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

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.

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

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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

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.

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

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.

This week on the Island Woman Podcast, I’m thrilled to bring you a powerful conversation with the wonderful Karin Wilson Edmonds, the founder of Bloom, a thriving online wellness membership specifically for women over 40.

Karin, who joins us from Jamaica, perfectly embodies our season's mandate: exploring how Caribbean women can maximise their contribution to regional economic development while protecting their well-being. A former corporate professional and consultant, Karin’s wellness-driven decision to spend less time “hunched over a laptop” set the stage for a massive career pivot over 15 years ago. She became a Yoga/Pilates Teacher and later a Certified Wellness Coach.

In this must-watch episode, we unpack Karin’s journey from the high-pressure corporate and consulting environment to creating a path for a successful Online Wellness Empire.

We discuss:

• An Unexpected Opportunity to Scale: How the COVID-19 pandemic catalysed Karin’s business from local to global.

• The Intentional Living Mandate: The personal challenges that jump-started her new career in wellness.

• The Core Questions: The non-negotiable advice she gives to every Caribbean woman entrepreneur: You must first answer, "What life do you want?" and “What’s your risk tolerance?”

If you are a Caribbean woman founder scaling a business, or simply striving for intentional living, this episode with Karin Wilson Edmonds is for you.

🔗 Connect with Karin Wilson Edmonds

web🌐karinyogalife.com

Instagram, Facebook & YouTube: @KarinYogaLife

I’m thrilled to share this conversation with a woman who is the absolute embodiment of purpose-driven leadership: Anushka Varsha Sonai.

Anuskha joins us from Suriname, where she is driving digital transformation across the region as the President of Creative Tech Hub Caribbean and the American Chamber of Commerce, Suriname. I have been impressed and inspired by her since we first met, and her accomplishments speak for themselves—from winning the prestigious Anthony Sabga Caribbean Excellence Award to receiving a nomination for the Women in Tech Global Leadership Award.

In this episode, we uncover an essential blueprint for true Caribbean economic development, a plan that must be led by Women, Alliances, Talent, and Technology.

Chapters

00:00 Introduction to Anushka Varsha Sonai

02:54 The Caribbean Survival Kit for Women Entrepreneurs

07:23 The Role of Women in Shaping the Caribbean's Future

12:38 The Importance of Competence and Ambition

20:41 Anushka's Journey Beyond Leadership

24:45 Balancing Ambition and Well-being

30:18 Creative Tech Hub: A New Business Model

Anushka reveals her unique vision for how women can maximise their contribution to regional economic development while still maintaining a purpose-driven vision for their own wellbeing.

• Women as Drivers: Anushka strongly asserts that women are not beneficiaries of development; they are the drivers of economic expansion. She shares compelling data that links the development of women to 30% less poverty in the region.

• Talent Retention & Brain Drain: We discuss her core mission to create "better futures" at home to halt the flow of people leaving the Caribbean, ensuring our talent is retained to build sustainable businesses.

• Alliances over Division: She shares a unique call to action for Caribbean leaders, emphasising the need to move from "playing the victim card" to "speaking from strength" by actively building powerful alliances and an inclusive private sector ecosystem.

• From Consumptive to Productive: Learn how Creative Tech Hub is leveraging technology and workforce development to strategically pivot the region from a consumer-based economy to a productive, digital-first industry.

If you're interested in genuine Caribbean leadership, women in tech, or the strategy behind regional development, this episode is your roadmap.

• Creative Tech Hub Caribbean: creativetechhub.online

• Connect with Anushka: (Search for Anushka Varsha Sonai on LinkedIn)
  🔑 The Blueprint for Caribbean Growth📲 Connect with Anushka & Creative Tech Hub Caribbean

  
  

  👇 If this episode inspired you to think bigger about Caribbean development, please Like this video, Subscribe to the Island Woman podcast channel, and Share this blueprint with a friend! Let's build a stronger Caribbean together.