Confessions of a leader who cares a lot
A story of good intentions and bad cookies
I worked as the Director of Strategy at a large healthcare organization during the later stages of the COVID-19 pandemic. Remember that long, strange stretch when the adrenaline had worn off and no one was quite sure when, or whether, things would ease?
While many of my colleagues were on the front lines in gowns and N-95s, I spent most of my days on Zoom, looking at faces in squares and sustaining momentum on longer-term strategic priorities. Somewhere along the way, a quiet, heavy sense of guilt settled in my chest.
In a tearful session with my Executive Coach, it finally surfaced. It felt wrong to be so far removed from the challenges of front line work.
So, with the support of our leadership team, I did something. It began with spearheading a small but meaningful staff appreciation initiative.
The concept was simple: greeting staff on every shift with cookies and handwritten notes of appreciation. The execution, however, involved a lot of thought.
Infection control. Fiscal responsibility. Dietary needs. Healthy options. Packaging. Sustainability.
I eventually found the perfect ethically sourced, allergy-friendly, vegan, and individually wrapped cookies, and drove across town to pick up enough boxes to fill the back of my mid-sized SUV.
The day itself went beautifully. My management colleagues and I stood at entrances handing out cookies at shift changes. I went home tired, feet sore, and quietly proud to have stepped out from behind my screen to show care in a more direct and immediate way.
The next day, a colleague came into my office, closed the door, lowered their voice, and said something that made me want to both laugh and cry:
“People are talking about how disgusting those cookies were.”
Despite all the care and intention behind the gesture, the thing that lingered, for some, was… disgusting cookies.
Ugh.
I share this because I know so many leaders who can relate.
You care deeply. You think things through. You do your best to act with integrity and consideration.
And sometimes, it lands sideways.
Moments like this reveal the inner side of leadership — the quiet tension between intention and impact, pride and doubt, caring and exhaustion. They remind us that leadership isn’t just about what we do; it’s about what we carry inside while we do it.
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This is the terrain The Collective was created for: a space where experienced leaders explore that inner landscape alongside others who truly “get it”.
Together, our members cultivate the inner steadiness to keep showing up with care and energy — especially, when things go sideways.
We currently have space for two Executives to join The Collective starting in February.
If this story made you smile, wince, or think “oh yes, I’ve been there,” you’ll feel right at home among the big-hearted leaders in our group.
