Starting a business while homeless is rarely a choice — it’s often the last option left when traditional jobs are inaccessible. When I was unhoused, unemployed, and carrying a criminal record, entrepreneurship wasn’t a dream or a passion project.
It was survival.
This post explains what it actually looks like to build income without stable housing — not the sanitized version, but the reality of working, earning, and holding yourself together when the system offers no safe alternatives.
I Didn’t Choose Entrepreneurship — I Ran Out of Options
I’m terrible at business-y details. What I am good at is doing what needs to be done and finding a way through impossible situations. Those are skills you learn in prison.
Starting a freelance writing business wasn’t about passion or freedom. It was about necessity. When you’re homeless, unemployed, and carrying a criminal record, you don’t get to “follow your dreams.”
You get to figure out how not to drown.
Homelessness, Depression, and the Breaking Point
By late spring of 2021, I had been homeless for sixteen months.
I was deeply depressed — dangerously so. My husband, Irish, was collecting cans all night, every night, often getting less than $50 for hours of work. It was a traumatic cycle of Irish heading out each day in the late afternoon, and me spending the night alone at the RV, often in a different part of town than where Irish was canning. It would be another 3-4 months before we rescued Barney from his abusive circumstances, so I didn’t yet have him standing guard over me at night.
Irish would show up in the mid- to late-morning, sometimes needing me to accompany him to the bottle drop because he had too many cans and bottles to redeem on his own. We’d use the canning money for our daily expenses, including generator gas, vehicle gas, and any needed household items. He’d grab a few hours of sleep, eat, and then get ready for another night of rummaging through garbage cans and dumpsters for a haul of cans and bottles.
We were living hand-to-mouth, exhausted, and stuck in survival mode.
I needed something to hold onto — something that reminded me I still had agency and a purpose. Work had always given my life structure and purpose, but now it felt unreachable. The barriers I was facing weren’t ones motivation could solve.
Why Freelancing Became the Only Option While I Was Homeless
Looking for a local job wasn’t realistic. Not because I didn’t want to work, but because the system wasn’t built for someone in my position.
- We didn’t have a reliable vehicle
- I often had no money for public transportation
- I didn’t have work-appropriate clothing
- I had access to a shower once a week
- I rarely got a full night’s rest
- I have a criminal history
None of these are things you can “power through” in a job interview. I slowly came to the realization that I would need to find a creative way to earn a legitimate income, so I began researching how full-time RVers and van lifers make a living.
The Moment I Stopped Believing I Wasn’t “Allowed” to Be a Writer
For months, I’d been thinking about using my English degree and looking for remote writing work. I had a Chromebook I’d bought on sale the year before, and I wasn’t new to online work.
But I’d look around at the inside of the motorhome we were living in and think: Writers don’t live like this. Writers have their shit together. You’re never going to be a writer.
That belief kept pulling me back under.
Then one night, I read Jon Morrow’s article 7 Life Lessons from a Guy Who Can’t Move Anything but His Face. Talk about a wake-up call of what’s possible if someone simply will not give up. (If you’ve never read the article, you should.)
When I finished the article, I put my phone down and said out loud:
“I have no more excuses. Not one fucking excuse.”
The perspective shift changed everything for me. It was suddenly clear that because I had nothing, there was nowhere to go but up. Options I hadn’t been able to consider earlier in my life were finally on the table.
I just needed to take the first step.
How I Started Freelancing Without Housing
Finding the First Opportunity
I spent the evening Googling “best job sites for beginning writers,” reading list posts, and bookmarking anything that seemed remotely possible.
The next morning, I found a listing for a freelance recipe developer and blog post writer. The application was simple: write a cover letter explaining why I was a good fit for the role.
I loved cooking. I loved writing. I loved photography. This felt… possible.
Telling the Truth
For the next 2-3 hours, I wrote and rewrote my cover letter. I explained (in great detail) how recipe writing combined my favorite hobbies. I also shared that I was homeless and living in an RV, but I assured the job poster I could cook, photograph, and deliver quality work.
I hit send and waited. Anxiously.
That afternoon, I received an email inviting me to complete a paid “audition” post so that the client and I could see if this was a good arrangement for both of us.
It was definitely a “trial by fire” experience! I was brand new to blogging and WordPress, and I knew nothing about best practices for “web optimized” content. Calling my first recipe blog post “green” is an understatement. But the client liked the final result and asked me to contribute weekly blog posts going forward.
Irish and I celebrated by hiking in a nearby park. We took photos to mark the day I became a published writer.
What Working While Homeless Actually Looked Like
Writing From an RV and a Generator
At first, I worked primarily from the motorhome. We had a generator for electricity, which powered a countertop Ninja oven and microwave for making recipes. It also allowed me to keep my Chromebook and phone charged. A propane camp stove provided stovetop cooking when called for.
My phone ran on prepaid service, so I bought monthly plans with hotspot data and tethered my laptop for online access. It wasn’t an elegant setup, but it gave me what I needed to bake, cook, write, edit, and create 1-2 blog posts each week.
Cars, Malls, and Free Wi-Fi
When I joined Irish on can-collecting trips, I worked from the car. He parked wherever we could find free Wi-Fi to conserve data. I wrote, edited photos, and drafted WordPress posts from the passenger seat.
