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How One Article Has Paid My Mortgage the Last 23 Months


“Hey man, I think this post is pretty good. But the title of “9 Decisions That Led to a Life I Love” isn’t doing it for me. Got any suggestions?”

“Yeah, it’s a bit dry,” my friend replied 38 seconds later over Slack. “Try throwing ‘How to Wake Up Smiling’ in front of it as you reference that in the intro.

I woke up the next day hoping the stats from the article would indeed make me smile. But that didn’t happen. Whatever upward trajectory it initially hit was short-lived. By the time I went to bed that night, I’d officially written it off and moved onto the next idea.

But something interesting happened while I was sound asleep in my bed in Spain. Something gorgeous. While I was dreaming, a famous blogger 6,000 miles away in NYC was typing. And somehow, a sentence from my post ended up on her blog.

“I think I’ve written my first viral article!” I screamed to my wife the next morning from the old mattress I was laying on next to our kid’s crib. “Someone named Cup of Jo must’ve shared it! It’s already got 8,000 views and it’s only 8 AM!”

For the following 47 hours, I was a despondent husband and absent father as I stared at my phone watching the numbers go up and up and up.




By the time Monday morning rolled around, this beautiful stranger — who I’d quickly learn was one of the top bloggers in the world — had single-handedly driven 100,000 views to my article via her website, Facebook group, and newsletter — setting it onto a path to eventually top the quarter-million mark.


Two years have passed and despite having a few posts that jumped immediately out of the gate, I’m yet to experience a flood of engagement like I did from that one. It not only launched my writing career, but also moved my coaching business from red to green.

  • 500+ Linkedin messages in the first 2 weeks and hundreds more since.
  • 3,000+ new Linkedin connections who continually support my work.
  • 27 coaching clients and counting.
  • 5,600+ fans and 30,000+ claps with less than 100,000 internal views.
  • Countless new followers on this platform.
  • Interest from a book agent.

In short, this 1,576-word article that I published when I only had a handful of followers and had never made more than $300 in a month from writing, has easily paid my mortgage for the last 23 months.

And the best part is, if there was ever an article that I’d want out in front of my name — this would be it.

I didn’t try to sell anything. I didn’t provide any bullet-proof tips on how to break out of mediocrity to be extraordinary. I didn’t make a list of lessons people learn too late in life or any of the other recipes that consistently lead to online virality.

I simply told my story in a way that made other people want to tell me theirs.

The “One”

Since it’s coming up on its two-year anniversary, I’ve been thinking about what made that one stand out and I’ve narrowed it down to a few things.

  • Countless people told me including mentions of depression and drug and alcohol use would damage my coaching practice and turn readers off. In the end, I found the opposite to be true as most of the people who contacted me cited my openness as the driving force behind reaching out to me. The realization I didn’t have to be cool in my writing, only honest was a game-changer.
  • Using a not-so-famous thought-provoking quote from a very famous person in the intro to explain why I was writing the post was super effective as it got people in the door quickly.
  • The first point was especially strong. It includes a highly relatable thought from my dad, followed by supporting lines that are highly Tweetable.
  • The mix of vulnerability and humor (self-deprecating at times) helped to separate it from other self-help articles that often tell instead of show. To this day, I don’t think I’ll ever write a better sentence than — “I’m not sure what the Myers Briggs code is for a stutterer with ADHD who never really listened to anyone, but I am pretty sure it is D I C K.”
  • The takeaway exercises I shared are extremely practical and easy for other people to do if they’re looking to smile more too.
  • I’ve since stopped using quotes as endpoints as much as I prefer to try to make my own thoughts sing. But I think the mix of common and uncommon quotes silently encouraged people to keep reading.

Lastly, and I think this one is key — most of the points hint at the theme that over time it’s our scars that make us beautiful — which is a message that a lot of people connected with.

You never know when your writing will take flight

I was asleep when a beautiful stranger sprinkled her magic fairy dust on my work. Within 90 days, thanks to the flood of messages, as I was able to quickly move from writing for fun to doing it for a living.

Maybe when you wake up tomorrow you’ll find that the world has caught on to what you’re doing too. Or maybe it’s the next day. Or the one after that.

For me, this is what makes this whole world of art so much fun.

We sit down and fight to find our voice and when we get the message right, some people decide to stick around to see what else we have to say.

One day, 23 months ago, I wanted to tell my story in a way that let people know that life has a funny way of changing as long as you yourself are willing to change.

It’s far from perfect. But looking back on it, I think that played a massive role in why it took off — for once, I was me.

One article.

One Tweet.

One mention from a stranger is sometimes all it takes.