We’re excited to introduce you to the always interesting and insightful Eileen Rose Miles. We hope you’ll enjoy our conversation with Eileen Rose below.

Eileen Rose, appreciate you joining us today. Owning a business isn’t always glamorous and so most business owners we’ve connected with have shared that on tough days they sometimes wonder what it would have been like to have just had a regular job instead of all the responsibility of running a business. Have you ever felt that way?

I think happiness in our work isn’t just about feeling good all the time. It’s about fulfillment, reward, and enjoyment. And yet, there are times when I don’t feel happy at all. Instead, I feel overwhelmed, exhausted, and stretched beyond my limits. In those moments, I catch myself thinking:

“Maybe if I had a regular job—one where I could just clock out at the end of the day—I wouldn’t feel this way.”

It’s a tempting thought, especially on the hardest days. The days when putting myself out there feels like too much, when things don’t go as planned, or when self-doubt creeps in and whispers: ‘Wouldn’t it be easier to slip into something more predictable?’

One of those moments hit me hard recently. I made a big business decision to take my virtual Meditation Teacher Training and turn it into an in-person retreat experience. It felt like the right move—an expansion, a deepening of my work and the ability to connect IRL. But the reality was, I was in over my head. The timing, the logistics, the cost…it didn’t come together the way I had hoped. And ultimately, I had to cancel the experience.

The emotions that followed were heavy. Shame, embarrassment, and most of all, self-judgment. I questioned myself and my choices. Why did I take this risk? What if I had just stayed in my comfort zone?

But then, I remembered something I’ve learned through this journey: Nothing is a failure, it’s a redirection. Every risk, even the ones that don’t go as planned, are an opportunity to learn. And that’s what keeps me here. The ability to continuously grow and to explore limitless possibilities.

Still, the constant momentum can feel exhausting, and the idea of stepping back, of choosing the easier path, is tempting. But deep down, I know that I—we—are meant for more. And it’s that knowing, that quiet but persistent call toward something greater, that always brings me back.

Because then, there are the moments that make it all worth it like the message from someone who tells me my meditation was exactly what they needed, the student who finally feels confident enough to lead their own class, the reminder that the work I do has a real impact. Those moments outweigh the heavy, hard days every single time.

As a business owner, I get to choose when to step into the arena. I get to decide how I show up, what risks I take, and how I evolve. And yes, that kind of freedom comes with uncertainty. But it also comes with something even greater: the chance to build a life and a career that feels truly aligned.

So, am I happier as a business owner? Maybe happiness isn’t always the right measure. But am I more fulfilled? More challenged? More deeply connected to my purpose? Absolutely. And that’s why I stay.

Eileen Rose, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

My name is Eileen Rose Miles and I am an Intuitive Meditation Guide and Meditation Teacher Training Facilitator.

I started practicing yoga at 12 years old and continued throughout high school and college. In 2014, I took my first yoga teacher training, followed by another transformative yoga teacher training in 2018. But it wasn’t until 2020, when the world felt chaotic and uncertain, that I stepped into leading meditation. Like many, I was searching for something to anchor me. I joined the Insight Timer app and, with no formal background in audio production, taught myself how to record and edit meditations. It wasn’t pretty at first, haha! I stumbled my way through poor audio quality and awkward recordings but I kept going. Over time, I refined my skills, found my voice, and built a practice rooted in intuition and authenticity.

Now, with over 10,000 followers on Insight Timer, I help individuals find calm in their daily lives, guide corporate meditations and lead Meditation Teacher Trainings. My training isn’t just about learning how to guide meditations; it’s about becoming an intuitive leader and someone who can hold space with confidence, connect deeply with their students, and guide from the heart rather than relying on a script. I’ve now led five rounds of this training, watching students transform from hesitant beginners to skilled and empowered guides.

Since 2022, my husband, our dog Sadie, and I have been traveling full-time in our camper van, exploring 49 states (Hawaii, you’re on the list, but we can’t drive there!). From the road, I’ve grown my meditation business, proving that location doesn’t define success—intention and consistency do. My virtual Meditation Teacher Training runs twice a year, and I keep it small by only accepting 10 students at a time to ensure deep connection, support, and growth.

What sets my work apart is how intuitive it is. I don’t teach people how to recite scripts—I teach them how to trust themselves, to lead with presence over perfection and to cultivate an unshakable confidence in their ability to hold space for others. I believe meditation isn’t just something we do; it’s a way of being. And helping others step into that space as guides is one of the things I’m most proud of.

For anyone curious about meditation, guiding others, or simply deepening their own practice, my work is here to help you feel more confident, calm, and connected—both to yourself and to those you serve.

How did you build your audience on social media?

When I first started sharing my work on social media, I had to let go of obsessing over followers and views. Growth doesn’t come from chasing numbers. It comes from showing up consistently and authentically. Instead of trying to align with the algorithm, I focused on sharing content that truly reflected my voice, my values, and my mission.

If you’re a meditation guide looking to grow, the best platform isn’t necessarily Instagram—it’s Insight Timer. Unlike social media, where people are mindlessly scrolling, Insight Timer is a space where people come with the intention to pause, breathe, and meditate. It’s a powerful place to get discovered and make a real impact.

So my advice? Show up consistently, be yourself, and share content that resonates with you first. Engage with others, ask thoughtful questions, and prioritize building a strong sense of community. Growth will follow. And if you’re a meditation guide, get on Insight Timer—you won’t regret it.

Can you talk to us about how your side-hustle turned into something more.

After graduating from Oakland University with a degree in Exercise Science and Nutrition, I began my career as a fitness practitioner at a gym. During that time, I started leading meditation on the side, initially as a way to balance the physical aspect of fitness with the mental and emotional well-being that meditation offers. Meditation was always a personal passion of mine, but it wasn’t until I discovered Insight Timer that I realized it could become something more.

At first, it was just a way to share my practice with others, but as I grew my following on the app and began connecting with more people, I started to see the potential. As we embarked on full-time van life, I transitioned into part-time work with a mental health company. This allowed me the flexibility to continue expanding my meditation work. Slowly but surely, the income from leading meditations on Insight Timer began to grow, and I started gaining corporate meditation clients, as well as expanding into groups like teachers and other small communities.

One of the key milestones was when my Meditation Teacher Training program took off. This was a huge turning point because it gave me the opportunity to offer a more structured, high-impact service that allowed others to become confident, intuitive meditation guides. Over time, these different streams of income started to add up, and it became clear that my side hustle had evolved into my full-time business.

Today, my meditation work has fully replaced my part-time and fitness jobs, and I’m fortunate to be able to support myself and my family with a typical full-time salary through the meditation business I’ve built. The key was consistently showing up, finding the right platforms like Insight Timer and continually evolving my offerings to best serve my community.

Contact Info:

• Website: https://www.eileenrose.me
• Instagram: https://www.instagram.com/eileenrosemiles
• Linkedin: https://www.linkedin.com/in/eileen-miles-a86134bb/
• Other: https://insighttimer.com/eileenrosemiles
  https://www.eileenrose.me/meditation-teacher-training
  https://open.spotify.com/show/45Z3cMVyEYLroan0oWWAoD?si=7aaa4b403786440f

Image Credits

Nicole Rall Photography
Sydnee Rayl Photography