one thing straight:
ADHD is not a character flaw.
It’s not laziness. It’s not a lack of discipline. And it’s not something a new planner can fix (ask me how I know).

ADHD is a neurological difference in how we regulate motivation, attention, and dopamine. That’s it. That’s the secret.

When I talk about “pebbling,” I’m talking about layering those small, thoughtful acts into the way you serve your clients. It’s the unexpected follow-up. The remembered detail. The DM that says “Hey, that hotel you loved? They're running a flash sale—should I check it out for your next trip?”