Three Ways Writers Evolve Over Time

Before hitting ‘submit’ or turning in your article, ask yourself if it’s too stiff.

Over the past five years, I have changed careers. Part and parcel of being a professional writer and speaker is regular blogging. Beyond that, I have written two books with a third just recently released. To say that I have learned a great deal about writing is a vast understatement. In this post, I will discuss how I have evolved as a writer.

Getting Clearer to Get the Point Across

Like most writers, I look back at some of my blog posts from about two years ago and cringe a little. I see where I was going but in many cases, I never quite made it there. Often I had a valid point to make but I didn’t write it in a way that others would find accessible. I used esoteric examples when a more generic one would have been more effective.

Dennis Miller is the one person I know who successfully pulls off the “you had to be inside my head to get it” standard. If you’re in the audience and you follow one of Miller’s obscure references, you feel like you’re super smart, like you’re part of the inner sanctum. On the other hand, if you don’t, then you kind of feel like an idiot.

Simon Says

Unless you’re writing for a particular niche, try to err on the side of expansiveness. No one wants to read the first paragraph of an article, book, or post and feel out of the loop and ignorant. Be inclusive. Make everyone feel welcome.

Getting Less Formal for More Engagement

I’ve embraced the second person. That’s not to say you should never use different perspectives, but I’ve found that it’s easier for me to present a casual tone if I write in the second person. I’ve found it’s really important to avoid an overly formal tone if you’re hoping to keep people interested as they read your work, Second person helps me do that.

Try to err on the side of expansiveness.

Several people who’ve read my books mentioned to me that I write like I talk. That made me feel good, because these are people who like hanging out with me in general. It also made me realize something very important: people like to feel comfortable engaging with someone, even if that person is in the pages of a book.

Overly formal writing makes them feel like they can’t relate to you, and that means they don’t want to hang out with you or your writing for very long.

Simon Says

Before hitting ‘submit’ or turning in your article, ask yourself if it’s too stiff. Is it possible to insert a little humor or laid-back language in places? If the answer is yes, then go for it. You’ll build a reputation as a serious writer who can introduce levity in key places.

Giving More Examples for Better Interest

My favorite writers draw me in with interesting narratives, making their points without being preachy.Malcolm Gladwell’s book Outliers, wouldn’t be the success it is if Gladwell had spent the whole book citing dry statistics drawn from business data. But reading about Bill Gates slaving away at terminals when nobody believed computers would ever be in every home is a great story.

It sticks with you. It drives home Gladwell’s point about success being as much about hard work as luck.

In contrast, I recently picked up a short technology book that was lamentably devoid of case studies, stories, and examples. The author wrote solid prose in a welcoming style about interesting content but I couldn’t get through the book. I can only read so many pages of truisms and recommendations. After a few pages, I thumbed through the remaining chapters, looking for anecdotes.

When I couldn’t find any, I put the book down for good.

Use examples, case studies, and personal experiences to illustrate broader points.

To communicate, garner and retain reader interest, tell stories like that one. Show us how this works in the real world. Make us feel something about disappointment or hope or excitement. That’s how people get engaged.

Simon Says

Use examples, case studies, and personal experiences to illustrate broader points. This is especially true if they’re central to the overall point to your piece. No, not everything needs a story, but rare is the point that couldn’t be improved by one. Use them liberally and keep the human element alive. We all need to feel like we’re not alone, and stories help us get there.


I initially wrote this for Men with Pens. Click here to read it there.

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