Personal loss and work upheaval as Kathryn turned 50 convinced her she was due for a change. She left her longtime career in finance to start her own business leveraging her love of travel.
Tell us a little about your background.
My younger brother and I grew up in the northwest suburbs of Chicago. Our parents owned a few companies and were constantly working. I majored in political science at Lake Forest College. When I graduated, my grandfather asked if I would like a tour of Europe (the kind where you’re in a different country each day) or money. I chose the tour!
My grandfather had grown up during the Depression and was kicked out of his house at the age of 13. He put himself through school and became President of a company. He did one of the condensed management programs at Harvard. That group of alumni came from all over the world and had a reunion each year in a different country. Add to that, my grandfather was an avid orchid collector (one is named for my grandmother) so he’d travel throughout jungles cutting down orchid samples. That started his addiction to travel, which he was more than willing to pass on to his grandchildren. He had an entire room in his house filled with slide carousels from floor to ceiling. As he had hoped, once I took that trip to Europe, I couldn’t wait to travel the world.
I held a few diverse jobs after college—I lived in Mexico, opened a restaurant, and thought about interior design school while working at a design firm. I finally ended up with a finance job in downtown Chicago. I started as an assistant for a well-known venture capitalist and eventually moved to Golder, Thoma, Cressey & Rauner, where I worked for 25 years. I did everything, including trading, analysis, client relations, and portfolio management.
Today, I live in Chicago with my 16-year-old son, Teddy, who goes to high school at Walter Payton College Prep. I moved him from the suburbs after I divorced and he was entering 6th grade. I sweated it out for a while, hoping I had made the right decision. I knew that I would love living in the city and be close to work and home eliminating the commute, but what if he hated it? Shortly after we moved, he told me, “Mom, isn’t it funny that we had to move to the city for me to make good friends?” I finally breathed a sigh of relief!
When did you start to think about making a change?
I went through an extremely rough year when I turned 50. My dad married a woman who I strongly disapproved of and shortly thereafter became sick. My longtime boss sat me down and said his goddaughter was going to take over the business. All of a sudden, the bottom of my life seemed to fall away. The two men I was closest with and looked to for support and guidance seemed to abandon me.
It took a year of agonizing—and I’m sure working on it subconsciously—to come to the realization that I should change careers and do something that I was passionate about: travel! I’ve been to 50+ countries and my son has been to 32+ so you could say I’m addicted to travel. There is so much about travel that I love. There’s the educational aspect; there’s the giving back aspect; there’s the whole aspect of relaxation that we don’t get enough of; there’s the understanding of different cultures—I’m convinced there would be less prejudice in the world if people traveled more.
What is your next act?
I am a travel agent—or as we like to call ourselves, a travel advisor. I have my own business, Kathryn Theodore Travel, which I launched in 2015 at the age of 51.
I have the best job in the world. I help people make their dreams come true! When I help plan a client’s trip, I feel that I’m going on the trip with them. I get so enthusiastic and love to plan, especially unique experiences like a birthday party, a treasure hunt for the kids, or an incredibly romantic dinner in a venue they will never forget. For example, I had three weeks to plan a vacation for a single woman in between careers who wanted to travel in Europe. I organized a five-week trip for her through Portugal and Spain. When I met her after the trip, she said that it had been life changing! I also planned a family vacation to Italy. Upon hearing that one daughter would love to learn how to make pasta, I arranged a special excursion into Tuscany for a pasta-making lesson with a renowned chef. I also love organizing wellness trips for women after divorce—and watching them come back with a new lease on life.
I have a specialty in wellness travel. While I book all types of travel for diverse clients, my passion is wellness. We Americans are stressed, over-scheduled, and don’t take time for ourselves. This is especially true of women. My goal is to provide clients with a trip that includes at least one wellness aspect. Whether it is detoxing from your electronics, learning a new exercise, or listening to a wellness specialist, my hope is that my clients come home feeling much better than when they left and having learned something to incorporate into their everyday lives. I am also planning groups to experience a wellness resort for a long weekend or a week. These wellness resorts offer 50+ activities per day, healthy meals, luxurious accommodations, and wellness classes. You can do as little or as much as you like.
How hard was it to take the plunge? How did you prepare?
It wasn’t an easy process. I had traveled with my family with the help of an advisor who was part of the Virtuoso network. This is a consortium of the top travel advisors in the world who get special perks for their clients and vet thousands of properties. They have an amazing continuing education program and support. I just returned from one week in Las Vegas for Virtuoso Travel Week which is like the Academy Awards of travel. Over the span of a week, I met with 250+ suppliers and was introduced to so many new properties.
So when I decided I wanted to be part of Virtuoso, I called them and told them that I was changing careers, needed a mentoring program, and it had to be a Virtuoso agency. They gave me three names of host agencies and I did due diligence on each (I am an independent contractor with my own LLC—Limited Liability Corporation—but hosted by a major agency). The agency that I ended up with, Largay Travel, is the most amazing place. They’re a family business based in Connecticut. They now have about 100 Independent Contractors and are still growing. They are prominent in Virtuoso and had a wonderful 6-month mentoring program.
I plunged into the program while I was still working my finance job. This wasn’t that difficult but once I started building my book of business and booking trips, it became much more challenging. Some weeks I was working 80 hours. I was reluctant to give up the finance work because it was paying my bills and allowed me to have funds for marketing and other programs for my travel business. There were many times when I questioned my sanity! Especially at the age of 50. And raising a teenager at the same time was not the easiest thing. But every time I became discouraged, I’d read about some incredible woman who had faced far greater obstacles than me and prevailed.
I had no social life and my friends didn’t understand. I knew I didn’t have an alternative though. I wasn’t going to have a job in finance forever; I wanted to continue working and wasn’t fond of growing old in the “old boys’ network” of finance. What other choice did I have? And every time I finished a mentoring class or learned about a new property or planned a trip for someone, I was giddy! I loved every minute of it. How could I not continue?
How supportive were your family and friends?
My mom and brother have always been very supportive. I knew I was also setting a good example for my son to show that hard work can yield results and in general how to be an entrepreneur. I want him to learn that it’s okay to take risks—even at the age of 50!
My friends were a different story. It’s hard to understand something until you actually go through it. Divorce is the same. My friends didn’t understand why I was working every weekend and couldn’t go out. They thought I was throwing my life away. But at the same time, I’ve met so many new friends who own their own businesses and thoroughly get it.
What challenges have you encountered?
Besides the time challenge, I’ve had to educate people about exactly what a travel advisor does and the advantages of using one. Being a travel advisor is akin to being a wealth advisor. When online trading became prevalent, everyone thought they could manage their own money. The same happened with the advent of online travel booking via Orbitz, Travelocity, and all of the others. Now I’m not opposed to a client going to the Internet to do travel research, but when a problem occurs (which it inevitably does in travel), are you going to get better results calling 1-800-ORBITZ or calling someone like me, who knows exactly where you are and how to handle your problem?
We monitor our clients’ trips and sometimes know about a problem before they do. I am your advocate. Through Virtuoso, we also secure certain perks for our clients such as VIP status, upgrades, credits, early check-in, late check-out, and more. We travel ourselves a great deal, meet the general managers of the best properties, and get to know our suppliers. We have in-depth knowledge and can provide you with special events and experiences that you would never find online.
The other challenge I’ve had is marketing. In finance, the clients came to us by referral. I’d love my business to grow that way, and it does, but the most successful travel companies say that marketing and networking never ends.
What did you learn about yourself through this process?
I’ve always doubted my persistence and really didn’t consider myself disciplined. I learned that I actually do possess these traits. It takes a lot of discipline to go out and market yourself when you’ve never done so before. It’s tempting to come home after working a full day and lie on the couch. I have spent the day at my computer when it’s a beautiful summer day. I’ve forced myself to go to one to two networking events each week. But as a consequence, I’ve met the most wonderful people and I feel so good about myself!
Looking back, is there anything you’d have done differently?
Yes. I’d have started in my 20s! I’m joking—I wouldn’t trade my career in finance. I learned SO much and every day was new. I obtained skills that surprisingly I use in travel. And I learned something about myself: I have to learn a new thing every day to stay alert. I love meeting new people every day. Fate has a way of making everything work out, although at times you definitely doubt it and can’t imagine a good ending.
What advice do you have for women seeking reinvention in midlife?
Just do it! You have to go with your gut. Your friends and family will give you a ton of different opinions but only you know how you feel and what you want to do. Listen to your inner self. It took me over a year to listen to my inner self tell me to start a travel business. It takes patience, especially when we’re older.
What advice do you have for those interested in becoming travel advisors?
We have a huge number of travel advisors getting ready to retire. This presents many openings for new people. Anyone interested can go the route I did or get a job with a reputable agency. Most will train new advisors and give them opportunities to travel as well. There are also careers on the sales side working for the hotels, resorts, cruises, and airlines. These won’t have the pressure of building up a client roster. The CTA designation is not necessary but I would advise gaining it, especially for someone new to the industry. It gives additional credibility.
You’re never too old to get a mentor. I have wonderful mentors in my Largay colleagues and I’ve applied for a mentor at PWCC. I believe in listening to everyone’s advice. You may not use it all, but listen.
I also love Meetup groups and subscribe to a myriad of travel websites (even my competitors’) to stay alert. I subscribe to Google Alerts for different tag words such as “Luxury Travel”, “Wellness Travel”, “Family Travel”, etc.
I use Vistaprint to make all of my marketing materials. It’s the easiest thing ever.
My accountant, Ted Galatsianos, is wonderful (Ted@opsaccounting.com).
What about your favorite resources for travel lovers?
I think I subscribe to every travel magazine, domestic and foreign, out there! I have a library of travel books. Here are some favorites: Travel & Leisure, Afar, Conde Nast Traveler, Departures, Virtuoso Life, Virtuoso Traveler, and the 111 Places series of travel books.
I follow competitors to see what they’re doing. I look for travel leaders on social media and follow them. I entered a Google Alert search for “luxury travel”, “travel”, “family travel” and “wellness travel” so I get alerts to articles posted on the web. You can never have too much information in this industry!
What are some of your favorite destinations you’ve visited and why?
That’s like asking who your favorite child is! I would say that the required trip for everyone is an African safari. Words cannot describe how you change after being on one and the incredible things you see. People are hesitant to do one, but I would encourage everyone to take the plunge.
What are your bucket list destinations?
Egypt (where we’ll be going to this year), Jordan, Japan, the “Stans”, Iraq, Patagonia, and many more African safaris!
What’s next for you?
I’m working on my CTA (Certified Travel Advisor) designation. I have dreams of starting a wellness consortium in Chicago so when my clients (or anyone else) experience a new wellness treatment or are introduced to something, I can connect them with practitioners to continue once they return home.
I’d also love to start a women’s support group for women going through divorce, career transition, loss of a loved one, adapting to being an empty nester, etc. I’d like to have monthly meetings with speakers, group sessions, and retreats.