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The Paid to Breathe Mastermind Presents


The Expansion Retreat

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

📆 When

20th – 23rd May 2026

📍 Where

Crete, Greece

100% of the attendees at our last retreat have rebooked for this upcoming retreat!

It won't just change your business — it will change you as a person.

- Michelle, Past 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

Integration Pool Day

Day four is for integration, celebration, and connection. Process everything you've learned while enjoying the pool with your new business besties.



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

📍 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

Absolutely lifechanging in strategy and elevating in sisterhood & standards. Just do it!"

Nisha Ryan

Nisha increased her prices, sold out and doubled her recurring revenue in 4 months since leaving the retreat.

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

A total rebrand / rebirth of your business and how to position yourself.

Kennedy Risby

Kennedy increased her prices significantly and started selling to premium luxury buyers (without imposter syndrome!)

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

Sandra Chuma

Sandra Chuma built an 8-figure business by doing what high-achieving women are taught to do. Work harder. Stay disciplined. Push through.

And she burned out. Twice.

The problem wasn’t her ambition or her drive. It was the model of success she had been following.

That insight led her to create the WORTHY Framework™, a self-leadership approach for high-achieving women who want to succeed without sacrificing their health, peace, or sense of self.

WORTHY isn’t about wanting less. It’s about leading yourself in a way that doesn’t require self-sacrifice. Because if it costs you yourself, it’s not success.  

Sandra’s work is grounded in lived experience and informed by extensive training across identity, behaviour, and subconscious change modalities. 
She built this framework because she needed it herself. In Greece she joins us to support you in a deep focused session on identity, money mindset and becoming the woman who makes money without relying on adrenaline.

Meet our guest speaker

Stefanie Sword-Williams

Founder of F*ck Being Humble. Forbes 30 Under 30. Best-selling author. TEDx speaker. Trusted by Google, Apple & Nike.

Stefanie Sword-Williams is one of the most influential voices in the world of personal branding, visibility, and self-promotion — and she’ll be joining us for the entire retreat.

Stefanie is super selective about the rooms she enters, but when I told her about the calibre of the women coming - she said yes straight away. She'll be hosting two powerful sessions:

F*ck Being Humble
  • A workshop on owning your expertise, celebrating your achievements, and dropping the instinct to shrink.
  • Because the version of you who creates £50k months doesn’t apologise for being good at what she does.

Presenting with Gravitas & Conviction

  • A masterclass on speaking with authority — on stage, on sales calls, and online. You'll learn how to find your own key-note talk and how to get booked on the worlds leading stages.
  • You’ll learn how to command a room, sell without second-guessing yourself, and communicate from stage in a way that makes people instantly trust your leadership.

This is the skill that amplifies every strategy you already have. You can have the best ideas in the world. But if you don’t know how to present them with conviction, they won’t land.

Stefanie does. And she’s going to teach you how.

Meet our guest expert

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



£2,000

dm jenna "crete" to apply

Payment Plan


× 2 monthly payments


£1,000

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Choose the option that works best for you

The retreat runs Wednesday 20th May – Friday 22nd May 2026, with an integration pool day on Saturday 23rd May. 


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 20th May – Friday 22nd May 2026, with an integration pool day on Saturday 23rd May. 

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 May 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.

dm jenna "crete" to apply