We caught up with the brilliant and insightful Sidney a few weeks ago and have shared our conversation below.

Alright, Sidney thanks for taking the time to share your stories and insights with us today. Being a business owner can be really hard sometimes. It’s rewarding, but most business owners we’ve spoken sometimes think about what it would have been like to have had a regular job instead. Have you ever wondered that yourself? Maybe you can talk to us about a time when you felt this way?

As a business owner, I wear a lot of hats — CEO, head of marketing and social media for both Instagram and TikTok, customer service, HR, and most importantly, lead travel agent. Being a business owner is a challenge, but it’s also one of the most rewarding decisions I’ve ever made.

I’ve officially been a business owner for two years and a travel agent for three. During this time, I didn’t abandon the security of a traditional 9-to-5 — I juggled both. I started out in Fairfax, Virginia, as a travel agent and outreach manager for a nonprofit. Then I moved back home to Detroit and started laying the foundation for my business while also working full-time in Detroit Public Schools. This past year I switched roles and began teaching 9th graders Orton-Gillingham literacy curriculum by day — and running my travel agency by night (and sometimes early mornings, weekends, and lunch breaks too).

Because I’ve done both — the business and the 9-to-5 — I don’t wonder what it would be like to choose just one. I know what it’s like. And let me tell you — it means late nights, long hours, and a constant balancing act between your professional life, personal life, and passion projects. Sometimes, it means delaying your true calling. Sometimes, it means burnout. Especially when you know you’re not in the right sector or living fully in your purpose.

So when I think about that question — “Do you ever wonder what it would be like to have a regular job?” — the last time I had that thought, I was probably sitting at my desk after a long day of teaching, knowing I still had travel clients to call, trips to book, and content to create before I could even think about sleep. That moment reminded me that while teaching is noble, it’s not my forever. My passion is in travel — curating experiences, exploring new places, and helping others do the same.

That’s why I’m proud to announce that I’m finally stepping into full-time entrepreneurship. Soon, I’ll be a full-time business owner — no side job, no backup plan. Just me and the dream I’ve been building for years.

I’m honestly happiest when I’m working solely on my business. There are no ceilings on my creativity. I can try a new strategy, bring on a new vacation vendor, or design a new trip experience without anyone telling me no. I’m the boss, and that means I get to let my imagination run wild — and that freedom allows me to help others discover the world, one adventure at a time.

Sidney, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

My name is Sidney Lynn Arrington-Ashford, and I’m the CEO and Founder of Arrington Adventures Travel Agency LLC.

My love for travel started during my sophomore year at the University of Michigan, when I studied abroad in Palestine. That was my first international flight — I had only been on a plane once before. I remember feeling every emotion: excitement, nervousness, curiosity. But when I arrived, it was breathtaking — more than I could’ve imagined. That experience led me to travel blogging, which became a way to reflect and share my journey in an educational and meaningful way.

In 2019, I graduated with a Bachelor of Arts in Political Science. After that, I lived abroad in London, researching gentrification and community systems in Brixton. Living in London made me feel alive in a way I had never felt before. I was fully immersed in the culture and pace of the city, and that experience solidified that travel wasn’t just a hobby — it was a lifestyle. It represented freedom, adventure, and exploration.

Fast forward to 2021, I moved to Virginia to work for a nonprofit. While I had once dreamed of that opportunity, I realized it wasn’t aligned with the life I truly wanted. So, I followed my heart and officially became a travel agent, launching Arrington Adventures on June 7, 2022.

My agency offers full-service travel planning: vacation consultations, payment management, itinerary and excursion creation, group coordination, booking services, and more. Whether you want a domestic trip, international getaway, hotel stay, cruise, Disney adventure, or all-inclusive resort, I handle everything — down to the smallest detail. I’ve even helped clients plan elopements in Vegas, milestone birthdays, honeymoons, and anniversary trips.

What sets me apart is that I’m not just a travel agent — I’m a certified, registered business owner in the state of Michigan, and I’m virtually with my clients every step of the way until they land safely back home. I take care of everything from the research and bookings to itinerary building and group logistics. My clients only have to worry about their bags and souvenirs.

So far, I’m proud to say I’ve successfully booked and coordinated 44 trips — and that’s not just 44 people. Some trips included up to nine travelers! My mission is to help others discover the world, one adventure at a time — and I can’t wait to see where we’ll go next.

How did you build your audience on social media?

Yes! I launched my Instagram about three months after starting my travel agency, and honestly, I was nervous. I knew how to run a personal Instagram, but not a business one. Still, I decided to make it fun, amp it up, and do a big launch and reveal of me becoming a travel agent. That moment helped set the tone — fun, vibrant, and real.

From there, I made sure to stay consistent and work on my brand. Knowing how you want things to look and feel is important. You can always grow and adapt, but you don’t want to be a chameleon all the time. Consistency builds trust with your followers — they should know what to expect from you.

I also just launched TikTok, and with the way the algorithm works, I try to post every single day. Even when I’m super tired, I pick anything travel-related, post it, and just do it anyway. My biggest advice? Post scared, post late — just post. Put yourself out there. You never know who’s watching or who needs what you’re offering.

What’s been the best source of new clients for you?

Word of mouth has been the best source of clients for me. I received an influx of clients, inquiries, and followers after I sent a trio friend group to Montego Bay, Jamaica, for their friend’s birthday. I knew the birthday girl from high school, but she was only my fourth client. After they safely returned home, she and her friends gave me an amazing review on Instagram, describing how I catered to their needs and captured every detail of how she wanted to spend her time in Jamaica — including extending the trip by an extra day.

That moment helped folks realize the benefit of having a travel agent. It showed them that my services were legit — not a scam — and that I was a real person who sent a group all the way from Detroit to Jamaica and back with care. I love when my clients review me or tell their friends and family. Word of mouth has grown Arrington Adventures tremendously, and I’m so appreciative of it. I truly hope folks keep talking and spreading the good news of having a travel agency with you from brainstorm to landing safely back home.

Contact Info:

• Website: https://arringtonadventures.org
• Instagram: https://www.instagram.com/arrington.adventures
• Other: Tiktok: https://www.tiktok.com/@arrington.adventures