Island Woman Podcast

Dianne N Squires
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Do you aspire to an uncomplicated and fulfilling way of life? Join me, Dianne Squires AKA D-Anne, an island woman living on the island of Barbados and walking my path to a big and simple life. Walk with me and learn with me. Welcome to the Island woman podcast.

  1. MAR 8

    Caribbean Women Find Your Voice II: No More Podcast Burnout

    Podcasting is an excellent way for Caribbean women to find, shape, and use their voices on the global stage. But podcast burnout can come quickly without planning for expected or unexpected realities. Dianne Squires of the Island Woman Podcast and Mialisa Garnes of the Wellness & Growth Journeys Podcast, with over 70 episodes between them, talk about podcast burnout, how it happens, how to avoid it and the tech tools they use to streamline their processes.  ----------------- The Island Woman podcast is back for Season 4, and we’re kicking off with a special International Women’s Day collab episode with the Wellness & Growth Journeys podcast with my fellow Island Woman podcaster Mialisa Garnes. We’re covering “Caribbean Women Find Your Voice” using the power of podcasting in two parts. On the Island Woman podcast, we’re revealing the realities of podcast burnout and the tech we’ve been using to simplify our processes. On the Wellness and Growth Journeys Podcast channel, we talk about how we got started in podcasting, what visibility via podcasting has meant for us and how it can go beyond personal branding to be economically empowering. Start here and then head over to the Wellness & Growth Journeys podcast to get the full conversation.  ---------- ➡️Connect with Dianne Website: diannensquires.com LinkedIn: @Dianne Squires Learn about the Rooted and Ready Strategic Visible Authority programme for women: https://www.diannensquires.com/rooted-and-ready-visibility-programme-for-women ----------- ➡️Follow The Wellness & Growth Journeys Podcast YouTube: https://youtube.com/playlist?list=PLl2SAz7ot8YzCAvwONVYSZBgo1_VaVw3U&si=nDZLw5y2nKenKKio Spotify: https://open.spotify.com/show/653PlFZ7LxJvZNf0Nh6crj?si=d2e22906e1604f47 ➡️Connect with Mialisa:  Instagram: @itsmialisa LinkedIn: @Mialisa Garnes ------- Where BIG ambition meets uncomplicated living and paves the way for holistic wealth and wellbeing - that’s the Island Woman Big and simple life™ philosophy. If this is your path, subscribe for more Caribbean Island stories on women in leadership, intentional living, entrepreneurship, and legacy-building.  YouTube channel link: https://youtube.com/@islandwomanpodcast?si=aopEY35yFMd9DYmf

    33 min

  2. FEB 15

    The Truth About Work & Ageing for Caribbean Women

    As many Caribbean women cross milestones of 35, 40, and 50, we start to wonder if we've outgrown the career roles we once worked hard to attain. We assess how we can continue to maximise our economic impact while protecting our wellbeing. With regional pensions under threat and the risk of noncommunicable diseases rising as we age, we have to get honest about our work, aging and our Caribbean reality.  In this episode, I’m sharing why I chose to "peel it back to the studs" and how we can all work stronger, not just harder.  Chapter Timestamps: 0:00 - The Reality of Ageing and Work in the Caribbean  2:15 - Life After 35: A New Perspective on Career  4:45 - The Truth About Pensions and Economic Stability  7:10 - Outgrowing Your Role: The "Tight Shoes" Analogy  9:30 - Maintaining Well-being & Managing Health Risks  12:15 - Upskilling: Are You Willing to Learn Something New?  15:00 - Using Your "Total Skill Range" to Earn Income  18:30 - Redefining Work I have more questions than answers, but I know this: we don't have to work until we drop. We can choose a life that allows us to execute at the highest quality while remaining whole. Let’s think through these transitions together. Join the Conversation:  If this resonated with you, please leave a comment—are you ready to learn a new skill, or think of new ways to harness your potential?

