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