The Joys and Frustrations of Stepping Outside My Writing Comfort Zone

Photo by Matthew LeJune on Unsplash

For the past year and a half, I’ve been making a concerted effort to write outside of my usual comfort zone.

My writing background is in the academic and legal world. I’m comfortable with heavily researched academic papers, and confident when it comes to all manner of legal briefs and motions.

I enjoy those types of writing, but they both have a very limited audience. Most of my legal writing has been meant for just a few readers (the judge in a case, and a handful of lawyers). I had always wanted to try writing something that would reach a wider audience.

I was worried though. Would being a good legal and academic writer translate to being a good writer in general? Or would I have to start over from scratch, learning to write from the ground up?

The reality of it fell somewhere in the middle.

I started expanding out of my comfort zone by writing op-eds. I stuck to legal subjects, but with a far more conversational tone than I had ever written in before. I found immediate encouragement when my first op-ed was quickly picked up by a mid-size newspaper, and my second was published in another paper a few months later.

Having these op-eds published was really exciting for me. I had never had anything reach so many readers before. It made me eager to expanding my writing even further. In the following year, I tried my hand at fiction, blogging, and poetry.

My posts here on Medium have been my latest attempt to try something new. For the first time, I’m writing about my personal experiences, including some of the most serious struggles in my life.

So, has stepping outside my comfort zone been worth it?

The Frustrations

I’ve enjoyed experimenting with new times of writing, but it hasn’t been completely smooth sailing. Having the op-eds published so easily was mostly just good luck, and since then I’ve learned the hard lesson that it can be very tricky to get things published.

I’m sure most writers know to expect more rejections than acceptances, but it can still be hard to see your work rejected again and again.

The writing itself has been difficult too. The op-eds came fairly easily to me, but fiction has been incredibly hard. It’s so different from what I’m used to writing, that I find myself needing to spend way longer writing than I ever have before. I also have to break some habits that work well in legal writing but not in short stories. (Getting the tone right is especially hard for me).

Frankly, even after a year my fiction still sucks. It’s been getting better, but it’s still the worst writing that I do.

Writing these personal posts on Medium was also very hard in the beginning, although it’s gotten easier. Again, I think finding the right tone has been my biggest struggle. It’s tough for me to write honestly and openly without coming off as too cheesy.

Finally, with a bigger audience, I’ve started to get a few haters. (Fortunately not too many). I’ve read again and again that everyone gets haters, and it’s just an inevitable part of publishing your writing. Despite that, it still gets to me. I hope that as I write and publish more, I’ll eventually learn to tune it out.

The Joys

Overall, branching out into new types of writing has been a great decision and I’ve enjoyed it a lot. It’s been hard, but I do feel like I’m slowly getting better. Learning to write in these new styles has even helped improve my academic and legal writing, by helping my tone become a little less dry.

Even though my previous writing experience hasn’t translated completely to these new styles, it has still given me a running start. Knowing a bit about structure and grammar has definitely helped me with every type of writing I’ve tried.

Another benefit I’ve experienced is that trying to write fiction has transformed the way I read books. I’ve always loved to read, but I’m finding a new appreciation for more “literary” books that I used to typically avoid.

As I read, I find myself paying more attention to details like the writer’s word choice, and how they structure a sentence or paragraph. Having these new things to look out for has actually made reading even more fun for me.

Also, to counter the “haters” that I mentioned before, I’ve received far more positive comments from readers. It’s really an amazing feeling to get positive feedback, and I don’t think I’ll ever get tired of it or take it for granted.

On Medium, I’ve mostly written about my struggles with sobriety, and the best kind of comments I’ve gotten are other people who have gone through (or are going through) the same things. It’s exciting to share these kinds of connections with strangers, and I had never really expected it when I started writing.

Overall, I’m glad I’ve expanded out of my comfort zone, and I’d recommend it to other writers who want to try something new. It’s hard, and I still have a long way to go, but it’s been fun and exciting, and I’ve learned a lot along the way.

I’m a lawyer and teacher from North Carolina. I write about sobriety, mental health, running, and more. Buy me a “coffee” at

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