    18 min

  3. FEB 8

    Big Ambition, Less Chaos: The Efficiency of Discomfort

    Learn why intentional growth doesn't have to be chaotic as I share lessons for Caribbean entrepreneurs on building business efficiency through the power of discomfort. In this unscripted episode of the Island Woman Podcast, I’m looking back at 2025 to unpack a hard truth: big ambition does not require a complicated life. It requires the courage to do simple, often uncomfortable things. From moving your plan off the paper to "building muscle" through tension, I’m sharing how to stop the busy work and start making every moment count toward your vision for 2026 and beyond. What You’ll Learn in This Episode: How to find the "Efficiency of Discomfort" in your daily routine. Why letting people know what you want is a 30-second shortcut to success. The difference between being busy and being effective in your marketing. How to treat your business strategy like a gym workout to build real strength. Timestamps: 0:00 – Intro: The Big Realisation: Ambition vs. Chaos  1:15 – Reflecting on 2025 Lessons 3:18 – Lesson 1: The Power of Asking for What You Want 4:51 – Lesson 2: Moving the Plan from Paper to Action 7:58 – Lesson 3: The Necessity of Patience (The Tortoise vs. The Hare) 9:28 – Lesson 4: Building Business Muscle through Tension 12:22 – Lesson 5: How to Make Every Day Count Toward Your Vision 16:53 – Final Thoughts: Managing the Discomfort Muscle 18:56 - Outro: Leave a Review & Connect Connect with Me:  Subscribe to the Channel: 🔗https://www.diannensquires.com/islandwomanpodcast[Link to Apple/Spotify] ➡️Connect on LinkedIn: @Dianne Squires  🌺Join the Visibility Program: https://www.diannensquires.com/rooted-and-ready-visibility-programme-for-women

    20 min

  4. FEB 1

    How I Stop Self-Doubt and Keep Going: 5 Founder Truths

    From my late Father's timeless advice on stopping self-doubt to the vulnerability of asking for help, I share how I’m building my 'keep going' muscle. Whether you call it perseverance, consistency, or 'stick-to-it-ive-ness,' it is a must-have for Caribbean women in leadership. And I’m sharing my candid tips in this unscripted episode of the Island Woman podcast.  00:00 – The Unscripted Truth: Navigating Technical Difficulties 01:24 – The Most Asked Question: "How Do You Keep It Going?" 02:18 – Pillar 1: Making the Decision to Stay the Course 03:10 – Lessons from my first podcast "Backstage with Bajan Brands" 04:42 – Setting KPIs for Entrepreneurship in 2026 05:25 – Pillar 2: My Father’s Advice on Overcoming Self-Doubt 06:20 – The "Common Entrance" Lesson: Trusting Your First Instinct 09:12 – Pillar 3: Reducing Self-Judgment & Finding Your Voice 10:30 – Why Caribbean Voices Belong on the Global Stage 11:25 – Pillar 4: Giving Yourself Permission to Evolve & Iterate 14:10 – The Vulnerability of Unscripted Content 15:35 – Pillar 5: Breaking the "Strong Woman" Cycle & Asking for Help 16:55 – Navigating the "Change of Life": Business during Perimenopause 19:40 – The Backyard Gym: How Expert Help Changed My Results 24:15 – Rooted and Ready: Strategy for the Visible Female Authority 26:30 – Recap: The 5 Pillars of Caribbean Resilience 28:10 – Final Thoughts: How to Support the Island Woman Journey 🌿For more info on the Rooted and Ready programme  Email: diannensquires@diannensquires.com ➞ Follow Dianne on LinkedIn: @Dianne N Squires  Where BIG ambition meets uncomplicated living and paves the way for holistic wealth and wellbeing - that’s the Island Woman Big and simple life™ philosophy. If this is your path, subscribe for more Island stories on Caribbean women in leadership, intentional living, entrepreneurship, and legacy-building.

