Healing the Heart. Rebuilding Life. Rediscovering the World.
Grief coaching and transformational travel experiences to help you grow from loss and reclaim your purpose—inside and out.
Growing From Grief Coaching
Grief doesn’t follow a timeline—and you don’t have to navigate it alone. Whether you're grieving a death, a divorce, or a life that didn’t go as planned,
Growing From Grief offers a structured, compassionate path forward. This program helps high-achieving women process pain, release regret, and gently rebuild their lives with clarity, confidence, and meaning.
Through guided reflection, weekly support, and real emotional tools, you’ll move from surviving to living fully again—with purpose and peace.
Enneagram Coaching
You’re self-aware, but still getting stuck in the same patterns—overgiving, overthinking, or second-guessing yourself.
Enneagram Coaching helps you understand the deep inner drivers behind your thoughts, reactions, and relationships.
Using this powerful personality framework, we’ll uncover your core motivations and map out what growth looks like for your unique type.
Whether you’re seeking better communication, self-leadership, or healthier boundaries, this insight-based coaching helps you live, lead, and love with authenticity.
Coaching For Growth
You're accomplished—but secretly feeling off track, overwhelmed, or burned out. Growth Coaching is for women ready to reconnect with who they are beneath the roles, titles, and to-do lists. Using evidence-based Co-Active coaching tools and values-led leadership strategies, I help you clarify what matters most, set aligned goals, and make empowered decisions. Whether you're navigating a life pivot, leadership challenge, or identity shift, this is your space to grow with intention—and create a life that fits the
real you
.
Not sure which coaching path is right for you?
Whether you're processing grief, exploring personal growth,
or want to better understand yourself through the Enneagram—
I’m here to help you decide what fits best. Let’s talk through it together in a free clarity call.
Travel That Transforms You
Sometimes the most powerful healing happens when we step away from the familiar. Through Delivering Dreams Travel, I design soulful getaways, wellness retreats, and custom travel experiences that nurture growth, connection, and renewal. Whether you're craving rest, adventure, or a fresh perspective, these journeys are crafted to inspire your next chapter—mind, body, and soul.
About Jennifer
I’m Jennifer Waugh—Certified Professional Co-Active Coach, Grief Recovery Specialist, and founder of Delivering Dreams Travel. I help high-achieving women heal from loss, rediscover their purpose, and live with intention. Whether through coaching or curated travel, my mission is to guide you back to yourself—with clarity, compassion, and a deep belief that you’re not broken… you’re becoming.
Client Love
"Working with Jennifer helped me reconnect with who I am and what matters most. Her coaching gave me the structure I needed and the compassion I didn’t know I was missing. I left each session feeling clearer, stronger, and more confident in my next steps—personally and professionally."
Healthcare Leader
"Jennifer created a space where I could be honest, feel deeply, and finally move forward. Through her guidance, I was able to process my grief, find meaning again, and make decisions that truly reflect the woman I’m becoming. I’m so grateful for the transformation that’s come from this work."
Tech Executive & Mom
Why I Do This Work
I believe healing and transformation happen when we create space—space to feel, reflect, connect, and reimagine what’s possible.
Whether through deep 1:1 coaching conversations, the shared wisdom of group coaching, or intentional travel experiences, my mission is to help women grow through what they’ve gone through.
I guide you to reconnect with your true self, make empowered choices, and step into a life that aligns with who you are now.
This work is about more than moving forward—it’s about coming home to yourself.
My Core Values
Compassion
– Meeting every journey with empathy, gentleness, and grace
Clarity
– Creating space to uncover truth, intention, and aligned next steps
Courage
– Holding space for brave conversations and bold transformation
Connection
– Building deep relationships—with yourself, others, and the world
Wholeness
– Honoring every part of your story as part of your becoming