About Cassandra
I’m a therapeutic coach for high-achieving men, CEOs and entrepreneurs, over 40, who feel stuck or disconnected. I help them break free from outdated ideas of masculinity, embrace emotional growth and rediscover purpose. Working globally with top leaders, I’ve also just written a book called ‘Unlearning Masculinity’ (out spring 2025), to support men in building lives that truly fulfil them.
We asked Cassandra to look back and reflect on her younger self
Q&A’s
How would you describe yourself at 18?
I was independent and ambitious, with a boundless belief that anything was possible. Hard work wasn’t something I shied away from; I embraced it. I was also the caring one in my group of friends, the one people confided in when they needed a listener.
What inspired you to start your own business?
I’ve always had an entrepreneurial streak – finding ways to make money without relying on others or being bossed around. I launched my first business at 25, a recruitment agency, followed by a cupcake business (I know – what possessed me?!). My current business is my third and, now seven years old, it truly reflects who I am today.
If you could go back knowing what you know now, what three things would you tell yourself to do when you first became a business owner?
- You’re the Sales Director now – own it. Selling is a skill you can’t avoid, so get comfortable and embrace it. It’ll serve you for life.
- Progress, not perfection.Stop worrying about getting it ‘just right.’ Nobody’s paying as much attention as you think and imperfect action beats perfection every time.
- Your network is your net worth.Relationships matter. Nurture them and pay it forward. Generosity and connection will open doors you didn’t even know existed.
What are the biggest lessons you have learnt professionally?
Everyone sees the world differently. The key is to get curious, not judgemental. Don’t assume you know better – listen and understand the perspective of others.
How did you deal with a big mistake, and what did you learn from the experience?
In my 20s, my first business was both a success and a failure. Rapid growth outpaced my ability to manage cash flow and instead of seeking advice, I pushed through alone. The stress mounted and things spiralled. At the same time, I was grieving my father’s death and my marriage was on the rocks. I’ve done significant healing since then and now see it as a financial lesson that shapes how I run my business today. I learned that success isn’t about having all the answers – it’s about knowing when to ask for help.
What are your ambitions for the future?
My ambition is to continue building a successful coaching business that gives me the freedom to live life on my terms while making a meaningful impact. I’m passionate about serving men and helping them redefine success, and my book is a key part of that vision.
What does the future have in store for you personally?
Gosh, who knows?! While I have a vision, I’ve got my oars up, ready to let the universe guide me. What I do know is that I’ll continue my own coaching and growth journey. I also want to travel, explore and soak up life’s richness.
Feeling stuck, trapped, or disconnected from who you are? ‘Unlearning Masculinity’ is for high-achieving men over 40 who are ready to redefine success and create a life of clarity and freedom. It dives into the beliefs, values and relationships that shape your life, offering practical tools to uncover and shift limiting beliefs. Walk away feeling seen, heard and empowered. Register on my website for book updates and exclusive early offers.
Photos of Cassandra taken by Chris Ball.
