The Lifestyle-First Business Model Retreat
A 3-day intimate retreat for established business owners ready to redesign your business model around your actual life, capacity and goals.
October 5-8, 2026 • Ladysmith, BC Canada
October 5-8, 2026
Stop Choosing Between Your Business Goals and Your Life
You're an established business owner and you're great at what you do. But you can't shake the feeling that you're never quite getting it right.
Everything just feels harder than it should. The leads are hard to generate. The messaging feels muddy. The sales feel like luck instead of a system. You're bouncing between client delivery, content creation and DM conversations … never feeling like you've done quite enough.
You've convinced yourself that you just need to work harder or longer hours for just a little bit longer. But that temporary hustle has become your permanent reality.
You don't know if you have another year of white-knuckling your way to your revenue goals in you. Another year where your health pays the price. Another year of your family paying the price. Another year of time you can't get back.
It's time to be really, really honest with yourself: Are you building a massive company with a huge team and infrastructure? Or do you want a lifestyle business?
A lifestyle business that's sustainable, built to last, something you can actually stick with and that makes your life better today – not in a year, not in 5 years, but right now.
This October, join a small group of established Canadian business owners for 3 days of strategic business model work facilitated by someone who's helped thousands scale sustainably. Design a business that honours your real-life capacity, clarify your positioning, build a revenue plan with actual numbers and leave with a Q4 action plan to make it real.
Strategy meets ocean views. Cozy fall vibes. Wine nights. No border crossing required.
EQUAL PARTS RESTRUCTURING, RECHARGING AND RECONNECTING
The Retreat Experience
The Lifestyle-First Business Model Retreat is a 3-day experience that's equal parts restructuring, recharging and reconnecting for established business owners who are ready to stop choosing between their business and their life. Set in a beautiful oceanview villa, surrounded by forest trails and fall colors – this is the perfect setting to redesign your business while actually recharging.
Mornings at the House
Wake up to crisp fall air and the smell of fresh coffee. Start your day with breakfast masterminding with your fellow retreat guests. Casual peer connection before we dive into the strategic work. These early conversations set the tone for real, honest business planning.
Afternoons of Strategy
Facilitated workshops where you'll work through your business model step-by-step. Individual reflection time, hot-seat feedback from Hailey and peer masterminding with business owners who understand exactly what you're working through. This is where the magic happens.
Evenings on the Ocean
As the day winds down, gather for dinner, wine and the kind of conversations that only happen when you're away from the day-to-day. Connection without the pressure. Strategy without the hustle. Space to breathe.
YOU'RE OFFICIALLY INVITED
The Lifestyle-First Business Model Retreat
Over 3 days, you'll redesign your entire business model using my 6-step Lifestyle-First framework – in a container that's equal parts strategic work and actual rest. Here's what you get:
Accommodations & All Meals
3 nights at the retreat house in Ladysmith, BC with your own private bedroom. 3 dinners, 3 breakfasts, 3 lunches and snacks throughout – so you can focus on the work without thinking about logistics.
2.5 Days of Facilitated Workshops
Guided sessions where you'll work through the complete 6-step Lifestyle-First Business Model Design Process with your retreat workbook and all materials provided.
Hot-Seat Coaching with Hailey
Get strategic feedback on your positioning, offers and business model from someone who's done this work thousands of times.
Peer Masterminding
Real connection and collaboration with other established business owners who understand exactly what you're working through.
Evening Wine (or Mocktails) & Reconnection Time
Unstructured evenings to decompress, connect and have the kind of conversations that only happen when you're away from the daily chaos.
Ocean & Forest Walks
Outings during breaks to recharge and let clarity hit while you're moving – because breakthroughs don't just happen in workshops.
Retreat Swag Bag
Thoughtfully curated items to support your retreat experience and remind you of what you built here.
BONUS: Post-Retreat Q4 Mastermind
Continued accountability and support through the rest of 2026 as you implement your new business model.
