What Nobody Tells You About Becoming a Travel Advisor
- Jennifer Ormesher
- 5 days ago
- 9 min read
When my fourth graders walked across the graduation stage on May 28, 2021, I walked with them.
Most people didn't know it at the time, but that day marked the end of my 30-year career in education.
I wasn't retiring. I wasn't moving to another district. I was walking away from the only career I had ever known and stepping into something completely different.
The journey that led to that moment began a year earlier when COVID changed the world.
One afternoon, an announcement came over the intercom asking teachers to check their email. That was the moment we learned we needed to pack up everything we might need to teach from home for the remainder of the school year.
Like so many educators, I adapted. We all did.
But when I returned to the classroom the following year, something felt different. For the first time in my career, I realized I was only giving 90%.
Now, some people might read that and think 90% is still pretty good. But I had made a promise to myself years earlier. If there ever came a day when I couldn't give my students everything I had, I would leave. The students were too important for anything less, and I was never going to be one of those teachers everyone said should have retired earlier.
Once I realized I wasn't giving 100%, I knew it was time to find a different path.
So when graduation day arrived, I celebrated with my students, hugged them goodbye, and quietly closed a chapter that had defined most of my adult life.
Table of Contents
Leaving the Classroom
I didn't have a perfect plan.
In fact, one host agency asked to see my business plan during the application process. I remember telling them that if they meant a piece of paper with the words "Business Plan" written across the top, I could provide that. Beyond that, I had no idea what I was doing.
I wasn't being flippant. It was the truth.
I knew I loved helping people. I knew travel had changed my life. I knew I wanted more control over my time and the direction of my career. But if you're looking for a story where I had every step mapped out from the beginning, this isn't it.
What I had was curiosity.
I spent the next several months immersed in training. I learned everything I could. I asked questions. I found mentors. I took notes. I tried things.
Then fall arrived and all of my teacher friends were heading back to school. It felt like standing at a train station watching a train pull away. I loved everyone on that train, but I didn't want to go where it was going.
That feeling was both terrifying and freeing because, for the first time in a very long time, I was betting on myself.
Betting on Myself (Literally!)
I took out a loan to start the business.
It was the first loan I had ever taken that wasn't attached to a house or a vehicle. There was no physical thing attached to it. The only thing backing that loan was my belief that I could build something meaningful.
People often ask what my biggest fear was when I became a travel advisor.
The answer wasn't learning the industry, finding clients, or mastering the technology. It was wondering whether I could actually do it.
Could I build something from scratch?
Could I create a business that served people well?
Could I make it work?
One of my mentors, Cyndi Williams, often says, "Fearful and forward or crappy and comfortable."
I chose fearful and forward. But that doesn't mean the journey was smooth.
The Mistake That Changed Everything
One of the first trips I ever planned included rodeo tickets.
There was just one problem.
I bought all 13 of them for the wrong night.
Yep. You read that right. Thirteen tickets... For the wrong night.
I still remember the feeling when I realized what I'd done. My stomach dropped and I thought I was going to throw up. I questioned everything. Had I made a terrible mistake leaving education? Was I really capable of handling people's vacations and hard-earned money?
In the end, I did what I hope every good advisor would do.
I fixed it.
I purchased new tickets so my clients could attend on the correct night. It cost me money, but it taught me something far more valuable.
Every system we have today exists because of a lesson learned somewhere along the way.
That mistake forced me to improve my processes, create better checks and balances, and become a better advisor. It also taught me that success isn't built on getting everything right. It's built on taking responsibility when things go wrong.
What Being a Travel Advisor Is Really Like
As the years passed, I discovered something else.
Being a travel advisor isn't really about travel.... At least not in the way most people think.
If I'm being completely honest, the job is probably 92% running a business and 8% travel.
Even when I travel, I'm looking at everything through the eyes of a travel advisor. I'm evaluating hotels, talking with suppliers, looking for experiences clients would love, asking questions, and taking notes.
Travel is wonderful, but building a business is the actual job., and many aspiring advisors are surprised by what the day-to-day reality actually looks like.
That reality surprises many people who are considering becoming travel advisors. The advisors who succeed aren't necessarily the ones who travel the most. They're the ones who treat it like a business. They complete training because they're genuinely interested in learning, keep up with expenses, build relationships, and show up consistently even when nobody is watching.
The same skills that helped me succeed in the classroom turned out to be incredibly valuable in this career. Planning, organization, building relationships, managing multiple priorities at once, and helping people feel seen and cared for all transferred beautifully.
My work location changed, but many of the skills stayed the same.
Building a Team
Around year three, the business began changing in ways I hadn't anticipated because I started building a team.
That year was probably the hardest of all.
I was updating the website, creating onboarding systems, helping advisors grow their businesses, taking care of clients, and learning how to think less like a travel advisor and more like a CEO.
There were moments when it felt overwhelming and moments when I wondered if I was doing any of it well.
But there were also moments that made me realize the effort was worth it.
Today, one of my greatest joys is watching other advisors succeed.
I love celebrating first bookings, milestone sales, completed supplier trainings, and professional breakthroughs. In fact, I get more excited watching my advisors succeed than I do watching my own accomplishments.
That wasn't something I expected when I started this business, but it has become one of the most rewarding parts of the journey.
The Champagne Moment
For years, I had carried the weight of that startup loan. It represented the biggest professional risk I had ever taken.
Then one day, it was gone.
The business had generated enough income to pay it back. Every dollar came from work I had done, clients I had served, and relationships I had built.
Brad and I enjoyed a champagne toast before going to dinner.
That was the moment I realized this wasn't just an idea anymore. This was real. Not because of the money itself. Because the gamble had worked.
For the first time, I knew I had built something sustainable.
What Success Looks Like Today
Today, when I think about what I'm most proud of, it isn't revenue.
It's our reputation.
The trust our clients place in us is something I never take lightly. The relationships we've built with suppliers around the world matter deeply to me. The fact that I can land on almost any continent and know there is likely a smiling face waiting to welcome me still amazes me.
Most of all, I'm proud of our team.
Our reputations wasn't built by me alone. It's the result of a group of people who care deeply about clients, suppliers, and each other. I wouldn't want to do this job without them.
The Freedom I Didn't Expect
The biggest surprise of all wasn't the business, it was the freedom.
My dad has dementia.
Every Friday starts the same way. I take care of the company books, wrap up any client tasks that need immediate attention, and then drive to my parents' house.
We usually spend the first hour talking together before my mom heads off to play Mahjong. That's when Dad and I begin our day.
I make lunch for us, and we sit down to eat. There's always chocolate afterward. Dad likes Hershey's Special Dark. I like milk chocolate with toffee and almonds.
After lunch, we take a short walk to check the mail.
Some days he's tired after that, so we watch old episodes of The Rifleman or Wagon Train together.
Other days he wants to talk. Most of the time, he's somewhere back in the 1980s and needs my help with a work project. We have conversations that make perfect sense to him and absolutely no sense to anyone else.
But no matter what, there's always laughter.
One day he asked where I was going, and I told him South Africa.
He looked at me with complete seriousness and said, "No. You need to get back to college."
So I promised him I'd get straight A's.
He's sweet. He's funny. And even though he doesn't always remember who I am, we still have a wonderful time together.
If I were still teaching, these Fridays wouldn't exist. Flexibility is one of the things that attracts people to this profession, but it's important to understand what that flexibility really looks like.
When I left education, I thought I was building a travel business. Five years later, I realize I was building something much bigger than that.
I was building a life that allowed me to show up for the people who matter most.
Thinking About Becoming a Travel Advisor? Here's My Advice
Five years later, I still don't claim to have everything figured out. I still make mistakes. I still have questions. I still learn something new every week.
But if someone is sitting at their kitchen table wondering whether they should explore becoming a travel advisor, here's what I'd tell them:
Ask the questions.
Have the conversations.
Talk to your spouse.
Learn everything you can.
Then decide if it's right for you.
Because the truth is, most successful business owners don't start with certainty. They start with curiosity.
The confidence comes later.
Five years ago, it felt like I watched a train pull away from the station. Today, I can honestly say it was the right train to miss.
If you're curious about becoming a travel advisor and want to learn more about what the journey really looks like, I'd love to have a conversation. No pressure. No sales pitch. Just an honest discussion about what this career can look like and whether it might be a good fit for you.
FAQ Section
Is becoming a travel advisor a good second career?
For many people, yes. Skills like relationship-building, organization, problem-solving, and communication transfer well into the travel industry. Many successful advisors come from careers in education, healthcare, administration, and customer service.
How long does it take to build a successful travel business?
Every business is different, but building a strong book of business often takes several years. Consistency, training, and treating the business professionally are key factors in long-term success.
Do travel advisors travel all the time?
Not usually. While travel is certainly part of the industry, the majority of the job involves serving clients, running a business, managing relationships, and continuing education.
What skills are most important for a travel advisor?
Communication, attention to detail, relationship-building, self-motivation, organization, and a willingness to keep learning are often more important than sales experience.
Can I become a travel advisor while working another job?
Many advisors begin part-time while maintaining another career. Over time, some grow their business into a full-time profession.
What surprised you most about becoming a travel advisor?
The amount of trust clients place in us. Helping someone plan a dream vacation is a responsibility I never take lightly.
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