magine yourself traveling to far-off countries, walking through landmarks you’ve only read about in history books and seeing sights that previously had only existed in your imagination. Now, imagine getting paid for it. That’s exactly what Gina Greenlee, author of Postcards and Pearls did. Here, Gina talks about some of the ups and downs of travel writing, but, more importantly, she shares how she summoned the courage to achieve the life she’d always dreamt of, how you can do that, and more.

Gina Greenlee is not only the author of Postcards and Pearls: Life Lessons from Solo Moments on the Road, but also of a series of illustrated inspirational gift books: Cheaper than Therapy: How to Keep Life’s Small Problems from Becoming Big Ones and Cheaper than Therapy: How to Take Risks to Create the Life You Want: The Lesson of the Chopsticks

She was a columnist for The Hartford Courant and has written for The New York Times Magazine, Essence, and The St. Petersburg Times. When she isn't writing, she is reading, traveling, ballroom dancing, or whooping it up with friends.

WOW:  Gina, I loved reading all those inspiring postcards from women. What inspired you to do this book?

Gina:  In 2000, I took a solo trip around the world and wrote about it for a newspaper’s website in a weekly column called Journey with Gina. During those five months, women from across the United States emailed me, not to ask about my geographic journey, but my existential one. Specifically, they wanted to know, “How do you find the courage to travel on your own? How do you keep from getting lonely? Don’t you feel self-conscious eating out alone?” After the first 30 emails like these I thought, “There’s a book here.” The moment I had that epiphany, I knew that Postcards and Pearls was not, at its core, a travel book. Rather, I would use solo travel—the context from which the epiphany sprang—as a metaphor for how women could cultivate, nurture, and delight in being in a relationship with themselves.

WOW:  I think that being in a good relationship with yourself is so important for anyone. So, then, how did you find the women who wrote the passages? Can you describe the process for gathering all this information?

Gina:  When I first conceived of Postcards and Pearls, the plan was to use stories only from my travels. However, over the years, as I began to talk to women about the book’s core theme, it became clear that if I only used my stories then my message would not be as universal as I intended. I wanted the broadest spectrum of women readers possible to see themselves in these experiences and feel that the lessons born from them had relevance to their lives. 

So, I put out a call for stories to various networks I belong to, including writers groups, in the form of a six-question, open-ended survey. The answers to the questions organically told each woman’s story. I included the stories that met my criteria: each had to contain a believable, relatable lesson; the lesson had to be one that could apply off the road because the “pearls” are not travel lessons but life lessons; and the story had to show how the traveler stretched beyond her comfort zone. Also, I wanted to include as much variety as possible—in geography, the life experiences of the women, and the type of solo journeys taken. Finally, I wanted the book to be entertaining, so I also chose stories that were just plain fun.

WOW:  Well, I definitely think you selected a great variety of stories. Were there any challenges in collecting your material? How did you overcome it?

Gina:  No, not in gathering the material. Because I had documented my five-month trip around the world in an online newspaper column, those travel details were nicely preserved. Also, stories from my other trips were easy to gather because I’ve always kept travel journals. My best experience with getting stories quickly and easily from other women was with an email blast on listserves.

WOW:  That’s so amazing and rare how smoothly it went for you. How did you compile and organize all the letters after you received them? Was there any specific plan involved behind the organization?

Gina:  The book’s structure was a challenge. I was always clear that I wanted Postcards and Pearls to have a daybook format, where each entry was self-contained and stood on its own. I envisioned women reading only one or two postcards at a time, and not in any particular order but skipping around as the spirit moved them. So each entry had to have its own beginning, middle, and end. At the same time, I also knew that if women chose to read the book from page one through the end, the entire book had to work as a singular narrative, and the stories as a collective had to have a narrative arc. I struggled with that. Should I organize the singular narrative thematically? Geographically? Based on the details of my personal history, some of which comes through in my stories? How do I tell 118 mini stories within a larger story and still have all the pieces fit together and flow for the reader? Because my stories come from travels over a 20-year period, my editor made a great suggestion for me to organize the book into thirds: travels before my world tour, during the tour, and post-tour. It made sense chronologically and that became the foundation for my thought process and the book’s organization. Within that core structure, I wove in the stories from the other women as well as grouped stories thematically.

