The Clarity Retreat: Find Your Direction for the Year Ahead
The Clarity Retreat is a self-paced course for anyone ready to pause, reflect, and choose a clear direction for the year ahead.
Through four guided sessions and a thoughtful workbook, you’ll review where you’ve been, clarify what you want, and begin moving toward what matters now.
Clarity isn't something that arrives. It's something you create.
Most years end in a blur: a little time off, a few half-formed intentions, and then the new year begins before you’ve had a chance to truly reflect.
The Clarity Retreat creates the space you’ve been meaning to give yourself — to look back honestly, vision boldly, and move into the year ahead with genuine direction rather than good intentions.
The Clarity Retreat is designed for you if:
You end every year feeling like it went faster than you planned and mattered less than you hoped.
You've been meaning to do this kind of reflective work for years — and keep finding reasons to put it off.
You're a whiz at strategic planning in your workplace, but you've never applied those skills to your own life.
You want clarity but aren't ready — or don't have the time — for an eight-week deep dive.
You're at a transition point and need to get clear before you can move forward.
You're tired of starting each new year with good intentions that fade within a month.
This isn't a course. It's a ritual.
Four recorded sessions. Each session is 90 minutes and guides you through one step of the process: reviewing your year, creating your Life Vision, examining your beliefs, and setting intentions. Watch them on your schedule, pause when something lands.
A digital workbook. This is where the reflection happens. You'll analyze twelve months of your own data, write a holistic vision across every area of your life, and set intentions you actually want to pursue.
Lifetime access. The process deepens with repetition. Return every year — many participants say their second or third time through produces their most significant insights.
Begin at any transition point. Year's end is popular, but the process works equally well at the outset of an empty nest, sabbatical, or birthday that ends in zero.
What clarity actually looks like.
-
Clarity on the past year
Twelve months of data, thoughtfully reviewed. You'll know what worked, what didn't, and why — with a fuller perspective than whatever you feel right now.
-
A Life vision that excites you
Your life is far bigger than the work/family binary. You'll create a holistic vision of the life you truly desire — instead of organizing your life around other people’s expectations.
-
Goals that move you towards your vision
Grounded, achievable goals aligned with the life you want to create — instead of random resolutions, “should” goals, or another year of vague good intentions.
-
![]()
"After the Annual Clarity Retreat, I've become better at balance."
"The most important insight for me from the Annual Clarity Retreat was the full appreciation for all areas of my life. While, conceptually, I knew that there was more to my life besides the work I do — in reality, work had shaped most of the decisions I'd made and governed how I spent my time. After the ACR, I've become better at BALANCE. I'm intentional about prioritizing time for relationships, creativity, my money, and my health. I still have room to grow but I'm happy with the shifts."
Shanique Brown, PhD, Professor
Detroit, Michigan, USS -
![]()
"It taught me to clarify the frameworks of my values and intentions.."
"Completing the Annual Clarity Retreat helped me process what had been a big year of change for me, but even more importantly it taught me to clarify the framework of my values and intentions. Having this written out has helped me with direction and decision making through this past year."
Kelly Holman, Architect
Seattle, Washington, USA -
![]()
"Going through the process last year, I got so much closer to my ideal lifestyle!"
"Last year I redefined my goals so that they were all within my control. And I achieved most of them, despite so many macro changes! It was also great to look at my life so holistically, daydream about my ideal life, and actually have a timeframe for my goals. Just by going through the process last year, I got so much closer to my ideal lifestyle!"
Anya Chernyshova, Business Coach
San Francisco, California, USA
I'm Kerry Ann Rockquemore, PhD — a guide for women navigating midlife transitions.
In 2006, my husband and I looked successful from the outside — good jobs, a beautiful home, full lives, endless opportunities. But inside, we were exhausted workaholic perfectionists wondering, Is this it?
Then one year, we snapped. We quit Christmas, left the country, and spent December rethinking how, why, and for whom we were living. We emerged with clarity, a plan, and a set of practices we've repeated every year since.
Twenty years later, that ritual helped us build a life that is genuinely ours — financial freedom, meaningful work, real adventure, deeper joy, and success by our own definition.
The more this process changed our lives, the more I wanted to share it. The Clarity Retreat is that same annual ritual, distilled into four recorded sessions and a digital workbook you can follow at your own pace.
Since 2019, I've guided more than 1,500 people through it. Many return every year — not because they failed to find clarity the first time, but because the process deepens with repetition. For them, it has become a cherished annual ritual they don't skip.
One retreat. A clearer year ahead.
Investment: $99
What’s included:
4 recorded video sessions
A digital workbook
Lifetime self-paced access so you can return to the process each year
Frequently asked questions
-
Each of the four recorded sessions runs approximately 90 minutes. Most people complete the retreat over one to two weeks, working at their own pace. Plan for six to eight hours total, including the sessions and workbook exercises.
-
Yes. The self-paced Clarity Retreat is available year-round, and you can begin today. Many people use it at the end of the year or the start of a new one, but the process works at any transition point: a new semester, sabbatical, birthday, career change, or season of reflection.
-
The self-paced retreat includes the same core process as the live version: four sessions, the workbook, and the full reflection framework. The live version, offered twice a year exclusively to Annual Members, adds real-time facilitation, group discussion, a buddy match, and the energy of doing this work alongside others. If community and live interaction matter to you, the Annual Membership may be the better fit.
-
Yes — and many people do. Partners often describe the retreat as one of the most meaningful conversations they’ve had in years. Families who use it as an annual ritual find that it creates a shared language around values, vision, and goals. Each person completes their own workbook individually, then shares as much or as little as they choose.
-
Many of our most committed participants return every year. The process doesn’t repeat; it deepens. Each year, you bring different experiences, questions, and desires to the same framework. What emerges is always different because you are different. Many participants say the second or third time through produces their most significant insights.