Don’t miss the full story. Listen to the episode now.
Every once in a while, I think it’s fun to step away from the business strategy and educational content and just…chat.
So consider this our virtual coffee date.
I’m answering some of the questions I get about my travel business, my life as a full-time teacher and entrepreneur, my favorite places I’ve traveled, what I actually spend money on in my business, and even a few things you might be surprised to learn about me.
And, of course, we’re talking about travel.
Let’s get into it.
How Did I Become a Travel Advisor While Working Full-Time?
I’ve always loved to travel.
In college, I studied abroad in Spain the summer before my senior year and absolutely fell in love with it. Once I became a teacher, I spent a lot of my summers traveling. I also traveled with my family, went to Disney, and took students abroad.
But becoming a travel advisor wasn’t necessarily part of some master plan.
In 2019, I was introduced to a travel MLM through social media. I was already very familiar with network marketing and had actually grown another network marketing business into the top 0.1% of the company.
The first time the travel opportunity was presented to me, I didn’t join.
Eventually, though, someone else I was connected with mentioned it to me and essentially said, “You travel a lot. Would you be interested in this?”
And I thought…why not?
I joined in July 2019.
Because I’m a teacher and had the summer available, I was able to spend time going through the training, getting organized, printing ALL THE THINGS—because apparently that’s who I am—and figuring out how the travel business worked.
But there’s another piece of the story that actually started several years earlier.
After my mom passed away in 2015, I started a travel blog called Loving Life with Lindsay. I taught myself WordPress, built my own website, and started writing about my travels.
Looking back now, it’s funny how everything has come full circle.
I was creating travel content before I ever became a travel advisor.
And Then 2020 Happened…
I started booking travel in July 2019 and was getting clients.
Then COVID happened.
Suddenly, instead of booking trips, I was spending hours and hours on hold canceling them.
There were days I was on the phone for five or six hours. Thankfully, I had a landline, so I could literally put the phone down and go do other things while I waited.
That experience made me take my foot off the gas.
For the next couple of years, I mostly booked travel for close friends and family. Around 2022, I started incorporating travel into my marketing a little more.
But it wasn’t really until late 2024 that I decided:
Okay. I’m actually going to give this a go.
People had started reaching out to me because they wanted to become travel advisors. I had spent years building businesses, learning marketing, coaching entrepreneurs, and creating content.
Eventually, all those pieces started coming together.
And that’s how something that started as a “second business” eventually became a much bigger part of my life.
What’s My Favorite Destination in the World?
This one is easy.
Spain.
Spain has been part of my life for years.
I first studied abroad there in college. Later, I completed a three-summer graduate program for teachers through Sacramento State that took me to Guatemala, Peru, and then back to Spain.
I’ve taken students to Spain multiple times.
I’ve attended an AP teacher conference there.
I even won a trip to Spain after being named a Spanish honorary advisor of the year.
I’ve been there during two Euro Cup wins, which is actually where I fell in love with soccer.
And I love pretty much everything about the country.
I love the Spanish language—especially Spain’s dialect. I love the lifestyle. I love how geographically diverse the country is.
You’ve got mountains.
Desert.
Beaches.
Vineyards.
Olive farms.
Oranges.
And so many completely different regions and experiences within one country.
Most of my trips have been during the summer, but I also once led a teacher training in Spain over Christmas break. I got to experience the Christmas markets and spend New Year’s Eve in Madrid, which was a completely different way to experience a place I already loved.
So if you ask me my favorite country?
Spain. Always Spain.
What’s One Trip I Think Everyone Should Experience?
This question is much harder because I don’t think there’s one perfect destination for every traveler.
But if I had to choose one bucket-list experience?
An African safari.
And personally, I would go to the heart of the safari experience in Kenya and Tanzania.
I did a 16- or 18-day Kenya and Tanzania safari, and it was incredible.
If you love animals and nature, there is something breathtaking about seeing them in their natural environment.
It’s also difficult to describe how the experience makes you feel.
There’s almost a spiritual element to it.
You’re out there surrounded by nature, animals, and these incredible landscapes, and it almost brings you back to a simpler way of experiencing the world.
Of all the bucket-list trips you could save for, this is one I think is worth the time, money, and effort.
What Does My Typical Day Actually Look Like?
This depends heavily on whether I’m teaching or on summer break.
But one thing that has helped me tremendously is using theme days.
During the school year, I try to assign certain types of work to certain days.
Mondays: Content planning, brainstorming, and planning for the week.
Tuesdays: Podcast day. This is when I record solo episodes and schedule podcast guest interviews.
Wednesdays: My agency Q&A happens in the evening.
Fridays: Follow-up.
Weekends: I usually spend some time in the morning wrapping up administrative tasks from the previous week and planning for the next one.
During the week, I’ll work on my businesses a couple of evenings after school, too.
Obviously, client needs don’t always fit neatly into my theme days. If I have quotes, payments, or something time-sensitive that needs handled, I’m going to take care of it.
But I also don’t believe everything needs to be handled at 10 p.m. just because I’m a business owner.
During the summer, my schedule changes.
