Women in Real Estate…Why Courage Comes Before Confidence

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November 21, 2025

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KAYLA MARI

Women in real estate are rewriting the rules of wealth, work, and financial freedom. More and more women are stepping into investing, flipping, and entrepreneurship—not because they feel fully prepared, but because they’re choosing courage over waiting for confidence. And that theme came up again and again in my recent conversation with real-estate investor and mentor, Stephanie Lombardo.

Stephanie didn’t set out to become a real-estate investor. She actually grew up in Canada riding horses, eventually moving to South Carolina in her early 20s. When her riding career didn’t pan out, she found herself studying accounting and later doing bookkeeping for a real-estate investor. That opportunity opened doors she never expected—and years later she’s done everything from flipping homes to building rental portfolios, earning her place as a leader in the women in real estate space.

The Decision That Comes Before Any Investment

One of Stephanie’s biggest pieces of wisdom is that confidence doesn’t magically appear before you begin. If you’ve never flipped a house or bought an investment property, how could you realistically feel confident?


You need courage first.
The confidence comes later—through experience, education, and surrounding yourself with people who’ve done it before.

Her advice for women wanting to enter real estate is simple but powerful:
👉 Make a decision.
👉 Take one step forward.
👉 Let confidence build through action.

Different Paths for Women in Real Estate

Stephanie broke down several types of real-estate investing, emphasizing that not every woman has to take the same path:

  • Fix & Flip – Active work, but highly flexible for moms who want income without a traditional schedule.
  • Rental Properties – More passive, but still requires management.
  • Private Lending – The most hands-off option, ideal for investors who want passive income without the rehab process.
  • Wholesaling – An active, hustle-driven way to break into the industry with low capital.

Each path serves different goals—some women want to replace their 9–5 income, others want long-term wealth, and many simply want the freedom and options that come with real-estate investing.

How Women Can Confidently Start Flipping Houses

Stephanie shared actionable steps for women who want to flip their first home:

  • Start on the MLS (yes—Zillow works!)
  • Choose your market intentionally—local if possible, but out-of-state is absolutely doable
  • Interview multiple contractors and get at least 2–3 bids
  • Use referrals from agents, paint stores, or local investor groups
  • Hire a home inspector to double-check contractors’ work, especially if you’re investing remotely

She reminded listeners: You don’t need to be an expert on plumbing or framing. You just need a system, support, and trustworthy professionals.

Breaking Generational Money Scarcity

One of the most meaningful parts of our conversation centered around money mindset. Stephanie grew up with a scarcity-driven view of money—something many women can relate to. Over time, she rewired that mindset by:

  • Paying attention to her language around money
  • Exposing herself to success stories
  • Reading books about abundance
  • Practicing gratitude for every dollar earned
  • Replacing “I can’t afford this” with “How can I afford this?”

This shift not only changed her finances—it changed her identity.

Women in Real Estate and Motherhood

We also talked openly about balancing business with motherhood—a topic that deserves more honesty. Stephanie shares her world with her daughter and chooses work that gives her flexibility. But she also admits to experiencing mom guilt, constantly weighing which “glass balls” she can’t drop that day.

Her philosophy is refreshing:
There’s no perfect balance—only harmony.
And sometimes harmony looks like a child on the floor with an iPad during a Zoom call.

Habits That Support Success

Some non-negotiables Stephanie swears by:

  • Prioritizing physical health for mental clarity
  • Giving attention to money management and mindset
  • Staying flexible and adaptable in entrepreneurship
  • Protecting her energy by surrounding herself with supportive people

These habits don’t just help her succeed—they help her remain present as a mom and intentional as a business owner.


Closing Thoughts

Women in real estate are powerful.
They’re redefining what financial stability, generational wealth, and career fulfillment can look like. They’re entering a traditionally male-dominated space and proving that courage—not perfection—is what opens the door.

Stephanie’s story is a testament to what happens when a woman decides to go for it… even when she doesn’t feel fully ready.

If you’re curious, intimidated, excited, or anywhere in between, remember this:

Why not you? Why not now?

Listen to “The Work We Keep” now:

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