“I was always challenging myself to enjoy the dream and not work so hard that I would sour its memory.”

WOW:  It all makes sense now! I completely see that looking back at it. What are some challenges of travel writing?

Gina:  I am not so much a travel writer as I am a traveler who writes. I’ve had wanderlust since age 14 (I’m now 48.), and I’ve always loved to write. As well, personal growth and self-awareness have always been top priorities in my life. Postcards and Pearls is an intersection of these three interests.

Taking a solo trip around the world had been on my “bucket list” for ten years from age 29-39. I never intended to publicly write about it. It happened though, that at age 39, when I made the decision to finally do it, I was working for a newspaper at the time and saw an opportunity to jumpstart a professional writing career. On that trip in particular, when I wrote my Journey with Gina column for five months, my biggest challenge was striking a balance between business and pleasure. I was living a long-held dream and frankly, just wanted to enjoy myself, not worry about hitting a weekly deadline from the road. Yet, this was my first big break as a professional writer, so I was always challenging myself to enjoy the dream and not work so hard that I would sour its memory.

WOW:  That makes sense. That would be hard for me. So, how did you balance having work with still having fun?

Gina:  It was tough and I probably didn’t do the best job. I was more writer than traveler than I wanted to be on my trip around the world. I found it hard to experience the trip without always planning my next column to the point where I was almost voyeur rather than participant in my own experience.

WOW:  It sounds to me, though, that despite the challenge, you were still able to strike a good balance. What, in general, did you learn from your travels?

Gina:  Travel is one way I’ve learned more about how the world works and about the history of different cultures. History and geography were not favorite topics of mine in school. Looking back, that is because to my mind, what happened in Rome in the 15th century, for example, seemed to have little connection to the life I was living as a girl and teen in the Manhattan of the 1960s and ’70s. Knowing the world only became interesting to me when I could experience it first hand, especially through its people. 

Also, travel has challenged a lot of my assumptions. For example, I assumed that the cultures of New Zealand and Australia were similar because of their geographic proximity. My assumption was not rooted in anything with real teeth, just a casual idea. These two cultures are not at all alike. And I much preferred one to other. Had I not visited New Zealand, I doubt I would have ever known that it was the first country in the world to give women the vote. That tiny but significant bit of information led me to study about the worldwide suffragette movement once I returned home. 

When I was in my 20s and early 30s, I had this idea that because I was naturally intelligent and could learn just about anything I put my mind to, that I was “smart.” Travel humbled me in a variety of ways—it showed me how little I knew and how much I had to grow, not so much in intellect, but from a place of compassion and connecting more meaningfully with others.

WOW:  That’s such a good point you make about being “smart.” I hope to be humbled this summer when I go traveling, too. What do you hope other readers will take away from this book?

Gina:  I want readers to walk away from Postcards and Pearls and believe they can do something they’ve always dreamed about, that they have what it takes to live their best lives, however they define that.

WOW:  I think that message in the book is very clear and that readers will see that after reading it. But, getting to writing more—how has traveling affected your writing?

Gina:  I’ve become much better at describing an environment in a way that puts the reader in that setting. Also, it’s taught me the importance of bringing in the larger, external world when writing about the personal interior world. Otherwise, in the past, it was more like navel gazing and not as universal.

WOW:  Detail is so important in any form of writing. That’s such a valuable skill to possess. I know you had plans go awry when your cruise went bankrupt. What advice do you have for people in regard to overcoming obstacles like this? How have your obstacles helped with your writing process?

Gina:  In the most practical terms, my advice is that travel insurance is not worth the money. Just about everyone on that cruise, including me, had travel insurance and the cruise company’s bankruptcy was not covered. I’ve since researched travel insurance thoroughly and found that there are so many loopholes and scenarios where Jupiter must align with Mars to collect on a travel policy that the best “insurance” is to 1) book with a reputable company whose business values are to do the right thing for the customer; and 2) pay with a credit card so that your money is immediately refunded and it is the credit card company that does battle with the travel vendor, not you.

“I learned so much from the experience, including how to ask for help and not feel bad about it and that yes, I do have what it takes to travel the world on my own.”

