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The Crossing

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Twelve weeks ยท Women crossing ashore

Yachting Exit Strategy: 12-Week Programme Outline

Week by week, what you explore and what you leave with, from your first cohort call to a written, dated plan already in motion.

Weekly live sessions every Wednesday evening: 90 minutes.

Week 01

Welcome to The Crossing

  • Meet your cohort and begin building trust and connection
  • Understand the 12-week journey ahead
  • Explore what has brought you here and what you hope this next chapter might make possible
  • Set your intentions for the experience ahead
  • Begin Before the Crossing | Week 2 Preparation

You leave with

A clear understanding of the journey ahead, connection to the women making it alongside you, and your first preparation ready to begin.

Week 02

The Power of Perspective

  • Explore the perspectives, narratives and assumptions shaping how you see yourself and your next chapter
  • Begin separating who you are from the role or title you've held
  • Recognise that many of the perspectives you carry are interpretations rather than facts
  • Recognise the transferable value of the experience and capabilities you already bring
  • Choose a more empowering perspective to intentionally carry forward

You leave with

Greater awareness of the perspectives shaping your thinking and a more empowering lens through which to begin seeing yourself and what's possible.

Week 03

Your Possibility & Potential

  • Reconnect with who you are beyond your professional role
  • Explore the strengths, natural affinities, interests, values and motivations that have followed you through different chapters of your life
  • Recognise the conditions in which you are in your element
  • Consider how you want to Work. Live. Be.
  • Give yourself permission to imagine without needing to decide

You leave with

A deeper connection to yourself, a broader sense of your potential and a more expansive picture of the future you might intentionally create.

Week 04

Career Exploration & Discovery

  • Explore where your strengths, experience, interests and aspirations could translate professionally
  • Begin seeing your yachting experience through the language of wider professional capabilities
  • Discover roles, industries, organisations and pathways you may not previously have considered
  • Learn how to research and investigate opportunities without immediately committing to a direction
  • Use conversations and small actions to gather information and create greater clarity

You leave with

Professional pathways worth investigating and specific actions you can take to learn more about what genuinely interests you.

Week 05

Business, Entrepreneurship & Meaningful Value

  • Explore business, entrepreneurship, consultancy, freelance and portfolio pathways
  • Understand how ideas and opportunities can emerge from problems, needs, experience and insight
  • Begin thinking entrepreneurially, whether or not you ultimately choose to run a business
  • Explore where something you bring could meet something somebody else needs
  • Consider what you value, the value you bring and what makes work a meaningful value exchange for you

You leave with

A clearer understanding of whether entrepreneurship interests you, where you might create meaningful value and what you could explore, research or test next.

Week 06

LinkedIn & Personal Brand

  • Translate what you've discovered about yourself into how you communicate professionally
  • Articulate your experience, strengths and value in language that makes sense beyond yachting
  • Build a professional presence that reflects where you're going, not only where you've been
  • Develop your visibility and begin building relationships in the spaces you may want to move into
  • Use LinkedIn intentionally for positioning, networking and opportunity creation

You leave with

A stronger professional presence that communicates the value you bring and begins positioning you for what comes next.

Week 07

Recruitment Pathways & CV

  • Understand how recruiters and organisations may interpret your yachting experience
  • Translate your roles, responsibilities and achievements into shoreside language
  • Strengthen your CV around capabilities, evidence and outcomes
  • Understand where relevant opportunities exist and how to approach them
  • Learn to communicate your experience as an asset

You leave with

A repositioned CV, a clearer understanding of how the market may see you and greater ability to communicate the professional value of what you've already achieved.

Week 08

Tax Foundations

  • Understand where you are tax resident and what that means
  • Explore whether you are declaring correctly and what may change when you transition ashore or relocate
  • Understand the financial responsibilities and structures that may come with your next chapter
  • Identify the questions you need to ask and the professional advice you may need

You leave with

Greater clarity on your tax position, what may change as you transition and the questions you need answered.

Week 09

Financial & Investing Foundations

  • Get clear on what you've saved while yachting and what to do with it next
  • Explore investing vs holding cash, plus options for your specific jurisdiction
  • Plan for property, retirement and pension gaps yacht crew often face
  • Build a financial plan around an irregular, high-income career and a safe exit from yachting
  • Spot the common mistakes when a tax-free salary ends and set up systems that match your lifestyle
  • Bring your situation to the session through a short pre-work questionnaire

You leave with

A clearer picture of your financial position, practical next steps and the start of a personal roadmap for life after yachting.

Week 10

AI Upskilling & Future Readiness

  • Understand how AI is changing the world of work and what that could mean for your next chapter
  • Build practical fluency with tools increasingly used across organisations and industries
  • Explore how AI can support research, thinking, productivity, career development and professional work

You leave with

Practical AI skills you can use immediately and greater understanding of how AI can support you in your next chapter.

Week 11

Integration & Action Planning

  • Reflect on the journey you've made across the programme
  • Bring together what you've discovered about who you are, what you want and what you bring
  • Identify what matters now
  • Translate your thinking into clear priorities and practical next steps
  • Build a written, dated 90-day action plan and share your commitments with the cohort

You leave with

A written, dated 90-day plan that builds on the action and progress you've already made and gives you clear priorities for what comes next.

Week 12

Celebration & The Next Chapter

  • Recognise and celebrate how far you've travelled across the 12 weeks
  • Revisit your Crossing Journal and notice what has changed
  • Articulate what you now know about yourself, what matters to you and what you're choosing
  • Share the commitments you want to carry forward
  • Join The Crossing Alumni community

You leave with

Greater clarity about who you are, what you bring and what you're choosing next, a plan already in motion and a community that continues beyond Week 12.

By Week Twelve

You'll have a clearer understanding of who you are, what you bring and what you want next, alongside a written, dated plan for intentionally building it.

You won't simply leave with ideas. You'll have taken meaningful action throughout the programme, built momentum towards what comes next, and gained a cohort of women who understand exactly what this crossing takes.

Build your exit strategy, before you need it.

Beyond the 12 Weeks

The programme ends. The crossing continues.

You'll join The Crossing Alumni, an ongoing community for connection, opportunities, introductions, continued learning and collaboration, leaving with the foundations, tools, relationships and momentum to keep building what comes next.

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