This season on the Island Woman podcast, I’m talking to Caribbean women founders, industry experts and thought leaders about how we can make maximum economic impact and protect our health and wellbeing.
Joining me in the season premiere is Tanja Gittens, chartered accountant, global nomad, budget guru and author of the book “Living Loud on a Budget: Authentic Financial Living”. Tanja has officially retired from the corporate world to build the Living Loud on a Budget™ brand. She talks candidly about:
➡️Why guts and gumption, not qualifications or experience, form the number #1 power package for Caribbean Women entrepreneurs
➡️How she took the unconventional nomad path while being a practising chartered accountant
➡️ Financial wellness, health and healing trauma to live out loud
➡️ Merging personal experiences, beliefs and professional skills to build a brand
➡️ The scale of her level of ambition and personal well-being
➡️ Prioritising health and wellbeing on the career path
➡️ Living out loud
➡️ Her advice for other Caribbean founders (having an emergency fund and more)
00:00 Empowering Caribbean Women Entrepreneurs
02:33 The Importance of Guts and Gumption
04:59 Breaking the Mould of Traditional Accounting
09:30 Choosing the Unconventional Path
14:52 Building a Brand: Living Loud on a Budget™
19:30 Understanding Emotional Spending and Cultural Influences
24:45 Balancing Ambition and Well-Being
27:35 Advice for Aspiring Caribbean Women Entrepreneurs
32:03 Defining Living Out Loud
35:30 Final notes
36:10 Podcast outro
We’ve reached the end of Season 2 of the Island Woman Podcast, and what a season it’s been. From the cultural power of breadfruit and the structure behind successful side hustles, to the surprising ways Caribbean women are shaping wellness and wealth, this season has been a celebration of our stories, our brilliance, and our potential.
In this final episode, I share 5 of my favourite moments from across the season and put out a call to Caribbean women founders, leaders, and experts to join the conversation in Season 3.
---
Season 3: Your Voice Is NeededWe’re dedicating the next season to the women shaping the future of the Caribbean: founders, innovators, culture shifters, and experts building solutions from the ground up.
👉🏽 Are you one of them, or do you know someone who is?
Email diannensquires@diannensquires.com with a short bio and links to your/their work.
Are you a Caribbean woman expert, founder, or creative ready to be more visible without the overwhelm? This episode is your roadmap to strategic visibility that builds credibility, authority, and high-value opportunities.
We explore what really counts when it comes to visibility: focusing on 2–3 core pillars that define what you want to be known for. Learn how thought leadership can amplify your authority, differentiate your business, and attract the right opportunities over time.
Why Visibility Matters:
Visibility is more than showing up; it’s a deliberate strategy to grow influence, establish trust, and expand your impact. If you’ve been wondering whether increased visibility is worth it, this episode offers clarity and actionable insights.
Go From Invisible To In-Demand With The Rooted And Ready Programme:
If you’re ready to start your visibility journey with guidance tailored to your expertise and goals, the Rooted & Ready 1:1 coaching programme is here to help.
👉🏾Email diannensquires@diannensquires.com with the subject line: Tell Me About Rooted and Ready to learn more.
Is it possible to be penalised for being successful? And does it happen more often to women? In this episode, I explore the “success penalty”, when achievements that should open doors end up creating backlash, especially for Caribbean women leaders.
We discuss research on intentional invisibility, real-life experiences of female leaders, and how to navigate these challenges without shrinking yourself.
If you’re a founder, expert, or creative ready to be visible with courage and clarity, this episode is for you.
Learn more about Rooted & Ready: Email me at diannensquires@diannensquires.com with the subject line Tell Me About Rooted and Ready.
#IslandWomanPodcast #CaribbeanWomenEntrepreneurs #Leadership #VisibilityMatters #HolisticWealth
What does it take to market women’s health and wellness in the Caribbean? My guest, Mialisa Garnes, has built a niche agency that bridges the gap between women looking for care and the professionals providing it. From her own journey into motherhood, she saw how little awareness there was around issues like midlife health and postnatal care, and she decided to do something about it. In this episode, we talk about choosing a niche, building trust in a sensitive sector, and the hard truths about how Caribbean women put ourselves last when it comes to our health and wellness.
