Careers on Vacation™ Mastermind

careers on vacation mastermind computer picture

This is my signature and most popular program. Careers on Vacation™ (COV) is my 12-week immersive mastermind program for aspiring, new or experienced agents (we have two learning tracks based on your experience). We are an ASTA affiliated travel school, as a graduating participant you will receive a Careers on Vacation™ certificate of completion and a watermarked logo that is industry recognized to use in your marketing.

We are focused on one thing – RESULTS. We offer full support as you set up your marketing machine, sales, service, and operational best practices. We support you in the real world set up and application, this is what is so different about our program and why we have the best results in the industry (don’t take my word for it, watch here). The Mastermind includes weekly calls and trainings; group calls with me, training sessions with our team of experts in various areas like social media, branding, and mindset. Each participant is assigned a private coach and has access to me and my amazing team of experts (the same team that got my travel business to 6-figures a month).

This is the program that teaches you everything you need to know to get your business optimized for scalable growth. COV is a “Learning while earning” model vs. the “learning without earning” that makes other programs or traditional travel schools fall flat in the results department. This means we support you in setting up my proven systems to launch & supersize. The faster you set them up, the faster you can start selling on a larger scale. Most of our clients are actively selling before graduation and get a quick return on investment; better yet, they know how to create amazing results going forward.

What exactly is the Careers on Vacation™
system and what does it include?

Careers on Vacation™ is so much more than a traditional travel school or general consulting practice because we provide the industry specific business application processes and systems that new and experienced owners need to be successful.  While you still get the benefits that traditional travel schools or a top tier consultant would provide, we take you light years ahead and support you through the planning, launch, and real-life application required to be as successful as possible in today’s marketplace.  Think of Careers On Vacation™ like a fast pass to get you in action and succeeding at lightning speed. Countless clients have told us that they wish they had found us before investing in travel school, university programs, franchises, or other coaching programs that didn’t yield nearly the result that our program did in less than 12 weeks. 

Travel hosts and franchisors retain a percentage of your earnings for the lifetime of your tenure with them, so it’s in their best interest to keep you under their umbrella.  In our program, we work directly for you, so our advice and counsel is always in your best interest. You will learn the best strategy for your unique vision, and how to map out your short and long-term growth plans for maximum earning potential through your career.   

Careers on Vacation™ is the only program on the market that works with both experienced and new professionals to personally understand your unique vision for both your life and business, and support you through the application and execution of your vision.  If you are new, you will avoid years of wasted time and money and fast track yourself to success. If you are experienced, you will blast past your current plateau to supersize and finally realize the success you’ve been craving. 

We will start by understanding your vision, and help you customize a strategic plan to execute your vision.  We will teach you tools to improve your confidence and implement a CEO, results-driven mindset. You will learn how to implement proven systems to powerfully get your marketing machine, sales systems, automation, and growth initiatives in action fast. 

The 12-week Careers on Vacation™ Mastermind includes:

• 10 jam packed (self-paced) on-demand training modules
• 9 Live Q&A calls with Cyndi
• Library of on-demand video trainings
• A Cyndi Williams certified Coach to personally mentor you, 3 private sessions
• Weekly training sessions with Cyndi’s team of experts to discuss social media optimization, branding strategy, adopting a 6-figure+ mindset & more
• On-demand support (M-F) with access to Cyndi, and our team of industry & marketing experts
• Video strategy training (how to leverage video for your agency)
• Resources, templates, talk tracks, tools & bonus content
• Lifetime access to the membership site, & any new content we add in the future
• Invitation to our graduate community to connect with your peers’ post-program
• COV graduates also receive invites and discounts to special events
• Careers On Vacation™ certificate & watermark logo to use in your marketing to show consumers you are a certified Careers On Vacation™ graduate.
• Exclusive student freebies and discounts on done-for-you marketing tools from
• Advanced training on how to leverage available marketing tools in your marketing plan or your business.

See a full breakdown of program inclusions here.

What results can I expect?

  • Have big breakthroughs and ah ha moments.
  • Become your own boss, and all the flexibility that suggests.
  • Launch your fully operational travel business.
  • Optimize your agency on the highest converting social media platforms.
  • Follow your BLISS into ABUNDANCE
  • Discover yourself, set goals and reach them.
  • Feel empowered & excited about the future.
  • Receive your own custom training and strategy plan. 
  • Gain unshakeable confidence in yourself – (a lot of my clients tell me that is worth the investment alone).
  • Reach your ideal clients in large numbers and inexpensively.
  • Learn proven techniques for launching, growing, and supersizing your travel business.
  • Get crystal clear on who your ideal clients are who will gladly pay you what your worth to help them solve their problems.
  • Create a compelling marketing message that will make your ideal client say, “Wow, that’s exactly what I need”.
  • Monetize your travel business, and increase your immediate cash flow.
  • Implement a recurring business model.
  • Leverage your time so you can begin selling one to many and make more money in less time.
  • Create a lead generating marketing plan.
  • Work smarter at building your business not harder.
  • Close the sale without ever feeling sales-y.
  • Position yourself as an expert in your field (and be perceived, and paid, as such).
  • Stay accountable to your vision and goals and achieve them.
  • Get proven techniques you can apply right away.
  • Learn how implement automation & improve your work life balance.
  • Receive specific tools, templates and scripts for you to use.
  • Create greater exposure and visibility for your business.
  • Learn time saving techniques that will dramatically cut down your learning curve.
  • Make more money than you’re making now, while enjoying being in business for yourself even more than you’re enjoying it now.
  • Implement systems so you consistently market your services easily and can finally stop struggling to get clients, for good.
  • Be clear, concise and strategic about your business.
  • Learn how to eliminate tire kickers from your business
  • Watch your best life unfold with ease.
  • Raise your self-esteem and self-confidence.
  • Rewrite your story.

Who are your clients?

I work with people just like you who have a passion for travel and want to turn their passion into their career.  Some of my clients want to break into the travel industry to build a portable (work from anywhere), profitable business that will allow them the freedom and income they desire.  Some of my clients have established travel businesses that they want to sky rocket to the next level of success.  I also consult with travel companies that want to motivate and inspire their management teams and workforces to increase company performance, improve operations, and increase profits.

If you have a passion for travel, even if you are in another industry, I can show you how to successfully make the transition into travel. We have had all types of amazing clients through our program; healthcare workers, retired military, realtors, event planners, police officers, attorneys, hair dressers, coaches, college students, influencers, teachers, bus drivers, DJs, those in and approaching retirement, and all walks of life. If your passion & motivation is there, I can show you how to make the leap into the travel industry successfully, and position you like a seasoned expert, even if you’re brand new.

Examples of clients I've worked with: 

Aspiring Travel Agents • Travel Agents (new and experienced) • Entrepreneurs • First Time and Existing Business Owners • Professionals • Sales Professionals • Leaders • Travel Agency Owners • Travel Business Leaders and Managers • Travel Franchisors and Franchisees • Management Professionals • Travel Enthusiasts • Travel Vendors and Suppliers • Resorts • Tourism Offices • Travel Company CEOs • Host Agencies • Tour Operators

What makes you different from other coaches and experts in the travel industry?

Well, besides being the original Travel Career Coach, and pioneering the niche, you will not find someone more motivated or experienced to help you (and your team) succeed.  With 25+ years of experience, and an award-winning travel agency of my own, my proven systems have been tested in hundreds of successful agencies, and are delivering amazing results across the industry. There is no other coach in the travel industry with over 100+ verifiable case studies and counting (feel free to watch some here). We are also one of the few available programs affiliated as a travel school with ASTA, the American Society of Travel Advisors.

In a complicated world of travel hosts, franchisors, agencies and multiple options it’s difficult to know where to start, or who is operating in your best interests.  As your personal consultants, my team of industry experts and I work directly with you on how to understand your vision and get the fastest results in the least amount of time. Most people make years of mistakes before realizing success in their business.  I support you in setting up and scaling your business the right way to map growth for years to come, and how to avoid costly mistakes and setbacks. 

Although we will occasionally cover time management, mindset and other “business coach-y” things, you have me and my team as your business strategy experts and consultants. We work on the inner and outer principals for success and look at your business and your sales results from a strategic, organic, and goals-based perspective. What that means to you is that you get an experienced, heart-centered, authentic, travel, sales, and marketing support. I’m not delicate, you’ll always get a straight to the point quick and honest response from me.

I’m concerned with how to get your highly profitable travel business started and growing in abundance.  You may not like what I have to tell you, but you can be sure I will always tell you the truth. The truth about what’s standing in the way of your success and how to get rid of it fast so you can start getting results in record time (and I throw in a healthy dose of humor and inspiration, which always helps).

What type of personality do you work best with and what is expected of me?

