Jill Cruse - VP of Guest Experience for Olivia Travel, OWN Ambassador


As VP of Guest Experience for Olivia Travel for 29 years, Jill Cruse has helped thousands of women become inspired by the world around them. She serves as an OWN Ambassador, promoting the Oprah network via social media and has appeared as a special guest on Oprah’s Super Soul Sunday. Jill is also an avid photographer (took home a first-place win in a national competition for InterContinental Hotels/National Geographic!).

I knew Jill for years through email and coordinated voyages for her groups. But I was so taken by her spirit and passion after meeting her in person that I had to reach out and invite her to the Explorers' Corner.

1. Starting big: You've traveled the world and have overseen guest experience for Olivia Travel for 29 years. That takes an incredible amount of energy and passion. What drives you? 

Gratitude! Every morning I say "Thank you" for getting to do something I love.  I am incredibly grateful for this work I get to do. I know that we change the world a little bit at a time when we do these trips. Whether it’s changing the life of our guest to have an experience they might not have had or to change the perception of our group with the staff and crew we work with, or with the people we meet in the countries we visit. The icing on the cake is that I get to travel the world. I take a lot of pride in serving our guests and making sure their experience and expectations are met.

2. What would you consider your biggest accomplishment? Biggest failure? From both experiences, what did you learn? 

Honestly, I never really have thought about this, and I struggled with an answer! My entire life I view as an accomplishment because I have lived it with passion. From that, my photography has become pretty good. I've won a few awards, and I've used my photos in our marketing materials and shared my photos on FB so that others who cannot travel can vicariously travel with me.  I can name drop and tell you I know Oprah, met with her 5 times and was on a Super Soul Sunday episode with her and don Miguel Ruiz, which was a great accomplishment and I hope inspired others. But really, I feel that anything that had to do with helping a young girl or even a guest feel better about who she is I think is a great accomplishment – Having been a camp counselor and camp director, coach and now my present job of VP-Guest Experience accomplishes this every day.  

I don’t think we really have failures.  We make mistakes, or stay at a job (or in relationships) too long that do not make us happy. We lose people we love and get our hearts broken. We move to a new place, and have no friends or support system. We can find ourselves alone and afraid.  Did I do the right thing? But as I look back on my life, I am grateful for all of it, because it lead me to my passion and made me who I am today.  They were all learnings and completely meant to be.

One example was that I was fired once from a private school teaching job.  They wanted me to teach something that I was not trained to teach, and they basically gave me a babysitting job after school for K-12. I was fired, but I quickly learned to be grateful it happened as I decided I would never do a job that I didn’t enjoy or feel good about. I never really worried about failures as it does not define who I am. I moved to San Francisco and changed jobs for a relationship that ended two weeks after I made the move. I mean, c'mon!  Really? But had I not moved here, I would not have had the job I presently have. I'm completely grateful for that! If that's a failure, then bring them on!

3. What advice do you have for young people interested in the travel industry? What common career advice should they ignore? 

I didn’t start out thinking I would work for the travel industry and have this dream job for the last 29 years, so unfortunately, I can’t come from a place of “You should take this class, or work at this place”. I would say make sure your intentions are pure. Is it something that feeds your soul, makes you happy and serves others? Or is it just because you want to travel? I have seen some great Travel Agents who really serve their clients well, and get the perk of travel, and I have seen others in it just so they can get free travel. Be pure with your intentions.

Dream big. Don’t worry about where the money will come from, how it will happen or when. Then WRITE IT DOWN.

My experience is a spiritual one, and I am presently writing a book about this journey. When I was 22, I wrote down in a journal that I wanted to travel the world, experience different cultures, do something to empower women and use my photography in my work. I had no idea what that would look like or how I would get there.  At the end I wrote “and how cool would it be to work for an all-women’s company like Olivia, which at the time was an Women’s Record Company (Independent label) and later became a travel company. This is where I presently workt. At the time I was a camp counselor and was about to start teaching High School Physical Education and coaching. So I am not even doing what I went to school for – most people I know are not. I truly believe I set that intention in motion when I wrote it down, with the Universe or God, whatever you believe, on that day. From there I lived my life doing my best at whatever I was doing, and moving on when it was not feeding my soul.


In short, my advice is to think about what in life you really want.  Dream big. Don’t worry about where the money will come from, how it will happen or when. Then WRITE IT DOWN. Your job is then to do whatever you are presently doing with love and passion, work hard at it, do your best, pursue what makes you happy and when it doesn’t, make an exit plan. Don’t settle, whether it's work or a relationship.  Good things always happen and work out when we take big risks.  That is, giving up something that may feel secure (home, job, health insurance, financial reasons). Go for what will make you happy and nurture your spirit. Figure out what you have to do for the money part, even if it's just scraping by and taking a part time minimum wage job. I quit a good paying, Community Services Supervisor recreation job at the age of 31. I liked it, but I could not see myself being there forever. I was no longer passionate about it. I looked at the parts I liked about it, like the creative side of making flyers, and decided to pursue computer graphic design. I took out all of my 401K to go back to school to learn computer graphics, and had enough to live on for 6 months.  It may not have been the smartest thing to do, but I loved this new chapter in my life and the possibilities. This risk lead me to a freelance graphic design job at the company I now work for. Having the right last name to be a Cruise Director actually worked out. The point is, all my experiences and the risks I took lead me here. That's another story and chapter in my book!  Trust that the money will come, but we have to sometimes make those sacrifices and just trust it will all work out in the end.  Because this I know for sure.  It always does.

4. Kodak Scenario: you're given the last roll of Kodachrome and can go anywhere to use it. Where do you go and what do you shoot? 

Great Question! I love nature photography, and I have two dreams, so I'll take 1/2 a roll in each place :-). I've been to Antarctica 4 times, but never made it to South Georgia. So my dream is to make it to South Georgia and photograph the King Penguins and Tonga and swim with and photograph the Humpback whales.   

5. What can you not travel without? 

Besides my camera, good coffee!

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