4 Essential Lessons in Midlife Leadership
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Hi, I’m Jason. If you are a midlife man in a leadership role, I’ve created The Prime Movement for you. It’s a community for those of us who believe in the power of progress - in leadership and in life. Dare to know. Dare to grow.
What’s coming up:
Prime Performance: This Week’s Best News, Views & Life-Hacks
The Prime Perspective: 4 Stoic Secrets for Modern Leaders
Lessons from the Trenches: The Team Dynamic That Blindsided Me
Be a Prime Mover: 1 Quote to Spark Change
Prime Performance: this week’s news, views and life hacks
READ 3 ways to avoid career irrelevance
Based on my interaction with leading midlife executives, the fear of becoming irrelevant in their careers consistently ranks as one of their biggest fears. Even entrepreneurs have these concerns when it comes to their business (and let’s be honest, their status - these fears are just as much emotional as they are rational). No-one likes to feel irrelevant. Rishad Tobaccowala’s latest knowledge bomb is essential reading if you’re in either group. As the man himself says: “Unless we plan to end our career in a year or less, we will have to begin future proofing right away whether we like it or not.”
WATCH 24 seconds on the danger of later
A 24-second Instagram reel from Hyrox Master Trainer Jake Dearden that hits hard. It’s a message you’ll have heard before, but it has extra resonance in midlife. Let’s vow to not leave it till later…
LISTEN 2 hours of the some of the best relationship advice you’ll ever hear
This week renowned psychotherapist and best-selling author Esther Perel joined Rich Roll, the ultra-endurance athlete and wellness advocate, to talk human connection. The podcast covers everything from loneliness in relationships through to intimacy and self-awareness. Whatever your current situation, I promise you that you will find something of value for you here.
The Prime Perspective: Personal reflections on leadership and growth
4 Crucial Lessons in Midlife Leadership (from my time with Ryan Holiday)
Last week in London I was fortunate enough to have a front row seat for Ryan Holiday's talk on modern stoicism and leadership. As I sat there watching The New York Times' bestselling author share timeless, practical wisdom, I couldn't help but reflect on how perfectly his insights spoke to the specific challenges we face as midlife executives and entrepreneurs.
I believe in the power of sharing knowledge - so I've distilled my detailed notes into the 4 most impactful lessons for our TPM community.
Holiday reminded me that the ancient Stoics weren't just philosophers - they were warriors, generals, and men of action. Socrates was a soldier, Seneca practiced cold-water immersion, and Marcus Aurelius trained in boxing. They understood something we often forget today: true leadership integrates mind, body, and emotional mastery.
For us as midlife leaders, this integrated approach has never been more relevant. We too must be gladiators in our own arena - ready to face the mental, physical, and emotional challenges that each day brings. It’s why Dr Brendon Stubbs and I are building the TPM Program.
He also explained that the four core virtues of the Stoics - Wisdom, Courage, Justice and Discipline - aren’t just philosophical concepts, they are practical tools for navigating life's complexities. As I sat there taking notes, I decided to distil them into lessons to help guide you on that path:
🧠 1. The power of curiosity (Wisdom)
Holiday spoke about how Socrates, even in his final moments of life, never stopped questioning and learning. In our midlife leadership roles, it's easy to fall into the trap of thinking we need all the answers.
True wisdom lies in maintaining genuine curiosity and embracing the journey of discovery. The moment we stop questioning is the moment we start declining.
Personal Reflection:
Where have you stopped being curious, in role and ln life?
What assumptions about your leadership, your capabilities, or your future have you left unexamined?
What questions you should be asking yourself are you avoiding?
🦁 2. The Bravery to Engage (Courage)
It's tempting at midlife to retreat into the comfortable, to focus on past achievements or regrets rather than future possibilities. Holiday emphasized that courage isn't about fearlessness – it's about choosing engagement over retreat. As midlife leaders, we often feel constrained by responsibilities, expectations, and past decisions, but the reality is that each moment presents a fresh opportunity to choose who we want to be.
True courage is choosing the right path… even when it is the harder one (those of you who read last week’s Prime Perspective know the harsh lesson I learned about this).
Personal Reflection:
Where are you running on autopilot?
Where are you actively choosing comfort over growth?
What possibilities are you avoiding exploring because they feel too challenging or create feelings of uncertainty?
⚖️ 3. The Network Effect (Justice)
Our actions as leaders create ripples far beyond our immediate sphere, in role and in life. Holiday spoke about how each choice we make – how we handle pressure, prioritize our health, treat our teams or families – doesn’t just have implications for ourselves, it sets standards for those around us. This 'network effect' means our personal growth has the ability to directly impact the organizations, families, and communities you are a part of. The clear message was that with great power, comes great responsibility.
Personal Reflection:
How are your current choices and behaviors influencing those around you (both intentionally or unintentionally)?
What messages do you want to send through your actions your team, family, and broader network?
What steps are required in order for you to do that?
⚔️ 4. The Integrated Life (Discipline)
Drawing on Roosevelt's 'strenuous life' philosophy, Holiday showed how the Stoics viewed physical, mental, and leadership development as inseparable. They understood that sustainable excellence requires integration – treating mind, body, and character development as one unified practice.
Their physical practices weren't separate from their philosophical work - in fact, they were essential to it. For today's midlife leaders, this integration is crucial. The challenges of executive leadership demand both mental acuity and physical resilience. Tthis means rejecting false choices between professional success and personal wellbeing. Leadership energy IS physical energy. The discipline to maintain an active lifestyle directly translates to the discipline needed in the boardroom.
