Homeless to Hopeful: How I Went From Poor & Pregnant To Being A Six-Figure Single Mom

Shannon Ashley


Photo by Kristel Hayes on Unsplash

Back in the fall of 2013, I was quickly crashing down from what I’d call a borderline delusion. About 8 months earlier, I fell in love with a man online and I quickly traded my life in the Twin Cities for the pursuit of a romance with him in Tennessee.

Our relationship read much like a soapy shojo manga. He was married and had 3 kids. He was also a chronic cheater and by mid-November I was pregnant… and then we were done.

One week, we were getting married. His divorce was finalized and he gave me my dream rose-gold and rose quartz ring. The next week, he was positive that he didn’t want to get married again because he’d “never been alone.”

At 32-years-old, I knew enough about men to understand that codependent guys typically use the statement that they’ve never been alone as a reason to break up and see other people. He was no exception and he informed me that he needed me to leave our shared 2-bedroom apartment so he could have his space.

Everything that transpired between us isn’t what matters today.

Thank god. But back then, I still had undiagnosed borderline personality disorder and I genuinely believed that my fiance leaving me homeless, heartbroken, and pregnant was the absolute worst thing that ever could have happened to me.

I lost most of my will to fight that winter. I have PCOS and doctors always told me that they thought I would struggle to carry a baby to term.

They were right.

Extreme morning sickness, anxiety, and prenatal depression took me out of work. I didn’t have it in me to fight T-Mobile for short term disability, so I didn’t.

Instead, I spent my days sleeping, crying on the shower floor, and Googling the least painless ways to die by suicide.

As much as my ex wanted me out of our apartment, I had nowhere to go. So, he arranged for me to spend a month in Iowa with an acquaintance on Facebook.

I slept on an air mattress on the floor which deflated by the time each morning rolled around. In those days, I couldn’t stand to listen to music or watch anything aside from true crime on TV. I wanted to die. I didn’t want to think or feel. I wanted to give up, but I didn’t want to feel so guilty about doing it.

But as much as I wanted to die, death scared me.

When the family I stayed with found out that their brother wanted to move in with them, I was looking for a new roof once again.

My next few months were spent in Missouri with an older Christian couple whom I’m sure meant very well. But they reminded me on the daily that I wasn’t “home” and that my future was seriously screwed up.

I attended classes at one of those pregnancy resource centers whose sole purpose is to get women to choose anything but abortion.

They wanted me to give my daughter up for adoption. Actually, a lot of people wanted me to do that and my ex had zero complaints about the idea.

Nobody seemed to think I should get to raise my child because I was homeless and jobless at 32. Plenty of people called me selfish for keeping my child at all.

The way I saw it, my daughter would always wonder why I gave her up, and I would always wonder if it was really the right thing to do.

I was also pretty sure that if I chose adoption, I would kill myself. I don’t know why I felt that way, and I don’t think many people understand, but adoption was never a viable option in my mind.

And as much as I didn’t want to be a single mother, I also didn’t want to be responsible for messing up a kid with my own dysfunctional family issues. It felt like a no-win situation.

My pregnancy was the most miserable time in my life.

The joy that mothers talk about while expecting was impossible for me. There would be no baby showers or baby books outlining the details of gestation. There was only the urge to kill myself, and simply getting through each day without doing giving in to those thoughts of self-harm.

It also turns out that getting help for single moms is harder than you might imagine. My age made people gasp, because I wasn’t the typical teen. More than one person called me “stupid” and I was turned away from a variety of crisis pregnancy homes all because I “should have known better.”

There’s something about an unwed 18 year old mother-to-be that sometimes inspires hope and charity among Christians. It’s different when that mother is 32. Nobody seemed able to see a bright future for me. And for a long while, I couldn’t see anything bright ahead either.

By the end of my pregnancy, I decided that I wanted to be a writer and blogger.

It wasn’t some random thing--I’d been writing all of my life. Meeting my daughter’s dad actually interrupted my work on a novel. He ran a blog when we met and was writing for The Huffington Post when we broke up. In fact, just hours before he told me it was over, I’d been helping him work on a story.

Back then, I simply lacked the confidence to believe that anyone would care about anything I wanted to write.

Yet, I kept telling myself that if I wasn’t going to end my life, I had to figure out a way to thrive. I decided that it was time to make writing work. I reasoned that some of the greatest success stories happened when people were desperate and I certainly fit the bill.

In early 2014, I began telling people that I wanted to write.

I didn’t write, not really, but I read a helluva lot and then wrote about wanting to write on Facebook. Really.

At that point, writing about wanting to write still wasn’t writing. It was more like giving the universe a wish list.

But I don’t think that was such a bad thing. It was more like the precursor to actually believing in myself. First, I had to be able to dream of a better future for me and my child.

But people genuinely thought I was nuts. They told me that I needed tough love because single moms don’t get to lead fun lives or follow their dreams. They worried that I was out of touch and that I wouldn’t be what my daughter needed.

I kept putting my intentions out there anyway, and a friend eventually asked for some writing samples and offered me a job.

I was hired for my first writing gig in November 2014, but I didn’t begin to get clients until February 2015.

My daughter was about 9 months old and we were living with a young Christian couple and a young new school teacher in a suburb of Minneapolis.

Financially, I got by on child support and food stamps. In lieu of rent, I chipped in with household supplies.

It was the most lonely time of my life despite our living arrangements, and it was during this time that I officially quit believing in God and any of the Christian lessons I’d been raised to believe.

The writing work started off slowly. It was pretty basic social media work--blogs, Facebook posts, and Tweets. I made $50 my first month and $150 the next. Even so, the writing made me feel useful. And I slowly began to feel hope again.

The husband who owned the home we stayed in had a mother who worked with a non-profit group called Families First. They worked to get parents back on their feet by offering a temporary reprieve through foster care.

She told me that my best bet for my daughter was to forget my writing dream and use their services instead. She and her son explained that I could have a church family take care of my baby for a couple of weeks while I found appropriate work.

The mother said that daycare work made the most sense for me, while the son suggested that I let him and his young wife adopt my baby instead. They didn’t seem to understand my unwillingness to be separated from my daughter while she was still a breastfeeding infant.

Writing with a child would only get harder as she grew up, they claimed.

When my daughter was nearly a year old, the couple we lived with said that God had told them to sell their house, which they’d owned for less than a year.

They explained that I needed to be out by the end of May and I agreed that I would oblige. Earlier, if I could find suitable arrangements.

After several uncomfortable weeks with my housemates making snide comments about how they were afraid I wouldn’t get out of their house (despite still not reaching their deadline), I finally made arrangements with another Christian couple who planned on letting the house they’d recently moved out of go into foreclosure.

I agreed to pay $600 a month under the table to live in their old home. Of course, the filthy state of the place along with a carpet beetle infestation was an unpleasant surprise.

But for about a year, it was home.

All the while, I kept working in social media marketing.

Every month, I asked for more clients, and for a while, it felt like a great gig. By the time my daughter was about 15 months old, I earned $1,200 to $1,500 monthly and I decided not to renew my food stamps or WIC services.

My daughter and I had to vacate the foreclosed home in early July, so I decided to move back down to Tennessee since rent is cheaper down here than in Minnesota. I had U-Haul take our belongings and keep them in storage until October 2016 when our new apartment was ready.

For the first time since getting involved with my daughter’s dad, I had a place that was mine. No more sharing space with overbearing housemates. No more bugs.

And it was glorious.

My social media gig carried me until things with the company got weird.

As much as I try to pick my battles, I can’t seem to quit being a squeaky wheel. It’s one of my biggest quirks.

And so, I was a squeaky wheel at work. I spoke up when I was assigned tasks for zero pay, like newsletters.

Management was dumbfounded. You’re not creating new content. Can’t you just copy and paste? I explained that even copying and pasting newsletters for 25 clients every month took hours to complete.

I should have known things were bound to end badly there. But I kept working.

At one point, I became a squeaky wheel because they reduced our pay for writing blogs from $25 to $10. Ultimately, the company responded by replacing me with a manager’s sister.

When I spoke up about the fact that I couldn’t support myself and my daughter on part-time work, they took more clients away from me, gave some sexist lecture about how I needed to smile more, and then tried to gaslight me into believing the problems at work were all in my head.

Luckily, I had an editor who was able to confirm to me that I wasn’t crazy. She witnessed the same sad scenarios as me, and I knew I had to do something to change my fate before that place fired me.

At the same time, I found myself a little envious of an old classmate from high school.

He kept sharing articles he’d written to Facebook and it reminded me that I didn’t want to do social media for other businesses forever. I wanted to write stories that meant something to me.

Just six months before, this website had begun paying writers and I kept thinking that I should try it out. But I was scared.

For one thing, finding the time to write and simply hope to earn decent money seemed crazy. And then, of course, I had to deal with the fact that I didn’t believe anyone would want to read my work.

I only took the leap and finally began writing online because I was so desperate to dig myself out of that hole.

It was April 2018 when I finally began writing for myself.

Back then, I merely wanted to stay afloat. But I also wanted to quit my social media gig. My day job sucked the energy out of me and I felt like the whole world was going to find out that I was a terrible writer.

Like I was good for nothing.

At the same time, I’d been reading and watching a lot of Fred Rogers, and his words kept replaying in my head. There was this gnawing feeling that maybe I was right where I needed to be, because maybe this was my chance to turn my life around.

Something about becoming a single mom kept making me wonder if I could take a tragic situation and use it for good. I wondered if I could radically transform my life by doing something that I love.

I was determined to make my own writing career work.

So, I did. I committed myself to writing whenever I could, and within months, I found myself only wanting to write for me.

After several months, the money was better than anything my social media job paid me.

Eight months into my efforts with online writing, I quit the social media gig. I was so scared that I was making an enormous mistake that would hurt my daughter and ruin our lives, but I couldn’t spend another day working a job that crushed my spirit.

That was in early December. As we head into the holiday season, I am reminded that it hasn’t even been a year since I quit my job to write full-time on a website that may or may not exist in a few years.

The jury is still out on whether or not this will turn into lasting success. But I don’t care.

All I really know is that I wake up and fall asleep with a whole lot of hope in my heart.

I have not always been a hopeful person. I am a natural idealist, but my spirit was deeply broken over the years.

It started with my family and my strange upbringing. It continued with the church, and culminated with society. All of the hopes I had as a child to lead a fulfilling and creative life were ultimately dashed to pieces by mundane or abusive experiences.

I spent my whole life being told that my dreams were unrealistic and that nobody really makes it in a creative career. Even my father, who was a freelance muralist did a lot to discourage me from holding onto a sliver of hope.

So, these days, when I wake up with hope in my heart and the belief that maybe there are better things ahead, I don’t feel like keeping these thoughts silent.

Mister Rogers was right all along.

He once said, “The world needs a sense of worth, and it will achieve it only by its people feeling that they are worthwhile.”

People have plenty of ideas about how to deal with folks who are struggling. Or how to deal with single moms and crisis pregnancies.

A lot of those ideas revolve around this notion that we just need some tough love. Or that we need to be put in our place. As if nobody ever told us the word no.

But here’s what I know.

Too many people have floundered because all they ever seem to hear is no. Sit down. Shut up. You’re not special. Who do you think you are?

Tough love isn’t making the world a better place. People aren’t rising to the occasion because they feel like dirt. On the contrary, people make terrible choices when they feel terrible about themselves.

I didn’t get involved in an unhealthy relationship because I felt good about myself. I did it because I didn’t feel worthy. And it’s the same reason why I didn’t pursue my writing dreams.

People need to feel worthwhile.

Dreams do come true.

I don’t really care if my current level of success doesn’t last. I’m not worried, because I now know that dreams come true. And that everybody has a story worth telling.

If I face a new patch of adversity I believe that I can survive.

My experiences with success might still be green, but I am more determined than ever to build a good life for me and my daughter. I believe more in the power of that determination.

Likewise, I hope my experiences inspire you to take big risks where it matters because perpetually playing it safe doesn’t serve anybody well.

You have something inside of you that the world needs, and perhaps the point of this whole journey is figuring out exactly what that is.

Don’t let anyone tell you that your dreams don’t matter.

You can prove them wrong.

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Single mama, full-time writer, ex-vangelical. It's not about being flawless, it's about being honest. I cover real-life issues, like family, parenting, relationships, and spiritual abuse.

Cleveland, TN

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