Some people dream small. They come to you, eyes full of hope, saying, “We just want a little two-night getaway.” How quaint. How adorable. What they really mean is, “We don’t yet realize that we deserve a three-week, life-changing adventure.”

And you, dear consultant, are here to show them the light.

Upselling isn’t about tricking people into spending more—it’s about helping them realize their true potential. They came for a weekend. They’ll leave with a month’s worth of memories (and a slightly dented credit limit).

Step 1: The “Slippery Slope” Strategy

No one wakes up thinking, “Today, I’ll spend three weeks in paradise instead of two days in a Travelodge.” You must guide them. Start small.

• “You’re doing two nights? Lovely! But, of course, three nights is where you really start to relax.”
• They nod. The seed is planted.
• “And, of course, if you’re doing three, you might as well do five—otherwise, it barely feels like a break.”
• They nod again. The wheels are turning.
• “And honestly, if you’re taking a week off work, why not go all-in? Have you ever considered two weeks? It changes everything.”
• Boom. Hooked.

Step 2: The “Once-in-a-Lifetime” Effect

People are terrified of missing out on life-changing experiences. Your job is to make them believe that a short break is a wasted opportunity.

Example:
Customer: “We just need a quick weekend away.”
You (visibly concerned): “Oh… I see. You don’t want to do the full experience then?”
Customer: “What do you mean?”
You: “Well, most people make incredible memories by doing at least two weeks. Imagine exploring those hidden beaches, discovering the local food, really unwinding… But hey, two nights should be… fine.”
Customer: Visibly distressed at the idea of missing out.

Step 3: The “It’s Practically Free” Logic

Nobody wants to feel like they’re spending more. Instead, make them feel like they’re saving money.

• “Flights are the biggest expense—so actually, staying longer makes way more sense.”
• “Once you’re there, the extra days basically pay for themselves.”
• “You won’t need a weekend break later in the year if you do this properly now.”

By the end of this conversation, they’re convinced that not extending the trip is a financial mistake.

Step 4: The Emotional Close

Logic is great, but emotions close the deal. Hit them where it hurts:

• “Think about how stressed you’ll feel coming back after just two nights.”
• “Wouldn’t it be nice to actually switch off and return feeling like a whole new person?”
• “Do this for future you. Future you deserves this.”

Now, they’re emotionally obligated to upgrade. Well played.

Final Thoughts

Selling holidays isn’t about “selling” at all—it’s about gently guiding people toward their best lives (which just happen to cost a little more). They came for a weekend. You gave them a journey they’ll never forget. And that, my friend, is why Paul is always right.

Now go forth and transform those weekenders into epic explorers.