How A Decade of Blogging Gave Me The Confidence To Become a Writer

Jacqueline Dooley
6 min readJul 2, 2021

I started my first blog in 2004 when I was 8 months pregnant with my second child. It was a bit of a blogging Renaissance back then. Google had recently purchased Blogger, one of the first platforms that made blogging accessible to the masses.

(Side note: I was today years old when I learned that Ev Williams not only founded Blogger, but is the person who popularized the term “blog.”)

Blogs gave rise to a form of independent writing (and content sharing) that set the stage for the social media and content platforms that dominate today’s digital ecosystem. It democratized writing — at least, in theory. Starting a blog was easy, but building a decent sized following was another thing entirely. Growing (and monetizing) a blog would ultimately elude most of us, but audience size didn’t matter much to me.

Back then, blogging was an exciting new way to express myself and connect with people. There wasn’t an easy way to amplify a blog because platforms like Facebook and Twitter didn’t exist. Even so, I’d shared a communal excitement with other bloggers and with my readers. We could talk to each other and leave comments. We could elevate and promote our favorite blogs via the almighty blogroll (a list of blogs typically located in the margin of your post and home pages). I started and abandoned half a dozen blogs before I launched one that finally stuck.

Cleftstories began as a personal journal about my younger daughter, Emily. We learned that Emily had a cleft lip and palate on my 20-week ulstrasound. The treatment we chose — a process called nasoalveolar molding — required that she be seen once a week by an orthodontist who would create a removable plate (similar to a retainer) to mold her face prior to surgery (infants’ faces are very stretchy).

The orthodontist was brilliant. He’d pioneered the procedure that would ultimately save Emily from having many surgeries. But he was located 90 miles away in Manhattan, a 6 hour round trip from my house in New York’s Mid-Hudson Valley. I took a train into the city each week while my husband stayed home with our older daughter. I carried Emily in a sling and brought an arsenal of baby supplies in a backpack.

There was no room to lug around a laptop (and no smartphones back then), so I wrote the first blog posts on the train in a tiny notebook while Emily nursed (from a special cleft-friendly bottle) or slept. When I got home, I transcribed them on the blog.

Blogging was an easy way to keep my family updated about Emily as we prepared for her first surgery at six months old. After that surgery, I maintained the blog for a few more years. I focused on her milestones and some of her medical issues, but I mostly wrote about both my girls, showcasing how normal our lives were despite having a child with medical issues. The cleft team at NYU referred all new parents to my blog. It helped me feel less isolated as a new mom, but also as the mom of a baby with special needs.

By the time Emily turned 4 or 5, I’d stopped posting regular updates, opting to post photos of her on her birthday or after her annual cleft team visits and again when she had her bone graft surgery.

I’d loved the daily act of blogging on Cleftstories and missed my audience of fellow moms when I stopped updating the site. I also craved another outlet for my writing. So, soon after Cleftstories fell dormant, several other blogs followed.

There was a toy review website, Toy Graveyard where I tried (and failed) to earn affiliate income by writing reviews about the many toys that came into my house (and never again saw the light of day). The blog languished, neglected, for a year or two before my guilt got the better of me and I took it offline.

Then there was a collaborative blog that I launched with a few friends. Its purpose was to rant about things (and people) that annoyed us.

It was the most fun I’ve ever had blogging. I even had a few posts go (slightly) viral, but it soon felt more toxic than fun. That’s when I realized that a blog that exists solely to complain wasn’t something that I wanted to be a part of, so I deleted it.

In 2009, I launched and soon discarded a blog called Mom In A Century. That was the year I started cycling. I was determined to ride a century (a 100 mile bike ride). I think I updated that one about four times before abandoning it.

I launched Search Marketing Trainer and Internet Marketing Advice around the same time — two blogs related to my consulting gig as a search marketer. I kept up with both of those blogs for a respectable few years, but could never find the time or motivation to update them consistently.

There are a handful of others — blogs I started with optimism and good intentions about topics I wanted to explore, but never found the time to write about.

At one point, I owned close to thirty domain names and had half a dozen live blogs that I rarely (or never) updated. I held on to them for no other reason than I thought that I should. I didn’t want to give up. I wanted (needed) to write, but blogging about any topic quickly became hollow without an audience.

The next blog that stuck was ultimately what led me to become a published writer.

In 2012, my older daughter was diagnosed with cancer. The first night in the hospital was terrifying. I felt desperately alone. I needed people to know what was happening. I needed them to reach out and hold us up. I recalled the support and community I’d gotten from Cleftstories and knew what I had to do.

I launched a new blog, Healing Ana, that same week.

The blog became my lifeline for the five years that Ana was sick. It had a readership of thousands, propelled by the growing ubiquity of social media and smartphones.

Ana’s blog invited people into our lives in a way that I’d never experienced before.

It helped my family raise money to cover medical expenses, travel, and bills. It connected me with strangers across the world. It brought me closer to my support system — the people who knew us and wanted to do something to help ease our burden.

Ana’s blog also did something unexpected — it gave me confidence as a writer. For the first time in my life hundreds (sometimes thousands) of people were regularly reading what I wrote. Readers constantly reached out to tell me that they loved my writing. They told me it brought tears to their eyes and that my words moved them and made them feel less alone. I was stunned and a bit conflicted. I finally had an audience, but it was for the most terrible topic imaginable.

Even so, the blog gave me the courage and confidence to begin writing essays about parenting a child with cancer. I started submitting them to publications like the Huffington Post where even more people read my words.

In 2016, I had my first essay published in the Washington Post where I went on to publish nine more essays. I’ve since published essays in many other publications including Al Jazeera, Longreads, Modern Loss, and Human Parts. Ana’s blog stopped being relevant after she died. It’s still online, although I’m not sure how much longer I’ll keep it going.

In the months that immediately followed Ana’s death, I shuttered most of my remaining blogs.

I backed them up using a tool that converted the posts into PDF and Word files and deleted everything, including the databases. I’d finally realized, after 13 years of blogging, that I could be a writer without keeping a daily blog.

Of course, me being me, I launched one more blog before calling it quits — The Halfway Path — where I wrote about grief.

I maintained this final blog sporadically for about a year. The last update was on December 23rd, 2018. This blog, like all the others, had became a self-imposed obligation. But my previous years’ of blogging experience helped me recognize that this wasn’t a project I needed to keep working on. I allowed myself to walk away from this last blog without any guilt. I just…let it go.

To my surprise, I was completely okay with that.

I don’t need a blog. Isn’t that wonderful? I’m writing more than I ever have, both professionally and personally. I’ve been a full-time freelance writer for nearly three years. I’m still amazed that people pay me to do something I love so much.

Blogging was a stepping stone for me. It helped me find my voice. It gave me confidence. I’ll always be grateful for that. It also taught me that most projects don’t go on forever and that walking away from something that feels done (even if it isn’t) doesn’t make me a failure.

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Jacqueline Dooley

Essayist, content writer, bereaved parent. Bylines: Human Parts, GEN, Marker, OneZero, Washington Post, Al Jazeera, Pulse, HuffPost, Longreads, Modern Loss