WOW:  I never knew that! That’s very good to know. Is there anything about your journey that you’d do differently?

Gina:  Not one thing and that includes getting on the Ship of Doom. I don’t like cruising. The only reason I did it was because I was afraid to travel the world the more conventional way—trains, planes, and automobiles. It felt too vulnerable to me. I wasn’t certain I could handle it on my own. Well, when the cruise went belly up, it was as if the Universe was saying to me, “Yes, you can, girlfriend! And I’ll prove it to you.” It was a stressful time to have to regroup and figure all that out, but I learned so much from the experience, including how to ask for help and not feel bad about it and that yes, I do have what it takes to travel the world on my own.

WOW:  I definitely believe that everything happens for a reason. Backtracking a bit though, you said before you even went on the cruise, you made a pact with yourself. Can you explain “The Pact” more? How did this plan really take off in your life?

Gina:  The “London Life Expansion Pact” was my written commitment to myself to live more authentically, and my most direct, conscious effort to apply in earnest the laws of attraction. 

Until I made that pact with myself in 1998, I had always come home from vacation depressed. I would have this great time in some fabulous locale only to return to a job that sucked me dry doing work I didn’t believe in, even though it paid well. At almost 40 years old, I felt I’d had enough of that. I asked myself, “If I could create these wonderful vacations for myself, why couldn’t I use the same resources—imagination, commitment, planning, intuition, and money—to create the life I really wanted?” It was a real shift in perspective for me. My challenge was that I didn’t exactly know how to do it. But I believed that by putting the commitment out into the world boldly, in writing, and then keeping that commitment foremost in my mind by literally reading it aloud every day, twice a day to myself, that I would attract the people, information, and other resources that would lead me to a more authentic life. 

The next year, I was hired by a newspaper as the director of strategic planning (after 13 years in a health care career) and that inside track led to freelance writing gigs with the paper while drawing a full-time salary. That was the same year I decided to travel around the world. Because I already had a writing relationship with the paper, it seemed natural to pitch the Journey with Gina column to them, which I did. And so, one short year after creating my Pact, I had significantly changed my life as I had dreamed.

WOW:  That is so amazing. I really applaud you for being able to accomplish your dream. That’s something I admire and hope to have in my life. How did you get into travel writing? What are some good resources or tips for writers looking to get into travel writing?

Gina:  I can’t say that I did get into travel writing as a pure genre. I wrote an inspirational book that uses solo travel as a metaphor. My first two books are not travel-related but personal-growth/inspirational related.

“I believed I had to remove the security blanket of a full-time job and salary to be sufficiently uncomfortable to make the leap into freelance writing.”

WOW:  That makes sense. I hadn’t thought of it that way. How did you get the courage to quit your job and start freelancing? Describe your experiences with this huge life transition.

Gina:  I find courage to be a skill that, to be useful like any other, must be practiced. I constantly look for opportunities to expand my comfort zone, to put myself in situations that force me to access resources I didn’t know I had. If I’m repeatedly doing that in smaller ways, then I’m better prepared to take on bigger risks when those opportunities present themselves.

I have wanted to be a professional writer since age five, the year I learned how to read. I was almost forty years old before I acted on that dream. That was because it took that long for me to be more uncomfortable with living an inauthentic life than taking a crack at my dream. As scary as it was to go for the dream (Am I good enough writer? Can I make money at it? Can I regroup if it doesn’t work?), not going for it and approaching middle age, was even scarier. I didn’t want to look back on my life and regret not having tried.   

I believed that if I had made arrangements to return to my full-time job after my world trip or sought traditional employment, that choice would cause me to relax back into a comfortable, familiar way of life. I believed I had to remove the security blanket of a full-time job and salary to be sufficiently uncomfortable to make the leap into freelance writing. I had already quit my job and had replaced it with a paid, five-month writing gig. I had momentum and I chose to run with it.

WOW:  That was so bold of you! I’m so happy for you that you had that realization and took that leap. In your opinion, what makes a good travel writer? How do you set yourself apart from other travel writers out there?

