Cave Days
Bring your idea. Leave with a plan.
Join us February 6, 2026.
Cave Day is a focused work retreat designed to help you turn a single project into a concrete plan you can execute. In one guided day, you’ll outline your goals, break your project into phases and tasks, identify what’s getting in the way, and build a clear three- and six-month timeline. You’ll leave with a completed project plan, immediate next steps, and simple systems to keep you accountable so you can start moving forward right away.
Deadline to apply is January 7, 2026.
Cave Day: The New Year Reset
Before the year gathers momentum, you deserve one intentional day to step back and get organized.
Cave Day: The New Year Reset is a guided work retreat designed for an exclusive group of people who are serious about moving an important project forward and want the structure to finally do it. The retreat will take place at the Howard County Conservancy, a nonprofit land trust that operates a nature center on the historic 300-year-old, 232-acre Mt. Pleasant Farm in Woodstock, Maryland. The Conservancy’s open fields, wooded trails, and restored farm buildings offer a quiet, grounded setting that makes it easier to think clearly and reset your pace. It is less than an hour from both Washington, DC and Baltimore, making it an accessible escape from the speed of the city.
This retreat is not about resolutions or visioning. It is a space to plan. A space to break down the work you want to do in 2026 and map out exactly how you will move forward. Because this experience is intentionally curated, we select participants who are ready to work with clarity, honesty, and momentum.
Throughout the day, facilitators and business advisors, Faye McCray and Sherry Samuels, will guide you through prompts that help you name the mental barriers that slow you down and the tactical ones that make big goals feel out of reach. You will choose one project or pivot to focus on, outline what success looks like, break the work into phases and milestones, and build a three-month and six-month plan you can trust. You will also receive executive-level feedback from facilitators with more than fifteen years of experience across multiple industries. Specially curated feedback groups will offer real-time insight and accountability to help you refine your plans and build momentum.
You will leave with a completed project plan, a clear timeline, immediate next steps, a strategy for working through mental and logistical barriers, and a renewed sense of clarity and momentum.
Who Should Attend
People preparing a pivot. Writers outlining a book. Entrepreneurs shaping a new offer. Anyone ready to stop circling an idea and start moving. Participants should come with one project in mind and a commitment to doing focused, structured work throughout the day.
The cost to attend is $199.
The event will take place on February 6, 2026, at the Howard County Conservancy. Applications will be accepted on a rolling basis, and applicants will be notified of their status within 48 hours. The final deadline to apply is January 7, 2026.
“Start where you are. Use what you have. Do what you can.”
— Arthur Ashe