My Careers on Vacation Mastermind™ , products and events were created for people who are absolutely excited and serious about running wildly successful travel businesses while enjoying the independence of traveling whenever they want, or working from wherever they want.  It means not running around all day long, beating yourself up anymore saying: “I hate my job, I can’t wait until my next vacation.”  They were created for you to put systems in place within a few months (sometimes weeks), which will eventually lead you to making more money, working for yourself, working from anywhere in the world, and traveling our beautiful world at highly discounted (sometimes free) rates.

Being a Travel Entrepreneur myself, I’m known to work best with other entrepreneurs and people who are committed to their success no matter what.  People who are ready to get going and just want a proven roadmap to create, run, or expand their travel businesses.  My clients often tell me – “Just tell me what to do and I’ll do it!”  Consider what you’ll do with me to be a high-octane crash course on everything you need to know to make a huge income while traveling the world.  You will be expected to take serious and consistent action. No excuses anymore, just a very different way of thinking and full support while you achieve this incredibly exciting goal:  Building a wildly successful travel business, up-level your lifestyle financially and emotionally, and finally have the time to enjoy your life and travel the world at your leisure.

For what type of professionals are your programs NOT going to work?

Please know I’m very selective in who I work with and I cherry-pick my clients, choosing to (gently) turn away people who aren’t suited for my programs and won’t get the results for which they would have signed up for. (It wouldn’t be fair to them.)

The Careers on Vacation™ program is not a fit for those who have no money coming in and are absolutely financially desperate, at least not right away. It’s been my experience that people in financial crisis do not trust the recommendations I give them and do not do the work (probably because they are worrying about where they are going to get next month’s rent check or mortgage payment.) If you fall within this category, it’s absolutely OK. We’ve all been in times of financial crisis at one point or another.

Another type of personalities I won’t work with (without exception) are the whiner or the chronic skeptic, as well as individuals who consistently make excuses for not getting their assignments done or challenging every aspect of the program. If you are one of these people, I gently and respectfully ask that you not call and I hope you understand why.

Not sure if you're ready?
Doing these five things will really help you get primed for our work. Then when you’re ready, call me and we’ll get you started.

(I’m in no rush and will be here when you need me).

  1. Get some money coming in with a full-time or part-time job at the very least, and then call me. This will take the edge off and provide a little more peace of mind. Mostly, it will de-clutter your mind enough to focus on your Careers on Vacation™ assignments and the BIG picture. Once you start seeing the clients come in regularly as a result of our work, you can then start reducing the hours you work at that other job and focus on your own business.
  2. Sign up for the free Careers on Vacation™ Masterclass.  The free information will get you started towards your goals until you’re ready to work with me one-on-one. 
  3. Join the “Careers On Vacation” Facebook page.  The tips are helpful, and will give you LOTS to think about. 
  4. Subscribe & click the notification bell to receive all my free content on YouTube.  
  5. Check out our podcast

Does this really work?

Yes! The result of our work is an approach to shifting your mindset and putting a proven strategic business model in place so you will be able to confidently manifest your travel career at any level. Click on our testimonials link to read about our success stories.

There is no other company in the industry that can boast 100+ case studies and we’ve proudly earned over 100 five-star reviews across Google and Facebook.

Can I contact some of your former clients to see what it’s like to work with you?

Yes, I encourage you to! Please go to the Client Testimonials page and read all of them. See which ones you feel drawn to, either because the person has gotten the results you want to get to, or perhaps because that person is in a similar situation. Then feel free to email or call them and ask what they got from working with me and my programs.

Here are our most asked questions from our clients.

How Quickly Can I Expect Results?

That depends on how quickly you can make those inner shifts. Some clients are ready to go and open their travel business in a very short time frame, sometimes even a few weeks while others have a bit more work to do first. It also depends on the time and energy you can readily commit to getting started.  Some of my clients start their businesses as part-time while keeping their full-time employment, others go all in right away.  That’s the great part about this business, you can do either it just depends on your preferences and personal goals.

How Can I Guarantee Myself That I Will Have More Success, In Record Time?

Do all of your homework. Be totally committed to your success. Understand that this is a process, a proven one, that works if you take action and implement all of the steps. All my clients who have diligently applied every step of Careers on Vacation™ have successfully built travel businesses, and bigger abundance in much less time than they would have on their own AND have enjoyed the freedom of working for themselves from any location they choose, all while traveling as much as they’d like to.

Who is this program best for?

Brand new and aspiring agents (Newbie Track) that want to run their own portable, profitable travel business and have everything set up the right way from the beginning. Aspiring travel entrepreneurs (it’s ok if you’re never worked in travel that’s why you’re here) that want to skip years of frustration and learn from a mentor that’s already accomplished what they want to replicate. Those that are serious about substantial, serious growth. COV is designed to support those that want to transition to running a full-time travel business, or an extremely profitable hobby. If you have a huge passion for travel, want to be your own boss, want a substantial full-time income working in travel, and you want the roadmap (and skip the mistakes) to get the most results as quickly as possible, then this is the program for you!