JOIN US FOR STRATEGY & OCEAN VIEWS
Design Your Lifestyle-First Business Model
October 5-8, 2026 • Ladysmith, BC • $2,500 CAD All-Inclusive
YOUR RETREAT ITINERARY
Your 3 Days: Strategic Work, Ocean Air and Real Connection
While every moment feels intentional, we've designed each day to give you the perfect balance of focused strategic work and actual rest. Morning masterminds, facilitated workshops, hot-seat coaching, ocean walks and evening conversations where you finally feel understood.
Here's how the 3 days unfold…
1
DAY ONE
Arrival & Intention Setting
Today is about arriving and grounding. You'll settle in, meet your fellow retreat guests and begin the work of getting honest about what you actually want your business to look like. We're setting the foundation for the transformation ahead.
- 4:00pm: Arrival and Check-In (Get Your Retreat Swag Bag)
- 5:30 pm: Welcome Dinner
- Lifestyle Factors and Intention Setting
- Overview of the retreat ahead
- 8:30pm: Evening wine & connection by the fire
2
DAY TWO
Positioning & Your Offer Ecosystem
Day two is all about strategic clarity. You'll define your positioning, map your signature process and design an offer ecosystem that maximizes lifetime value. This is where the muddy messaging gets clear and your offers finally make sense together.
- Optional: Gentle Hike
- Breakfast Mastermind
- Clarifying Your Positioning
- Developing Your Signature Process
- Mapping Out Your Offer Ecosystem
- 8:00pm: Wine Night (Cozy, unstructured connection)
3
DAY THREE
Marketing Plan & Business Model Integration
Integration day. This is where your positioning, offers and revenue plan come together into one cohesive marketing system. You'll see how all the pieces connect and leave knowing exactly how to drive traffic, generate leads and convert sales. Then we celebrate.
- Optional: Gentle Hike
- Breakfast Mastermind
- Designing Your Marketing TLC Plan
- Business Model Mastermind
- Wrap-Up Dinner and Celebration
- Wine or Mocktail Night (Cozy, unstructured connection)
4
DAY FOUR
Implementation Planning & Closing
Today is about implementation. You have your complete business model – now what? We'll map your end-of-year action plan so you know exactly what to prioritize between now and December 31st. You'll leave with clarity, a roadmap and momentum.
- Breakfast Mastermind
- End-of-Year Sprint Planning
- 10:30am: Checkout + Goodbyes
RETREAT DELIVERABLES
What You'll Walk Away With
01 Complete Lifestyle-First Business Model Canvas
Every section filled in: lifestyle factors, positioning, offer suite and revenue plan mapped out with your actual numbers
02 Revenue Plan with Real Numbers
Not vague goals. Actual lead targets, conversion rates and monthly sales numbers you need to hit your revenue goals
03 Clarified Positioning & One-Liner
The problem you solve, the person you serve, your process and the transformation you deliver, distilled into one clear statement
04 Sustainable Offer Suite
Signature offer, upsell, downsell and entry offers designed around your capacity and profitability goals
05 Your Q4 Action Plan
A prioritized list of what needs to happen between October and December 31st to implement this business model
06 Beautifully Designed Retreat Workbook
Spiral-bound, thoughtfully designed, something you'll reference for years as you implement and refine
07 Expert Guidance & Community Connection
Strategic hot-seat coaching from Hailey combined with peer feedback from other established business owners. Real relationships that continue beyond the retreat through our alumni group.
JOIN US FOR STRATEGY & OCEAN VIEWS
Design Your Lifestyle-First Business Model
October 5-8, 2026 • Ladysmith, BC • $2,500 CAD All-Inclusive
A NOTE FROM YOUR HOST
Your guide for this strategic escape is Hailey Dale: content strategist, business coach and founder of Your Content Empire.
For over a decade, Hailey has helped expertise-based business owners scale sustainably without burning out. She's worked with thousands of coaches, consultants and course creators to build business models that honor real life, not hustle culture's version of what success should look like.
