When you think of a retreat, do you picture total silence, mushrooms, and a few awkward spiritual exercises?
Yeah… this is not that.

We are entrepreneurs and creators ourselves. We know what it feels like to have a thing you are building or dreaming about. A business idea, a creative project, or a side hustle that matters to you. We also know how easy it is to lose momentum, get stuck, or push your own dreams to the bottom of the list.

We created Waypoint for entrepreneurs, aspiring entrepreneurs, creators, and dreamers who are craving a pause from the noise. A chance to step out of the daily grind and into something more intentional, focused, and meaningful.

This retreat is for people who are tired of surface-level business advice and endless hustle culture. You want more than marketing tips. You want clarity about what you are building, why it matters, and how to keep moving forward without burning out.

You will connect with like-minded entrepreneurs, creatives, and visionaries. You will get space to think, reset, and create a plan to bring your next step to life. You will leave with clarity, confidence, and a renewed sense of purpose. 

Expect a small, supportive group of people who are in the arena with you:

• Entrepreneurs building bold, purpose-driven ventures
   
• Professionals with a business or creative idea they can’t stop thinking about
   
• Side hustlers bringing a passion project to life for purpose, joy, or extra income
   
• Creatives and visionaries looking for clarity, connection, and momentum

Whether you’ve already launched or are still working out your next move, you’ll be in good company at Waypoint.

We’ll gather at Whispering Springs, a luxury glamping oasis in Grafton, Ontario. Think cozy tents, heated blankets, forest trails, and beautiful grounds. The pictures say it all! It’s rustic in all the right ways, while still wildly comfortable.

You’ll be nourished by Hawley Crescent Catering, a Feast-On™ certified culinary team serving flexitarian, locally-sourced meals that fuel your body and creativity.

We love campfires. We love great food. We love real, unfiltered conversations with real people about things that actually matter.

So if you're ready to step out of autopilot and reconnect with your vision, Waypoint might be exactly what you didn’t know you needed.

Most retreats end the moment you pack your bags and head home. But we believe the real growth happens after you leave. That is why we include three months of post-retreat support to keep the momentum going.

You will stay connected with your retreat group via our Vienna Waits Slack environment, get ongoing encouragement, and have the accountability you need to keep moving forward on your goals. Whether you are refining your business, launching a new idea, or making space for your next big step, we are here to help you turn clarity into real progress.

A "waypoint" is a marker on a journey. It is a place to pause, recalibrate, and make sure you are still heading toward what you really want. That is what this retreat is: a purposeful stop along your business or creative path. A place to breathe, reflect, and choose what comes next...with intention.

Please review our full cancellation policy HERE. 

Please plan to arrive at Whispering Springs by 1:00 PM.

We’ll kick things off with a relaxed welcome and light icebreaker to get to know one another and ease into the experience. You’ll settle into your accommodations and have time to slow down and step away from the noise of daily life.

We’ll then gather for a guided walking tour of the grounds, led by the creators of Whispering Springs. You’ll hear the story behind this intentional space and get a deeper sense of the environment that will hold us over the next few days.

Day 1 is all about Pause.

This is your opportunity to step back, reset, and create space for what actually matters. Whether that’s connecting with others, enjoying the cedar sauna or saltwater pool, playing lawn games, or taking a quiet walk through the forest trails, this time is yours.

We’ll come together for a welcome reception and dinner in the Main Pavilion, followed by an optional (but highly encouraged) campfire under the stars.

Start your morning your way. Join a forest walk, a restorative yoga session, or a group trail run. Or take the time to relax, reflect, and enjoy the space before breakfast.

From there, we move into Prioritize.

This is where things start to sharpen. You’ll begin turning your thinking into clear direction, with guided sessions and practical exercises designed to help you focus on what matters most.

We’ll build in space throughout the day to step back, process, and think. Time to grab a coffee, get outside, or let ideas settle before moving forward.

A fresh, nourishing lunch will be served.

In the afternoon, we'll gather for a session with Jim Moss. Through stories and practical insights, Jim will explore how trust, care, and community can become your greatest edge as a leader, entrepreneur, and human.

The rest of the afternoon is yours. You can continue working through your ideas, recharge, or take advantage of optional one-on-one support and coaching.

In the evening, we’ll come back together for an elevated, seated dinner experience featuring Intentional Dining with Dana Shortt (one of her new workshops)!

We’ll close the day with s’mores, music, and meaningful connection around the campfire.

We’ll begin the final day with a morning session over breakfast, focused on Pursue.

This is where everything comes together. You’ll take what you’ve uncovered and turn it into clear, intentional next steps. Not ideas, but a plan you can actually move forward with, whether you’re building a business, launching a project, or stepping into something new.

We’ll create space for reflection, meaningful conversation, and a sense of closure so you leave grounded in what comes next.

You’ll head out with a packed lunch, new connections, and the clarity and momentum to keep going.