    29 min

  5. JAN 25

    4 Caribbean Women on Leadership, Pay Equity, and Economic Power

    My conversations with Caribbean women founders leaders and experts have been fuel for my BIG and simple life, where big ambition and wellness converge. In this episode, I recap some of those conversations that relate to leadership, pay equity and economic power for Caribbean women.  Key moments:  00:00 Embracing a Big and Simple Life 01:28 Women’s Economic Impact in the Caribbean 02:29 The Power of Everyday Leadership: Why you should never underestimate your role, regardless of your official job title. - Kim Butcher, Cultural Strategist & Founder of Okoye by Kim  04:24 A Vision for Total Development: Reframing women’s empowerment as a mission for an entire productive population - Anuskha Varsha Sonai, President Creative Tech Hub Caribbean 07:54 Valuing Invisible Labour: The urgent case for better compensation packages for women in the development sector - Karen Philip, Founder, Kainos Caribbean Consulting  11:33 Breaking the "Sticky Floor" and getting to the top - Racquel Moses, CEO, Caribbean Climate-Smart Accelerator and Global Ambassador for Race to Zero and Race to Resilience 15:10 Closing Thoughts and Call to Action ------ Loved the clips in this episode? Catch the full episodes with each of these incredible Caribbean women leaders. VEX Money to Caribbean Legacy: Kim C. Butcher, Okoye by Kim Founder | Island Woman Podcast https://open.spotify.com/episode/44kvgtwdxGS3CxaYGSu0HZ?si=kcpbHjFCRkKY7CbYTBb75w Anuskha Varsha Sonai: Women, Alliances, Talent, Tech for Caribbean Growth | Island Woman Podcast ​​https://open.spotify.com/episode/4ItZSxRvVQtaySStQgGwPo?si=_0txU2MUTIqvkiV5ATflfg Doing Good Better: How Women Lead Caribbean Social Impact with Karen Philip | Island Woman Podcast https://open.spotify.com/episode/52oBapcOeL4NJtYG8vxG40?si=v3wKuYZdSPSlNu9vlL5UNA Why Not You? Racquel Moses on Getting off the Sticky Floor in Leadership | Island Woman Podcast https://open.spotify.com/episode/4BDXp8MNH99lgZc7a6QiFb?si=Ln4cKNP2RkeN1Bic6Mio8g

    16 min

  6. JAN 18

    Why Not You? Racquel Moses on Getting off the Sticky Floor in Leadership | Island Woman Podcast

    As women, we hear a lot about "breaking the glass ceiling" – that constant pushing up against external boundaries to leadership. But what about when we, for whatever reasons, refuse to explore the edge of those boundaries? How do we elevate ourselves to top leadership and finally move beyond the "sticky floor" of junior and middle management? In this episode, I chat with the powerhouse that is Racquel Moses. As a global ambassador for the UN-backed Race to Zero and Race to Resilience campaigns and CEO of the Caribbean Climate Smart Accelerator, Racquel is a visionary redefining economic empowerment in the Caribbean. But beyond the global accolades, we talk about the grit, heart and desire it takes to lead. From the "survival kit" woman CEOs needs to the tough but necessary decisions that prioritise family over a paycheck, this conversation is a masterclass in Caribbean women and leadership. We explore how to grow your ambition, build a village that sustains you, and why "ridiculous" ideas are often the ones most worth pursuing. If you are ready to stop shrinking and start scaling, this episode is your invitation to grow bigger. In this episode, we explore: The CEO Survival Kit: Why practical habits and hydration are the foundations of Caribbean resilience and lifestyle. Breaking the "Sticky Floor": Moving beyond the glass ceiling to address the internal and systemic traps that hold women back. Leading for the Future: How sustainable living in the Caribbean isn't just an ideal—it’s a multi-billion dollar investment opportunity. The Power of the Village: Navigating the intersection of high-level career demands and the deep roots of Caribbean culture and community. Episode Timestamps 00:00 – Meet Racquel Moses: Global Ambassador and Climate Catalyst. 02:11 – The CEO Survival Kit: 3 essentials for the Caribbean woman leader. 05:30 – Getting to the Top: Why gender equity makes business sense 08:32 – The Sticky Floor vs. The Glass Ceiling: How to reclaim your ambition. 12:15 – Hard Decisions: Prioritising family, education, and the "village." 18:53 – Funding the Future: Connecting philanthropy to Caribbean innovation for climate adaptation. 24:09 – The Scale of Wellbeing: Rhythms, sleep hygiene, and the 12/10 ambition. 29:31 – "Why Not You?" – Final advice for the aspiring Caribbean leader.