From solopreneur to enterprise — how do we as Caribbean women entrepreneurs make the leap from side hustle to sustainable business?
In this episode of the Island Woman Podcast, I’m joined by Shauna Marshall, MSME development strategist and founder of SMB Consulting. We talk about what it really takes to scale our businesses with intention, structure, and vision.
We also dive into the cultural challenges Caribbean women face around sales, visibility, and leadership — and how embracing these areas can transform a “small business” into a lasting legacy.
If you’re a Caribbean woman entrepreneur looking to grow beyond survival mode into holistic wealth and intentional living, this conversation is for you.
What if building your business was more like training for the Olympics? 🏃🏽♀️
In this episode, I explore how Caribbean entrepreneurs can learn from elite athletes, their systems, discipline, and mindset, to build businesses that last.
What can Caribbean entrepreneurs learn from the discipline, mindset, and systems of world-class athletes? In this episode of the Island Woman Podcast, I explore how champions like Shelley-Ann Fraser-Pryce and Julien Alfred train, recover, and maintain excellence — and how those lessons translate into building sustainable, successful businesses in the Caribbean. 🏃🏽♀️
We cover:
The system of success behind elite athletes and how it applies to entrepreneurship
Reframing setbacks as part of the long arc of growth
Building a culture of discipline, resilience, and excellence in your business
Caribbean-specific insights on mentorship, support systems, and enterprise-building
If you’re a Caribbean entrepreneur, freelancer, or anyone navigating the challenge of building your own enterprise, this episode offers practical inspiration and actionable ideas to help you run your business like a champion.
What does it take to make your vision real? In this episode of the Island Woman Podcast, I share how my own vision took shape, why imagination is powerful, and what really matters when it comes to turning a dream into reality.
You’ll hear about the daily video diary practice that gave me clarity, how reflection shaped my Rooted & Ready programme, and why compounded action — the small steps done consistently — is the most important key to living the life you imagine.
✨ Inside this episode:
How to use imagination to shape your vision
The daily practice that rooted me in clarity and growth
Why compounded action matters more than one-time breakthroughs
A personal story about lessons in persistence and consistency
How to move beyond “what could be” into what is
If you’re a woman in leadership ready to embody your voice, presence, and power without overwhelm, explore the Rooted & Ready 3-month 1:1 programme. Email me at diannensquires@diannensquires.com for details.
🌴 The Island Woman Podcast is about cultural clarity, holistic wealth, and intentional living — rooted in the Caribbean, with a voice for the world.
Share your thoughts: Is having a vision important to you? How do you keep moving toward it?
Not everyone will choose you — whether it’s for a project, a friendship, or a role in their life. But that doesn’t mean you’re not worthy of being chosen.
In this episode, I share why choosing yourself matters, what it really looks like, and 3 small but powerful ways I’m practising it right now.
From the crowded buses of my teen years in Barbados to the lessons I’ve learned about podcasting, boundaries, and vision-setting, I explore how following your inner compass creates the space to breathe, grow, and excel.
If you’re ready to stop waiting for validation and start walking your unique path, this episode is for you.
✨ In this episode:
Why “choosing yourself” isn’t selfish, it’s sustainable
How a clear vision helps guide your decisions
3 daily practices to honour your own time and energy
A story of how not choosing myself once stalled my growth — and what I’m doing differently now
🌺 The Island Woman Podcast celebrates Caribbean women, Caribbean stories, and the pursuit of holistic wealth, rest and renewal, and intentional living.
📌 Share this episode with a friend who needs the reminder: choosing yourself is the first step toward freedom.
