Today we’d like to introduce you to Staacy Cannon.
Hi Staacy, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
In my twenties, my life was centered around wellness and mindfulness. I immersed myself in teaching yoga and leading retreats, sharing the joy of these practices with others. The serene, balanced life I led then took a sharp turn as I entered my thirties and was introduced to the exhilarating world of startups. I quickly became hooked on the thrill of the fast-paced, dynamic environment. But life had its challenges in store for me. A difficult divorce left me a single mom, and the pain of navigating a custody battle drove me to immerse myself even deeper into work. I founded a technology startup, inventing a cutting-edge system that used computer vision and AI to gauge consumer emotions in response to advertisements. Despite the eventual closure of the startup, I didn’t slow down. I plunged into executive leadership roles, including serving as president of an airline startup, always solving other people’s problems, avoiding my own heartache.
My relentless pace took a toll on me, and I became the stereotypical A-type personality, running on fumes, barely sleeping four hours a night. Deep down, I knew this wasn’t sustainable. My quality of life was abysmal, and I yearned for something better. In late 2019, I took a pivotal trip to Hawaii’s Big Island. For the first time in over 13 years, I allowed myself to rest. I worked with a local Hawaiian healer who helped me confront the immense damage my lifestyle had inflicted on my mind, body, and spirit. This healing journey reawakened my longing to lead retreats and share the peace and joy I once knew.
When I returned home, I made a bold decision. I left my secure job as head of growth just before the COVID-19 pandemic hit. I embraced consulting, with a promise to myself: I would only work with companies that aligned with my core values of freedom, truth, joy, and quality time. In 2020, I bought my first home as a single mom in Cardiff by the Sea. During the renovations, I spent time on the North Shore of Oahu, where I reconnected with myself and my Divine feminine energy. This period of self-discovery reinforced my calling to return to the retreat space.
Having spent years healing myself, I realized my purpose: to support high-achieving women in breaking free from destructive habits. Women who overwork to prove themselves, people-please to stay on top, and neglect self-care in their relentless pursuit of success. This led to the birth of Laia Retreats.
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?
Starting another business has definitely been triggering in some ways, yet despite the challenges, building Laia Retreats has been incredibly enjoyable. When I decided to embark on this new venture, I set a clear intention: to build it slowly and sustainably while ensuring my core values of freedom, truth, joy, and quality time are always at the forefront.
The road isn’t always easy. The echoes of past experiences and the fear of falling into old patterns of overworking and neglecting self-care often loom in the background. There are moments of doubt, like when it seems like a retreat won’t fill up. Each step forward requires a careful dance between ambition and self-compassion, constantly reminding myself of the lessons learned from my time healing in Hawaii and the memory of how I used to live—as an overworked people pleaser with a perfectionist mentality, completely disconnected from my truth.
One of the toughest struggles is resisting the urge to say yes to consulting clients when the phones for Laia are quiet. But I’m committed to staying true to my intention. I embrace a pace that allows for deep, meaningful progress without sacrificing my well-being, my time with my family, or the quality of my work. Like with all new businesses, there are uncertainties and moments when the future seems precarious, but these challenges only strengthen my resolve to stay aligned with my values.
Even in the midst of struggles, there are profound moments of clarity and triumph. Building Laia with intention has allowed me to create a business that not only thrives but also enriches my life and the lives of those I work with- this to me is gold! Each challenge overcome and each small victory celebrated has reinforced the belief that a smooth road isn’t about the absence of obstacles but about navigating them with grace and determination. This journey is a testament to the power of aligning one’s work with one’s deepest values and purpose, and it has me eager to watch Laia’s story continue to unfold.
As you know, we’re big fans of Laia Retreats. For our readers who might not be as familiar what can you tell them about the brand?
At Laia Retreats, we specialize in providing transformational experiences specifically designed for high-achieving women like startup founders and corporate executives. Our retreats are meticulously curated to offer a haven where women can rest, reconnect with themselves, and rediscover joy through exploration and play.
What sets Laia Retreats apart is our deep understanding of the unique challenges faced by successful founders, C-suite executives, and those still climbing the ladder. These incredible women often find themselves trapped in a cycle of overworking, people-pleasing, and striving for perfection, leaving them exhausted physically, mentally, and spiritually. Our retreats are a sanctuary where they can break free from these patterns and experience profound personal transformation.
Held at our breathtaking oceanfront property on the North Shore of Oahu, our retreats combine daily wellness practices such as yoga, meditation, and breathwork with cultural activities like hula dancing and lei making. These activities are designed to help primarily midlife women reconnect with their bodies, quiet their minds, and find inner peace. Additionally, we offer playful and adventurous experiences such as surfing, sailing, snorkeling, and dancing, allowing our guests to rediscover the joy and lightness that comes from true play.
Laia Retreats is proud to provide a unique environment where women can let go of their daily stresses and immerse themselves in a supportive community of like-hearted individuals. Our guests leave with a renewed sense of self, a deeper connection to their intuition, and practical tools to maintain balance and joy in their everyday lives.
One of the things we are most proud of is the tangible transformation our guests experience. Women who attend our retreats often report feeling more creative, connected, and joyful. They rediscover their collaborative spirit, improve their relationships with their partners and children, and return to their professional lives with a renewed sense of purpose, and clarity.
We’d be interested to hear your thoughts on luck and what role, if any, you feel it’s played for you?
Luck, to me, is a construct that often follows hard work, intention, and perseverance. In my journey, especially in building Laia Retreats, what some might call “luck” has been the product of relentless dedication and a commitment to my core values.
Take, for instance, my time in Hawaii. Some might say it was sheer luck that I found a local Hawaiian healer who helped me confront the toll my relentless pace had taken on my mind, body, and spirit. However, it wasn’t just luck—it was a culmination of years of pushing myself to the brink, realizing the need for change, and then being open to the healing process. The intention I set to reconnect with myself and heal was the real catalyst.
Similarly, the decision to leave my secure job and start Laia Retreats wasn’t a leap of faith born out of luck. It was a calculated decision made after deep introspection and a desire to create a life and business that aligned with my values. The journey hasn’t been without its challenges but every step forward has been driven by perseverance and a clear intention to build something meaningful and sustainable.
Even the successes that Laia Retreats has experienced, such as filling our retreats and seeing the transformative impact on our attendees, are not just strokes of luck. They are the result of meticulous planning, understanding the needs of high-achieving women, and creating a space that truly addresses their struggles and desires. It’s about offering real solutions, from rest and play to deep personal transformation, that come from a place of genuine understanding and care.
In essence, what might appear as good luck in my life and business is really the outcome of persistent effort, clear intentions, and an unwavering commitment to my values. Luck is just the byproduct of creating opportunities through hard work and being prepared to seize them when they arise.
Pricing:
- $2999-$5999
Contact Info:
- Website: https://laiaretreats.com/
- Instagram: @laia_retreats

Image Credits
Evan Campbell Jorge Moya
