I’m Starting a 30-Day Blogging Challenge

Published in

Writers Guild

6 min readDec 10, 2018

Dusted off the ol’ typewriter for this one.

When I was a sophomore in college, I was hired as a social media and marketing intern for a brand new startup company called SeatGeek.

I didn’t go on to work for that company after college, which is now worth tens of millions of dollars (due large in part, I am sure, to my contributions as a summer intern), but I did write a lot of blog posts during my time there.

My favorite was a post where we used proprietary data to track what seat in Yankee Stadium was the most likely for Alex Rodriguez’s 600th home run to land in. We pitched an exclusive to Wall Street Journal — very exciting for a punk 20-year old kid!

The projected path of A-Rod’s 600th Home Run. We were very wrong!

All that summer, I had the privilege to blog — amongst other responsibilities — for an existing audience of a really cool company.

I was emboldened to write elsewhere for a bit, and batted around the idea of a career in media.

Fast forward 8 years later, and I’ve basically only written business emails for the past 8 years.

And I’ve gotten really good at writing emails, but it’s not the kind of writing I’ve been wanting to do.

I’m inclined to blame Corporate America, yet I myself deserve equal if not greater criticism for my lack of content and for my lack of courage to put finger to wireless keyboard.

I’ve blamed lack of time, lack of energy, lack of practice, lack of a blog, lack of a social media strategy, lack of a monetization plan, lack of an audience.

So here I am today, with a fledgling Medium account and far less than 10,000 hours under my belt.

A year and a half ago, I quit my job and moved to South Africa.

I had a great job in the U.S., but I felt compelled to take some substantial risks. I wanted to pursue entrepreneurship, to create a lifestyle redesign, and to immerse myself abroad.

And so I did. I gave my notice, sold most of my stuff, and hopped on a one-way flight across the world.

I bought this stupid blue backpack only to have used like 3 times…

While I had no idea what was in store for me as an expat and a traveller, I felt that I had finally gained control of my life and was poised to built the ideal version that I had been reading and dreaming about.

Fast forward back to today — writing from Johannesburg, South Africa — and I’ve learned (the hard way) what it takes to build something successful — as an entrepreneur and as a lifestyle designer.

It takes a tremendous amount of time and patience and recurring effort; resiliency and an even keel; an intimate understanding of how things compound and accrue.

I’m at far less than 10,000 hours because I’ve written far less than 10,000 hours.

I haven’t had the patience, or the resiliency, to write for 10,000 hours.

Until now.

I’m starting a 30-day blog challenge because now I know what it takes to be successful.

If I actually want to build a sizable Medium following and/or get better at writing, I need to do the work.

I already knew this, but I hadn’t acted on this knowledge until now.

Cognitive dissonance.

I’m going to write every day for 30 weekdays straight (though we’ll see how it goes with the holidays coming up), and I trust that — in spite of my fears, my reservations, my impending discouragement, my impending writers block — that I will be better off, both objectively and subjectively, after these 30 blog posts.

And I don’t plan to stop there.

So what’s the plan?

The plan is to write every day — about life experiences, about culture, about learning, about decision making, and more.

Today’s actually already day two — I was annoyed by a company’s customer service, angrily typed up a blog post on Friday in a haste, and hit publish.

It was that easy!

(Shout out Tom Kuegler, whose writing emboldened me to take this challenge on, and whose daily routine I will be following.)

I’ve kept a list of topics to write about, and I’m going to keep adding to that list daily.

I believe I’m pretty well read, and have many references to share to corroborate my theses, but I do not want research to stand in the way from me hitting publish.

I plan to share via my personal social media platforms — feel free to connect with me there too. Facebook, Twitter, LinkedIn & Instagram.

I’ll also share via my Newsletter, in addition to my regularly scheduled email (sent weekly on Wednesdays, which shares interesting articles, podcasts and books I’ve come across).

Why am I writing?

I’m writing because I want to write. And that should be reason enough.

I don’t have a plan, or any intentions, to make money from blogging (though that would be nice).

This isn’t a content marketing exercise or a lead gen tool for business purposes.

I’m just writing because I want to.

I do also believe that putting my thoughts and ideas out there in the world will benefit my ability to think more constructively, and will benefit my mindfulness, as well.

And, regardless of readership metrics or audience development, it’s an exercise worth doing and an experience worth having.

Who am I writing for?

In my perpetual study of writing (one that wasn’t going to stop until I was “ready”) I’ve read that the best way to write is for an audience of one.

Well, my audience of one is myself.

I’m writing for myself.

As a reminder of the things I already know to be true.

As a challenge to myself — that I can do these things that are hard, and I can do them over a long, sustained period of time, even and especially when I don’t want to.

As a sense of pride, to share all of the of the things I’ve learned and experienced over the past year and a half.

I’m writing for me — but I hope that you find what I have to say useful too!

I don’t really like what I just wrote.