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A few weeks ago, I did a mastermind in Chicago, and I want to tell you why it was one of the most powerful days of my year.
No, it wasn’t a luxury retreat. There were no guest speakers, no swag bags, no high-ticket facilitator leading the way. It was six women, totally unpaid, coming together for 36 hours to go deep—not wide—on our businesses and our lives.
And here’s the thing: we weren’t starting from scratch. We’d already met up 90 days earlier, and instead of letting the momentum fade, we kept our little text thread alive—checking in, asking for support, celebrating wins, and keeping the conversation going.
So when we met again, there was no need for small talk. We picked up right where we left off… with trust, continuity, and so much more clarity.
Now, to be clear: I did spend money. I paid for the plane ticket, the hotel, and the meals. But the experience itself? It didn’t cost a thing to attend. It was free… and honestly, it felt priceless.
Over the years, I’ve done just about every type of mastermind—$25,000 masterminds with multi-course dinners and famous guest speakers, peer-led groups, even masterminds created to raise money for charity. But this year? The only ones I’ve said yes to are the free ones. The small ones. The ones built on intention, not investment.
I’m sharing this with you because I know how lonely the road can feel. Maybe you’re not ready for a high-ticket mastermind, or you’ve told yourself that’s only for her (the one with the big audience, the polished funnel, the team of ten). Maybe you’re duct-taping your way forward and wondering what you’d even bring to a table like that.
But what if I told you that you can still get the clarity, the breakthroughs, and the community your heart is craving, without paying to sit at the table?
In this episode, I’m unpacking what a mastermind really is, how to create one that works for you, and why it might be the exact space you didn’t even know you were missing.
Because here’s the truth: You are already worthy of a seat at the table. You just might be the one who gets to build it.
What Is a Mastermind?
The word mastermind can sound fancy or vague. But at its core, it’s simply a group of people committed to growth: who come together not just to chat, but to help each other move forward.
- It’s not a course.
- It’s not a coaching program.
- It’s not a networking event where you feel pressured to pitch yourself.
A mastermind is peers with different skills and struggles saying: “I see you. I’ve been there. Let’s work through this together.”
In a good mastermind, there isn’t a single guru with all the answers. Instead, the magic is in the perspectives you share, the coaching you both give and receive, and the clarity and confidence you walk away with.
So if you’ve been craving support, wishing you had someone to bounce ideas off of or just wanting to feel seen by people who get it—this might be exactly what you didn’t know you needed.
1. You Don’t Need Fancy to Go Deep, You Need Focus
This mastermind wasn’t held at a dreamy Airbnb or curated retreat. It was in a standard Marriott hotel with a normal lobby. But the women who showed up? They came ready to be intentional, honest, and present.
We skipped the alcohol, the distractions, and the surface-level chatter. Instead, we nourished our bodies, focused our energy, and honored the time we had together.
So many people spend time and money trying to make masterminds “look” impressive: swag bags, branded notebooks, Pinterest-worthy spaces. But none of that matters if the people in the room won’t go deep. Transformation comes from presence, not aesthetics.
2. Curate Energy, Not Just Expertise
Not everyone in our group was in the same industry or stage of business. And that made it better.
We weren’t comparing résumés. We were connecting from lived experience and desire. What mattered most was that we were all in the same season of wanting to grow, and we were willing to go there.
If you’re dreaming of starting a mastermind but don’t know who you’d invite, here are five tips to find your people:
- Start with your current connections. Think about the business friends you DM with, cheer on, or always reply to. Invite them to test the waters with you.
- Don’t stress industry alignment. Values matter more than identical business models. Look for generosity and honesty.
- Be the initiator. Stop waiting for an invitation. Build the table yourself, set a date, and invite 2–3 people.
- Use your voice. Post about it. You’ll be surprised who raises their hand to join.
- Join the Goal Digger Insiders Facebook Group. It’s full of entrepreneurs looking for connection and collaboration—perfect for finding your mastermind crew.
3. Structure Sets You Free (Even in 36 Hours)
With just a day and a half together, we knew structure mattered. Our plan looked like this:
- Dinner the first night
- 9AM start with movement + roundtable conversations
- Afternoon hot seats
- Evening reflections and connection
Each woman came prepared with her top 1–2 questions. My friend Bonnie even brought a mic, recorded every hot seat, and later created a tabbed transcript of everyone’s feedback so nothing got lost.
This structure gave us room for breakthroughs in real areas of our businesses—sales strategies, restructuring teams, balancing family with entrepreneurship, and even letting go of what no longer served us.
Structure isn’t restrictive, it creates freedom for real transformation.
4. Protect Your Energy So You Can Show Up Fully
One of the biggest game changers? Protecting our energy.
We prioritized healthy food, sleep, movement, and hydration. We minimized distractions and stayed off our phones. We honored the space so that every conversation had our full attention.
Because here’s the truth: without a plan to protect energy, a mastermind can just turn into a girls’ weekend with laptops. Intentional energy management made sure everyone walked away replenished, not drained.
5. Depth Over Width: We Didn’t Try to Do Everything, Just the Right Things
We weren’t there to cover every possible topic. We zoomed in on the issues that mattered most to each of us.
We listened deeply, challenged kindly, and offered solutions rooted in honesty and generosity. That’s what made those 36 hours feel worth every second.
If you’re planning a mastermind, here are five ways to go deep, not wide:
- Name your season, not just your goals. Get clear on the stage of life and business you’re in.
- Bring 1–2 specific questions. General questions create vague answers. Specificity sparks breakthroughs.
- Decide what’s off the table. Give yourself permission to stay focused.
- Use a hot seat format. Give everyone equal time and structure for feedback.
- Make space for integration. Build in quiet time, journaling, or reflection to let the insights land.
Final Thoughts
So if you’re sitting there thinking, “I want people in my life who get it, but I don’t know where to find them,” or “I’m not ready for a big investment, but I am ready for clarity and connection,” this is your permission slip.
You don’t have to wait for a big-ticket invite. You can build it yourself. Ask two or three women you admire. Book a hotel room, open your home, or gather at a coffee shop. Create the agenda. Protect the energy.
You’re not too early or too messy. You’re ready, and that’s enough.
And if this episode sparked something in you, don’t keep it to yourself. Share it with the women you’d love to mastermind with. Plant the seed. See what unfolds.
Join the Goal Digger Insiders Facebook Group to find your people and keep the conversation going. And if you try this? Message me. I want to know what it opened up for you!
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Jenna, I LOVED this episode! I am definitely going to get the ball rolling here. I truly appreciated how you highlighted what I should ask myself before showing up and starting a mastermind sooooo valuable.
Finally, I’ve tried joining your Facebook group-I answered the group questions- and I haven’t gotten in. I don’t recall the exact date I “applied “ but it’s been awhile.
That’s awesome, Darcy! Also, if you haven’t been admitted to the group, there might’ve been an error on the Meta side. You can cancel your pending request and reapply (which I am so sorry you might have to do!) Give it a whirl when you get a moment!