A Coastal Outing with Leigh and Jess - August 31st, 2026

Come spend a morning in community, by the sea, away from your work and for your work.

This was such a lovely gathering in late August 2026. We will definitely be holding more workshops and retreats in this vein - keep in touch to learn about what’s coming!

We are heading to the coast, with picnic baskets, journals, swimsuits, and good company. On the heels of summer when life can be so full and active. We are making space to touch base with where your work thoughts are at as we feel the first chill in the evenings.

Join Leigh Tillman Facilitation, Uproot Pie Company, and peers for this experience. This is a time to notice the wisdom of late summer as it pertains to your work. To make note of the ah-has, questions, curiosities, depletions, considerations, excitements, possibilities you are experiencing. Maybe this is a snapshot you will revisit in the quiet and coziness of January planning…maybe you want to ground some new awareness into how you shift into fall. Maybe you want space for questions you are holding.

There will be invitations to walk, sit, swim if you like, write, share, listen, eat delicious food…there will be time as a whole group, small groups, and solo.

Let this be a celebration, a break, a delving in, a time for working ON your business. Sometimes we need to step away to see it all from a different perspective.

This gathering is about a love for being out on the shoreline, in community, amidst the sea breezes, in our bodies, in the moment.…this is about the wisdom these spaces hold and offer us…this is about a love of gregarity and depth…and where the two dwell together allowing us to be both boisterous and still...to know and not know.

This workshop is for you if:

• You primarily do your big picture business thinking on your own and would value delving in alongside peers to offer and gain perspective and insight

• You want to make time to work on your business

• You want to gather with peers to consider and discuss what is feeling true in this season and what that means for where your work is headed from here

• The Group

  -Women* entrepreneurs and small business owners of noncompetitive businesses as well as contractors and women who want to look at their worklife picture in totality.

  -Women who want to do this together – to be in community, to support and be supported by in your work

  *This program is inclusive to all who want to join. Please feel welcome and that this is for you.

• Date, Location, Cost, and Registration

  This workshop will be held on the coast in Owls Head, Maine on August 31st, rain date, September 1st. (Please reserve both dates.) We will send directions out to participants. Meet 9:00am - 1:30pm. You are welcome to linger after.

  Cost – to cover costs we ask each participant to contribute $75. This includes the workshop, snacks, and lunch. If cost is a factor please be in touch about scholarships and work trade as we want this to be accessible to all who would like to attend.

  To Register – click here to register through the Uproot Pie Company’s website.

• What Participants Will Want to Bring

  A backpack or tote bag with these items:

  • Journal 


  • Small beach towel or shawl for settling in during conversations

  • Water bottle 


  • Layers for warmth and sun and shoes for walking

  • Watch (could be timer on your phone)


  • Swim suit (optional)

Leigh is thrilled to collaborate with Jess of the Uproot Pie Company for this workshop outing.

“Today’s workshop on the coast of Maine was truly a gift, and the best way for me to unofficially wrap up my summer that I can think of! Leigh and Jess were wonderful ... and this gathering of women business owners, at one of the most beautiful spots of coastal Maine that I have ever seen, was as much a gift to myself as it was from the facilitators to us. First of all, it was so well planned and thought out, that it seemed effortless. Of course, as a facilitator myself, I know how much work goes on behind the scenes to make it appear that way! The variety of the exercises, the solo, small group and whole group sharing times, and the AMAZING food were all part of this extraordinary experience. (And from the comments of everyone at the end, this was not just a wonderful, enjoyable pampering day of self-care for each of us; it was also rich in ideas and practical steps that each of us can actually use every day in our personal and professional lives to move forward.) Although I almost waited too late to sign up, I now see that I would not have wanted to miss this for anything in the world! I look forward to taking other workshops from Leigh, and unconditionally recommend others to do the same. You will NOT be disappointed.” 

-- Cathi Crowe, Historical Storyteller/Mixed Media Fiber Artist