Vanessa Wakeman: Balancing Strategic Silence and Bold Language in Challenging Times

On this episode of The PlayFull Podcast, host Kristine Michie welcomes Vanessa Wakeman, founder of The Wakeman Agency, for a rich and candid conversation rooted in strategy, courage, and language. Vanessa brings decades of communications leadership to this episode, but it’s her ability to blend intention with imagination that truly resonates. Whether you're navigating high-stakes messaging, questioning how to show up bravely in your work, or looking to bring more play into serious change-making, this conversation offers ideas that could shift your entire approach.

Key Takeaways:

• Nonprofit leaders should regularly assess whether their language still reflects their mission and audience; outdated or overly cautious terms can unintentionally undermine trust.
• Rather than avoiding sensitive language entirely, organizations can develop customized communication frameworks to navigate risk while staying aligned with their values.
• Consulting partnerships should be seen as opportunities for growth, where trusted advisors help uncover blind spots and introduce bold, necessary shifts in messaging.
• Leaders must consider not just what they say, but when and how they say it—sometimes strategic silence protects both people and progress.
• Integrating joy, humor, and creativity into work environments—such as implementing a team “Bucket List Fund” or encouraging personal play—supports team resilience and authentic leadership.
• Language strategy isn't about optics; it’s about reinforcing accountability to the people you serve and maintaining alignment with long-term equity goals.
• How stand-up comedy and art-collecting can be grounding practices that reconnect changemakers with purpose and presence.

"Fun is important. I’ve really tried to make [it] a source of resistance in my life." — Vanessa Wakeman

"Joy is really important to me, and so I want to make sure that I am not letting it happen, or hoping that by happenstance something joyful happens. I want to be in control of it." — Vanessa Wakeman

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