Caribbean realities are complex, from high youth unemployment to the rise of informal work, gender inequality, and climate threats. But alongside the challenges, there’s a deep well of hope, ingenuity, and resourcefulness we can tap into.In this episode of the Island Woman Podcast, I explore how we as Caribbean people can manage distractions, stay focused, and hold onto what’s real. Drawing on insights from the Caribbean Development Bank’s Labour Market Differentials in the Caribbean study, we’ll look at three truths that can keep us grounded: 1️⃣ The power of sharing and community: from backyard produce to collective entrepreneurship. 2️⃣ Turning off the noise: and protecting your mental space in a hyper-connected world. 3️⃣ Caribbean ingenuity: the traditional practices and mindset shifts that can fuel sustainable living and a stronger future.If you care about Caribbean resilience, sustainable living, and economic empowerment, this conversation will inspire you to see possibilities beyond the “doom and gloom.”
Are you over 35 and starting to feel niggles in joints you forgot you had? For me, it’s the ‘phantom pains’, the ones you can’t link to anything you did. If that’s you too, we’re not alone.
In the Caribbean, joint-related issues linked to NCDs and more sedentary lifestyles are showing up earlier and more often than we think. In this episode of the Island Woman Podcast, I’m joined again by Nutritionist Carla Ramsay.
She talks about 3 essential things you can start doing today to protect your joints and preserve your mobility as you age. From anti-inflammatory foods to muscle support and sunshine, this is a must-listen for every Caribbean woman who wants to move freely and live fully.
And tell your younger friends that nutritionist Carla says, “Don’t wait, start showing your joints some love from now. They’ll thank you as you age.”
👣 Whether you're already feeling joint pain or just trying to prevent it, this episode will help you take grounded, powerful steps toward long-term health.
Welcome to Season 2 of the Island Woman Podcast! We kick off with the first episode in a three-part health and wellness series. I’m joined by seasoned nutritionist
in Barbados’ National Nutrition Centre, Carla Ramsay, to explore the incredible benefits of one of the Caribbean’s most treasured staples — breadfruit.
Why does breadfruit belong on every island plate?
From its affordable, versatile nature to its rich nutritional profile, breadfruit offers a powerful alternative to more processed foods and expensive imports.
It’s a powerful food in the fight against non-communicable diseases, like high blood pressure and diabetes, major concerns across the Caribbean region.
We discuss practical ways to prepare, store, and enjoy breadfruit dishes that honour our heritage and support healthier living.
This conversation is packed with insights to inspire your next island meal.
🌿 Join our Island Woman podcast family as we explore what it means to live a BIG and simple life.
In this season finale, I reflect on the idea of courage and what it really took to leave corporate, pursue dance, raise a child while studying abroad, and carve out a life that’s both big and simple.
Is this way of life brave… or just bold and naive?
I share what “big and simple” means to me and why it’s not small, broke, or boring. It’s my personal manifesto for living well without the overwhelm.
Thanks for walking with me this season. Season 2 is coming soon.
Welcome to the final episode of the Clarity Series on the Island Woman Podcast, a space for Caribbean women who, like me, are rethinking success and ready to move with intention.
In this episode, “Clarity in Action: A Success Blueprint for Caribbean Women Over 40,” I’m exploring how to turn your clear vision into bold, grounded decisions without burnout, hustle, or upending your life.
Whether you're a seasoned expert, an emerging leader, or a purpose-driven creative, this episode will help you:
✅ Move toward your redefined vision of success
✅ Align your time, energy, and money with your vision
✅ Recognize and act on opportunities with confidence
✅ Let your Caribbean cultural values guide your leadership and voice
This episode is especially for Caribbean women who want more visibility, financial freedom, and ownership of their time without starting from scratch.
Ready to move from clarity to action with support?Explore the Clarity & Visibility Package — a 1:1 experience to help you define your vision, refine your message, and show up with cultural confidence. 📅 Book a discovery call: https://calendly.com/diannensquires/discovery-call
🎨Clarity Series Sponsor: Made Alive Design & Co.
For intentional visuals and video editing that bring your message to life.
