Evolving Beyond the Leader You Had to Become
/My Moment of Reckoning
I once thought the next stage of my leadership evolution was becoming a Vice President.
When my company reorganized, I applied for and became acting VP of Operations, overseeing IT and a broader operational vision the company hoped to grow into.
A few months later, I realized something uncomfortable: I could not succeed in the role as the organization currently existed.
Not because I lacked capability or commitment. But because the leadership alignment and operational support needed for the role to succeed simply were not there.
Eventually I sat down with the CEO and told him I wasn’t going to let the company fail by continuing to force something that wasn’t working.
We made an unusual agreement. I stepped back into a senior project management role while helping transition and orient the eventual permanent VP of Operations.
And something surprising happened.
I discovered I had far more influence and impact in that role than I would have expected.
The evolution I needed was not becoming a bigger version of the leader I thought I was supposed to become.
It was becoming more aligned with the kind of leader I actually was.
And there was something else I eventually came to recognize.
The role would likely have consumed far more of my time and energy than I wanted to give.
At the same time, I had already spent years singing with the Boston Gay Men's Chorus, which had become an important part of my life, identity, community, and expression.
At the time, I don’t think I fully understood how deeply that mattered.
I just knew that the version of success I thought I wanted was no longer fitting as cleanly as I expected.
The Leader You Had to Become
Many leaders evolve ways of thinking, behaving, and leading that help them succeed.
Over time, those adaptations can become so familiar that they stop feeling like choices and start feeling like identity.
Over time, many leaders begin telling themselves things like:
“Being needed started to feel safer than being replaceable.”
“I knew which parts of myself fit the culture and which parts didn’t.”
“My value has always come from having the answers.”
“I do my best work in crisis mode.”
“I got very good at staying analytical instead of vulnerable.”
“Visibility was never a simple yes-or-no decision.”
“Eventually I realized that integrating more of who I was made me a better leader, not a weaker one.”
These strategies may once have been necessary, effective, or even lifesaving.
But eventually leadership asks a different question:
“Is the version of me that succeeded before still the version needed now?”
Four Dimensions of Evolution
Leadership evolution rarely happens all at once.
More often, it unfolds gradually through shifts in awareness, identity, priorities, relationships, and the way we respond to ourselves and others.
Here are four dimensions of evolution I increasingly notice in myself and in the leaders I work with.
Awareness – Seeing Differently
You are still reacting from old patterns that no longer serve your current reality.
Perfectionism. Tight control. Constant urgency.
These strategies may once have helped you succeed. They may even have protected you.
But leadership evolution asks whether your reflexes are still aligned with the reality you are leading in now.
⭐ Create even a moment of awareness before your old reflexes take over, allowing yourself to choose instead of simply repeating what once worked.
Integration - Becoming More Whole
As you’ve aged, you’ve become more nuanced, more complex.
The ways you understand yourself — and the ways the world understands you — may have evolved too.
⭐ Make room for aspects of yourself you’ve minimized or set aside or left behind as you’ve progressed in your career. Let it all enhance your leadership, your voice, your authentic performance.
Sustainability – Releasing What Drains You
Let go of the constant urgency.
The vigilance. The pressure. The feeling that everything is critical and depends on you being constantly available and relentlessly good.
Your mind and body cannot sustain that forever.
⭐ Use the very skills that helped you survive pressure to instead meet life and leadership with more equanimity.
Impermanence - Letting Go Intentionally
Nothing is permanent.
Roles change. Relationships evolve. Cultures shift. New generations redefine what matters.
Over time, we inevitably let go of identities, expectations, capacities, and assumptions we once thought were fixed.
⭐ Be less about holding on and more about becoming intentional about:
what matters most
what we want to carry forward
and what kind of impact or meaning we hope to leave behind
Become You
For many leaders, evolution begins as a strategy for success.
But eventually it becomes something more personal. A question of:
what still fits
what no longer does
what you’ve outgrown
what parts of yourself are asking to return
and who you want to become next
You do not need to discard the leader you once had to become. But you can evolve beyond them.