Reclaiming the Narrative: Why Entrepreneurship is the Ultimate Escape Hatch for Justice-Impacted Women
I am a white, Jewish man. No matter how much I listen or how deeply I care, I move through the world with a set of cards that look very different from the ones dealt to a woman walking out of a correctional facility. I see the world through my own lens, and I recognize that.
In my time as the CEO of Breaking Free Industries and as a mentor to those navigating the "justice-impacted" label, I’ve had a front-row seat to a specific kind of resilience. I’ve watched women reclaim their lives from the wreckage of the system, from domestic violence, and from workplace harassment.
And through those observations, one thing has become crystal clear: Entrepreneurship isn’t just a career path for women in this position. It can also be an Escape Hatch.
When the W2 world shuts its doors—or offers a wage that barely covers the bus ride—starting your own thing isn't just an "option." It’s a strategy for survival and, eventually, for power.
The Freedom to Define Your Own Value
One of the most frustrating parts of the traditional job market is having someone else tell you what your time is worth. And honestly, that frustration exists for people who have not been justice-impacted too. But when you have a record, that number is almost always lower than it should be—if you can even get in the door. The "justice-impacted" tax is real, and it’s exhausting.
In entrepreneurship, both reality and the math change. For starters, while background checks are commonplace for W2 jobs, clients are usually more focused on whether you can deliver. If I need a website designed, your portfolio and reviews matter more than your rap sheet. If you do great work, do I really need to know about your outstanding parking ticket? (Note to self: when you start a business, ask for reviews.) There are exceptions, sure. But most of the time, in the entrepreneurial world, your work can speak for itself. The conversation becomes: what can you do for your customer? Your past gets a lot less oxygen.
Better still, you get to define your own economic worth. When you start a marketing agency, a website design firm, or a specialized cleaning service, you set the floor. You decide if you’re doing a project for $250, $500, or $5,000.
All this to say: charge a fair price—one that’s sustainable for you and competitive in your market. I use two checkpoints:
- If I’m at ~75% capacity, can I support myself (and my family, if that’s your situation)?
- Am I priced within about 10% of market for the work I’m doing?
Because if you’re working ten hours a day and still can’t take care of yourself, that’s not “hustle.” That’s a broken system—pricing, processes, sales, something. You will need a day off. You’re not a machine. And if one day off means you can’t make rent, that’s a blinking red light.
I also see a ton of returning citizens charging too little. If the average cost to clean a two-bedroom apartment is $100 and you charge $50, you’ll get work. You’ll be busy. But will you be stable?
How do you find market pricing? Blind shop people. Search online. Call a national brand. Then call a couple local companies. You’ll learn what the market will tolerate. Don’t be the cheapest option—someone will always work for less. Stand in your value. And it’s probably not a good idea to be the most expensive either.
Last pricing note: when you charge too little (because you’re trying to be “nice” or you feel like you have to), if something goes wrong you have nowhere to go but down. You eat the mistake. You lose money on the job.
When I was a CPA, in a life before incarceration, peeps would lie to me all day long. A prospect would call for a quote and start with, “My stuff is simple. Just a W-2.” I’d quote it. Then they’d show up with a folder chock-full of disorganized paperwork.
They lied.
I generally believe the best in humanity, but don’t build your pricing around optimism. When your customer participates in the quote process, assume it’s never as easy as they say—because if it was, they’d be doing it themselves.
You decide who your clients are. You decide who you won't work with. In a W2 job, you’re often stuck with a manager who doesn't respect your journey. In your own business, you are the gatekeeper.
The "Escape Fund" and the Side Hustle
We need to talk about safety. For a lot of women, entrepreneurship isn’t a cute “boss babe” thing. It’s a tool to get out of situations that are just as suffocating as a cell: domestic violence or toxic, harassing work environments.
Sometimes you need a way to build an “escape fund” that a partner—or an unsafe situation—can’t touch. A side hustle does that. It starts as pocket money and turns into “I can leave” money. Options where there were none.
And no, entrepreneurship doesn’t have to be a 60-hour-a-week plunge on day one. It can be the quiet engine in the background while you navigate your transition. It’s about building a place to go when you finally decide you’re done. Self-employment is a job that’s always waiting for you.
Beyond the Traditional: What Can You Actually Do?
When people think of "justice-impacted" businesses, they often default to the same three or four ideas. There is absolutely no shame in the traditional: I know plenty of women who have built empires in commercial cleaning or catering: but don’t limit yourself.
If you have a laptop and a WiFi connection, the barrier to entry is lower than it has ever been. Here are a few lanes I’ve seen women absolutely crush:
- Virtual Assistance: Organizing the chaos for other busy business owners.
- Specialized E-Commerce: Selling niche products, apparel, or even stickers. (At Breaking Free Industries, we have a zero minimum order requirement, including single-item orders, so you can start small without going into debt.)
- Marketing & Web Design: If you can navigate social media or basic web tools, there is a massive market for small businesses that need help looking professional.
- Travel Agency: Using your organizational skills to curate experiences for others.
- Life Coaching: Taking the hard-won wisdom of your journey and helping others navigate theirs.
- Hair / Makeup: I have seen many women monetize their creativity here.
- Commercial Cleaning / Food Service: These are staples for a reason: they are scalable and always in demand.
The point is: your past does not dictate your industry. Your skills and your grit do.
The "Nonprofit Trap": Put Your Mask on First
This is where I might lose some people, but it’s the most important advice I give.
A lot of people come out of the system with a real desire to “give back.” Start a nonprofit. Open a halfway house. Build a mentorship program. I respect it. I do.
But here’s the trap: mission without sustainability turns into self-destruction.
Nonprofits are hard. Like, paperwork-on-paperwork hard. And when you’re justice-impacted, there’s often a credibility gap with donors. Unfair? Yep. Still real? Also yep. You have to convince someone you’ll be a good steward of their money while you’re still trying to secure housing, income, and basic stability. That’s a brutal ask.
I’ve also seen way too many “free grant money” ads that are basically mirages. Most nonprofits struggle until they have success stories. But you can’t get success stories without funding. And you can’t get funding without success stories. That loop eats people alive.
Which brings us to the airline speech: why do they tell you to put your own mask on before helping your child?
The Airplane Metaphor (Fact-Check):
At high altitudes, if the cabin loses pressure, you have about 15 to 30 seconds of "useful consciousness" before you pass out from lack of oxygen. If you spend those seconds trying to mask someone else first, you both black out. The masks typically provide about 15 minutes of oxygen—enough time for the pilot to get the plane down to a breathable altitude.
So yes: put your mask on first. In real life that means securing your “oxygen”—income, stability, and mental health—so you’re actually around long enough to help anyone else.
Start Small, Build a Track Record
If your dream is to run a safe house, don't start by trying to buy a building and filing for a 501(c)(3).
Start by running an AA meeting. Start by volunteering for an existing org. Start by showing that you can run a program successfully for two years.
When you have a track record of "small" wins, the larger grantors—the cities, counties, and states—will take you much more seriously. They want to see that you can manage a project before they hand you a six-figure check.
In the meantime, build a for-profit business that feeds you. There is no shame in making money. In fact, financial independence is one of the most powerful ways to prove to the world (and yourself) that you are back in the driver's seat.
You Don’t Need Permission
The justice system is designed to take away your agency. It tells you when to eat, when to sleep, and what you’re allowed to do.
Entrepreneurship is the exact opposite. It is the ultimate reclamation of agency. You don't need a gatekeeper to tell you that you're allowed to start a business. You don't need an HR department to "overlook" your background.
You just need a plan, a bit of grit, and the willingness to start small.
If you’re ready to start putting your own mask on, we’re here to help you build the "merch" side of that dream whenever you're ready. Whether it's one shirt or a hundred (our sweet spot is usually 50–500 for risk and flexibility), the door is open.
Don't let the system's narrative become your own. You’re the one holding the pen now. Write something worth reading.
SEO Title: Reclaiming the Narrative: Entrepreneurship for Justice-Impacted Women
Meta Description: Entrepreneurship is more than a job; it's an escape hatch for justice-impacted women. Learn why starting small and focusing on sustainability is the key to reclamation.
Tags: justice-impacted, women entrepreneurs, second chances, business strategy, social enterprise, breaking free, nonprofit advice, financial independence