8 min 47 sec

ESL Teacher Turned Travel Planner Sends Clients on Surprise Vacations

An elementary school teacher creates a for-profit service to “whisk away” travelers to surprise destinations.
Customer Service Service Teacher Hustle Travel Unique Ideas

Subscribe Now For A Free Five Step Tutorial

What It's About

A seasoned traveler discovers a side hustle helping others plan their vacations.

Business Model
Skills Required
Research & Planning
Profit Potential

Words of Wisdom

When she was starting out, Charlotte was really impatient to book those first clients, but a friend of hers said something that really stuck with her: "You aren't selling $50 shoes. People aren't going to wake up in the morning and decide to buy a surprise trip on a whim. Give it time." And that friend was absolutely right!

What she’s selling is not only a big ticket item (she offers different budgets but clients have to pay for their entire trip up front), but it is also buying something with no idea of what you are going to get. She’s had to build trust with my clients—and also find the right people in the first place.

Fun Fact

Whisked Away's first clients were a couple that wanted to celebrate their honeymoon with surprise travel. Charlotte got the notification that there had been a new order while she was at an end of year school celebration with her colleagues...and she says she literally screamed out loud. Then she showed everyone, and it started a great conversation about going after things you are passionate about.

As it grew, clients came in through referrals. That first couple that booked a surprise honeymoon then referred their wedding photographers (also an engaged couple) and they booked a surprise honeymoon too!

Notes from Chris

Episode 346

Charlotte McGhee is an ESL teacher at an urban elementary school in Charlotte, NC. Until this year, she had never had a side hustle. She didn’t know about providing a service, creating a website, deciding on pricing, and so on—but what she knew is that she loved planning travel for people. She was good at it, and she noticed that other people often didn’t know where to start when planning a trip.

And while she would happily pass the time looking up options and sample itineraries, other people didn’t want to sit in front of a computer for hours after work to do all of the research.

Still, she’d only helped friends, and only for free, until one weekend when she and her husband were sitting in a bar in Savannah, Georgia on a quick weekend trip that she’d planned. She’d been pondering the idea of starting a trip planning service for a while, and he looked at her and said, “You should really do this.”

So she did!

This side hustle is called Whisked Away. Here’s how it works: the client goes on her website, which she created in a weekend using Squarespace, chooses the region of the world they'd like to travel in, chooses their budget, and their travel dates. Then, they fill out a short survey telling Charlotte what they love to do. The whole process takes the client about 10 minutes, and then she takes it from there. Each client gets a completely customized trip to a surprise destination in the region of their choice. It’s just 10 minutes for the client, but then Charlotte spends around 10 hours per trip doing all of the research and preparing a detailed plan.

Two weeks before they leave, clients receive an email detailing a) what time to arrive at the airport, b) what to pack, and c) what the weather will be like. One week before, they get a surprise envelope with their entire itinerary inside: flights, accommodations, restaurant recommendations, and activity suggestions. Charlotte is hardcore: she recommends that clients wait to open it until they get to the airport!

So far her profit has been $5,000. She’s working with a business coach to look at her pricing structure to ensure that she’s getting paid properly for the amount of time she puts into each trip. She says that's been a learning process.

  The best part is when clients send photos of them opening their surprise envelopes at the airport, and looking thrilled at where they are headed. She says “There really is nothing better than giving people an amazing experience with something you did.”


  • Whisked Away: Do you love to travel but lack the time to plan out the vacation of your dreams? Visit Charlotte's website and let her plan the trip for you!
  • SquareSpace: The website building platform that Charlotte used to create Whisked Away

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


Download all 2018 episodes from each month: JANUARY | FEBRUARY

Download 2017 archives: JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC



Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️

Learn More


Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

Learn More

Quote of the Day
"In the first few months, I recommend that you read everything you can and hustle it out. But once you have some things in place, try to sit back and let things play out a little bit. Surrender a little!"
—Charlotte McGhee #SideHustleSchool

Sponsors & Gratitude

Try ShipStation for 60 Days FREE!

Today’s episode of Side Hustle School is brought to you by ShipStation, the #1 choice of online sellers. 📦

To get a 30-day trial AND an additional month free, click the microphone at the top of their page and enter the word HUSTLE.

Get it Here

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau