Rooted at Last: How Squared Away Became Jordan’s Steady Ground

Beyond Orders

In the inaugural episode of Beyond Orders, host Michelle Penczak sits down with Jordan Streetman Cole, Chief Experience Officer at Squared Away, for a powerful conversation about the realities of military spouse life and the unexpected opportunities that can come from uncertainty.

Together, they unpack Jordan’s journey from applying to Squared Away out of sheer desperation to growing into a key leadership role within the company. Along the way, they explore themes of reinvention, resilience, and the deep need for stability in a life shaped by constant change.

This episode dives into the unique strengths military spouses bring to the workforce, the transformative power of meaningful assistant-client partnerships, and why building community and trust is at the heart of it all. Whether you’re navigating career transitions, PCS chaos, or simply looking for a story that reminds you you’re not alone, this one’s for you.

Because while military orders may move us, they don’t have to define us.

Jordan's book reference - Time, Talent, Energy

• The podcast aims to empower military spouses to rewrite the rules of their careers.
• Desperation often drives military spouses to seek new opportunities.
• Stability in employment is crucial for military spouses facing frequent relocations.
• Resiliency is a key trait of the Squared Away team.
• Building a community among military spouses enhances support and connection.
• Successful client-assistant matches require time and investment in understanding each other.
• Celebrating wins, both big and small, is essential for motivation.
• Reframing opportunities for military spouses can change perceptions in the workforce.
• Reinvention is about honoring one's potential and evolving into the best version of oneself.
• Leadership is about empowering others and leading by example.