One day might include answering client emails, taking my car for an oil change while working on my laptop, updating workflows in my CRM, RSVP’ing for supplier trainings, and recording a podcast.
Because why waste an oil change when you can bring your laptop? 😂
There’s Also a Nonprofit in the Mix
Along with my sister and an amazing board, I also run Cathie’s Magical Memories, a nonprofit created in memory of my mom.
We raise money to send children who have lost a parent on a Disney World trip with their new family unit.
We recently sent our second family on their trip, which was incredibly exciting.
Throughout the year, we have meetings and work on the nonprofit, but things get especially busy leading up to our annual auction in October. I’m pitching businesses for donations, organizing auction items, and getting everything ready behind the scenes.
And then somewhere in ALL OF THAT, I try to prioritize my health, too.
Realistically, I work out about three to four days a week. During the summer, I’ve also been intentional about walking more and listening to podcasts while I walk my dog.
And when I’m finally done for the day?
I love reading.
Interestingly, I’m not a huge TV watcher. I’m much more likely to binge shows during the winter than the summer.
So no, I don’t have a perfectly structured entrepreneurial morning routine followed by six uninterrupted hours of productivity.
My days are a mix of teaching, clients, agency leadership, content creation, podcasting, nonprofit work, exercise, and regular life.
And theme days help me make it all work.
What’s the Biggest Misconception About Travel Advisors?
Here’s one I hear all the time:
AI is going to replace travel advisors.
I don’t believe it.
Google didn’t replace us.
YouTube didn’t replace us.
Why would AI be any different?
Technology changes how we work. It gives consumers more information and gives travel advisors new tools.
But people still value expertise, service, relationships, recommendations, and having an actual person there when they need help.
I don’t think travel advisors are going anywhere.
If Money and Vacation Time Didn’t Matter, Where Would I Go?
ANTARCTICA.
I really want to check off my seventh continent.
The problem isn’t convincing me to go. The problem is making it work with my teaching schedule.
Antarctica cruises typically operate during our winter, and I haven’t found an itinerary that fits perfectly into the two weeks I get off around Christmas.
If money and vacation time suddenly weren’t factors?
Get me on that ship.
What’s My Best Travel Tip?
Travel insurance. Travel insurance. Travel insurance.
I didn’t prioritize it when I was younger.
We had insurance on student trips, but for a lot of my personal international travel, we simply didn’t buy it.
That has completely changed.
After my dad had an accident during a trip this past spring, our travel insurance ended up covering what was approximately $45,000 in expenses.
That experience cemented something for me:
I will never take a trip without some form of travel insurance again.
I have an annual travel insurance policy, but I also purchase individual policies for many of my trips because my annual policy has limits, particularly when it comes to cancellation and interruption coverage.
Travel insurance isn’t the fun part of travel planning.
Nobody is sitting at home saying, “You know what I’m excited to shop for today? INSURANCE!”
But when something goes wrong, it can suddenly become one of the most important things you purchased.
What’s Something People Are Surprised to Learn About Me?
I have two answers.
I’m Actually an Introvert
People often assume I’m an extrovert because I’m confident and loud.
Nope.
I’m genuinely an introvert.
And here’s probably the easiest way to explain it:
During COVID, while everything happening in the world was obviously awful, I personally thrived being at home.
I was perfectly happy being a stay-at-home dog mom, working online, and not seeing anyone for a month.
Give me my dog, my computer, and my own space, and I’m good.
I’m Also a Farm Girl
This one REALLY surprises people who didn’t grow up with me.
I grew up on a farm, and I still live on one.
Growing up, I showed all kinds of animals at the fair. My dad still has cows and chickens, and we’re constantly doing something at one of the farms we own.
So yes, I love skincare, travel, Disney, and looking presentable.
But I can also put on old work boots, shorts with holes in them, and a stained T-shirt and go shovel crap.
Both things can be true. 😂
Although, ask me how much I love farm work when it’s ridiculously hot outside and you might get a different answer.
What’s Been the Hardest Part of Owning a Business?
For me, it hasn’t necessarily been wearing all the hats.
It hasn’t been learning sales.
It hasn’t even been figuring out boundaries.
One of the hardest parts has been learning how to handle the emotional side of entrepreneurship—especially when people close to you don’t support your business.
Years ago, when I was selling LuLaRoe, I had someone I considered one of my very best friends invite me to hold a pop-up at the school where she worked.
If you know anything about doing one of those pop-ups, you know this wasn’t a “throw a couple things in the trunk” situation.
At the time, I drove a tiny Honda Civic.
I loaded it with probably ten giant IKEA bags of clothes, racks, and everything else I needed. I hauled it all in and set everything up.
People came.
They tried on tons of clothes.
And nobody bought anything.
Eventually, I walked into the bathroom and overheard this friend—the person who had invited me to do the pop-up—telling the women trying on the clothes that the products were poor quality, looked bad on them, and that they shouldn’t buy anything.
That hurt.
I packed everything up professionally, got in my car, and called my dad crying on the way home.
There were other issues in that friendship, and we were already growing apart, but that moment was essentially the final straw for me.
