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.