Three Ways Writers Evolve Over Time

Three Ways Writers Evolve Over Time

You know, I sat here for a long time trying to think of something to say about Phil. I mean, he’s got a goofy looking avatar, he’s shorn closer than a sheep and he sends me good posts. What more can I say?

Then it hit me – for all that I don’t know much about Phil, I know this: he observes and pays attention to his writing. Not just how he’s writing now, but how he used to write, and how he’ll be writing in the future. That’s a pretty neat thing to do.

Why not try it? Read, think, and then let us know your three favorite writing evolutions.

The last time Men with Pens saw me, I had just written a guest post for them entitled Get a Rush from Your Writing.

That was a year ago. Since then, I’ve been running a copywriting business, become a regular blogger, and have had two books published, with a third just recently released.

Moderation? No, can’t say I’ve heard of it.

With the amount of work I’ve been producing, I’ve learned a lot about myself as a writer and about writing in general. So for my next great endeavor, I’d like to discuss how a writer evolves.

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 a lot of 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.


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.

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.


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.

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.


Use examples, case studies, and personal experiences to illustrate broader points, especially if they’re central to the overall point to your piece. Not everything needs a story, but few points 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.

What about you? How have you evolved as a writer over time? Where have you relaxed your standards or improved your skills? Let us know in the comment section!

Post by Phil Simon

Phil Simon is a three-book author who consults companies on how to optimize their use of technology and speaks about emerging trends. He also writes for a number of technology-oriented media outlets. Check out his blog, listen to his podcasts, and watch his videos here.