Making friends is just as scary as an adult as it was when you were a kid. Maybe even more.
Making friends and maintaining relationships is hard at any age. Especially as we have gotten more and more distant and impersonal.
As we enter this ‘back-to-school’ season, think of how you felt on the first day of school. Are your friends that you haven’t talked to in a few months as close as they were at the end of last year? Or are they now connected to the group they went to summer camp with?
As business owners, we often view the summer months as ‘downtime’ or at least a slower pace. We all need those seasons. And then ramping up to Fall energizes us, but also causes panic as we are ‘back in the game’.
Let’s face it, relationships are hard and sometimes awkward, whether you are 8 years old or 48 years old. And online relationships, the new normal for the last several years, redefines the strange dance even more.
The secret to a real connection isn’t one more coffee chat on Zoom. We talked about the importance of this in Building Your Tribe: Finding Support and Strength in Community.
You know what no one tells you about adulthood?
Making friends gets weird.
Gone are the built-in social circles of school, sports, or playdates. Suddenly, you’re 40-something, juggling work and family, wondering when the last time was that someone invited you to brunch just because.
It’s not that we donât want new friendships or to invest in our old ones. Itâs that we donât always know how to find them anymore.
And even when we do⊠do we really have the energy to start from scratch?
The Connection Gap Is Real
As entrepreneurs, we talk a lot about networking, collaboration, and âgrowing your audience.â
But what about growing your friend circle?
Those are the people who just get it without needing a pitch deck. Conversations that arenât about metrics or monetization or scaling. Relationships built over shared values and not shared Wi-Fi.
This is the kind of connection that in-person events are made for.
And itâs something a well-designed retreat can foster better than just about anything else.
Why Retreats Are Friendship Accelerators
I love retreats because when women step into a shared space with aligned intentions, barriers drop fast.
You donât need six months of small talk. You just need shared values, a safe environment, and a schedule that allows for unstructured connection!
I’ve seen it happen time and time again, women who started as strangers walk away as soul-level allies.
They swap numbers, send gifts, and become each otherâs hype squad for years to come.
Because a real connection was baked into the retreat experience, intentionally.
How to Design for Adult Friendship (Without Making It Weird)
Whether youâre planning a small mastermind weekend or a full-scale retreat, here are five ways to create connection that sticks
- It’s important at the beginning to have a bit more structure and purpose to the first meetup with the group. Assign tables, have an icebreaker. Have everyone talk to the person on their right and their left, and then you introduce the person next to you to the group.
“This is Valerie. She partners with entrepreneurs to help them host in-person events. She has seven kids and nine grandkids! And she grew up in Vermont and now lives in Arizona.” Much more fun and less awkward than introducing yourself.
2. Schedule community-building moments..
Think beyond sessions and schedule at least one gathering that feels like friendship-in-action:
- A shared meal where everyone brings a story
- A sunset walk
- A collaborative art or journaling activity
đŹ 3. Invite Vulnerability Without Forcing It
Instead of saying âeveryone share something deep,â create invitations that give people a choice:
- You go first. Share a story and ask if anyone can relate.
- Ask open-ended questions that everyone can answer (if they choose to). Example-” What was the biggest obstacle you had to overcome to be here?”
- Stay away from clichĂ©s and overused phrases. Ok, just my opinion, but I don’t have a magic wand and money is always an object to consider, so find a more creative way to ask me to dream big.
Gentle guidance creates brave spaceânot pressure.
4. Mix Up Seating
Design your space to encourage movement. Assign seats. Then donât.
Encourage rotating partners.
Give people reasons to interact with someone new each day. We automatically feel safe with predictability but we grow with uncertainty.
5. Leave Room for Spontaneity
Some of the best bonds form in the unstructured time. That 20-minute break on the porch as opposed to ‘take a 10-minute potty break and come right back’.
The chat during cleanup. Don’t do everything for everyone. Let them participate and invest in the experience.
Laughing over late-night tea. Donât overschedule. Let the magic breathe. Those who want to turn in early or have some alone time should have that option, but those who want to enjoy each other’s company should have a place available, too.
Friendship Isnât a Perk-Itâs a Goal
If the only outcome of your retreat is that two of your attendees walk away with a new business bestie⊠Thatâs impact.
Because when women support each other, we grow faster. We show up bolder and we dare to push the boundaries of our comfort zone.
A transformational experience isnât just what happens during your workshop.
Itâs what happens when someone texts a new friend three months later and says,
âHey. I was thinking about you. Want to catch up?â
Build a Space That Builds Relationships
You donât need to host a massive event.
You just need to create the right environment for connection.
Start with your own clarity, and ask yourself…
- Who is your retreat for?
- What transformation am I promising?
- How can I make space for community along the way?
Thatâs what my 10 Essential Retreat Decisions Workbook is forâor we can walk through them together in a Retreat Planning Intensive.
Because youâre not just building an event.
Youâre building a room full of people who might just change each otherâs lives.
And thatâs the kind of ripple that goes far beyond your agenda.
Did you know I have a Facebook Group? It’s called Someday: the 8th Day of the Week, and we take a virtual road trip with friends to get our “Someday I’ll host a retreat” dream out of our heads and onto our to-do lists! Come check it out đ. We’d love to have you join đ.
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