The client began asking me for help with virtual assistant tasks and with editing other recipe writers’ work. Eventually, my time was split between creating a weekly recipe blog post and editing tasks.
When the weather turned cold, I went to a downtown mall where I could connect to free wi-fi. I mapped out which three electrical outlets in the food court worked and sat at those tables for 7-8 hours a day. I used a power strip to charge everything before Irish picked me up each evening.
This was my routine for the next 7 months.
My Career Grows, Irish’s Addiction Worsens
While I was working to develop and grow my new digital content skills, Irish flailed. His time was filled with heavy drug use, disappearing for days at a time, and hanging out in the part of town that felt comfortable to his addiction. He had numerous run-ins with the law, but because they always resulted in a “book and release” situation, he came to believe he was untouchable.
For months, I’d pleaded with him to stop staying out all night because eventually his luck would run out, and it wouldn’t be him who suffered. It would be Barney and me left to face the danger of the streets on our own. But my words fell on deaf ears, and Irish continued his downward spiral.
Working With a Dog and No Safe Place to Leave Him
In the late summer of 2022, my prediction came true when Irish was arrested. Unlike his previous arrests, this time the message was “Sit down and wait for your court hearing next month.”
For six weeks, Barney and I were alone in the worst possible circumstances. We were vulnerable to predators in the homeless community, and if something happened, calling the police for help was not an option. The outcome was far more likely to result in me being charged with illegal camping and having my travel trailer impounded than receiving help as the victim of homeless-on-homeless crime.
The first thing I did was carry on as though everything was business as usual to avoid tipping off those around us. I still had obligations to my client, which meant bringing Barney with me to the mall while I worked. Each day, we took the bus to be there when the doors opened, and I set up a mat, food, water, and toys for him under the table.
But after a week or so, it was clear he couldn’t handle being in that environment for hours. Leaving him in the RV wasn’t safe — by then, a heat wave had moved in, and temperatures were reaching over 100 degrees.
I joined a dog-friendly coworking space, so Barney and I could both be out of the heat. It provided the wifi and electricity I needed for my work, and showers were among the amenities. It was a daily refuge where we were safe until Irish was finally able to appear in court and be released on probation.
When the co-working space shut down a few months later, I discovered that the mall had disabled its food court outlets to prevent unhoused people from setting up day camps at the tables while charging devices and sleeping off whatever substances they were on.
From then on, I worked at tables in public libraries from open to close until the day we finally moved into an apartment.
The Hidden Cost of Being a “Professional” While Homeless
Eventually, the client stopped publishing recipe posts, and I transitioned into an editor role. Later, I became a senior copy editor, overseeing the editor team and helping train new writers entering the field of SEO copywriting.
Mentoring new writers was one of my favorite parts of being an editor. I guided each one through the same learning curve I once faced and celebrated with them as they began their journeys as paid writers.
But sometimes I would think: If these writers knew their work was being reviewed by a homeless person, they’d never take me seriously. I worried that the other editors working from their nice home offices would ostracize me if they found out. I was friendly while also keeping everyone at arm’s length, which created a peculiar kind of isolation with my peers.
Because the work environment was fully remote and freelance, I was able to keep my housing status private. But the fear and the shame lingered long after the work stabilized.
For me, professionalism meant doing my best to deliver high-quality results while working under unthinkable circumstances that I kept secret from others.
The Real Lesson Homelessness Taught Me About Risk
Years ago, I wanted to be a writer, but my lifestyle required the salary and stability of an IT job. I couldn’t afford to take risks.
Homelessness changed that.
When you’ve already lost everything, risk stops being scary. There’s nothing left to protect. The bizarre silver lining of homelessness was that all career options reopened, since some income is better than none.
When One Door Closes…
Sadly, the client had to shut down their online content business a couple of years ago — a victim of the 2022 “helpful content” update. Turns out Google updates cause significant damage to creators who rely on website traffic for revenue, even those who were doing everything right.
I was fortunate to find new clients quickly through the networking connections I’d made. Since then, I’ve continued to acquire and develop my skills in the digital content world.
The work I do is still anything but stable, and the feast-or-famine income creates its own special kind of stress. But I’m doing work I wanted to do long before homelessness forced my hand.
And I love that when people ask what I do, I get to say:
I’m a writer and editor.
Maybe one day, I’ll even get the business-y shit figured out.
Survival Is Not a Business Strategy — But It Becomes One
Starting a business while homeless didn’t make me resilient or fearless. It exposed how few options actually exist for people locked out of housing and traditional employment. Remote work and freelancing kept me afloat, but they were never a substitute for stability, safety, or support.
Entrepreneurship is often framed as empowerment. In reality, for many unhoused and justice-impacted people, it’s a workaround to survive when systems designed to help instead create barriers. The fact that I was able to build income at all had less to do with grit and more to do with access to a laptop, an internet connection, and a client willing to look past circumstances most employers refuse to see.
If you’re navigating homelessness, reentry, or financial recovery right now, know this: the struggle isn’t a personal failure. It’s structural. And finding a way to earn money under those conditions is not a moral triumph.
It’s proof of how hard the system makes survival.
If you’re looking for practical guidance rooted in lived experience, explore more stories and resources in my Entrepreneurship & Financial Recovery section.
You may also want to read about housing barriers after incarceration, because income alone is never enough without a place to live.
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