And it’s an example of something entrepreneurs don’t talk about enough.
Sometimes the people you expect to support you won’t.
Sometimes friends will know exactly what you do and intentionally buy from someone else.
Sometimes family members won’t understand your business.
Sometimes someone will actively discourage other people from supporting you.
And yes, it hurts.
Learning to deal with THAT has been one of the hardest parts of entrepreneurship for me.
What Are the Business Tools I Think Are Worth Paying For?
I am not someone who thinks you need to pay for every shiny new business tool that exists.
But there are definitely things I wouldn’t want to run my businesses without.
1. A Good CRM
For my travel business, that’s Tern.
I previously used TravelJoy, but after moving to Tern, I’ve been incredibly happy with it.
Having a strong CRM is absolutely worth the investment when you’re managing clients, workflows, automations, trips, and follow-up.
2. My MacBook
I use my computer for EVERYTHING.
I love the quality, storage, and ability to run all the different parts of my businesses from it.
3. Google Workspace
Having a branded business email alone makes this worthwhile for me.
I also use the other functionality, including things like PDF signatures, especially on the agency side.
4. Business Coaching
I’ve invested in coaching programs for years.
The programs I’m currently in aren’t specifically travel-related, either.
That’s an important distinction because sometimes the best thing you can learn for your travel business isn’t another destination or supplier training.
It’s how to run a better business.
5. QuickBooks Online
This is a newer investment for me as an agency owner, and I probably should have done it sooner.
Do I love paying around $70 a month for it?
No. 😂
Do I love that I can use it to run payroll and keep track of expenses?
Absolutely.
Sometimes paying for the right system saves you enough time and frustration that it’s worth every penny.
What’s My Advice for Someone Who Wants to Become a Travel Advisor?
START.
You’ve probably heard people say, “Start messy.”
I don’t necessarily want you to start messy.
But I DO want you to start before you feel completely ready.
Choose one mentor—or maybe one or two trusted people—to learn from.
There are so many people online telling you what you should do that it’s very easy to develop shiny object syndrome.
You keep consuming.
You keep learning.
You keep buying another training.
You keep watching someone else’s business.
And you never actually DO anything.
At some point, you have to start.
Start learning.
Start promoting yourself.
Start talking about travel.
Start putting yourself out there.
And please, please don’t become what I call a silent agent.
If nobody knows you’re a travel advisor, nobody can book travel with you.
Then you don’t make sales.
Your business doesn’t grow.
You get discouraged.
And eventually, you quit because you decide “this didn’t work.”
Except you never really gave it a chance to work.
So my advice is simple:
Start. In every sense of the word.
And Just for Fun…
We’ll finish this Q&A with a few rapid-fire answers.
Window or aisle? Aisle.
Carry-on or checked bag? Carry-on.
Mountains or beach? Beach.
Disney or Universal? Disney.
Ocean cruise or river cruise? River.
Favorite airport? Amsterdam.
Least favorite airport? Atlanta.
Coffee or tea? Coffee. Always.
Favorite country for food? Honduras. I was just there, and everything was delicious.
Favorite cruise line? Disney—but aside from Disney, Norwegian.
Favorite Disney park? EPCOT.
One travel item I never leave home without? Portable charger.
What’s always in my carry-on? My medications, liquids, and must-have toiletries.
Early morning flight or red-eye? Early morning. I will hate it. I will complain about it. I will dread it. But then I’m happy when I get there early and it’s done.
If I could move anywhere in the world?
Spain.
Obviously.
Take What Works and Make It Your Own
Hopefully this gave you a little peek inside my brain—and maybe a few ideas you can apply to your own life or business.
That’s one of my favorite things about learning from other entrepreneurs.
I don’t believe you need to copy exactly what someone else is doing.
Look at what’s working for people you admire.
Take the pieces that make sense for you.
Leave the ones that don’t.
Tweak them.
Make them your own.
And use them to amplify your own success.
And if you’ve been sitting on the idea of starting your own travel business, remember my biggest piece of advice:
Start before you feel completely ready.
Because you can spend another six months learning about what you could do—or you can start doing it.
Go out there, friend, and create your magic.
-Lindsay
🌎 Ready to plan your next vacation?
Book with At Last I See The World Travel: https://www.atlastiseetheworldtravel.com
Connect with Lindsay: https://lindsaydollinger.com
https://www.instagram.com/lindsaydollinger
💼 Curious about becoming a travel advisor?
Learn more here: https://www.atlastiseetheworldtravel.com/quiz
Join Paul Gowder’s OTW Pro Membership: https://www.onthewaycommunity.com/checkout/otw-pro?affiliate_code=8d5c36
DM me for the info about Adaptive Marketers that I mentioned!
Try Tern: http://try.tern.travel/7fQCVH
📱 Come hang out with me on social media for more travel tips, business strategy, and behind-the-scenes fun!
If you enjoyed today’s episode, I’d be so grateful if you’d subscribe, leave a review, and share it with a friend. It helps more travel lovers and travel advisors discover the show!
Thanks for listening—and until next time, keep chasing those passports, profits, and a little pixie dust. ✨
