Building a Team as a Travel Advisor: How I Scaled Beyond My Own Capacity
When I first started out as a travel advisor, I did what most of us do: I wore every single hat. I was the marketer, the salesperson, the admin assistant, the bookkeeper, the concierge, and the trip designer. I worked long hours, often late into the night, trying to juggle everything myself. For a while, that hustle worked. But eventually, I hit a wall.
I realized that if I wanted my business to grow—and if I wanted to enjoy the life I was building—I couldn’t do it all alone. I needed a team.
In this post, I want to walk you through the journey of how I built and scaled a team around me as a travel advisor. I’ll share the lessons I learned, the mistakes I made, and the practical strategies you can use if you’re thinking about taking this leap yourself.
Hitting Capacity: Why I Knew I Needed Support
The moment it hit me is still vivid. I had just returned from an incredible wine cruise in France with my mom. The very next day, I took a pregnancy test and learned I was expecting my second child.
That news changed everything. I knew that running my business the way I had been—burning the candle at both ends, answering every email, handling every detail—wasn’t sustainable. Not with another baby on the way, and not if I wanted my business to thrive.
For many advisors, the tipping point comes when your time, energy, and capacity are maxed out but your goals are still bigger than what you can do alone. If you’re finding yourself working nights and weekends just to stay afloat, or you’re turning down clients because you literally can’t take on more, that’s your sign: it’s time to consider building a team.
Takeaway: Pay attention to the warning signs—constant overwhelm, no room for growth, and life changes that demand balance. Those signals mean you’ve outgrown the solo model.
Making the First Hire: Filling Your Weaknesses
When I decided to hire, I didn’t start with the things I loved doing. I started with my weaknesses.
My first hire was Abby, a Disney genius. At that point, I was done with Disney. I didn’t have the energy or the passion for it anymore, but clients were still asking. Abby stepped in and handled every Disney lead with expertise and enthusiasm.
Next came Julie, who took over cruises—my personal kryptonite. No matter how straightforward they should have been, ocean cruises always seemed to go sideways for me. Julie loved them, and she became the go-to for every cruise inquiry.
By filling the gaps where I was weak or uninterested, I not only gave my clients better service, but I also freed myself up to focus on what I was great at.
Takeaway: Start by asking yourself: What am I weakest at? What do I dread doing? Your first hire should cover those areas so you can play to your strengths.
Scaling One Role at a Time
From there, my team grew role by role.
Concierge: Kelley joined to handle dining, tours, and the extras that clients love but that consumed my time.
Assistant: Emma, a former student of mine, came in and completely reorganized my inbox, apps, and systems. She “Marie Kondo’d” my digital life, and I’ve never looked back.
Specialists: Abby H. became my Fun-in-the-Sun expert, while Brenna specialized in Hawaii and Universal.
Not every hire was perfect—at one point, I even tried hiring my husband for a couple of weeks. Spoiler: it didn’t work out, and I had to let him go. But with each addition, the team became more well-rounded and capable of serving clients at a high level.
Of course, I had fears. Could I afford to pay them? Could I sustain them with enough leads and work? But the truth is, hiring is an investment. If you do it thoughtfully, the payoff is worth it.
Takeaway: Scale slowly and strategically. Don’t try to hire five people at once. Start with one role, see the impact, and then add the next.
Lessons From Early Challenges
Not everything went smoothly. One of the hardest moments came when I had to fire my first assistant hire. She wasn’t the right fit, and despite training, the quality of work just wasn’t there.
Another challenge was figuring out how to involve my team in client interactions without making clients feel “passed off.” Early on, a client described the process as “scammy,” and it broke my heart. But it also forced me to rethink how we communicated roles and value.
What I learned is that building a team is messy. There will be missteps. But those mistakes don’t mean you’ve failed—they mean you’re learning.
Takeaway: Expect bumps in the road. The key is how you respond: adjust, improve, and keep moving forward.
Creating Training That Scales
In the early days, I learned by sitting in my agency owner’s living room, listening to her client calls and watching her process. It was invaluable—but it wasn’t scalable.
