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Exploring Life & Business with Ali Sullivan of Ali’s Happy Desk

Today we’d like to introduce you to Ali Sullivan

Hi Ali, thanks for joining us today. We’d love for you to start by introducing yourself.
After graduating in 2017 with a degree in psychology and sociology, I set off on what was supposed to be a 3-month trip to Europe—but here I am, eight years later, still traveling. I lived and worked in France as an ESL teacher, and when the pandemic hit, I found myself stuck there for an extra three months. During that time, I lost my job, my apartment, and the contracts I had lined up for the next two years. With the world shut down, I knew I had to pivot.

I started teaching ESL online and launched my own business, which has since grown into something I love. Now, I still teach ESL, but I’ve also become a travel writer and virtual assistant, working with creators, bloggers, hostels, and travel agents. It’s been an incredible journey, and I’ve been able to create a career that blends my passion for travel with helping others in the industry.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It definitely hasn’t been a smooth road. I didn’t have much of a background in business when I started, so I had to teach myself everything along the way. There were times when I was screwed over for thousands of dollars by unreliable clients, and I’ve come close to quitting more than once. But at the end of the day, freedom is what I’m after, and I know this path will give me the most freedom to travel and see the world.

Learning everything from scratch has actually been a blessing in disguise—I’ve gained so many skills that now allow me to help clients in more ways than one. But the reality is, the world isn’t designed for people like me. Things like taxes, insurance, and retirement are all set up for people with traditional jobs, and I’ve had to figure it all out on my own. It’s possible, but it definitely feels like the world makes it harder for those of us living unconventional lives.

We’ve been impressed with Ali’s Happy Desk , but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
My business, Ali’s Happy Desk, is my freelance venture where I work as a virtual assistant and travel writer, specializing in the travel niche. When I first started, my focus was broad, but writing, SEO, and marketing quickly became my strongest areas—so that’s the direction I pursued. Now, I work with several clients, including hostels in the U.S., travel agents, and content creators, handling the behind-the-scenes tasks that many find tedious but that I genuinely enjoy.
Beyond that, after years of teaching ESL, I’ve expanded my work with my teaching company, doing online writing and SEO for them as well. My goal is simple: to make other people’s lives easier and be the helping hand I wish I had when I was first starting out. What sets me apart is my firsthand experience in both travel and online business—I understand the industry inside and out, and I bring that knowledge to every project I take on. I’m especially proud of how much my business has grown and how I’ve been able to carve out a career that blends my love for travel, writing, and helping others.

Who else deserves credit in your story?
While Ali’s Happy Desk is something I built entirely on my own, I’ve definitely had support along the way. It took a few years for my family to come around to my unconventional lifestyle—honestly, I don’t think they fully understand it even now—but after eight years, they see how important and meaningful this is to me. Even when they don’t fully get it, they try to support me as much as they can, and I appreciate that.

Surprisingly, one of the biggest factors in my journey was the pandemic. As difficult as that time was, it ended up being a blessing in disguise. If it hadn’t happened, I don’t know if I would have had the courage or the push to start my own business. It forced me to take a leap, and I’m grateful for that.

Beyond Ali’s Happy Desk, I’ve also expanded into two other ventures: Ali’s Happy Adventure, my travel blog, and Ali’s Happy Office, my travel shop where I sell premade travel plans and itineraries. They’re still in the works, but I’m excited about where they’re headed.

Pricing:

  • $27/Hour or Packages Deals Avaliable (va)
  • $70/1000 words (writing)

Contact Info:

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