Women’s Strategic Planning Retreat

This program is full. Contact Leigh about participating in the winter 2026 retreat.

Join a small group of women entrepreneurs* in getting clear on crafting your business to fit your life. Make space for yourself to envision and map out the year ahead (and beyond). Use your planning muscles to actualize what you envision.

The Plan

An initial gathering in January to prepare and a day and a half retreat in February designed to support you in clarifying, articulating, and mapping out where you are headed with your work and how you intend to get there. This is followed by a check-in Zoom meeting one month following the retreat. Doing this as a small team of women allows us to explore together, learn from one another's unique perspectives, and gain valuable insight on our business planning.

The initial gathering, the retreat, and the check-in Zoom meeting will be facilitated by Leigh Tillman. Leigh will guide you through a collaborative process to shape the unfolding of your business and thoughtfully integrate it with your life.

*This program is inclusive to all who want to join.

As one of Leigh’s partnering organizations explains this intention: “CEI aligns with the definition of women and female that explicitly includes not only cis women, but also trans women and femme/feminine-identifying genderqueer and non-binary individuals.”

Please feel welcome and that this is for you.

• Participants Will Come Away With:

  • A compass setting that honors your life and your business – that honors you

  • Clarity on where you want to go and how you want to get there

  • A roadmap of what you are doing – with who and by when

  • Enhanced understanding of an array of planning techniques and how to cater them to your planning intentions

  • A team to engage with in the year ahead to support the unfolding of the course you’ve set

  • Gratitude toward yourself for making this time for you and your business

• The Group:

  • Women entrepreneurs and small business owners of noncompetitive businesses

  • Women who are in it – i.e. your business is your primary form (or one of your primary forms) of work and source of income

  • Women who want to do this together – to have a team to support and be supported by in your work

• Dates, Times, Locations, Cost, and Scholarship Funding:

  This retreat happens every winter in Maine. Details will be posted for next winter’s retreat later this year.

  Contact Leigh to learn more.

• To Register:

  Registration is not currently open. Join the mailing list to stay informed about when it will open later this year.

This program is now full. To inquire about joining next winter’s retreat, please fill out this form:

Open "Inquiring to Register" Form by Clicking Here

Women's Strategic Planning Retreat 2025

A big thank you to the Opticliff Law team for generously providing scholarship funding for the 2025 retreat.

With Opticliff Law’s generous support, Leigh Tillman Facilitation is thrilled to offer a scholarship specifically for a local farmer or food producer here in Maine to attend this winter’s Women’s Strategic Planning Retreat.

Other scholarship funding is also available - write Leigh directly to inquire.

Participant Testimonials

“Leigh is a dream to work with. Her ability to move you through your vision and goals while holding space for your humanness is impressive. This was my second time joining a group with her and I am so inspired!”

Hedda Campbell, Primal Blossom Landcrafting and Plantcare, 2024 Participant

“Leigh is an incredible facilitator. As a woman-owned business owner, she knows well the challenges we face and the joys we experience. The content of the retreat, the purposeful and thoughtful work, helped me refine my vision and create a workable plan going forward. The group of women was amazing. I feel energized and inspired.”

Stephanie Noyes McSherry, Executive Director, Merry Barn Writers’ Retreat, 2024 Participant

"The Women's Strategic Planning Retreats led by Leigh provide an outstanding opportunity that women shouldn't miss! Leigh has brilliantly mastered a transformative workflow that took me to surprising places, deconvoluting my many ideas and organizing the complex process of launching my new business into achievable bits. Her retreats bring together women across generations and backgrounds, each with unique aspirations yet aligned in values and success metrics, which adds tremendous depth to her platform. Not only have I optimally broadened my network, built accountability and grew from interacting and listening to those amazing women, I have also acquired clarity and knowledge that I am implementing right now as my company forms! Thank you, Leigh!"

Pascale Richalet, Ph.D., Portland, ME, 2025 Participant

“Leigh creates a program and holds a space for leaning into that program in a profound and graceful way. I felt so held, informed, and nurtured as I was given the space to dive into my business plan and all the life that goes with it.”

Seren Sinisi, Old Crow Ranch, 2019 Participant

“This Strategic Planning Retreat is a must for any woman, at any stage of her career/life. The intentional exercises, thoughtful feedback and venues were perfectly curated to create a productive and meaningful process. I will be doing this again in three years with Leigh!”

Angela Cleveland, The Place Above the Notch, Bethlehem, NH, 2025 Participant