Travel with Life: Say “Yes, And” to the Journey

Aug 17, 2025 | Entrepreneurship, General, Leadership, The Losses We Keep, Travel with Life

Some chapters announce themselves with a whisper, others arrive like a wave that knocks you off your feet. I’ve lived through both. Certain chapters of my story were not ones I ever imagined writing. I’ve lived through the heartbreak of four miscarriages. I’ve learned to make room for chronic pain. I carry a rare diagnosis—well-differentiated papillary peritoneal mesothelioma—without a predictable path forward. For a long time, I thought these realities closed doors I hoped to walk through. What I didn’t see then was that they were inviting me to respond differently. To evolve my dreams. Travel gave me the space to do that. It didn’t erase the hard things; it helped me breathe around them, reconnect with my people, and choose the next right step.

That choice is the heart of Travel with Life.

This post is a welcome and a guide. I’m sharing why Travel with Life exists, how my “yes, and” mindset informs it, the places that shaped me, and the services that bring this work to life—reset retreats, group retreat planning, personalized coaching, a community membership, and a podcast designed to support how we respond when life happens.

The “Yes, And” Mindset That Grounds Me

I grew up in a high school theatre program that took the craft seriously—on par with many community theatres in the Twin Cities. That experience trained me in collaboration, responsibility, and taking care of the details that make a show work. While I’m not established in improv, I understand its principles, especially “yes, and.” You acknowledge what’s true in the moment, and you add what keeps the story moving. If you want an approachable intro to improv, there’s a wonderful episode of Julie’s Greenroom on Netflix with Julie Andrews that explains it beautifully.

“Yes, and” is how I move through my days:

  • Yes, I live with uncertainty—and I can plan a weekend away that gives me clarity for the next step.
  • Yes, I carry grief—and I can choose experiences that help my family laugh together and feel connected again.
  • Yes, my energy ebbs and flows—and I can design rhythms, retreats, and trips that honor this while making room for wonder.
  • Yes, there are unknowns—and I can keep building community and creating experiences that put good into the world.

This mindset doesn’t ask us to ignore hard things. It invites us to acknowledge them and create forward motion with intention and care.

How Travel Keeps Me Connected, Grounded, and Growing

Travel weaves through my life as a practice. It supports my family during heavy seasons, helps me integrate what I’m learning, and gives me language for joy.

 

Walt Disney World: An Escape, a Reset, a Way to Remember Magic

 

I didn’t start out as a “Disney” person. I stumbled into it as a response to the trauma our family was living through. Walt Disney World became our shared escape from reality—a place where we could reconnect, step outside reality, and soak up the magic together. Over 30 trips later, those memories matter immensely. We love rope drop mornings that stretch into 16-hour park days, and we love night swimming at the resort (a real treat for Minnesotans!). We seek out the latest snacks, see our favorite shows, meet characters, make the most of Lightning Lanes, and visit our favorite restaurants. Those days remind us that joy lives here, too—and that we can choose it together.

 

France: Roots, Home Tables, and a Well of Ideas

 

France is my travel root system. My mother’s roots planted a launch pad for me—cultural and literal—that shaped my 20s and beyond. I’ve spent time in French homes, soaked up the rhythms of daily life, learned to cook, and integrated French culture into our Minnesota routines. The table matters there. Conversation matters. The pause matters. Those values seep into how I design travel, plan gatherings, and build community.

When I began shaping Travel with Life, I returned to France to work—and I lit up with ideas. I recorded videos, wrote drafts for this platform, visited friends in different cities, and switched between French and English at dinner tables where stories flowed. I explored cultural connections that bridge continents and asked how travel can support the way we respond to life. Those roots in France sparked an aliveness in me—clarity, creativity, and the conviction that this work needed to exist.

 

Learning to Slow Down—Even at the Beach

 

I love being on the go. Navigating medical hurdles and chronic pain challenged that part of me. I’ve been known to throw myself into work because building and serving energize me. When we decided to give our kids real beach experiences, I had to learn a new rhythm. The ocean asks for a different pace. Day one can feel restless. Day two softens the edges. Day three finally lets your shoulders drop. That learning changed how I plan: arrivals with margin, early nights, slow mornings, and enough space for the body to catch up to the heart.

 

From Vacations to Travel with Life

My entrepreneurial path began with Engage! Community Building for Nonprofits, where I partnered with associations and nonprofits on leadership, strategy, and meetings that build trust. That work taught me to listen well, hold space during transition, and design experiences that serve real people.

The dream of working in travel stayed with me for years. In late 2021, I found a coaching program and built Engage! Travel Co from the ground up. My goal: help people make their dream vacations happen. Today, I’m also growing a team of agents who share that mission. We plan Disney trips that balance magic with margin, craft European itineraries that weave culture and ease, and create getaways where couples and families reconnect.

As we served more clients, a pattern stood out. People wanted travel aligned to their season of life—grief, healing, new beginnings, big decisions—and they wanted support returning home with more than photos. Travel with Life grew from that insight. It brings together my community-building background, planning expertise, love for France and Disney, and lived experience with health challenges into a holistic way of designing travel that supports how we respond to life.

I also wrote a chapter in The Losses We Keep, which reflects my commitment to naming hard things and offering practical, compassionate tools. That work sits at the center of Travel with Life.

What Travel with Life Offers

Travel with Life is a philosophy and a set of services designed to help you create space, reconnect with what matters, and move forward with clarity. Each offering supports a “yes, and” approach—accept what your life holds, and add what helps.

Reset Retreats: Create Space to Begin Again

A reset retreat is not therapy, and it doesn’t replace business or transition coaching. It complements them. I draw on transition work, meeting planning, strategic facilitation, and travel skills to design the reset you need right now.

