Meet Annie Sim

Alright – so today we’ve got the honor of introducing you to Annie Sim. We think you’ll enjoy our conversation, we’ve shared it below.

Annie , we’re thrilled to have you on our platform and we think there is so much folks can learn from you and your story. Something that matters deeply to us is living a life and leading a career filled with purpose and so let’s start by chatting about how you found your purpose.

As a child, I was always confused by the question, “What do you want to be when you grow up?” It sounded so daunting and finite…and…it was. How was I supposed to know at 5 years old where my life would take me and what passions would develop over the next few decades? And then whether those passions would persist for decades to come.

Throughout my childhood, I was confident that ‘doing the next thing well’ would put me on a trajectory. Get good grades, to get into good classes, to get into college, to excel in your class, etc. Then it hit me like a brick wall at graduation that I had no clue what I wanted to do next.

I stumbled through odd jobs (restaurants, manufacturing facilities), passion pursuits (a road trip funded by a grant for college students, an internship with a local TV station), and mini-careers (telecom and project management). I attended a career workshop and the speaker shared some wild statistics about fear being the biggest inhibitor of career progression. Fear of looking stupid, of being embarrassed, of not making progress. So much of the reasoning had to do with ego and external factors. At that juncture, I vowed to take time to find what made me overcome my fears – what lit me on fire and made me want to bring value to the world.

From that point forward, I quit my job and spent 6 months traveling the world, and ultimately it led me to a career in travel, connecting people, communities, and cultures around the world.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

At The Table Less Traveled, we’re all about bringing people and communities together through unforgettable travel experiences. Imagine going on a small group trip with like-minded travelers and there is one seasoned traveler who has extensive knowledge about your destination, has planned the entire trip, is there to handle all the trip logistics, and on top of that is introducing you to their friends in that destination and getting you access to experiences you wouldn’t find on your own. This style of travel frees you up to be fully present for every moment of your trip.

Our trips were recently named “fab for foodies” by The Boston Globe and it’s not the first time we’ve been voted the best foodie tours. Sharing a meal is one of the best ways to connect with people, their stories, and their culture. This is why we weave so many culinary experiences into our trips from cooking classes and market visits to tastings and in-home dinners.

Even though we’ve been doing this for over 10 years, each day still feels like a new adventure. We’re super excited about adding three new destinations in 2025—Portugal, France, and the UK—to our lineup of amazing shared journeys. And to top it all off, we’ve recently acquired Savor Seattle Food Tours, a local (to Annie) gem that shows off the best of Pike Place Market’s food scene. It’s all part of our mission to help travelers make genuine connections wherever they go.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

– Resilience: No matter what you are trying to achieve, having resilience allows you the patience to see things through in the good times and the bad. The bad times will get bad – you will be stressed, and making the discomfort go away can be somebody’s primary goal. However, having long-term vision and the determination to keep on keeping on allows for greater success in the long run.

– Passion: Even on the toughest of days, I reflect on WHY. Why am I doing this? Why does it matter? Why do we want to create what we’re building? Passion for WHY is the foundation that keeps us going even when things are difficult. I encourage people to find their passions and pursue where they are most grounded in ‘why’.

– Integrity: A cornerstone of success is following through on the things you say you will do. In my experience, the network we’ve built and the relationships we have are the most valuable thing about our business. They are also what make us most human. Honoring our promises is a critical piece to the consistency that our partners, vendors, and clients come to expect from us. It’s part of what makes us who we are, and why people can rely on us. It’s part of what then gives us the passion to continue bringing value to our community.

What was the most impactful thing your parents did for you?

The most impactful thing my parents did for me was give me unconditional love. Did I disappoint them? Yes. Did I make bad choices? Yes. Did I make good choices, but ones they didn’t agree with? Yes.

At the end of the day, whether they agreed with me or not, I knew they still loved me. And as an adult, I think this built a quality of self-esteem and resilience that allowed me to dream big and step outside my comfort zone. I knew that taking risks was never going to damage the thing that was most important to me – my family foundation and love from my parents.

I recognize that it’s a quality that we (as children) are not privileged to pick and choose from our parents. I’ve had many close friends, partners, etc. that have not had the same experience I had. And the common thread throughout was less a focus on what could have been done better by their parents, but more an emphasis on learning and where they’d like to do better for generations ahead.

Luck gave me parents that showed me love. And hopefully that luck gives inspiration to others to continue on for their children.

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