When I started building my own team, I knew I couldn’t spend hours with each person in my living room. So I created a training tool called on.board—a seven-video series with homework assignments that walks new advisors through every step of the process.
It took a huge time investment to build, but now it’s evergreen. Every new hire gets consistent training, and even my experienced team members revisit it when they need a refresher.
Takeaway: If you’re serious about building a team, create systems and training tools that scale. They’ll save you time and ensure consistency across your business.
Learning to Lead: Letting Go of Control
As a former teacher, I was used to being in charge. But leadership isn’t about control—it’s about trust.
I love the story of Moses’s mother in the Old Testament. She placed her baby in a basket and let it float down the Nile, trusting that it would end up where it needed to be. For a long time, I was “white-knuckling the basket” in my business, refusing to let go. But I realized that if I wanted my team to flourish, I had to loosen my grip.
Delegation doesn’t mean lowering your standards. It means trusting others, giving clear feedback, and allowing your team members to thrive in their roles.
Takeaway: Leadership requires letting go. If you try to control everything, you’ll stifle your team and stall your growth.
Delegation by Design: The Quadrant Matrix
To figure out what to keep and what to delegate, I created a simple four-quadrant matrix:
Things you love doing and have to do.
Things you love doing but don’t have to do.
Things you hate doing but have to do.
Things you hate doing and don’t have to do.
For me, consult calls landed in quadrant one: I love them and I need to do them. Invoicing landed in quadrant four: I hate it and I don’t need to do it—so it was the first thing I delegated.
The hardest box is quadrant two: things you love doing but don’t have to do. For me, that included building proposals. I loved it, but it wasn’t the best use of my time. Delegating those tasks freed me to focus on higher-level work.
Takeaway: Use this matrix to make delegation decisions. Start with quadrant four, then move to quadrant two as your team grows.
The Payoff: Freedom, Impact, and Growth
The first real payoff came during maternity leave. I actually got to enjoy it. My team kept things running, and I was able to be fully present with my newborn.
Another moment came in Costa Rica, where two of my teammates joined me on an agency FAM trip. Seeing them there—living out dreams they once thought impossible—was deeply rewarding.
And then there are the smaller, everyday wins: a teacher able to retire early, a mom supporting her family through travel advising, a young bride funding her dream wedding. Those stories remind me why I built this team in the first place.
Takeaway: Scaling isn’t just about revenue growth. It’s about creating freedom for yourself and opportunities for others.
The Hard Truths Nobody Talks About
Here’s what most people won’t tell you: scaling often costs more in the beginning than it brings in. Training takes time. Mentorship takes energy. And while you’re investing in your team, your own sales may temporarily dip.
That’s why you need to “dig the well before you’re thirsty.” Build your team before you’re desperate, because by the time you truly need them, you won’t have the capacity to train them properly.
Takeaway: Be proactive. Build before you need it, and prepare for a short-term investment that pays off long-term.
Advice for Advisors Ready to Scale
If you’re on the fence, here’s my advice:
Look 12 months ahead. What do you want your client load, sales, and work-life balance to look like a year from now?
Work backwards. Identify the team roles that will get you there.
Adjust your expectations. No one will do things exactly like you, but if they can do it 90% as well, that’s a win.
Give yourself a runway. Training takes time. Plan for it.
Just start. The first hire is always the hardest, but once you take that step, the path forward becomes clearer.
Takeaway: Scaling is as much about mindset as it is about strategy. Dream big, plan smart, and trust the process.
Building a Business That’s Bigger Than You
At the end of the day, building a team allowed me to create a business that was bigger than me. It gave me back my time, empowered my clients to receive better service, and opened doors for others to pursue their dreams in travel.
It wasn’t easy. There were challenges, mistakes, and moments of doubt. But looking back, I wouldn’t trade the journey for anything.
If you’re a travel advisor wondering if it’s time to build your own team, I hope my story gives you both encouragement and practical steps to start. You don’t have to do it all alone—and honestly, you shouldn’t.
Learn More: Building a Team
I discussed all these lessons and more on a recent episode of Masters in Travel. You can listen to the full conversation here: Ep 241 Building a Team.