Personal Retreat

An intentional & customizable outdoor getaway.

Ready for a shift?

It’s time to disconnect from the noise and reconnect to something deeper within. This purpose-built men’s retreat balances fun and adventure with rest and reflection, all while being fully immersed in the great outdoors.

This is your chance to get away from the grind, find new inspiration, explore new habits, talk about your next idea or business venture, and take some intentional time to check in on the heart, soul and mind.

LOCATION:

Bend, OR

TRIP LENGTH:

2-3 days

STARTING AT:

$399

SEASONS:

All 4 seasons

Here’s the idea…

Join me for an approachable and transformational one-on-one men’s retreat here in the outdoor playground of the Pacific Northwest.

The goal is to help you reconnect with the part of your soul that longs for adventure, beauty, meaning, and connection.

Let’s go on a soul fueling

adventure.

What we’ll do:

Get off the grid and out of the grind for an outdoor experience customized to your interests. We’ll follow the sun, find some fun, and talk about the things that matter most.

Choose your style of adventure:

This personal retreat is personalized to your likings and curated by me for the best possible experience. I believe mood follows action, so we’ll get after it in someway or another. This can be an adrenaline pumping activity, or something more relaxing and peaceful, whatever is most helpful in connecting your mind to your body and boosting your mental health and wellness.

Action Sport Adventure

Push your limits with an action-packed trip that will get the blood pumping and keep the stoke level high. It can be introductory (noobs are my fav type of people!) or we can get extreme with your favorite sport/skill.

  • Summiting a peak, rock climbing, mountain biking, river wave surfing, paddling (kayak, SUP, raft), backcountry ski/snowboard, etc. are all on the table (although you may have to rent specialized gear out of pocket - see upgrades below). We’ll eat on the run and chase some fun in the sun.

    • Mtn Bike rental: $150

    • Ski lift ticket: $100 | Rental: $50

    • Moto adventure: $250

    • Private whitewater raft: $400

Nature Exploration

If you prefer a slightly slower pace (but still want to get after it) this style of trip is focused on being outside and actively exploring nature. Whether that’s fishing, hunting, paddling, hiking, climbing, or e-biking out in nature.

  • This could include things like an e-bike ride in the mountains, a waterfall hike, a tour of some local natural wonders (lava caves, mountain peaks, waterways, canyons, etc.), nature photography, finding some beautiful views, or even doing a tasting tour of some local grub & grog. We will still do some unique outdoor activities, but it will be less physical and at a calmer pace than the action sport option.

    • Scenic chair lift ride: $50

    • Fishing gear & license: $100

    • Small game hunting license: $50 - $100

Relax & Recharge

This is the most low-key option, but still one my all-time favorite ways to retreat. Primarily focused on finding calm and clarity in nature in order to boost your mental health and wellness.

  • Whatever we do will be designed to increase your mental and physical wellness. We’ll have some fun and eat some great food, but the trip will be slow and steady and feel more like a quiet retreat to help you find more peace, quiet, and clarity in life.

    We’ll explore several different daily well-being practices to see what helps you most. Or if you already have practices you use, we can focus on using those throughout our day to optimize their benefits.

    • Turkish Bath: $50

    • Hotspring tipi ceremony: $300

No matter which style you choose…

It will be my absolute honor to help guide you on a personal retreat that is helpful, tasty and fun, while clearing out the mental clutter and reigniting the spark within. You’ll see who you are and where you’re going next with much more confidence and clarity.

We go outside to explore inside.

We’ll get clear on your commitments and help build momentum to tackle the obstacles ahead. We’ll challenge the body and find stillness for the mind. Most of all, you’ll get the encouragement and support needed to keep going.

You don’t need external advice, you need internal clarity.

  • Serial Entrepreneurs

  • New Entrepreneurs (my fav)

  • Creatives (my other fav)

  • Workaholics (me too)

  • Age: 30’s & 40’s (I’m 42)

  • Need some time outside

Who it’s for:

It’s for men who are searching for a change of pace and a shift in perspective - a jolt back to life by chasing fun, adventure, stillness, calm and clarity.

It’s for men looking for experiences that will challenge and inspire, but also bring a deep sense of renewal.

It’s for men who know that something’s gotta change for them to become a better version of themselves—one with more purpose, more depth, and more connection—and want to jumpstart that process.

The types of things we can see & do together:

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Practical Details:

General info:

  • I’ll take care of all the essentials (ground transportation, snacks, drinks, lodging, basic recreational gear, etc.) so all you guys have to do is say ‘yes!’ and get out here.

  • One-on-one is the goal, but sometimes having a buddy or business partner is more helpful (especially if we’re talking in depth about your business and higher level changes). For this reason we can add a couple more to this retreat.

  • This trip is completely customizable to your likings (and the weather/season). We can make it chill or get the adrenaline pumping. Either way we’ll check in on the mind, body and soul in intentional ways during our time together.

    We’ll talk about what it’s like being men in this modern world, what we’re committed to and how we’re showing up. We’ll look at work/life balance and our role in shaping whatever is coming next in life.

    And we’ll explore a few bio-hacks to help boost our mental health and wellness (think breathwork, cold plunges, hot soaks, wolf walk, etc) - of which, they are all optional, but encouraged.

  • What’s included:

    • I’ll take care of all creature comforts, but do be prepared to rough it.

