Who’s Holding Your Ladder? by Deborah Gray-Young

Deborah Gray-Young is a former advertising agency executive who now serves as a trusted advisor to senior executives and SMB CEOs. Known for distilling complexity, challenging assumptions, and clarifying high-stakes situations, she brings candor, strategic insight, and a grounded perspective that helps leaders see possibilities and lead with intention.

Happy New Year to each and every one of you and your families.

As we begin this new year, it’s the perfect time to take stock of our support systems. One of the most common and least discussed roadblocks to success is the absence of a strong support system. This is especially true for women who have been raised to be self-sufficient and self-reliant. While those traits are often celebrated, they can quietly work against us in certain professional environments, particularly for women of color.

For many women of color, independence is deeply ingrained. Asking for help doesn’t come naturally. We are quick to support others, often without being asked, but far more reluctant to seek support for ourselves. When challenges arise, our default response is to work harder, push through, and figure it out alone. And when that stops working, we don’t always look for help; we look for a way out.

Instead of looking for an exit, consider this question: What does your support system look like? More specifically, who’s holding your ladder? Who have you intentionally chosen to be part of your inner circle, both professionally and personally?

In his book Who’s Holding Your Ladder?, leadership coach Dr. Samuel Chand describes an experience that offers a powerful metaphor. While waiting to speak at a church, he noticed a painter working on a building across the street. The man had climbed as high as he comfortably could and stretched as far as his arms would allow—but no further. Chand couldn’t see the base of the ladder and wondered aloud who was holding it steady.

The insight came quickly: the painter wasn’t incapable of going higher. He simply wouldn’t, and shouldn’t, do so unless someone was holding the ladder. The work required help.

Dr. Chand applied this lesson to leadership in ministry. When I first encountered this story, I saw something broader: a metaphor for leadership, career growth, and life. At the end of the day, most of us aren’t asking for special treatment. We want a fair chance to demonstrate our ability. One of the most effective ways to create that advantage is to stop going it alone and build the right support system.

Friends and family who cheer you on matter. We all need people who believe in us. But we also need at least one person who will tell us the truth, hold us accountable, challenge our thinking, and call us out when necessary. Not with judgment or criticism, but with honesty rooted in love and respect. The kind of truth-telling that risks temporary discomfort for long-term growth.

While the new year is still young, take a moment to reflect. Who’s currently holding your ladder? And whose ladder might you be holding for someone else? Support systems aren’t static. They require intention and, sometimes, adjustment. Who knows how far you could climb if your ladder is strong and sturdy?

Until next time,
Deborah Gray-Young

Twitter: @coachdgrayyoung

IG: @d.grayyoung

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