Women Who Lead, Retreat
By: Cindy Free
What Does Retreat Mean to You?
I have asked myself that question many times for many reasons. I’m single and a sole provider for my kids. I lead a team of all-women professionals and a growing company. I’m an entrepreneur, and my mind never stops wondering and wandering. I have high expectations for myself that I just can’t shake sometimes. I have eight pets and a small hobby farm. I have a lot going on.
Life gets busy. The world is uncertain. I lean into so many beloved things, and at the same time, constantly struggle with what competing demands to choose and when. Work over kids? Kids over travel? My team over myself? An animal over a fun night with friends?
A few years ago, a client shared that they had taken their entire management team of about 20 people on a trip from Oregon to Hawaii. I saw the pictures…beaches, luaus, tropical drinks. They temporarily closed their business to go. Another client who had two partners told me they were each taking a month off over the summer. They would alternate and hire a new GM to ensure the operations were handled so they could leave. I was inspired, and dang it, my limiting beliefs told me that those were really great things other people could do, but I could never take the time away or afford the money to do any of that.
The optimist I am, I put a picture of a beach and a palm tree on my vision board, shut those limiting beliefs down, and told myself, “Yes, maybe.” Seven company retreats across Oregon, California, and Washington, 5 retreats with Entrepreneurs’ Organization (EO), and four personal retreats to Central America later (one where I brought my kids), and now curating my own retreat for Women Who Lead in Costa Rica in April 2026, here’s what I’ve discovered.
High-Performing Women Are Choosing Retreats Over Traditional Leadership Development
Don’t get me wrong. I love good leadership development. As part of HR Annie Consulting, we have our own online training platform and offer in-person training for managers and leaders. Retreats are different. More women are seeking holistic support to navigate life.
From books to blogs to podcasts to life coaches, women are seeking support and coaching for burnout, fatigue, and uncertainty, and want this outside of a traditional classroom or virtual meeting. We are craving immersive connection in a moderately disconnected world.
The Hidden Cost of Doing It All: Why Women Leaders Need Time Away to Lead Better
Women are Holding. It. All. Together. Professionally, family, parenting, people leading, and being the literal glue to their organizations, families, friendships, relationships, and more. Retreats aren’t indulgent; they are a recovery strategy. Stepping away helps us return with clarity and be more sustainable leaders and hosts of our lives and all we love. If we don’t retreat, we risk the urge to run away instead of stepping away.
Connection is a Competitive Edge: Transformation Retreats Build the Networks Women Actually Need
Do people even use business cards anymore? I see them still sometimes, plus QR codes, phone tap technology, and don’t get me started on the elevator pitch. I forget my cards everywhere I go, because that isn’t how we foster relationships, rather that’s how we build our rolodex.
Curated retreats with like-minded people, looking for similar experiences and surrounding themselves intentionally, create trust, valuable networks, innovation, and personal resilience and vulnerability.
When we retreat together, we develop a common understanding that we are all in this together, that we want to continue to be together in life and business, and that we have a deeper level of support. It’s not just kumbaya, but it is that too, and that shared experience builds networks.
Purpose-Driven Life Design: Women Leaders Are Using Retreats to Redesign the Next Chapter of Their Lives and Careers
There are certain inflection points that women in leadership, running an organization, or entrepreneurs hit. Scaling companies, shifting roles like becoming the CEO, facing reinvention, or craving a more aligned way to lead.
Women who lead, retreat.
It’s not letting go; it’s letting all the stuff rest, so you can rest too. Part of rest means the opportunity to recharge, reignite, and rise. Rest and retreat might mean breathing room, or it could mean a big, long, well-deserved nap on a beach chair.
I was talking to a colleague of mine recently, and they said they were going on an off-site retreat the next day. Of course, I wanted to know all about it. Would it inspire me for my next team retreat or a location for my EO forum retreat? Then he confirmed. It was an off-site to talk about their strategic plan in a fancier office than at their company. I laughed, in a caring way, and simply said, “That is a business meeting disguised as a retreat.”
Women who lead, retreat. The focus is on allowing personal and professional transformation as a strategy, not just a spa day—although that’s part of the gift of retreats too.
We cannot confuse business offsites for retreats. Call it what it is, because those of us who know, we know!
- Want to join me at SUYO: A Retreat for Women Who Lead in Costa Rica, April 24-May 2, 2026?
- Want some awesome ideas for hosting your own company offsite retreat? Let’s connect.
You CAN take a month off. Ask me how I did it with some 1:1 leadership coaching.
