"Caution in midlife is perhaps the most fatal to true happiness..."
Inspired by my colleague Eleanor Mills's astute adaptation of Bertrand Russell's famous quote about love, this week I'm unpacking our need to Go For It in midlife.
Yesterday I listened back to the latest Debrief episode of the Queenager podcast. Host Eleanor Mills and I were discussing three takeaways from her interview with Avivah Wittenberg-Cox and Eleanor suggested that “caution in midlife is the worst kind of caution” - à la Bertrand’s Russell’s wonderfully romantic observation about love. Her words struck a chord, because I’ve recently been deliberating about fear and low confidence - and how many women (including me!) get to midlife and think: “FFS, it’s time to release the stranglehold fear has on my life!”
It’s interesting to focus on caution, because caution is the result of fear and lack of confidence. Fear makes us cautious, and then we step back from opportunities - seeing them as just too risky. Caution is aligned with playing small - something we often only see in retrospect. We look back and see how our lives simply veered gradually into the shadows where we then hid from all that felt scary.
I’ve been inadvertently tapping into this with my current series of videos on LinkedIn about fear of public speaking. They’re prompting some really interesting observations about how we perceive this specific fear - and what we think we can do about it. Because the most obvious way to deal with a fear of public speaking - is to not do it! This, I only realised recently, was a solution I too could have adopted a long time ago. What can I tell you, I’m a slow learner…
I jest of course. Because although I had crippling anxiety around public speaking dating back to my pre-teen years, it never crossed my mind to not keep stepping up and doing it. And I guess that’s because I was a keen and capable performer from childhood. I was a massive and happy show-off at the family dinner table from an early age, and sang THE nativity solo aged about 5 or 6 dressed as the cutest sheep ever in the massive local church. My confidence was then to be crushed over the next handful of years as life, and cruel others, did their thing. Yet there remained a determination: I was going to get over my nerves and own the spotlight again whatever it took, and however painful the process might be!
I now see that my determination to overcome something I found so overwhelmingly scary was pretty awesome, but in the context of my family dynamics it was nothing short of revolutionary. Because my Dad was a decidedly cautious man. He firmly believed that dwelling on the worst that could happen was the best approach to life. For him, there was a right way to do things and decisions should always be made in line with the safest and most conservative option. My siblings and I were directed to study ‘sensible’ subjects and get ‘proper’ jobs. Having not adhered to the latter, his diminishment of my successful career in media (“But when will you be reading the news?”) was ongoing and painful to endure.
However, like many of us, my more youthful frustration and at times anger at my parent’s critical stance softened over the years into a greater understanding. Although I’d always known of his brutal experience in central Liverpool during the war - his home was bombed; the family spent nights under the stairs as the city burned; he was evacuated to the Isle of Man as a small boy with his sister and Mum - it took the passing of many years for me to suitably comprehend the deep impact those early experiences had on him.
What had been a thrilling story for me and my sister as children - knowing we were staying in the ‘box room’ that had been bombed clean through decades earlier - became an insight into my Dad’s cautious demeanor. Of course these experiences left a lasting imprint on him. He even spent his entire professional life in insurance assessing risk - the signs were literally always there! So naturally, going on to transmit his caution to his children appeared sound to him, even if in reality it was unhelpful at best .
I don’t know what specifically had me commit to throwing myself onto stages and into endless gut-twisting situations in the hope that at some point I’d ‘get over’ my nerves. Possibly the need to shed this shameful ‘weakness’ which I believed it to be. But I similarly don’t know what had me go so massively against the family culture and follow my passion of pop music and radio.
Unfortunately, however, my massive actions in pursuit of confidence weren’t enough to recalibrate it to its original setting on their own. Just following my passion, i.e. performing - which I’d already shown myself and others I could do well - couldn’t break the spell of anxiety. I consequently spent decades struggling with my ongoing panic attacks.

Midlife was the turning point, as it is for many. It’s a particular phase where a mind blowing cocktail of events and changes vie to overthrow our status quo - whether it’s been happy or otherwise. This maelstrom’s often not much fun and can manifest as multiple challenges and endings like redundancy, divorce and bereavement. If you’re there, you know what I’m talking about! But there can also be a silver lining inside all these stressful life events: we can shift our perspective and start shaking ourselves out of cautious living.
