The Art of Speaking Up: Why Midlife Is Your Moment for Courageous Conversations
By Helen Jarvis, Founder of Ripple Learning and Second 50 member
There are moments in life when you know a conversation matters deeply.
You can feel it before a word is spoken, with a tightening in your chest, the flutter of nerves and your thoughts beginning to race.
Part of you wants to say the thing that has been sitting quietly for weeks, or even years, while another part urges you to stay silent and keep the peace.
For many women, this tension feels especially familiar, and in midlife it can surface more strongly than ever.
Through my work as a mediator, counsellor and coach, and my own midlife transitions, I have come to see these moments not as problems to avoid, but as invitations into what we call courageous conversations.
These are the conversations we often put off because the topic feels sensitive, emotionally charged or uncomfortable. They might involve different perspectives which are strongly held, or when a reaction is likely. The stakes can also feel high because it touches something precious, such as a relationship, our own wellbeing, or our sense of fairness.
Yet these are the very conversations that often shape our lives.
Midlife conversations that matter
Midlife is full of conversations that shape our lives. Conversations with partners about changing needs and expectations. With adult children about independence, contribution and boundaries. With ageing parents and siblings about care, roles, responsibility and money. And at work it can be about flexibility, leadership, relevance or the possibility of change.
Yet many of these conversations never quite make it out into the open. Instead, they are replayed internally, repeatedly, as we wrestle silently with who we are becoming and what we are no longer willing to carry.
In my work, it is often midlife women who describe feeling this pull most acutely, as long-standing patterns of accommodation meet a growing need for more wellbeing and self-respect.
Many women have spent decades smoothing things over, holding things together and staying quiet to preserve harmony. While this pattern is deeply ingrained, it often comes at a cost to women’s wellbeing, particularly as life becomes more complex in midlife.
Over time, a desire emerges for greater honesty alongside kindness, and for ways of speaking up that do not damage important relationships.
I know this is something that resonates with many Second 50 women. We have a shared sense that this stage of life is not about shrinking or enduring, but about choosing to live with more intention and joy.
But even with that clarity, many women (like most people) find they have never been taught the skills to speak up with confidence.
Supporting courage with skills
It is important to highlight that having a courageous conversation is not about winning or proving a point.
It is about being conscious and purposeful in the way you engage when emotions are strong and the outcomes matter. It is also about protecting both our relationships and our wellbeing.
When we lack the skills to navigate these moments, our nervous system takes over and we slip into fight, flight or freeze mode. We may say too much or nothing at all, and leave the conversation feeling unheard, misunderstood or explosive.
Sometimes we retreat and tell ourselves it was not worth it. Or we push too hard and damage the very relationship we were hoping to preserve.
None of these paths tend to serve us well.
What I have learned, and what I love sharing, is that when we understand what is happening in our brains and bodies under stress, we can move from being reactive to intentional.
We also stop judging ourselves and feel confident to make conscious choices about how we show up and speak up.
Finding your courageous voice is a learnable skill
One of the most hopeful things is that having courageous conversations is not a personality trait, but a learnable skill set.
Skills like grounding yourself when emotions rise, listening in ways that de-escalate tension, and speaking assertively without aggression can all be learned, practised and improved.
So can naming what matters while staying connected, and knowing when to lean in, and when it is time to step back.
These conversations are always contextual and often quite personal, so practising them in a psychologically safe spaces matters enormously.
Through our Ripple Learning training programs, I have seen time and again that when people practise these kinds of conversations with the right support and thoughtful feedback, their confidence grows. Not because the conversations become easy, but because they become navigable.
Why this work matters beyond the individual
When people build the capacity to have courageous conversations, they do far more than change a single interaction.
They begin to change patterns of behaviour at home and at work, strengthen their relationships and protect everyone’s wellbeing. They also model something powerful for others, including their children, colleagues and friends.
When someone has the skills to speak clearly, calmly and with compassion about what matters, it creates a ripple effect. Ripples of understanding, respect and courage that extend far beyond one conversation.
A different way forward
I often hear people say, “I know I need to say something, I just don’t know how”. Or, “I am afraid it will all fall apart if I speak up.” Or even, “I have waited so long, it’s too late now”.
My experience tells me something different. It is rarely too late, and the world usually doesn’t collapse when the truth is spoken with skill and care. More often, something opens.
If you find yourself standing at the edge of a conversation you have been avoiding, I invite you to pause and get curious.
What matters here? What are you protecting? And what might be possible if you had the skills and support to speak with both strength and compassion?
Courageous conversations are not about being fearless. They are about being willing to understand yourself better, stay grounded when you speak, and care for the relationship at the same time.
Practised with care, courageous conversations can open new possibilities, not just in one moment, but in how you move forward from here.
invited me to write this piece for Second 50 because these themes have been surfacing again and again in our community. I am deeply grateful to be part of an ecosystem where women are willing to reflect honestly, learn together, and build skills that support both wellbeing and connection.
I am really looking forward to continuing this conversation with Second 50 women who are curious about this work, whether through shared reflections, questions, or learning together in person at our upcoming Sydney workshop (see below).
About Helen Jarvis
Helen is a Nationally Accredited Mediator, Family Dispute Resolution Practitioner, Counsellor, Coach, Facilitator of Restorative Engagement conferences and Clinical Supervisor in private practice. She brings an in depth mix of change management experience, mediation and corporate coaching. Helen facilitates conversations between workplace employees who are in conflict or going through rapid change; providing a safe forum for them to discuss the underlying issues and make decisions together. She has extensive experience mediating for non-profit, health, education, construction, call centres and local councils. Helen is also a lecturer for the College of Law. She teaches the Mediator Training Programme and subjects of the Graduate Diploma of Family Dispute Resolution. Helen's volunteering commitments are focused on the mental health and wellbeing of youth. Learn about Ripple Learning here.
Courageous Conversations: A One-Day Learning & Wellbeing Workshop in Sydney
This workshop grew out of conversations in Second 50, where we heard the desire for practical ways to navigate important conversations. We are proud to be partnering with Ripple Learning to co-host this wonderful day of immersive learning, connection and courage for our community.
WHEN: Friday 27 March 2026, 9:30 am – 4:00 pm
WHERE: Cuppa Co-Lab, Barangaroo, Sydney
COST: $149 (includes lunch, refreshments and all materials)
Helen is generously donating her time and expertise. Your ticket price simply covers the cost of running the day and engaging a photographer/videographer to help Ripple Learning strengthen its impact storytelling. All profits will be directed to Ripple Learning’s youth mental health charities. This partnership supports the confidence and wellbeing of Second 50 women, while also amplifying a cause that creates positive change far beyond the room.
You do not need to be confident or outspoken to join, just open to learning alongside other Second 50 women.