When one woman planned a surprise trip for her husband’s 30th birthday, it sparked an idea that became a thriving side hustle for travelers who love surprises as much as savings.
Challenge
Roshni A. has always been the planner in her relationship. As an accountant, she loved precision, organization, and most of all—getting the best deals. Her husband Jeff, an engineer and fellow travel enthusiast, shared her passion for exploring new places.
So when Roshni stumbled upon an incredible discount on flights to Chile, she jumped on it. She secretly planned an entire trip to Patagonia for Jeff’s 30th birthday, from hiking routes to penguin encounters. When she finally revealed the surprise, Jeff was stunned—and delighted.
After returning home, their friends couldn’t believe how much the couple had experienced in just one week, or how little they’d spent doing it. One friend joked, “You should plan my next trip—I’d actually pay for that!”
That offhand comment became the spark for their new venture.
Action
Roshni and Jeff realized that many people love traveling—but not the planning that comes with it. Between researching destinations, finding good deals, and comparing hotels, vacation planning can feel like a second job.
That insight led to The Vacation Hunt, a business offering surprise vacation packages.
Here’s how it works: travelers fill out a short questionnaire about their interests, travel dates, and budget. Roshni and Jeff then research, plan, and book the entire trip—flights, hotels, and itinerary included. The twist? The travelers don’t find out where they’re going until shortly before departure.
To make it fun, the couple mails teaser clues leading up to the big reveal, building anticipation before the trip.
With Jeff handling the website and Roshni managing marketing and social media, they built their first site on Squarespace for under $300. Within weeks, they received their first order—from a complete stranger.
Their first official package sold for $1,200 per person, and the thrill of that sale confirmed they were onto something.
As they gained experience, they refined their pricing. They timed themselves while planning a few trips for friends to understand the workload—about ten hours on average. Then, they set their rates to fairly value that time while staying accessible:
- $750 per person for domestic surprise trips
- $1,200 per person for international adventures
They also offered a smaller “custom trip planning” service for travelers who wanted help with logistics but not the surprise element, starting at $150.
Result
From the very first month, The Vacation Hunt was profitable. The model was simple, the startup costs were minimal, and the excitement around the “mystery trip” concept attracted natural word-of-mouth buzz.
Their customers—mostly busy professionals and couples planning honeymoons—loved the convenience and thrill of handing over control to seasoned travelers. Roshni and Jeff received glowing feedback from clients who said they never would have gone to those destinations otherwise.
The couple continues to refine their process and expand their reach, carefully balancing their side hustle with their day jobs. What started as a birthday surprise has become a growing business that funds their own travels and helps others see the world in unexpected ways.
Lesson
Roshni and Jeff’s story shows how powerful it can be to turn your personal strengths into a service others value. They didn’t reinvent travel—they reimagined how people experience it.
Their success also offers a simple reminder for anyone starting a side hustle: your time is valuable. When you price your work, start by asking, “What is my time worth?” and build from there.
Because when you respect your own effort, others will too.
Inspired by a true story originally featured on Side Hustle School by Chris Guillebeau. This rewritten version is independently produced and fully original.