Annual Clarity Retreat
Annual Clarity Retreat
Kerry Ann Rockquemore

Welcome to the Annual Clarity Retreat!

Welcome to 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, had 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 28 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 17 years, we’ve built a life that is delightful, fulfilling, meaningful, and successful (by our own definition).

While I’ve written about our Annual Clarity Retreat in the past, it’s hard to capture the depth of the process (and the internal work) in a single blog post. While I can describe the steps, it’s qualitatively different to do the work for yourself.

So every December (since 2019), I guide a group of people through the Annual Clarity Retreat. It's a free, 4-module course that requires 3-hours per module of intense personal work. You can do the modules all at once, over a weekend, or over four weeks. All the information is available at the beginning of the course, so your pace is up to you.

I have to warn you up front! 

Every year, about 1/3 of participants drop out after the first step when they realize this isn't superficial resolution-setting or magical thinking, but a time and labor-intensive process. Another 1/3 get to the middle of ACR, realize they are in deep emotional waters and swim away. And the other 1/3 -- probably the people who invited you here -- finish all four steps of the retreat and find it profoundly transformative. 

How Does the Course Work?

The Annual Clarity Retreat is set up as a 4-step course:

  • There is a video describing each step, providing tips for new participants, and suggesting advanced moves (for people who do the retreat annually). 
  • There are weekly co-working sessions for participants who want to do one-step per week. It's a great opportunity to do the work of ACR and get any questions you have answered on the spot.

If you’re ready to dig in, reflect, and work towards creating a meaningful life, we welcome you!


Kerry Ann