Gina:  I think of travel writing in three categories: 1) The essayist or storyteller who uses travel as a way to entertain and/or express something specific about the human condition; 2) the writer who informs on the logistics of travel such as the 411 on where to eat, what to see, and what hotels to lodge in at a particular locale; and 3) the writer who is telling a thorough history of a place. Africa is a continent that travel writers love to explore over and over again in a strong historical, biological, and sociopolitical context. 

What I learned when I was freelancing is that the second category—the 411 on a place and its attributes—is the one where a freelancer can have the most impact because the market is larger. It is larger because it is directly tied to commerce, selling a reader on a place to visit. And there is advertising to support that. Category one is more for books and essays, and the personal essay market is small and we all know the challenges with getting our books to the marketplace. Category three is found in more high-end scientific, literary travel journals and magazines. And the travel writers in category three usually are scientists or scholars who are also writers as well as travel/adventurers—Jacques Cousteau types.  

The kind of travel writing I like is category one, an introspective take on the intersection of the personal and the external world. I’m an essayist, which means the travel writing market for me is negligible. I don’t like Category two travel writing. And I don’t have the scholarly credentials for category three. This all basically means, I’m not truly a “travel writer.”

“Know what kind of writing you like to do and what you’re good at.”

WOW:  I think it’s the contrary. I think you are a travel writer. You’re just a category one travel writer. From your experience, is there anything people should beware of when getting into travel writing?

Gina:  It’s not so much a warning as awareness. Know what kind of writing you like to do and what you’re good at. This makes writing for money so much more pleasant than it otherwise would be. I learned that the hard way.

WOW:  I think that’s a good awareness for anyone to have when writing. But, switching gears a bit, what was your experience with Aventine Press? Would you recommend them over another subsidy publisher or self-publishing? Why or not?

Gina:  I love Aventine. I’ve used them to print all three of my books. I wrote and published all three books while working full-time jobs and doing many other things such as traveling, ballroom dancing, and running marathons. I knew my plate would be plenty full with finding a designer for the book, developmental editor, copy editor, marketing and more. If there were steps I could delegate to a vendor such as obtaining ISBN numbers, getting my book on Amazon and other online booksellers, I needed to do that because my time was limited. 

So, I went with a one-stop operation that was top-notch and professional, but small enough to give me the personal attention I needed. When I call Aventine, I speak only to the owner versus a different customer service rep each time. I like knowing that I can pick up the phone and get the same person and personalized, customer-friendly answers to my questions.

WOW:  That’s so rare with companies these days! I’m tired of talking to a computer when I call places. What has been the most effective way you’ve found for publicizing yourself and your books? Any tips for people looking to do the same?

Gina:  The most effective way I have found is to help potential readers make a personal connection to you and your book.  That’s when they are most inclined to buy it. There are any number of ways to do that both in person and in the digital space. For me, I do well when I speak to groups. At a recent talk I did at a bookstore in Florida, a woman in the audience said it best when she approached me to sign the book she’d just purchased: “I don’t know anything about your book or your writing but I liked what you had to say.”

WOW:  Well, I know that woman will like your book as well, just like I did! My last question is just what was your favorite postcard from this book and why?

Gina:  It is the postcard titled, “Right Now” (page 62) about an experience I had in Nepal one New Year’s Eve. I love this postcard for many reasons. The experience was truly hilarious and the feedback I’ve received is that it reads precisely that way. I never get tired of reliving the punchline moment and it cracks me up every time. Also, that experience is highly representative of the solo travel dynamic of starting the evening out on your own, but winding up having an unexpected adventure because of the very fact you are solo; friendly strangers gravitate toward you because your energy is directed out into the world versus concentrated on the people you would be traveling with if you were not solo.

WOW:  Thanks so much, Gina!  I have loved learning more about you and your inspiring book, Postcards and Pearls. You can read even more about Gina on her website https://www.ginagreenlee.com.

Amy Robertson is a freelance writer, reporter, and graphic designer, living in Orange County, Calif. She is currently finishing her last year at California State University, Fullerton, majoring in journalism and graphic design. She’s so excited to move to the Big Apple in June where she’ll be interning for Us Weekly. When she’s not busy with school, work, or her two internships, she most likely can be found singing her heart out at a karaoke bar or line dancing the night away at a country club.