Available for new & aspiring agents in: US, Canada, and Australia

Experienced agents (Experienced Track) that want to supersize their travel businesses. Quickly fix what’s broken, get real marketing and proven systems in place, and learn from a mentor that’s already accomplished what they want to replicate. Experienced agents that are serious about substantial, serious growth. COV is designed to support those that want to transition to running a full-time travel business, or an extremely profitable hobby. If you are tired of lack-luster results, but don’t want to give up on your passion. If you’re wondering how others are successfully growing their agencies in the on-line space, but can’t figure out what you’re doing wrong. If you want to transition quickly to working in travel fulltime, and you just want the roadmap to get the most results as quickly as possible, then this is the program for you!

Available to: experienced agents world-wide.

Are you experienced & not sure which program is best for you? Check out our program comparison here.

Do I earn a certification?

Yes! Upon successful completion of the program you will receive a certificate of completion recognizing you as a Careers on Vacation™ graduate. You can also then proudly display the industry recognized Careers on Vacation graduate watermarked logo on your website, and on-line.

Are you an ASTA affiliated Travel School?

Yes, our training is ASTA affiliated. ASTA (American Society of Travel Advisors), is the leading global advocate for travel advisors and they are recognized industry-wide.

However, we are much more than a traditional travel school, we consider our programs to be an evolved model; delivering education with real world execution. Think Travel Industry Education + Consulting + Tools & Resources + Support. This formula is what allows our clients to achieve such incredible results compared to traditional travel schools.

How does the Careers on Vacation™

Mastermind compare to other training programs?

I am glad you asked, good vetting should be part of your screening process no matter who you hire to support you in your growth initiatives. Please don’t invest in anyone (even me) until you’ve vetted them to see if they are a match for you. Remember, the cheapest solutions are rarely the best for tangible results. It’s always best to go with someone who works in our industry, and can show you proven results. We have over 100+ case studies from our clients, watch some of them here. Also, here’s a free checklist to help you see how we measure up against the competition.

Quite simply, the Careers On Vacation Mastermind™ is the only program of its kind, delivering the type of results that we do in the industry. We are unique in many ways, but to point out some of the most important differences between us and everyone else out there, it would be…

• Everything we train has been tested in actual travel agencies (you’d be surprised how many “coaches” don’t actually have their own agency).
• I started in the Travel Industry over 25+ years ago, and have a track record of multiple 6-figure years for over a decade.
• I spend over 100K+/year (so you don’t have to) on ad testing & marketing to make sure we are bringing you the best, highest performing marketing solutions.
• I hire the best experts (which would typically be out of reach for a home-based agent’s budget) and make them available to you in the mastermind format.
• There are tons of marketing “experts” that may be amazing at what they do, but they don’t understand the travel industry. Furthermore, marketing managers will require ample testing budget to “figure out what works” during your honeymoon period. We’ve already done that for you & we already know exactly what works best.
• I have the most amazing team of coaches (all travel veterans) ready to support you in making your vision a reality.
• You get personalized, custom support, this is not an e-program that will end up sitting on your hard drive collecting dust.

The same path doesn’t work for everyone, which is why cookie cutter programs, marketing “gurus” from other industries and taking a DIY approach just doesn’t work when you want exponential growth quickly. If you’re looking to work with an award-winning travel expert, that’s already done what you want to do, and has 2 decades of multiple 6+ figure years under her belt than welcome aboard! I’m here to teach you everything I know, more importantly what to avoid to save yourself years of frustration. You get all the good stuff; all my tricks, secrets, systems and proven systems in this program, and I can’t wait to change your life!

Cyndi, based on everything I’ve read and heard about you, I know you’re the one I want to learn from. What are my options for getting started with you?

Congratulations on making a decision for success! I’m happy to work with you to achieve your business goals. The best way to work with me is to apply for my 12 week Careers on Vacation™ program. Click below to apply!

OK, I’m ready to do this for myself, but I have a couple of additional questions. Can I call you?

Good, sounds like you’re ready to be pulled into your future! Please review our program comparison chart. If you still have questions, just e-mail us at and we will be happy to walk you through the different options to see which one will be the very best for you. I can’t wait to see you succeed and am honored to be the one to help you.

Let's get traveling!