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Key Takeaways
- Building a strong entrepreneurial community requires intentional connections that balance challenge and support.
- True freedom in business comes from embracing vulnerability and integrating all parts of your life
Twenty years ago, my husband and I made a decision that would transform our lives.
I had just quit a government job that had me traveling the world. We had two young children and no clear plan. We gave ourselves six months to figure out our next move.
What followed was both unnerving and beautiful.
Each day, Enrique and I would go to the gym, drop the kids off at the free daycare and ride stationary bikes side by side while mapping out our future. That rhythmic hum of the bikes, the kids’ laughter in the background — it became our strategy HQ.
Enrique, then finishing his MBA, turned our future into his final project. We evaluated three potential businesses and eventually chose a cleaning franchise that aligned with what mattered most to us: time freedom and financial independence.
That season taught me something I’m still learning to this day: Freedom requires structure — and that structure is built from the people you surround yourself with.
The power of anchors
In the early days, “community” didn’t mean networking events or masterminds. I wasn’t ready for all that.
What I needed were anchors — one or two people who could keep us steady when everything felt uncertain.
One was Enrique’s strategy professor, who helped us evaluate business models with clarity. The other was a friend working at the Small Business Development Center — a free, often-overlooked resource for entrepreneurs. He became a steady guide during those critical early months.
He had one simple, unwavering rule: “Don’t come see me until your financial statements are done.” His point was clear — if you don’t know where you stand financially, you’re not running a business.
Later, when I faced tough employee decisions, he didn’t sugarcoat things. “Yes, you need to do that.”
I’d cry. Then I’d do it. And I’d return stronger. Those tears weren’t weakness — they were part of becoming who I needed to be.
Because freedom requires facing what scares you most.
Finding the right circle
As the business stabilized, I realized I needed more than anchors. I needed peers — people who understood the weight and wonder of entrepreneurship.
That’s when I began seeking out entrepreneurial communities. For example, groups like Entrepreneurs’ Organization offer spaces where people live not just big businesses but big integrated lives. It shifted my view of what was possible — not just professionally but personally.
I also realized that real entrepreneurial success isn’t about separation — not work versus life — but integration. You’re not building a business while life happens on the sidelines. You’re weaving it all together.
The right circles support that. They don’t just celebrate wins — they hold space for the full journey: the doubts, the pivots, the personal growth.
Vulnerability as a superpower
A major turning point came when I gave a talk about my entrepreneurial journey.
It wasn’t just a business story. I talked about surviving abuse. I talked about parenting. I talked about building a company from scratch. For the first time, I brought my full self to the stage.
What I had once viewed as liabilities — the hard parts I kept hidden — were actually my greatest strengths. Owning my full story didn’t diminish my credibility. It deepened it.
In that moment, I realized: Vulnerability isn’t a liability — it’s your leverage.
Related: Want to Be an Entrepreneur? Start With These 4 Simple Steps.
Community as a container without walls
That experience reshaped how I think about community. The best communities aren’t rigid. They’re more like containers without walls — strong enough to hold you, yet spacious enough to let you grow.
Now, my sense of community is more fluid. Every morning, I walk five miles listening to podcasts — business leaders, spiritual thinkers and health experts. One idea leads to another, one voice leads to a new connection. Mentorship is everywhere if you know how to listen intentionally.
That’s the evolution — from needing a handful of anchors to building a global network of voices. Proximity matters less now. What matters more is alignment.
The future of the entrepreneurial community
If I could redesign the entrepreneurial community of the future, it would look different than most rooms I’ve walked into.
We’d break down artificial hierarchies. No more sorting people by revenue tiers or exit size. Instead, we’d gather around shared values — resilience, generosity, curiosity and purpose.
We’d see that the entrepreneur with a $1 million business could teach the billion-dollar founder something they’ve forgotten. And vice versa. Vulnerability would become currency. Wisdom would flow in all directions.
Final thoughts
Those exercise bike sessions twenty years ago were the foundation of something much bigger than a business.
They taught me that success isn’t a solo journey. It’s shaped by every mentor, every challenge and every honest conversation that helped me become more of who I truly am.
We often chase freedom as a destination. But I’ve come to believe this: Freedom doesn’t happen when you escape the hard stuff — it happens when you embrace it with the right people beside you.
Key Takeaways
- Building a strong entrepreneurial community requires intentional connections that balance challenge and support.
- True freedom in business comes from embracing vulnerability and integrating all parts of your life
Twenty years ago, my husband and I made a decision that would transform our lives.
I had just quit a government job that had me traveling the world. We had two young children and no clear plan. We gave ourselves six months to figure out our next move.
What followed was both unnerving and beautiful.
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