Here’s what makes it powerful:
  • It doesn’t erase the hard things you’re facing.
  • It fills the gap of how to get away, where to go, and what will actually fill YOUR tank.
  • We honor the differences between introverts and extroverts in our planning, solo time and together time, ocean air and city energy.
  • We choose a location and a rhythm that match your season—forest stillness, a beach with built-in margin, a Disney stay with downtime, or a France itinerary that feeds your senses.

You leave with language for what’s next, clarity you can trust, and a plan to carry it home.

Group Retreat and Meeting Planning: Gather with Purpose

I bring years of association and nonprofit experience to design gatherings that foster trust, connection, and results. We start with purpose. Then we choose a place and craft an outline that serves that purpose.

Ways we work together:
  • Leadership team retreats that turn alignment into action
  • Community experiences where people feel seen, supported, and energized
  • Entrepreneur cohorts that blend strategy sessions with restorative downtime

Most often this is meeting planning services (location selection, logistics, registration, etc) and clients often have speakers or a draft agenda from which we will work.

Personalized Coaching: Design Travel That Fits Your Life

Sometimes you want a guide who listens and helps you build a travel-based plan that fits your energy, time, and budget. In coaching, we:

  • Clarify what would truly support you, right now
  • Select destinations and experiences that align with your season
  • Design a solo reset blueprint, a Europe exploration itinerary with art and café time, a writing retreat, or a series of micro-getaways that nurture you throughout the year
  • Integrate the gains so the benefits last after you return

You get a plan you can actually live—not a wishlist that gathers dust.

Travel with Life Community Membership: Beyond Cold Crowdsourcing

This community isn’t another crowd-sourcing or a space driven by AI-generated responses forum where you toss a question into the void and sift through conflicting opinions. It’s a space shaped by shared values and guided connection—where stories, strategies, and support flow in context.

The Travel with Life Community is an invitation to join real people integrating travel with the ever-changing seasons of their lives. Beyond once a year big grand vacations, and full digital nomad lifestyle. We will learn about using points and miles with travel – and also not restrict to *only using that as a tool.

Here, we move beyond surface-level recommendations to dig into the “why” of your travel dreams and intentions—whether you’re navigating a life transition, seeking joy after loss, or looking to find adventure after a long season of routine, you want to bring more types of travel into your family life, etc.

What makes this community different:
  • Conversations that start with your season of life and work toward solutions that fit you
  • Space for honest conversations about what you’re truly seeking—not just where to go, but why it matters right now
  • Discovery of new types of travel you may not have tried, from restorative retreats to community-led journeys to solo micro-adventures
  • A trusted circle where you can ask nuanced questions and receive thoughtful, human answers
  • Opportunities to connect with people who value travel as a practice for connection, reflection, and growth
  • Support that addresses both logistics and heart: we talk about schedules and budgets – we also share ways to infuse daily life with small joys and “yes, and” moments

The Travel with Life Podcast: When Life Happens, How Do We Respond?

The podcast is a companion for navigating life’s challenges and transitions through the lens of travel and beyond. Inspired by the Travel with Life philosophy, episodes explore how we respond when “life” happens—how we create space to reset, how we find clarity and purpose, and how we carry both the hard and the hopeful.

What you’ll hear:
  • Stories from people who use travel to navigate change and find connection
  • Practical ways to integrate travel into real life, regardless of budget or schedule
  • Conversations about grief, resilience of spirit, and joy in small moments
  • Journeys that happen without a suitcase—inner work that shapes how we show up
  • Entrepreneurial stories rooted in service and purpose

It’s about the messy, beautiful paths we walk—and the tools that help us keep going.

How It Comes Together

My consulting background taught me to design for people, not checklists. My years planning meetings and retreats gave me the structure to turn purpose into plans. Building Engage! Travel Co sharpened my ability to translate dreams into journeys that work in real life. Time in France and Disney refueled my creativity, joy, and sense of story. And my direct work with mesothelioma patients—a cancer that is devastating—reminds me every day to make the most of our time here. I carry many friends’ stories in my heart. Their courage and love push me to show up fully, to create spaces where people feel held, and to help others claim moments that matter now.

Travel with Life brings it all together. We center your story and your season. We use place and pacing as tools for connection and clarity. We keep “yes, and” at the heart of every decision—acknowledge what is true, and add what helps you move forward.

Next Steps: Let’s Travel with Life

If you’re at a crossroads, if stress sits close to the surface, if you want to reconnect with yourself or your people, I’m here.

  • Explore a reset retreat. We’ll design a plan that fits your energy and your season.
  • Plan a purpose-filled group gathering. We’ll shape a space where connection can do its work.
  • Work with me one-on-one to design travel that supports your life right now.
  • Join the community for warm, thoughtful connection that goes far beyond cold crowdsourcing.
  • Listen to the podcast for stories, tools, and conversations that keep you moving.

My first business—Engage! Community Building for Nonprofits—taught me how to hold space. Engage! Travel Co taught me how to turn dreams into journeys, and I’m growing a team of agents who share that mission. Travel with Life integrates it all so you can create room to breathe, reconnect, and step forward with clarity.

Yes, life holds unknowns—and you can shape the next right step.

Yes, your story includes loss—and it also includes love, wisdom, and joy.

Yes, the journey keeps changing—and we can choose how we travel through it.

Let’s say “yes, and” to what’s here—and design the next scene together.

Let’s connect about projects and speaking engagements. I would love to be invited on your podcast!

Email me: katie@katiejamieson.com

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