I’ve been writing for the web since 2007. I started on my own site, The Writer’s Coin, which (at the time) was about personal finance, writing, and advertising.

Eventually, I focused on writing about money, but at the time I was pretty intent on making it work as some rare, three-headed monster where I’d write about money, writing, and advertising. And part of my routine in those early days was to publish three posts per day.

I saw Trent from The Simple Dollar (the mecca of money blogs at the time) and figured that’s what I needed to do to get some traffic.

So I did.

That meant that some posts weren’t nearly as good as others—and all those early ones were pretty terrible. But eventually my writing got better, the posts got better, and I started seeing some decent traffic.

On one of those early days, I had two posts ready to go but needed/wanted a third. I had seen an interesting picture on the cover of my Poets & Writers magazine that month, so without hesitating I grabbed the image from the web, saved it to my desktop, and put it into a post.

I gave a little background to the picture, some stuff I learned about it via a quick google search, and then segued into a personal story of mine that was tangentially related to the picture.

Tired of all the abstractions?

Here is the the post.

It has gotten over 74,000 pageviews since i first published it .

Here’s what happened when the traffic spike hit:

That’s right: a post about Marilyn Monroe reading Ulysses has been the most popular piece of content I’ve ever written out of 500+ posts in my life—most of them about money, writing, or career related topics.

But a tiny little piece I threw together in 15 minutes so I could hit my daily quota has been the big winner.

Sad? Somewhat. Depressing? Kind of. Hilarious? Totally.

You Just Never Know

That’s what I took from this anomaly. Whenever I get an idea that I think is decent and I start trying to shine some light on it, there’s that little voice that tries to shut it down. That says, “Eh, it’s not very good, let’s just move on to the next one.”

The voice is smart. All it wants is to get you to stop, to quit, to stay still and never grow. And it’ll say whatever it has to in order to achieve its goal.

“You can do better than that…can’t you?”

“Try something a little different, this one’s a little weird. Even for you.”

“Even your wife won’t encourage you on this one.”

But you just never know. You owe it to yourself to push as many ideas like this as you can to fruition because we just aren’t very good judges of what’s good or bad.

Some comedian said that once on a podcast, I just can’t rememeber his name. The jokes he thought were good were the ones that bombed. So he just started trying out all his material first and noticed that the laughs came from the jokes he didn’t think were all that good.

A famous photographer said the same thing about taking pictures: he had to take thousands of pictures in order to come up with a handful of great ones.

You just never know.

The lesson is you have to just ship it. Ship as many things as you can and see what happens.

One day I woke up and told myself I would have a first draft of a short story before I went to bed that night.

So after work I went to the DePaul library in Lincoln Park and sat down with pen and paper. I forced myself to sit there for two hours. I started writing and had a decent-sized paragraph when I realized it was crap but now that the crap was out of the way I was ready to start with what sounded like a pretty interesting story.

So I did. And two and a half hours later I wrote the ending. A couple of days worth of editing and I decided it was good enough to send in to a contest.

A month later I got a letter in the mail. My girlfriend at the time (now wife) happened to be with me when I opened it and read it.

I had gotten an honorary placement in the contest. I didn’t win and I wasn’t getting published, but I was invited to the celebration event and I got a $300 prize.

I was blown away.

I wanted to cry. I looked at my now wife and told her how awesome it was that she was with me when I opened the envelope because it was such a cool moment. After that day, I felt like I could really become a writer if I wanted to.

Honestly, I felt invincible.

One little story written in a couple of hours and tweaked over a couple of days.

You just never know.

That girlfriend and now wife?

I was at a dive bar with a friend of mine and it was completely empty. So I told him we should get out of there. He told me it would get busy soon. I said, “We never come to this part of the city, so let’s at least go where the people are.”

So we did.

And when we got to the next place (which I’d never been to either) we managed to get a table before it got crazy busy and everyone was asking us if it was OK for them to put their drinks on our table. We said OK to the girls that asked.

Then two girls came asking if it was OK for them to actually stand at our table with us (not in a hitting on us kind of way, more of a “wow it’s crowded and we need some space”), and we said sure.

The one girl across from me was cute. I tried talking/screaming to her a little bit but it was loud. So I smiled a lot and she didn’t seem to mind that. So on my way to the bar I came up to her and talked a little bit so she could hear me. I bought her a drink. Later, we even danced a little bit (I hate dancing).

It was fun, innocent dancing, by the way.

I told her how I always forget to ask for phone numbers from girls I want to get to know and then they leave and it’s too late and I feel like such an idiot. So, sorry that it’s really early in the night and all, but could I please have your number? I don’t want to forget later on. She wrote it on a napkin and said, “OK, but you have to call me tomorrow. If you don’t, don’t call me at all.”

The next day, I did.

Now we’re married and have a four year old daughter two kids.

You never know.

I was looking for a new job because I was desperate to leave the one I was in. So I went on Craigslist and found something that looked interesting. It was as a writer for a web startup that wanted articles teaching people the basics of investing.

Remember The Writer’s Coin? I had a TON of content on that topic and it was a lot of fun. The Craigslist post seemed a little iffy, but I sent an email and they got back to me with some more info about the job. I looked the company up and the website was terrible. Could’ve been fake for all I knew.

But I wanted out and so kept going back and forth.

Eventually, I got an interview.

So I show up and when I get to the front desk it hits me: this place is real and it’s like a modern art museum. Whoever designed their website did them a MAJOR disservice.

Not only is this place real but it’s amazing. I get taken into a little meeting room with glass doors and as I go I can see that the whole floor is wide open, the ceilings are like 150 feet high. And the view out the window overlooks LaSalle Avenue going north because we’re in the Board of Trade.

Amazing.

In the little meeting room is a print on the wall. It looks funky and edgy and interesting. So I look for the name. It’s says: Robot drowning in nanobots:

That’s when I said, “I have to work here.”

And I did. For four years. I learned a whole bunch of new skills that would propel me to different jobs in the future. I met friends that I still have today.

You just never know.