There aren't many opportunities in life to step away from the day-to-day and give yourself the space to think INTENTIONALLY about where you are, where you're going, and what actually matters to you.

That's why we created Waypoint.

Now heading into our third year, Waypoint brings together entrepreneurs, aspiring entrepreneurs, creators and thoughtful people who are building something, changing something, figuring something out, or simply asking themselves what comes next.

For three days, we step away from the noise and into a beautiful setting with really good people.

We talk about life, work and life's work. We make room for the conversations that don't always fit into everyday life. We ask better questions. We share what we've learned. We challenge each other, support each other and spend some time figuring out what we want more of, what we might need to let go of, and what deserves our attention next.

We won't give you the answers.

But we will give you the space to find your own.

One of the most meaningful parts of Waypoint is the people in the room.

We intentionally bring together people from different backgrounds, industries, stages of business and seasons of life. People who are willing to be generous with their experiences, their questions, their encouragement and their friendship.

There are facilitated sessions and exercises, but some of the most important moments happen around the dinner table, on a walk, sitting by the fire, or in a conversation with someone you didn't know a few days earlier.

There is space to think. Space to talk. Space to laugh, rest, connect and be challenged.

And there is a lot of care in the details, from the people we invite and the experiences we create to the food, accommodations and beautiful setting where it all happens.

You may arrive with a specific goal or a big decision in front of you. You may feel stuck. You may be in the middle of a transition. Or you may simply know that you've been moving fast for a long time and could use some space to consider what's next.

You don't need to have it all figured out before you come.

That's kind of the point.

Waypoint is a chance to step away, surround yourself with thoughtful people, have authentic conversations and come home with a clearer sense of where you are and where you want to go next.

One of the best parts of Waypoint is the people you'll meet.

We intentionally keep the group small and bring together thoughtful, curious people from different backgrounds, industries and seasons of life.

You'll meet:

• Entrepreneurs building and growing businesses they care deeply about

• Aspiring entrepreneurs figuring out what they want to create next

• Professionals navigating a change, transition or big decision

• Creatives and big thinkers bringing ideas and projects to life

• People asking some of the same questions you are about work, life, purpose and what comes next

Some will arrive with a clear goal. Others will be figuring out their next move. Some will have decades of experience to share, while others are just getting started.

What they have in common is a willingness to show up, be real, share generously and support the people around them.

You won't just leave Waypoint with new connections. You'll leave with people in your corner.

Waypoint takes place at Whispering Springs, a beautiful glamping retreat tucked into the forest in Grafton, Ontario.

For three days, you get to step away from your usual routines and surroundings. You'll stay in comfortable safari tents, eat really good food, spend time outside, gather around the fire and have plenty of space to slow down and think.

There will be thoughtful sessions and conversations, but Waypoint isn't about filling every minute of your day.

Some of the best moments happen in between. Over dinner. On a walk through the woods. Sitting around the fire. Doing yoga in the forest. Laughing with someone you met the day before. Or finding a quiet spot and having absolutely nowhere else you need to be.

It's a beautiful place to spend a few days.

And an even better place to figure out what you want to take home with you.

The few days we spend together at Waypoint are just the beginning.

As part of Waypoint, you'll automatically be enrolled in the October 2027 cohort of our UNBLOCK Yourself™ program.

If you leave the retreat with something you want to get after, a goal to move forward, an idea to bring to life, a decision to make or a change you've been putting off, UNBLOCK Yourself™ gives you the structure and accountability to keep moving.

You'll also stay connected to the Waypoint community through Slack, where the conversations, support and encouragement continue after we leave Whispering Springs.

And throughout the year, you'll have access to our Workshop Wednesdays. We cover a variety of topics related to life, work and everything in between, and often bring in guest speakers to share their expertise and perspectives.

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. 

More details to come!

More details to come!

More details to come!

More details to come!