    35 min

  7. JAN 11

    Kimalene Regis: Be Unapologetic About Wanting More In Business

    Is it possible to be fiercely ambitious without sacrificing your soul? In this episode, I sit down with Kimalene Regis, founder of Kimalene Regis & Co (KRC), a marketing and project management powerhouse based in Grenada. We explore the reality of Caribbean women and leadership, moving beyond the highlight reels to discuss the "heavy" seasons of entrepreneurship and why "wanting more" is actually a radical act of self-care. Kimalene shares her journey from a high-impact corporate role to building a remote-first agency that serves the regional financial sector - all while navigating the complexities of motherhood and personal fulfilment. From her "Rose-Colored Glasses" planner to her survival kit for the Caribbean entrepreneur, this conversation is a masterclass in Caribbean resilience and lifestyle. Join us as we discuss how to build a business that honours your well-being, the power of economic empowerment in the Caribbean, and why you should never shrink to make others comfortable. Timestamps 00:00 Introduction to Kimalene Regis and Her Journey 06:35 Creating a Survival Kit for Caribbean Women Entrepreneurs 12:20 Catalyst for Entrepreneurship: Kimalene’s Journey 17:44 The Importance of In-Person Events for Women 23:22 Balancing Ambition and Well-Being 29:04 Final Advice for Women Entrepreneurs 33:31 Podcast outro.mp4 Connect with Kimalene: Website: kimaleneregisconsulting.com  LinkedIn: Kimalene Regis  Connect with Dianne: Website: diannensquires.com LinkedIn: Dianne Squires N Squires

    34 min

  8. 12/14/2025

    Caribbean Women Build Wealth: Financial Literacy Strategy | CPA Megan Samuel-Fields

    I was honoured to spend this episode chatting with Antiguan Megan Samuel-Fields, who is a woman on a mission to improve financial wellness for Caribbean people. As a certified public accountant (CPA), Attorney-at-Law, PhD candidate, life coach and the CEO of Samuel-Fields Consulting, her plate is full, and her passion for making every second and every cent count is unmistakable.   This episode continues exploring the essential question: how do we, as Caribbean women, maximise our contribution to regional economic development while protecting our wellbeing? We discuss the real barriers - the knowledge gaps, the tendency to follow only what our parents practised - and the specialised strategy required to move beyond them. In this conversation, Megan shares her insights on: The Power of Layering: How combining disciplines (like accounting, law, and finance) has created a powerful, integrated advantage for her as a Caribbean business leader navigating regional and global markets. Her scores on the Island Woman Ambition/Wellbeing Equation™: A candid discussion on balancing a 9/10 ambition with a sustainable 8/10 wellbeing, and the discipline required to maintain that equilibrium. The Founder's Foundation: Practical steps and a "survival kit" for Caribbean entrepreneurs seeking growth and resilience in their ventures. Redefining Financial Health: Moving past traditional definitions to understand financial wellness as a holistic life practice tied to intentional living, not just the balance in your bank account. Chapters 00:00 Introduction to Megan Samuel-Fields 01:51 Survival Kit for Caribbean Women Entrepreneurs 06:01 The Role of Samuel Fields Consulting Group 11:55 Passion for Learning and Financial Literacy 17:51 Likkle Byte Ideas: A Family Collaboration 23:49 The Importance of Financial Wellness 29:55 Advice for Aspiring Women Entrepreneurs If you are a Caribbean woman who is building something - whether it’s a business, a career, or a legacy, this is  a conversation that will empower your next move. CONNECT & SUPPORT: Find Megan at: 🌐 www.SamuelFieldsConsulting.com Facebook: SamuelFields Consulting Group  LinkedIn: Megan Samuel-Fields If this conversation resonated with you, please like, share it with a friend, and leave a review.

    33 min
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About

Do you aspire to an uncomplicated and fulfilling way of life? Join me, Dianne Squires AKA D-Anne, an island woman living on the island of Barbados and walking my path to a big and simple life. Walk with me and learn with me. Welcome to the Island woman podcast.

Information

  • Creator
    Dianne N Squires
  • Years Active
    2025 - 2026
  • Episodes
    36
  • Rating
    Clean
  • Copyright
    © Dianne N Squires
  • Show Website
    Island Woman Podcast