Cards & Conversation: Five of Pentacles
Taking stock of your losses to discover the bounty you maintain.
Welcome to Cards & Conversation, a space for personal reflection and community conversation on the intuitive side of leadership—the “gut check” we all need to stay aligned to our values.
On the Bosscraft Podcast and in the Bosscraft Community, we often discuss the reality of sustainability in your consulting practice, including finances. But today, we’re looking at the energy behind it. Success isn’t just about the “up” moments; it’s about how we navigate the “down” ones. Are you leading with a scarcity mindset, or can you see the light through the window?
The Card: Five of Pentacles
Take a moment to look at the card. Traditionally, it depicts two figures walking through the snow, past a glowin stained-glass window. In my deck, the stained glass window is shattered, breaking the beautiful facade. What do you see? Do you see the struggle of the strom or the proximity to warmth? Is there help waiting, if you looked up to see it?
I use the Vindur Tarot deck, developed by Leah Pantéa, which is now out of print, but I recommend learning a deck that strongly reflects the Rider-Waite imagery.
The anatomy of the card:
The Suit (Pentacles): In tarot, Pentacles represent the element of earth. they govern the physical world: finances, health, career, and material resources.
The Number (Fives): Upright, Fives often represent a moment of instability, conflict, or change. It’s a transition point in the cycle where things feel off balance. Reversed they may be more about an internal change or sticking point.
In the upright position, the Five of Pentacles represents a period of material or financial winter. It’s that moment in which resources feel thin or you feel excluded from a warm inner circle, of sorts. Maybe you are equating the stability and warmth that material resource provide with happiness and fulfillment. However, it is also a card of resilience. It reminds us that help is often available, but we are frequently too focused on our own struggle to ask for it. It may also remind us of what we have, and call us to use our own material wealth to support others who need it.
For mission-driven folks, the energy of the Five of Pentacles calls for a different kind of strength. It shows up when:
You find yourself in a “losing” season—a launch didn’t go as planned or a key partner walked away—and you realize this is the moment to see what core truths remain once the external fluff is stripped away.
You catch yourself falling into the “scarcity trap,” where your decisions start being driven by a fear of “not enough” rather than the deep, guiding mission that started your practice.
You confront the “lone wolf” fallacy, realizing that struggling in silence because you think a leader “should” have it all figured out is actually the only thing keeping you out in the cold.
You stop staring at the closed door and finally notice the “stained glass”—the community support, personal health, and dormant wisdom that have been right next to you all along.
You trade the exhaustion of “powering through” for the grace of radical honesty, understanding that asking for help isn’t a sign of failure, but a strategic move toward sustainability.
The Bosscraft Take: Embodying the lesson of the Five of Pentacles isn’t about wallowing in a hard season—it’s about having the humility to look up. This card is an invitation to stop pretending you are an island and to start leading from a place of communal resourcefulness. When you are aligned with this energy, you don’t just survive a downturn; you use it to build a more honest, resilient foundation and look for opportunities to support others. It’s time to stop trying to be the hero of a tragedy and remember that the light in the window is meant for you, too.
The Conversation
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This week’s prompt: The Five of Pentacles asks us to look up from our struggle and notice the support available to us. What is one area where you’ve been “walking in the cold” alone, and what is the “warm window” (a resource or person) you’re ready to reach out to?
I’ll be in the comments sharing a recent moment where I had to trade my “I’ve got this” armor for a little bit of community warmth.