As they say - two things can be true at the same time.
And although it wasn’t a direct path (ha - what ever is?), my journey to healing my public speaking anxiety clearly began a few years ago after I was sideswiped by a serious health challenge. It included not one but two significant and reckless misdiagnoses that had me - for an extended period of time - believing I was terminally ill. There’s nothing like thinking you’re about to die to have you reassess what matters and what needs to go!
And fear had to go. I had to get a handle on it, because I felt that its insidious presence was doing me no favours and had itself perhaps played a role in the illness I did have. More immediately back then, if I was dying I didn’t want my remaining time to be spent in overwhelm and chronic fear. I was pragmatically clear about that.
So with that powerful - if massively unwelcome - motivation, taking steps to access my fear, own it and release it became imperative. And facing that fear had me start unpacking what other fear might be residing in my body and my life. I then began pursuing options and protocols that I would have been way too scared to undertake were it not for my terrifying diagnoses. Oh the irony!
My intense and overwhelming experiences with my health over a period of a few years was the prompt I needed to make long overdue changes. I established new practices of self-care, set boundaries and began taking decisions that enabled me to step into a far better life and way of being.
I perhaps hadn’t been cautious per se - doing stand-up comedy to get over your performance anxiety is no-one’s idea of cautious I know! But I hadn’t been taking the bold action I needed to really make the difference my health and psyche required. I had been on autopilot for so long I didn’t really register the pain I was in and the resistance I had to accessing the support and healing I needed.
So I share my story to illustrate how we can get stuck in caution. I remained stuck in my fear by dealing with it and hiding it in ways that aligned with the cautious culture of my family. It was only when I embraced new ways of thinking and being that were totally outside my experience and upbringing that my life changed in necessary - and incredible - ways.
I don’t want you to wait for life’s car crash to prompt you into action. Sure, we humans resist change and we tend to hold off from taking any action until the pain of staying where we are feels utterly unbearable. But what if you threw caution to the wind right now and considered how you might be being cautious in ways that are impeding your happiness and well being? If you’re honest - what bold actions might you be avoiding - and what beautiful possibilities might open up if you dared to move beyond cautiousness?
What if you took a breath and saw where things are already unbearable and gave yourself a break?
Do me a favour - as someone who had to get not one but two massive wake up calls - give it at least a little consideration. Because life’s short: let’s not waste time being scared of it.
DFY recommends…
Watch this…
There’s nothing like an incredible documentary about an extraordinary individual and real life superhero to have you appreciating life and sobbing in your biscuits. Super/man: The Christopher Reeve Story is that documentary, and it’s currently streaming on Amazon.
Featuring intimate home-video footage and contributions from his family and many celebrity buddies, the film is a celebration of Reeve’s extraordinary life. With warts-and-all footage showing the courage and strength that saw him through almost a decade paralysed from the neck down, the film’s a humbling tale of high, lows and ultimately, love.
Book this…
A great way to move out of caution without doing anything too scary, is to book a FREE taster coaching session with me.
Because if you’ve hit a wall and realise you need to do something different with your life, you might just need coaching support to make those necessary shifts.
So if you’re ready to make real change, just click here and arrange a 30 minute slot where we’ll explore your midlife reinvention and how you might best achieve it.
You’ll leave your powerful 30 minute session with:
Your personalised goals and achievable outcomes.
A new awareness about your professional and personal skill gaps and what’s been holding you back (it might not be what you think!)
Renewed motivation to do things differently and take charge of your destiny.
A next-step action plan for exploring new options, acquiring new skills, and stepping into a new professional phase that aligns with your ambitions.
I’m foundations certified in Women’s Centred Coaching, which is an evidence based framwork that’s proven to specifically tackle the ways in which women are held back in life.
So whatever success looks like to you - overcoming public speaking and performance anxiety, raising your game professionally, finding true love, following your neglected dreams - and yes, releasing your fears! - I can personally vouch for how this is genuinely transformative coaching.
It’s likely the missing piece you didn’t know you were looking for.
Email wendy@dramafreeyou.com with any questions you don’t see answered at my website www.dramafreeyou.com
What are you waiting for?
It’s time to reset your midlife - let’s do this!
That’s it for now - keep on reaching for your best self, and reaching out to those who might help you.
Because Drama belongs in the movies, not in your life.
Until next time,
Wendy