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The Paid to Breathe Mastermind Presents


The Expansion Retreat

3 days in Crete, Greece to become the version of you your next level requires

šŸ“† When

21 – 23 October 2026

šŸ“ Where

Crete, Greece

"The magic of this event is that Jenna really creates an environment where she guides and leads, but she left space for us to connect with each other and tap into our own selves and our creativity in this amazing, gorgeous space."





- april roberts, may 2026 Retreat Attendee

You didn't build this business to feel stuck at the same level.

Your business is working. You're making money. You're booked. You're busy. But there's something you can't quite name, a ceiling you keep bumping into. Not a strategy problem. Not a tactics problem. Something deeper.

You know the next version of your business requires a next version of you. But you can't think your way there from inside the noise of your day-to-day.

You need to step out to step up.

That's exactly what this retreat was designed for. Four days in a stunning villa in Crete, surrounded by ambitious women who get it. A place to finally create the clarity, strategy, and identity shift that takes you from where you are to where you're meant to be.

This Retreat Is For You If...

You're craving connection with other ambitious women who understand the weight of building something meaningful


You want strategy AND soul — real frameworks for growth alongside the identity work that makes it stick


You know you need to step away from the day-to-day to gain real perspective on what's actually holding you back

You're beyond the startup phase — your business is generating revenue and you're ready to build the infrastructure (and mindset) for multi-6 figures

Funnel Strategy Workshops

Deep-dive sessions where we map your entire funnel - from relying on adrenaline to scalable systems. Leave with a complete roadmap you can implement immediately.

Mindset & Identity Work

The real reason you're stuck isn't strategy. It's the beliefs and identity keeping you playing small worried what people will think - this retreat will rewire that in 4 days.



Breathwork Experience

A facilitated breathwork session to release what's been holding you back and open space for the version of you your business needs.



Branding Photos & Content

Walk away with stunning, elevated photos that match the next level you're stepping into. Content that converts, captured on location.



Intimate Group Hot Seats

Personalised feedback and strategy sessions in a small, curated group. Real solutions for your specific business challenges.



Your 4-Day Experience

Integration Pool Day

Day four is for integration, celebration, and connection. Process everything you've learned while floating in the Greek sun.



Funnel Strategy Workshops

Deep-dive sessions where we map your entire funnel — from lead magnet to high-ticket offer. Leave with a complete roadmap you can implement immediately.

Mindset & Identity Work

The real reason you're stuck isn't strategy. It's the beliefs and identity keeping you playing small. We'll rewire that — together.



Breathwork Experience

A facilitated breathwork session to release what's been holding you back and open space for the version of you your business needs.




Branding Photos & Content

Walk away with stunning, elevated content that matches the next level you're stepping into. Content that converts, captured on location.



Intimate Group Hot Seats

Personalized feedback and strategy sessions in a small, curated group. Real solutions for your specific business challenges.



Your 4-Day Experience

Our Stunning Retreat Venue

šŸ“ Where

Crete, Greece

Totally transformational. Worth every penny and more to be in a room like this.

Sophie Sherief

Sophie since leaving the retreat has sold out all high ticket packages, her retreat and has 4x her income in 4 months.

Hear from the women in the room

I've built a whole new program and I have the confidence to launch it. I've had conversations with the incredible women in the room, who have said like 'yes I need that'. I've also had the identity shift that means that I can hold the program and actually bring it to life.

sophie morris

This was a strategic, ready steady go experience — everything I needed to start implementing my vision.

Katy Schweiger

Katy left with complete clarity and confirmation on the direction of her business and launched her podcast

Here's what's included

Surprise gifts and elevated details throughout








Facilitated breathwork experience



Intimate hot seats and personalized feedback





Integration pool day celebration






Complete funnel mapping and business strategy sessions


Connection with an incredible room of ambitious women







4 full days of strategy, mindset, and expansion work

Hi, I’m Jenna O'keefe

For over a decade, I worked as a marketing strategist inside and alongside award-winning agencies, leading multi-6 and 7-figure pitches, directing high-converting campaigns, and crafting messaging that made brands unforgettable.

Today, I bring that same strategic precision to the world of online coaching - mentoring 6, multi-6 and 7 figure coaches, creatives, and agency owners to scale with simplicity, clarity, and zero burnout.

For 3 years I focused solely on confidence coaching, honing my craft and leading the UK market. I'm a genius at helping women to dissolve performance pressure and guiding them to lead with conviction and gravitas (so they can get paid to breathe too!) 

My gift? Turning your messy drafts and half-baked ideas into messaging that moves money, magnetises premium clients, and positions you as the one to hire - before you even say a word!

Meet your retreat faciliator

Your Investment

Please note: This investment covers your retreat experience only. Flights and accommodation are booked separately - we'll send you our villa recommendation and travel details upon booking. 

Pay in Full

One-time payment



Ā£1,750

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Ɨ 3 monthly payments


Ā£641

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Choose the option that works best for you

payment plan

Ā£800

Ā£2,200

FIRST 5 TICKETS ONLY DISCOUNT !! šŸ‘‡

The retreat runs Wednesday 21st October – Friday 23rd October 2026, with an integration pool day on Saturday 24th October. 


What are the exact dates?

Accommodation and flights are booked separately. Upon booking your spot, I'll send you the details of our stunning villa in Crete so you can arrange your stay and travel.


Is accommodation included?

Yes! If you're a current mastermind member, the retreat is included in your membership. Simply let me know you'll be attending.



I'm already in the Paid to Breathe Mastermind — is this included?

This is an intimate experience with limited spots to ensure everyone receives personalized attention and support. Once it's full, it's full.


How many spots are available?

If May 2026 doesn't work for you, join the waitlist for future retreats. But if you can make it work — this is your sign.


What if I can't make these dates?

What are the exact dates?

The retreat runs Wednesday 21st October – Friday 23rd October 2026, with an integration pool day on Saturday 24th October. 

Is accommodation included?

Accommodation and flights are booked separately. Upon booking your spot, I'll send you the details of our stunning villa in Crete so you can arrange your stay and travel.


I'm already in the Paid to Breathe Mastermind — is this included?

Yes! If you're a current mastermind member, the retreat is included in your membership. Simply let me know you'll be attending.


How many spots are available?

This is an intimate experience with limited spots to ensure everyone receives personalized attention and support. Once it's full, it's full.


What if I can't make these dates?

If October 2026 doesn't work for you, join the waitlist for future retreats. But if you can make it work — this is your sign.



You already know what staying the same looks like.

This is your invitation to step into the room, the strategy, and the version of yourself that makes your next level inevitable.

secure your spot