Raw, real, and held: Why small groups change everything
If you’ve never felt this, I pray that sometime in your life, you will.
What am I alluding to? The most basic yet elusive aspect of human existence, of course: belonging.
Belonging goes both ways. I belong to you. You belong to me. We belong together.
It also has an active component; in order to truly belong, you must feel seen, heard, understood and accepted. Fully.
If you have felt this with someone, or a group of someone’s, or even looking into your dog’s eyes as they wag their tail in utter joy because, duh, you are the coolest human they’ve ever seen, you know what I’m talking about. If you haven’t, let me tell you how to find it, or build it.
All the business and personal growth books say: If you want to get somewhere you’ve never been, you must do something you’ve never done.
In other words, if you are broke, unhappy and want to break free from that pattern, don’t hang out with a bunch of other people who are broke, unhappy and happily fly their “if you’re broke and unhappy, come sit at our table” flag. If you want to change your results, you can’t keep surrounding yourself with people who normalize staying stuck.
In business, and in wealth, the goal is to surround yourself with people who are further along than you, or at least, who are hellbent to get there. They (also) are willing to take big leaps, challenge themselves, look stupid temporarily in order to get where they know they’re going, etc.
I used to think belonging was something you either found or you didn’t. Lately I’ve been sitting with a different idea: it can be designed—not manufactured, not forced—just carefully held, the way a good container makes it safer to be real.
In order for these groups to work, here’s what I’ve noticed that leads to achieving that “magic”:
They must be small – Too many people, and any one of them could fade into the woodwork, Irish goodbye, or secretly be struggling and no one would notice. Too small, and one strong personality can dominate the others. The sweet spot: 6–12 people.
They must be raw and real – I mean willing to bare all in service of the group’s unspoken (or perhaps spoken) agreement upon formation: We will share everything with each other—the good, the bad, the ugly and the beautiful. If we don’t, why else are we here? Surely, they’ve tried sharing only the good (Instagram), or only the bad (therapist), but what about the “I tried and fell on my face” (ugly) or “We finally won that contract, gosh darnit!!” (beautiful). The financials, the poor decisions (understood mostly in retrospect, but sometimes our intuitions saw them coming), the “Oh God, how do I get myself out of this mess.” Insert: the next criterion.
They must have each other’s back – These groups agree that no woman will be left behind. She will not be overrun by her emotions, hormones, negative beliefs, societal pressure, excuses. She will not freeze—she will move through the problem to the solution. And we will get her there.
They will ask each other hard, embarrassing questions – At a recent conference, I found a picnic table at a winery mixer near the edge of a bluff. A colleague I knew was sitting there, and another joined. We started cracking jokes. I asked people what they got in trouble for in high school. Asked them to introduce each other (many of them had never met, our table kept attracting strangers as people heard our raucous laughter lilting across the winery), when they didn’t even know their name, job, background, at all. This was a professional conference. About investing and startups. By putting people outside of their comfort zone as soon as possible, we broke the ice to allow the real water to flow. Your front—the self you present to the world—is manicured and trained to perform a certain way in front of your peers. The goal of this step is to shatter that image completely. To let the real you out. Afterward one of those colleagues and I got lunch, and called out how rare that kind of effortless aliveness is—and how much we want to recreate that “picnic table magic” in real life, in our own community, not just at conferences.
There will be no judgment – You are where you are with your business, and I am where I am with mine. What you are working on feels just as hard to you as what I am working on feels to me. No one “should have seen _____ coming,” otherwise we wouldn’t be here, in this group. Life is learning, not losses. We are going to try until we fall, and be caught by the rope. If we don’t, we aren’t challenging ourselves. We aren’t exploring beyond what we’re already doing to discover what actually works.
A shared goal – Often, successful groups form when seemingly disparate people realize they’re all struggling with the same thing. They’re all fighting cancer. They all have the same classic car. They all really really really want to finish writing their book. That niggling feeling, the one that keeps them up at night, either with determination or excitement, is enough to push them to see that the answer lies in community. Their goal is strong in and of itself. It is 100x stronger when mirrored and reflected in others.
A shared manifesto – I once joined a virtual group for women professionals that was all about women power, pumped up playlists, getting sh*t done. I made some great contacts from it. I also felt deeply uncomfortable. This group had a shared, revered culture of what I call “rah rah feminism.” Man-hating. This was not for me. In order for a group to really perform, they need to agree on certain tenets. Align around enough shared beliefs that the group commandments are there, while preserving plenty of diverse perspectives to allow fruitful conversations (more on that next).
Diversity isn’t welcome, it’s necessary – Similar to the AA bumper sticker, “If nothing changes, nothing changes,” if you’re stuck in a rut, and you’re looking to your group to help you get out, look closely: Do they all look like you? If so, enjoy staying that way forever. To expand your worldview, you must expand your demographic. People from other cultures, ages, tech-savviness, philosophies. More diverse teams perform better than homogeneous teams, period. Because if the room only reflects what you already know, you’ll keep getting the same answers—no matter how badly you want change.
I’ve experienced this kind of belonging in the business world twice, maybe two and a half times.
The first was in a small group cohort led by a dear colleague. We had nearly every quality listed above, and when our nine months together came to an end, I cried. I went through withdrawals. But I grew, and I had the other women to thank.
The second was my “business besties”—two women also with marketing agencies who were 100% committed to making it work, and willing to share everything about how they were trying to get there, and receive feedback on other tactics to try.
The third was a large business program, a 40-member 3-month cohort which ended with flying to NYC and shaking hands in heels on the 43rd floor of a building in the finance district. Powerful, engaging, elevated. But also distant, and too big to really connect. I preserved some contacts from the experience, I learned too fast and licked my wounds, and forgot the names of the rest of my peers.
…
On belonging, there’s a reel my partner and I have been quoting for at least a week. A licensed therapist turned internet sensation posted a “GRWM luteal” (Get Ready With Me) clip in which she screams, hisses at her husband, tackles a garbage can and throws an egg at their microwave, sexily looking at the camera, “Breakfast is ready.” (That’s the part we quote.)
The reel received 449K views, was forwarded 369K times, reposted 19K times, and prompted 9,354 comments. I read a hundred or so of them. In it, women (and men) shared that they had “never related to a reel more in their lives.” That “no one understands me like you do.” That, “this only begins to scratch the surface.”
Let’s go deeper.
What’s under your poised entrepreneur exterior? What are you dreaming to build? What’s holding you back? What would you do if you knew you had a community so strong behind you, that when you fall, you’ll simply bounce back, like a trampoline, laugh, and keep going?
If you’re carrying a private fear—about money, momentum, visibility, the decisions you regret, the ones you’re avoiding—this is your reminder: you weren’t meant to white-knuckle it alone.
509 Female Founders is one of the ways we practice that kind of belonging on purpose: small enough to be seen, structured enough to move, real enough to tell the truth.
If you want details on the 2026 cohort, read the fact sheet or book a call.