Contact them:
Instagram: @madealive.design;
Email: akeem@madealive.me
Other Episodes in the Clarity Series:
EP. 9 - Career Fog to Focus: 4 Clarity Anchors for Women Redefining Success
EP. 10 - Speak Clearly About Your Work Without Being a Showoff
#IslandWomanPodcast #CaribbeanWomen #RethinkSuccess #VisionToAction #ClarityAndVisibility #IslandWomanEthos #CaribbeanVoices #CulturalConfidence #DianneSquires
Do you want more opportunities to do what you’re great at, but feel awkward talking about your work? You're not alone. In this episode of the Island Woman Podcast, I share how women, especially Caribbean women can show up and speak clearly about their work without feeling like a showoff.
You’ll explore:
✅ Why clarity is the first step to meaningful visibility
✅ How to speak about your value without self-promotion that feels icky
✅ Cultural nuances that make visibility more complex (and more powerful)
✅ Three core tips to get grounded in how to speak clearly about your work.
Whether you’re pivoting your career, building a consulting business, or just ready to be seen, this is your invitation to do it in a way that’s clear, honest, and aligned with your values.
🔗 Mentioned in the Episode:
Clarity & Visibility Package — a 1:1 strategy experience by Island Woman Media & Messaging
Book a discovery call: https://calendly.com/diannensquires/discovery-call
🌴 Connect with Dianne: linkedin.com/in/dianne-n-squires-a2389132
Sponsored by: Made Alive Design & Co. Motion graphics and podcast video editing for creators who want to show up beautifully.
Contact: akeem@madealive.me;
Instagram: @madealive.design
In this first episode of the Island Woman Clarity Series, sponsored by Made Alive Design & Co., we explore how to move from career fog to focus with 4 powerful clarity anchors every woman (or man) needs when redefining success on her (his) own terms.
Whether you’re shifting from a 9-5 to consulting, entrepreneurship, or simply seeking a new path, this episode will help you root yourself in your values, define success your way, and build the confidence to show up and be seen.
Mentioned in the episode:
Rooted & Ready Clarity & Visibility Package →
Book a discovery call: https://calendly.com/diannensquires/discovery-call
Episode Sponsored by Made Alive Design & Co.
For motion graphics, video editing, packaging design
Instagram: @madealive.design; Email: akeem@madealive.me
In this episode, I reflect on how Caribbean women like me are redefining success. From being raised to value financial independence to walking away from traditional corporate careers, we're still choosing big ambitions, but in new ways.
Tune in if you're rethinking your version of success too.
Sometimes the right YES can’t happen because we’ve said yes to too many wrong things. In this episode, I share a personal story about missing a dream opportunity — and the powerful lesson I learned about the importance of saying NO.
This is a reflection for women who do too much, give too much, and rarely put themselves first. Especially island women like me.
Let’s talk about boundaries, burnout, and making space for a BIG, simple life.
My experience of nature growing up in St. Philip Barbados has given me some of the most powerful memories of my childhood. In this episode of the Island Woman podcast, I’m sharing my nostalgia for nature back then and the joy it brought me. I discuss how the shift from an agricultural economy to tourism has transformed our landscape in Barbados, leading to some loss of that natural beauty. While I mourn that loss, I believe we can still create a nature-nourishing industry for the future starting with each household. I’d love to hear how nature has changed in your area—share your thoughts in the comments below!
Call it #stayathomework or #workfrom home; it doesn’t matter. It is currently the work-life that I think works best for me.
In this episode, I share my thoughts on my home being my workplace and how remote work measures up based on three ingredients I desire for my 50-plus Island Woman work-life.
➡️ Autonomy over my time
➡️ Creative freedom and
➡️Robust health
You won’t believe the traffic challenges in this island life that make stay-at-home work life-changing! Plus I’ll share my number one productivity tip for working from home to juggle everything from creative projects to focused work. So, grab a cup of tea and tune in to hear how working from home can redefine what a fulfilling Island Woman life looks like!
If you liked this episode share it with a friend and follow the channel for more updates on living a BIG and simple life.
❤️Your Island Woman,
Dianne AKA D-Anne
#BigandSimpleLife