    • Lodging, meals and snacks, beverages, local transportation, basic outdoor gear for excursions (SUPs, river surf boards, hardtail mtn bike, e-bikes, etc), conversations that matter, and daily well being practices.

    What’s not included:

    • Travel to/from Bend, Oregon (Fly into RDM, or drive). We’ll figure out the best travel plan (fly or drive) together.

    • If we end up needing specific higher-end recreation gear (downhill mtn bikes, backcountry ski setup, white water raft rental, fishing license, etc), you’ll have to get such items out of pocket.

  • Together, we’ll figure out the best travel plan (fly or drive) to get you to Central Oregon. Airport code: RDM

Days/Dates:

This is typically a 3 day, 2 night experience that you can book whenever is most convenient for you. These retreats are meant to be flexible with your work/home schedule (even if you only have a 48hr window away), and they are customizable to whatever will fill you back up so that you come home recharged and ready to tackle what’s next.

I have three options for which days of the week to choose from:

  • SUNDAY - TUESDAY

  • TUESDAY-THURSDAY

  • FRIDAY - SUNDAY (weekend rate: add $250)

Itenerary:

  • We’ll meet in Central Oregon and it will be my pleasure to show you around this gem of an area.

    If you can arrive earlier in the day we’ll do a quick biking & snacking tour through my tasty town. Then we’ll head out into the forest to find a wild (dispersed) campsite. We’ll have all the gear we’ll need for the coming days packed in the truck. It’s time for a proper overland adventure into the wild!

    Welcome Dinner: Tacos, salad, chips & salsa, cerveza.

    Evening hang: Sunset fire at our first campsite, s’mores, cigars, and we’ll do a powerful exercise centered around your story thus far. And we’ll talk openly about where your story might be heading next.

  • We’ll take in the sunrise from a mountain peak, a hotspring, or out on the water with coffee in hand. Followed by a hearty breakfast while we prepare for our first big outing - likely something fast paced and fun.

    After a proper morning adventure, we’ll share a charcuterie styled lunch somewhere magical and with stunning views. Where we’ll talk about what’s getting in your way at work and at home.

    We’ll spend the rest of the day chasing fun in the sun, doing some target practicing or skeet shooting, and we’ll be sure to include some quiet times of reflection throughout the day as we discuss and process what changes are needed for your next big move in life.

    We’ll find our next campsite before dinner time, then we’ll get to work on a delicious meal (Elk Burgers) while we attempt to light a warming fire by hand with a bow drill.

    We’ll catch the sunset from a mountain peak or out on the the water and we’ll wind down with a fire back at camp while we continue our discussions before we head out on a headlamp night adventure that will test our grit.

  • A relaxing morning with coffee and breakfast at camp before we find a quiet place in nature to reflect and create a list of actionable items so that you know exactly what changes to make when you return.

    You’ll feel equipped and ready for your next big move.

    If time allows we’ll go on midday adventure (with lunch on the run), and then we are officially done.

    Airport shuttle run or drive time for you to head back home.

    *Although I do my very best to adhere to the schedule above, the itinerary is subject to change for numerous reasons beyond my control, including weather and terrain conditions.

Investment:

I’ve made it my goal to offer approachable and affordable trips that work best with your hectic schedule. We’ll start in beautiful Bend, Oregon and explore all that the area has to offer. You get 3 days of adventure, authentic connection and tons of fun. Upgrades are available if you want to ‘send it’ on a particular activity or type of accomidation, but even the base price below and what it offers will be an incredible experience.

*Price is per person. Pay full amount to secure your date. This trip is non-refundable, but fully transferable to another date or person.

Personal Retreat in Bend, Oregon:

$399 per person

Accommodations explained:

Depending on the season and the activities, we got options.

Experience the great outdoors in comfort and style. We’ll have the basic creature comforts covered, but be prepared to rough it to some extent. Rain, sleet, snow or shine we’ll be out there! Accommodation options include a rooftop tent, hammock, backpacking tent or inside the adventure trailer. You can even upgrade to a Tipi with your own personal hotspring nearby. Point being, together we’ll create an uncommon and amazing experience for you.

Warmer weather options:

  • The off-road capable Adventure Trailer

  • Tent camping or backpacking

  • Rooftop tent on the 4x4

  • Waterfront hammock camping via SUP (standup paddle board)

  • The off-road capable Adventure Trailer

  • Tipi Hotspring package (Upgrade: $300.00)

For colder season adventures, we’ll camp out on my property and take shelter at ‘Out There Headquarters’ (my outfitter & supply shop) - which has a wood fired stove, gear and games, mini-bar, outdoor kitchen, bonfire pit, camping spots, and has many sleeping arrangements.

I’ve been hard at work customizing this space for optimum hang-time with the guys. It’s where we gear up for excursions and unwind after a long day of getting after it.

Colder weather options:

Everything you change changes you.

Book your personal retreat.

Use the form to sign up for your customizable retreat here in Central Oregon. I only offer a couple of these per month. First come, first served.

Next steps:
After you fill out the form, we’ll schedule a call/Zoom to kick things off. We’ll finalize pricing and all those kinds of details depending on the activities and who’s coming. You’ll get a detailed packing list, liability waiver and final payment info later in the process.

What other men are saying:

“Talk about a life tonic for the soul. I’ve lived better because of my time with Gary. Forever grateful.”

— Anders Lindwall

“That was the most helpful retreat! Space to breath. Room to ponder. Opportunities to deep dive in meaningful conversations about work & life.”

— Mike Caston