Personal Reflection:
What stories do you tell yourself about being "too busy" for physical engagement?
How are you currently viewing the relationship between physical and mental performance?
What would true integration look like for you?
A Note on Real Change
Let me be direct: I’m not going to insult your intelligence with shallow prompts or "one simple trick" solutions. You've led teams, built businesses, and navigated complex challenges - you know meaningful change requires more than a morning routine checklist or a productivity hack.
The wisdom shared by Holiday isn't about quick fixes. It's about the deeper journey of integrated leadership development. If you're looking for easy answers, there are plenty of internet gurus happy to sell you those. But if you're ready for real transformation - the kind that creates lasting impact across your professional and personal spheres - then it's time to consider a different path.
The Path Forward
These virtues aren't separate domains to master or quick fixes to implement. They're interconnected aspects of the same goal: becoming the most effective leader you can be. This integration of physical, mental, and emotional mastery is exactly what we champion at The Prime Movement.
The ancient philosopher-warriors understood what many modern leadership programs miss: you can't separate the development of the mind from the training of the body, or the growth of the individual from their impact on others.
The question isn't which small habits to change, but how to begin this larger journey of transformation. The arena of life awaits. How will you show up?
Would you like guidance on taking the first steps of this journey? Let's talk.
Lessons from the Trenches: Real life leadership challenges
Every week, I address real challenges faced by leaders like you. These insights come from both TPM readers and anonymized coaching experiences. Because when one of us faces a challenge, we can all learn from it.
CHALLENGE:
"I'm struggling with finding the right balance of closeness with my team. Everyone says 'don't be too friendly, don't be too distant' like it's obvious, but I'm finding it much more complex in practice. How do you navigate this, especially as teams become more diverse?"
MY TAKE:
When an entrepreneur I’m friends with recently dismissed this as "coaching bullsh*t" - just basic common sense about not being too close or too distant - it reminded me of a pivotal moment in my own leadership journey that proved just how wrong that simplistic view is (spoiler alert: we’re still friends!)..
I had been working closely with a team member who was going through some personal challenges. Over several months, I'd helped him navigate these difficulties and this coupled with our growing professional respect for one another was forging bonds. At a company social event, he approached me and gave me a heartfelt hug of gratitude, also taking time to thank me for my support. In that moment, it felt like leadership at its most authentic - a genuine connection, visible growth, mutual respect.
Shortly after I was chatting with a senior female member of the same team and she expressed concern that my relationship with this team member, culminating in that public display of camaraderie, was creating a perception of a "boys' club" that made others feel excluded. Several team members had noticed the pattern of attention and worried about favoritism.
A younger me would have been on the defensive immediately and would have potentially felt the need to explain to her why she was wrong.
Instead, I took this as a learning experience. This was a wake-up call. What I'd seen as supportive leadership was inadvertently creating division. The simple act of accepting a hug - which felt natural and human in the moment - and spending a disproportionate length of time with that individual, had sent unintended signals about access and inclusion to the wider team.
The lesson? The right’ leadership distance isn't a simple calculation - it's a complex matrix that includes:
Individual relationships
Team dynamics
Gender dynamics
Organizational culture
Public vs private interactions
Precedent-setting
Power dynamics
MY GUIDANCE:
Be intentionally consistent in how you show support and recognition
Consider the wider audience for your interactions
Create structured opportunities for connection that are accessible to all
Be explicit about your support mechanisms and how people can access them
Regularly seek feedback from diverse team members about team dynamics
Remember: What feels like authentic leadership in one context can create unintended consequences in another. The goal isn't to reinvent the wheel here, as you’re clearly coming from the right place, it’s simply to be more intentional about how that support is structured and displayed.
If you’ve got a situation you want guidance on, message me at jason@theprimemovement.com.
Be A Prime Mover: Wisdom to inspire action
“We live on an island surrounded by a sea of ignorance. As our island of knowledge grows, so does the shore of our ignorance.”
John Archibald Wheeler, Physicist
MY TAKE:
When Ryan Holiday shared this quote at his London talk last week, it struck me as a profound truth about knowledge and humility that I'd never encountered before, despite decades of learning and leadership (just realised that sounded like a humble brag - not the intention!).
The metaphor is deceptively simple but extraordinarily powerful: as our knowledge (the island) expands, so does our contact with what we don't know (the shoreline). The more we learn, the more we realize there is to learn.
Intrigued, I went down a rabbit hole to learn more about Wheeler. This wasn't just any physicist - this was the man who worked with Einstein, coined the term ‘black hole’, and mentored Richard Feynman. Ironically my lack of knowledge about Wheeler served only to prove his point!
For midlife leaders, I believe this insight is particularly valuable. We're at a stage where our expertise and experience can sometimes become a barrier - leading us to think we've ‘done enough’ or "know all the important stuff”. Wheeler's metaphor, much like the Stoics, reminds us that true wisdom lies in maintaining our curiosity and humility, especially when we think we know the answers.
This isn't just philosophical musing - it's a practical reminder that leadership in your prime years requires both confidence in what you know and humility about what you don't.
Your challenge this week: Identify one area where your expertise might be blocking your curiosity. Step back to that shoreline and ask some new questions.
Dare to know, dare to grow.
If you enjoyed this, please consider forwarding it to a friend. We are stronger together.
Your thoughts are the fuel that keeps us moving forward, so message me at jason@theprimemovement.com.
