Frequently Asked Questions

How Do I become a Travel Agent or get started in the Travel Industry?

There are actually several options to get started, and it really depends on your personal goals, comfort level, experience, and even the type of travel you’d like to sell.  I actually created a free masterclass to help you understand all your options for getting started in the industry. This is the best place to begin your journey.

I am a Travel Agent but I am struggling with getting business, and generating leads. Is this something you can help me with?

Absolutely! Our programs are designed to help new, experienced, and agencies of all sizes grow to the next level.  If you’re ready to grow, I’d recommend booking a free Discovery Call so we can learn more about your goals and match you with the program that will help you best.  We have learning tracks for new, experienced, and agency owners.

If I participate in one of your masterminds do I actually get to work with you personally?

Yes!  We only accept a limited about of clients each month to ensure each client gets personalized support.  I host weekly video calls, and both myself and my team are available to you via our secret facebook group for any and all questions you’d like to personally ask while in the program.  You’ll also have access to our program mentors, and experts.

I am an Agency Owner, can you help me with my growing company?

Absolutely!  One of my favorite things to do is to help experienced agency owners, hosts, and travel companies evolve their business models and grow to new heights. I’ve supported companies with up to 1000+ agents in growth initiatives, evolving infrastructure, automation, and increasing profits.  Whether you are new to hosting or have thousands in your sales force, we can help.

Can you really make money in the travel industry?

Yes!  I started in the industry over 25 years ago and there has never been a better time to work in the industry.  The earning potential is incredible, and flexibility to work from home or while you travel is a huge benefit.  Travel suppliers pay YOU a commission, for all the travel you book for yourself and others, and there are also ways to monetize your agency to be more profitable faster.

What is the benefit of working with you?

Quite simply, faster and better results.  If you’re really serious about making a career out of your travel business, and generating a full-time income you’ve come to the right place.  Our typical clients want to transition from other careers into doing travel full time, and they don’t want to waste years making mistakes, or being stuck in “hobby” mode.  They want a clear roadmap, systems that generate fast results, and the knowledge, tools, and resources to start and grow quickly.

I have another full-time job, and a busy life will I have time to do this program?

We recommend you plan to commit 10-12 hours a week while you’re in the program.  However, the program is self-paced, and you keep the curriculum and training videos for life so you can do the program on your time schedule.  The last week of each month we only offer bonus classes, so you can also use that as make-up time too. Most of our clients work full time, and have families so I created the program with that in mind.

Should I get started and get some experience before I apply for your Mastermind?

In most cases, no.  The most common thing we hear from our clients is, “I wish I would have found you before I started. I wouldn’t have made so many mistakes.”  If you want to set your business up the right way, from the beginning, avoid costly mistakes and frustration, then you’re in the right place.  When you participate in our mastermind, you get access to me and my team of experts as your personal consultants to support you on your path. Unlike hosts, Travel MLMs, or even agencies that all want you to join with them because they have a vested interest in you doing so, we give you the advice, counsel, and recommendations that are best for YOU, not them.  Deciding how you set up at the beginning will set the stage for your success or failure, so we take special care to match each client based on their goals and needs.

Are you a Travel Host?

No, we are not a travel host. That would be a conflict of interest in supporting you in growing your own highly successful business.  We never keep any percentage of your commission, and you do not work for us in any capacity. We teach you the effective systems, marketing, and best practices to grow your agency every month, then you can create results for the duration of your career.

Can’t I just work for your award-winning agency?

While I am flattered, Tripsy Travel is not hiring at this time.  We have an elite team of high performing, luxury travel planners and Tripsy Travel remains our proof of concept model for everything we teach you in our mastermind programs.

Can I just start with a Travel host?

You can, but it’s important to know a host does not help you grow or generate leads.  In short, they will give you agent logons, in exchange for keeping a percentage of your commission on everything you sell.  It is still your responsibility to set up your own business and find your customers. It’s also important to know there is a lot of misinformation, and travel MLMs that can lead you down a path that will leave you discouraged, or disheartened with lackluster results.  Sometimes hosting is a good fit at the beginning, but selecting the proper match is critical. Unlike travel hosts, MLMs, or even agencies, that want you to join them because they will ultimately retain a percentage of your commission for years to come, we work for you and provide advice that is always in YOUR best interests.  This includes matching you appropriately, and giving you a plan for earning 100% of your commission as you grow. If you’re still considering hosting, definitely read this.

Is there post program support?

Once you participate in one of our Mastermind programs, we consider you part of our family.  After you graduate from either of our Mastermind programs, you will be eligible to participate in our secret Graduate Group which is filled with amazing women and men that are all using the Careers On Vacation™ (or Wanderlust CEO) systems.  This community will become like a second family to you as you proceed on your journey. It’s filled with like-minded, high achieving, and positive people.

How can I apply to work with Cyndi?

The best way to work with me is to apply for one of our mastermind programs

For The Careers On Vacation™ Mastermind,  you can apply here.

For The Wanderlust CEO Mastermind, you can apply here.  

Not sure which Mastermind is right for you?  Check out our program comparison here.

*Limited seats available


If you are not a COV Graduate [or] under 300K+ in annual sales (don’t have to count 2020 due to COVID19) than you should start with Careers on Vacation™ so we can make sure you have a solid foundation in place, including your marketing and automation systems so you are prepared to scale growth quickly. The good news is we offer a program credit towards the Wanderlust CEO Mastermind™ to all COV graduates.

COV Grads are allowed to start without reaching sales minimums, because they have been trained our proven systems and have often not completed a full year of selling. They can move without interruption from Careers on Vacation™ to the Wanderlust CEO Mastermind™ (provided space is available).

If you are a COV graduate [or] your annual sales exceed 300k+ and you want to scale a top performing team quickly than the Wanderlust CEO Mastermind™ is the perfect fit for you.

Do You Have a Calling to Travel?

If you’re feeling the call to travel and turn your wanderlust into a viable, portable, profitable, abundant travel business there is a reason you found your way to this page.  I have helped hundreds of people successfully transition into making travel their new way of life. I’ve been honored to support the launch of over 100+ unique travel brands, and I specialize in helping clients map their businesses to 6+ figures and beyond.  No longer tied to stressful, structured jobs my clients enjoy the freedom of traveling as much as they want while running their travel businesses from anywhere in the world. I invite you to start your journey by taking my free masterclass today.

Learn the simple systems our clients use to create wildly successful, portable, profitable, travel businesses in record time. In our new masterclass you’ll discover:


  • Simple and effective ways to launch your travel brand
  • How to attract your first clients
  • Avoid common pitfalls new travel agents make that cost them thousands of dollars
  • The keys to monetizing your travel business
  • How to position yourself as an expert in hot travel niches that sell
  • Take advantage of top travel perks and discounts while you travel the world on vacation