She holds a Master's in Communications, is the bestselling author of “Your Content Rebellion” and has helped countless clients design lifestyle-first businesses that consistently generate $10K+ months. Her approach is strategic, systematic and refreshingly anti-hustle.
When she's not coaching or creating content, you'll find her drinking decaf almond milk lattes, rewatching Gilmore Girls for the cozy vibes and building a business that supports the life she actually wants to live (not the one she's trying to escape).
With Hailey facilitating, expect strategic clarity, hot-seat feedback that actually helps and a retreat that feels equal parts productive and restorative.
– Hailey
Got Questions?
Frequently Asked Questions
01. Who is this retreat for?
- Have been in business for 2+ years and are generating revenue (at least $5K months or higher) but feel maxed out or stuck at a capacity ceiling
- Are tired of white-knuckling your way to your revenue goals and know you can't do another year like this
- Want strategic business planning, not just another tactics workshop or motivational pep talk
- Crave connection with other established business owners who understand what you're working through
- Are ready to stop pretending you need to build like a venture-backed startup and design a business that actually fits your life
- Want to walk away with a COMPLETE business model, not just ideas you'll never implement
- Value intimate, curated experiences over massive conferences where you're just another face in the crowd
02. If I prioritize my life and design around my capacity, won't I make less money?
No. The opposite is actually true. Your current model has a revenue ceiling because it's broken – no amount of hustling harder will fix a business model that's working against you. When your foundation actually works (clear positioning, strategic offer suite, capacity-based revenue planning), everything on top of it (messaging, marketing, sales, delivery) gets easier and MORE profitable. A business model designed around real capacity doesn't mean lowering your goals – it means building a model that can actually GET you there sustainably.
03. What's the refund policy?
All sales are final. Because this is an intimate retreat with only 7 spots and significant advance planning required, we cannot offer refunds. However, you may transfer your spot to another qualified attendee with at least 30 days notice and our approval.
04. I've been to business retreats before and left inspired but never actually implemented anything. How is this different?
You don't leave with inspiration – you leave with a DESIGNED business model. Your canvas is complete, your offers are mapped, your revenue plan has actual numbers and you have your end-of-year implementation roadmap. We do the work during the retreat, not after. Plus you get post-retreat mastermind support for accountability through Q4.
05. Do I need to be in Canada to attend?
Nope! Anyone can attend. But one of the benefits of this retreat is that it's hosted in Canada, so Canadian business owners don't have to deal with border crossings, exchange rates or the current political climate south of the border.
06. What if I have dietary restrictions?
We'll send a pre-retreat questionnaire to gather all dietary needs and restrictions so every meal works for you.
07. How do I get there?
Ladysmith is located on Vancouver Island, approximately 20 minutes south of Nanaimo.
By Air:
- Fly into Nanaimo Airport (YCD) – 20 minutes from Ladysmith
- Fly into Victoria International Airport (YYJ) – 1 hour 15 minutes from Ladysmith
- Fly into Vancouver (YVR) and take the ferry to the island
By Ferry:
- BC Ferries operates routes from Tsawwassen (Vancouver) to Duke Point (Nanaimo)
- From the Nanaimo ferry terminal, Ladysmith is a 20-minute drive
By Car:
- If you're already on the island, Ladysmith is easily accessible via Highway 1
08. How is this different from your coaching programs?
The coaching programs are ongoing support over 3-12 months. The retreat is an intensive 3-day immersive experience where you complete your entire business model redesign in one focused container. Both use the same Lifestyle-First framework, but the retreat includes the in-person experience, peer masterminding and the strategic + restorative elements you can't get on Zoom.
JOIN US FOR STRATEGY & OCEAN VIEWS
Design Your Lifestyle-First Business Model
October 5-8, 2026 • Ladysmith, BC • $2,500 CAD All-Inclusive