The Joy Collective
The Joy Collective
Kerry Ann Rockquemore

The Annual Clarity Retreat


I'm Kerry Ann: Angel, Mentor, and Cultivator of Joy!

I retired in 2017 and now spend my time doing what I love most: reading, writing, mentoring leaders, investing in women led start-ups, and supporting grassroots organizing. And my passion project in retirement is sharing the process that has had the greatest impact on my life: the Annual Clarity Retreat.

What is The Annual Clarity Retreat? 

Back in 2006, my husband and I were miserable, workaholic perfectionists careening towards midlife crises. From the outside, our lives looked like the American Dream. We had great jobs, a wide circle of friends, a beautiful home, lived in an amazing city, and had opportunities to travel the world. But on the inside, we felt exhausted and miserable. We were two hamsters on a wheel, running ourselves ragged every day.

We did everything we were supposed to do to be "successful": earned college degrees, got married, got good jobs, bought a house, saved for our retirement, went to church every Sunday, and volunteered in our community. But instead of feeling happy or successful, we were working all the time, killing ourselves to advance other people’s agendas, and left wondering: is this it? 

Then one year we snapped. 

We quit Christmas and left the U.S. to avoid over-eating, over-consuming, and over-doing the holidays. That December, we spent our time re-thinking how, why, and for whom we were living our lives. It wasn’t pretty, but we emerged with a radical sense of clarity, a plan for the new year, and a set of practices to keep us grounded. We called the process our Annual Clarity Retreat and it truly transformed our lives.

Since we started our Annual Clarity Retreat, we:

  • Quit the jobs that were making us miserable
  • Started, scaled and exited 2 companies
  • Spent 10 years as "snowbirds"
  • Traveled to 30 countries, 
  • Became Financially Independent and Retired Early (FIRE)
  • Unplugged from Social Media and plugged in to our real lives
  • Fell deeper in love with each other
  • Celebrated 25 years of marriage and partnership
  • Supported entrepreneurs, activists, and community organizations in creating positive change, and
  • Stopped chasing happiness and found our joy

To be clear, our life isn’t perfect, our marriage isn’t perfect, and we aren’t perfect. But using this process for the past 15 years, we’ve built a life that is delightful, fulfilling, meaningful, and successful (by our own definition).

Now every December, I guide a group of people through the Annual Clarity Retreat. It's a free, 4-week course that requires 3 hours per week of intense personal work. If you’re ready to dig in and work towards generating your own clarity, I welcome your application to join us.

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