The Long and Winding Road to Become a Professional Writer

A note to readers: This post constitutes my entry in a writing competition called “Writing Contest: You Deserve to be Inspired” hosted by the Positive Writer blog. Positive Writer is one of my favorite blogs about writing – check it out if you’re looking for an excellent writing resource.

I shuffled the papers into a neat stack, stapled them, and strode confidently into my supervising attorney’s office, handing her the memorandum I had painstakingly prepared on some arcane legal issue over the last several days. I nailed it. Or so I thought.

I was a first year attorney at Skadden Arps. I fancied myself a skilled writer and communicator, but I was, in fact, neither.

When I got back to the office the next morning, something bearing resemblance to the memo was sitting on my chair. It was a sea of red ink and looked more like something my three year old daughter would create – full of circles, x’s, and squiggly lines – than a polished legal document.

After wading through the document, I realized that it was not my grip of the facts, analysis or conclusion that was lacking. The substance was there. The form was not.

I had a lot to learn about writing well.

In his essential book, The War of Art, Steven Pressfield distinguishes between “professionals” and “amateurs.” An amateur is someone who hopes and dreams, but never does. A professional “commits full-time.”

There were four stages, each of them long and arduous, in my journey from amateur to professional writer.


I learned a great deal during my first year in the “real world” as an attorney. The most important lesson was that while my formal education had just ended, my real education about writing was just beginning.

I had two choices after digesting the comments to that disastrous memo I wrote. I could either respect or reject the feedback.

Fortunately I chose the former and began working to acquire the most essential skill of a good lawyer: the ability to inform and persuade using the written word.

I picked up copies of White and Strunk’s The Elements of Style, and Zinnser’s On Writing Well and began studying. I identified and sought counsel from skilled writers in my firm, and learned about structure, brevity and tone. The most important lesson I learned was the need to ruthlessly self-edit.

Over time my writing got better. I acquired the skill.


After about six years of practicing law, it was time to make a move. I wanted a more entrepreneurial existence. I joined my wife in her fledgling marketing business and off we went.

This transition presented a steep new learning curve. I had been accustomed to writing legal briefs and memoranda for judges and other lawyers. Now I had to write in an entirely different way for vastly different audiences. And I was on my own. There were no more filters between my work and the reader’s eyeballs.

I learned a lot during this phase in my career. In particular I learned what it took to get hired by clients to produce persuasive copy for disparate audiences and in different mediums. I learned how to get paid to write about someone else’s ideas.


After several years of writing for clients, I decided it was time to take the next step. I no longer was content just being a copywriter for someone else. I was ready to put my own ideas out into the world and I started this blog.

This is a big step for any writer. Fear of scrutiny and judgment stops many talented writers from ever sharing their gifts with the world. Author Bryan Hutchinson describes the fear that stops many would-be writers in a post on his blog: “The self-destructive thoughts our minds come up with may be irrational, but when they’re raging inside of your head, well, they seem very real and very serious, and they can be utterly devastating.”

I was fearful but decided to take the plunge nonetheless. I started blogging.

Putting my point of view and ideas into the world was scary. As with most things in life, it got easier with practice. Every time I published a new post my confidence grew. I wasn’t getting paid for this work but I was finding my voice.


A funny thing happens when you work hard and try to add value to the world. Sometimes the world gives back.

When I started my blog, I knew I needed to look outward to grow my audience. So I sought opportunities to write for other platforms with existing audiences in order to get noticed and drive traffic back to my own site.

I started publishing most frequently on a website that also publishes books geared toward lawyers. After publishing three or four articles there, the site’s publishers approached me about writing a book.

I said yes, got to writing, and about 18 months later my first book was printed.

While holding that book in my hands I knew I had entered a new stage in my career as a writer. I was a rookie, still rough around the edges in many ways, but I had turned pro.

And you know what happened then? I realized much I still had to learn! Writing a book is one thing. Selling it is an entirely different animal. The need to learn and grow as a writer never ends. This lesson, like others, was learned the hard way.


My experience is relevant not because it’s extraordinary, but rather because it’s not. It’s the story of almost every writer, marked by struggle and frustration, but also the occasional triumph that keeps your butt in the chair.

My writing evolution has been slow and full of fits and starts. But no matter how plodding, I’ve always been able to maintain some momentum. No matter where this journey takes me, I’m always going to remember that every stumble is a step forward.