From Strength to Purpose: Redefining Leadership in Midlife

What if the qualities that got you here - certainty, drive, expertise aren’t what will carry you forward?

In this conversation, Brett Wright reflects on a personal and professional shift that many high-achieving leaders eventually face but rarely talk about: what happens when your identity has been shaped by performance, and suddenly, that’s not enough?

Brett Wright is Chief Revenue Officer at Tortoise and has held senior roles at Macquarie and AXA Investment Managers. He's also the founder of Leadership Nexus, a community focused on navigating personal and professional change. Brett is passionate about redefining leadership through humility, intention, and meaningful relationships.

He shares what it was like to go from a Penn State football player taught to never show weakness, to an executive learning that vulnerability might be the most powerful form of strength. That showing up with “I don’t know, let’s figure it out together” builds more trust than pretending to have all the answers.

In this conversation, we explored leading with clarity, crafting a more connected second chapter, and navigating uncertainty.

Key Takeaways:

• Building community is essential for personal and professional growth.

• Leadership is about connection and caring for others.

• Navigating uncertainty requires focusing on the process, not just outcomes.

• Vulnerability is a strength in leadership and relationships.

• Finding purpose is crucial for a fulfilling life.

• Loneliness can be a significant issue later in life.

• Crafting a life involves understanding your values and experiences.

Leadership That Evolves

Early in our conversation, Brett shared a shift that changed the way he operates:

“I used to think strength was never showing weakness. Now, I think it’s being honest when I don’t know and inviting others to figure it out with me.”

It’s effective, particularly in high-stakes scenarios where trust is more important than control.

Brett’s approach, what he calls the “how might we?” mindset, isn’t just about collaboration. It’s about stepping away from needing to be right and focusing on creating space for better thinking.

Apprehensions That Show Up in Midlife

We identified several common concerns that often arise in midlife, even when your career appears to be progressing well. These appear in subtle ways: how you lead, how you connect with others, and how you handle uncertainty. Many high performers are excellent at solving external problems but haven’t taken the time to pause and ask what they genuinely want now and what they’re ready to stop doing.

Brett’s story is a reminder that successful people can still feel stuck, not because they’ve failed, but because something deeper is grabbing their attention.

What Joe Paterno Got Right

Brett’s leadership foundation was shaped early by his football coach at Penn State, Joe Paterno. But it wasn’t about game strategy; it was about how you treat people.

“He sat at your kitchen table and told your parents, ‘I want to help your son become a better man.’”

That kind of care stuck with Brett. It shaped his belief that leadership is personal before it’s professional. That people are more willing to grow, stretch, and perform when they know they’re being seen, not just evaluated.

Community That’s Built, Not Inherited

For Brett, community isn’t just a side effect of career success; it’s something he’s deliberately built with care, consistency, and a sincere desire to go beyond the transactional.

He explained that, over the years, he has built spaces, such as his annual ski and golf trips and, most recently, the Leadership Nexus group, not for networking, but for authentic connections. These events weren’t about exchanging business cards; they focused on conversation, friendship, and being genuine.

“The magic doesn’t happen at the event, it happens on the chairlift, the walk down the fairway, or over a beer when someone opens up about their life.”

The conversations weren’t about deals or titles. They were about kids, aging parents, self-doubt, marriage, and purpose. And over time, those repeated, honest conversations grew into a network of support.

What Brett has learned, and models, is that sustaining real community in midlife requires intentionality. You can’t just wait for it to show up. You have to create the conditions: regular time together, mutual curiosity, and space to be vulnerable. And perhaps most importantly: You don’t just need people you can lean on; you should also be the person others can call when they’re struggling.

Community, in this sense, becomes more than connection. It becomes a source of accountability, grounding, and a mirror for your evolving self. Especially when you’re navigating change, stepping out of a title, or rewriting the story of who you are.

From Resume Values to Eulogy Values

At a certain point, the accolades, titles, and achievements, the resume values, stop feeling like a complete picture of success. Brett described this shift clearly: the resume might still look great, but the question becomes, Would any of this show up in my eulogy?

He referenced David Brooks' idea of the "second mountain", that stage in life where the pursuit of performance gives way to a deeper desire for purpose. That transition isn’t always smooth. It often starts in a low point, when a job changes, the identity connected to it diminishes, and you're compelled to ask yourself: Who am I when I’m not being productive?

Brett started to shape his life around the values he wanted to be remembered for: presence, trust, generosity, and growth.

The shift from resume to eulogy values doesn’t mean abandoning ambition. It means grounding your choices in something that endures when the title fades and making sure the way you live reflects what matters.

Drop the Outcome. Focus on Process.

When facing uncertainty, it's common to focus on outcomes, such as the next job, role, or clear sign that you're "back on track." However, Brett suggested an alternative approach: releasing the urge for quick answers and instead concentrating on what is within your control. He described how, in a moment of professional transition, he felt off-balance, not just because he didn’t have a next step, but because the structure that once defined his days was gone. Rather than rushing to replace it with another goal, he turned inward and rebuilt his rhythm from the ground up.

The goal wasn’t efficiency. It was stability, clarity, and agency in the face of the unknown.

His process became the anchor:

• Daily movement to stay grounded in his body

• Meditation to build mental space and focus

• Reading to feed curiosity and insight

• Regular connection to stay in relationships, not isolation

“You don’t land where you want to go by accident,”

Brett said.“

You land there by what you do consistently.”

By focusing on the process, rather than the outcome, he created a sense of momentum, even when the destination was unclear. The process became the point.

Questions Worth Asking

This conversation didn’t provide clear formulas, but it raised valuable questions, particularly if you’re going through a period of change.

What part of your identity no longer fits, but you’re still holding onto?

• Where are you defaulting to control when curiosity would serve you better?

• Who are you in community with, outside of your professional role?

• What small structures could help you stay grounded in what matters?

Then write down whatever comes to mind. Write down your answers, honestly, without editing. But even small shifts in awareness can change the direction you’re heading. If you want to improve your leadership, creativity, and contribution, this is where it starts, not with more output, but with greater self-awareness.

If this resonates with you, you’re not alone.

Even high achievers need to understand their motivations. Contact me if you're ready to rebuild with more clarity and connection. Coaching can help you make space for what matters.

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