Leadership Is Rarely Black and White

Leadership would be a lot easier if every decision were black and white.

Designing Board Meetings for Meaning, Momentum, and Mission

Across the association community, I am hearing a consistent refrain from board members who care deeply about mission and impact: time is precious, and tolerance for low-value meetings is shrinking.

For years, through Healthy by Association, we’ve talked openly about wellbeing in the association and hospitality communities — movement, nutrition, rest, boundaries, and community. But over time, I’ve noticed something deeper happening in conversations with colleagues, clients, and friends: Leadership is taking a heavy toll on people. Not because they’re doing anything wrong — but because the role itself has changed.

Today’s leaders are juggling:

• constant travel
• nonstop expectations
• year-end pressures
• organizational change
• shrinking teams and expanding workloads
• culture-building responsibilities
• the emotional labor of supporting everyone else

And while so many leaders are committed to creating healthier workplaces, they often feel they can’t talk about their own burnout, loneliness, or mental health challenges. That gap — that silence — is why The Leadership Wellbeing Series was born.

This new podcast, co-hosted with my friend and colleague Tara Puckey, creates space for honest conversations about what it really takes to lead well without losing yourself in the process. Each episode features leaders who are willing to speak candidly about stress, boundaries, stigma, resilience, and the power of connection.

Season 1 explores six themes we know leaders are craving space to talk about: