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Conversations with Gennean Woodall

Today we’d like to introduce you to Gennean Woodall.

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
While I am originally from California, I moved to Nashville in 2013, just one-year post-grad. I was ready to experience living in a new place and had a gut feeling that Nashville might be a great fit for me. It’s actually pretty crazy to think back to what the city was like almost 10 years ago because it really has changed so much!

After moving, I got a job as an administrative assistant, where I worked for 4 years. During that time, I also took up a bunch of side gigs to make extra money in order to try to pay off my student loans, which had quickly become a goal of mine. I knew that my job wasn’t “it” for me, but I also knew I wanted to take care of that aspect of my finances in order to have more freedom and flexibility to do something I was more passionate about.

Two years later, my student loans were paid off, and I decided to celebrate by taking a 2 week trip to London, but knew I would need to save up for it. Then during that process of saving and starting to plan, something shifted, and I realized I needed to travel longer than 2 weeks, which would require quitting my job and taking a massive leap of faith.

In time, I made that decision permanent, quitting my job and moving back to my home state for a few months to start planning my trip. Long story short, I ended up solo traveling around Europe for almost 5 months, visiting over 65 cities across 13 different countries and having the time of my life.

Upon my return back to the states, I stumbled into a part-time remote job that gave me the opportunity to continue traveling, so I road-tripped around the U.S. for another 8 months, which gave me the chance to spend quality time with friends and family all over the country! Then I went back to Europe for another 4 months while spending extended time in cities like Paris, London, Edinburgh, and cities across Ireland.

After those travels, I moved back to Nashville just a few months before the pandemic hit, which obviously halted all of our travel plans. While I continued working remotely as a freelancer in the web design space, and despite having adopted a dog at the beginning of the pandemic, I started feeling the itch to travel again, and to help others do the same.

So I planned a few domestic trips to visit a few friends and a few new places (like Alaska!), and also decided to start a travel business! I created an online course for solo travelers, curated digital city travel guides, and even helped a few friends plan their own trips.

Gennean LLC became official earlier this year, and now I have the opportunity to take my insight and knowledge as an experienced world traveler and help others plan their own amazing trips to destinations all over the world… and I am having the best time!

Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
Is anything ever really a smooth road? Rarely, if ever.

Quitting my job — and all of the securities that came along with that — was something I battled with for months. I was terrified at the thought of not making money, not having traditional health insurance, not having a community, or even failing at pursuing my dream of travel.

But when I chatted with others who were either older or wiser than me, I kept hearing the same thing: “You have to do this!” or “I wish I would have done what you’re doing!” That helped me tremendously because I knew I never wanted to live with that kind of regret.

But that doesn’t mean that it was an easy decision, either. It felt like I was going against societal “norms” or the status quo of what I *should* do (e.g. save for a house, settle down, etc.). But I knew it was something I needed to do for myself, and I’ve never regretted it.

And there were plenty of struggles throughout my years of solo traveling, too. From causing a rental car to break down in Ireland to getting stuck on a ferry from Italy to Croatia to being stranded in France during a train strike, I had to learn how to deal with things that unexpectedly and unfortunately popped up along the way, and I think I am a better traveler (and human being) for it.

Simply put, struggles always happen. Thankfully, we get to choose how we respond to them.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I’m a travel planner and digital content creator who is passionate about helping others more easily and confidently explore the world. While I have a soft spot for helping other solo travelers, I truly love getting to help anyone make their dreams of travel a reality, whether that means hopping on a call to answer questions, creating a new travel guide, or partnering with someone to plan their trip from start to finish!

I am known most for being a solo traveler — namely, because I spent 2 years traveling solo and continue to today — as well as a budget-friendly traveler, as I’ve learned plenty of ways to make my money go as far as possible when I travel. What sets me apart from others is that I am an “everygirl” of sorts; I am not an “influencer” who takes paid-for or sponsored trips or who promotes things I haven’t actually tried and love.

If I talk about or share something, I actually use it. If I take a trip, I’ve most likely paid for and done the research for it on my own. Basically, I’m just like you… just maybe a few steps ahead. And I am most proud of creating a brand and business that keeps it real, shares the good bits as well as the challenging ones, and genuinely cares about helping others explore the world in any way they can!

I currently offer one-on-one travel planning and consulting services as well as a collection of digital city travel guides on my website, including “The Simple Guide to Solo Travel.”

What do you think about luck?
I think I’ve been surrounded by some amazing, supportive human beings who have believed in me, my dreams, and my desire to help others travel more easily and confidently.

I have friends and clients who have trusted me to help them plan their dream trips, which is something I never take for granted. And I’ve had a lot of grit to keep saying yes to myself even — and especially — when it was challenging.

I don’t really believe in luck. But I do believe in showing up, pushing forward, and surrounding yourself with amazing people.

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