If I Had to Do It Over…

I never planned to be a writer. And yet here I am. I kinda wish I’d approached a few things differently along the way.

I never planned to be a writer.

When I entered college in 1975, I had no plan at all. I had a vague interest in electronics, and seeing that on my application, the University of Washington saw fit to put me into College of Electrical Engineering.

It was there that I encountered what would become my career’s passion.

Engr 141

I’ve often told the story that Engineering 141 — Introduction to Fortran Programing changed my life.

A required class for all engineering students at the UW, it was the first time I’d used a computer of any sort … and it was love at first sight. Things just clicked. I walked out not only with a perfect grade, but with the giddy realization that people would pay me to do this.

They’d pay me to have fun.

Over the rest of my college career, the roots of what twenty years later would become Ask Leo! were sown as I helped friends with technology and worked the local help desk from time to time — often for free.

The real world

My first job out of college was with a small company that got smaller over time — unintentionally.

But I was having fun.

In a small company, being a “jack of all trades” is an asset. As a result, I worked on a number of different things, from software maintenance and bug-fixing to feature addition and more. I also wrote end-user documentation for our tools, and even ended up writing and editing a monthly newsletter sent to the company’s customers.

Eighteen years at Microsoft followed, where I not only worked on a variety of projects, but was introduced to email (my first email address was, indeed, @microsoft.com), the internet, and web development. Once again, as a “jack of all trades” I alternated between being an “individual contributor” writing software, and being a manager of same.

Not long after leaving Microsoft, I fell in with some internet entrepreneur types, and, to make a long story short, Ask Leo! happened.

After doing Ask Leo! for just a little while, I came to an unexpected conclusion.

Not only was I writing, I was a writer.

And I had been, all along.

Had I known that, I would have done some things a little differently.

If I had to do it again

I would have paid more attention in English class. Heck, I would have taken more English, grammar, and writing classes.

The problem was that I hated writing in school, absolutely hated it. It wasn’t until I started working a real job that I discovered that not only could I write relatively well (though I couldn’t spell to save my life — I still can’t), I actually kinda sorta enjoyed it.

That customer newsletter I put out at my first job? Not only was it my idea, but it was pretty fun. Writing documentation because, in the end, I was the software department? It worked. What did I do well at Microsoft? Communicate via email — which is, of course, writing. I even got my first published article in one of Microsoft’s early developer magazines.

But it didn’t dawn on me that I was writing.

Do what you love? Write what you love!

What I hated in school wasn’t writing; it was writing about things I knew nothing about and wasn’t interested in. Once I got past that, words started to … well, to trickle out. I’m certainly not about to write the next great American novel. But I do write.

And if I’d paid more attention and made a few different choices back then, I’d be a better writer today. Much better.

Which brings me to my point….

We are all writers

Regardless of your profession, writing, especially in this internet-enabled age, is becoming more and more critical. The ability to express yourself, clearly and even entertainingly, is often the difference between being good at a job and being great at it; a blog post being shared or ignored; an email being understood or discarded.

A question being answered … or not.

I bring this up because of the number of people who write to me who, to put it very bluntly, simply can’t.

Now, to be clear, there are two distinct camps: non-native speakers, for whom English is a second language, and those who’ve grown up speaking English, but still couldn’t write a coherent sentence if their life depended on it.

I have a lot of sympathy for the first group (very technically, English is my second language — it’s a long story). I’ve found myself trying to explain the rules of English to my overseas relatives and friends, and absolutely, it’s hard!

But, to be completely honest, I have very little sympathy, and less and less patience, for the second. After growing up and being educated in an English-speaking country, there’s very little excuse for not being able to express yourself in your native language. It doesn’t have to be eloquent, and it doesn’t have to be prose, but it needs to be understandable.

I think you’d be shocked at how many fail that simple test.

You are being judged

Sad as it is, both groups are at a severe disadvantage.

It’s probably not fair, and it’s certainly not politically correct, but the reality of the internet is that speaking and writing English well matters. Not only are vast amounts of resources and content in English, but it’s the closest thing we have to a common tongue among the masses online who speak a variety of other languages.

Your use of English — particularly as a native speaker — heavily colors how you are perceived. It can be a barrier or an aid to getting your ideas across, your position understood, your desires met, and more.

There used to be a commercial for a vocabulary product that began, “People judge you by the words you use …”. And this isn’t even about vocabulary.

It’s not fair, but it’s very, very true. You may be the smartest, coolest, most wonderful, knowledgeable, and professional person on the planet, but if your email, posts, and other writings sound like a spoiled teenager who didn’t finish high school, don’t be surprised if that’s exactly how you’re treated.

The ability to express yourself clearly and coherently in your native language — and in English, if that’s not your native tongue — can make a huge difference in your success online.

And in life, for that matter.

If I had to do it all over again, I’d make it a priority. I hope you will too.


This article was originally posted on Ask Leo! where it’s received a fair amount of positive feedback. That article, in turn, was a expansion on a podcast episode I’d published even earlier.

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.