How an undisciplined person was able to blog for 200 weeks in a row

I still remember this all-nighter in college, writing on my trusty Smith-Corona typewriter. That undisciplined person is me.

I'm someone whose list of things to do is scrawled on scraps of paper. I put off things I don’t enjoy doing, like taxes and even the smallest of administrative tasks. Occasionally <ahem> I’ll eat and drink too much.

Despite my lack of discipline in some areas, though, I’ve managed to write a blog post every week for 200 weeks. By sharing how I did it, maybe I can help others who want to write more too.

The beginning

It was about six years ago when I first started writing. Looking for some kind of creative outlet as I was changing roles at work, I began using a low-tech blogging platform that was available inside the company, and the early posts were therapeutic. I wrote about things I was interested in, and with each post I felt like I was developing a useful skill.

I wrote only half a dozen times that year, but one post about trying to use Gmail at work attracted over a thousand comments. I was amazed at how a simple essay on a social platform could make it possible to connect people and build a movement. Something clicked. I saw that by making my ideas and work visible, I could shape my reputation and get access to opportunities I wouldn’t have known about otherwise.

I started to take writing more seriously. My friend Eric, an author and journalist, helped me by editing my work and offering support. I gradually started writing more, enjoying the feedback, and after 18 months or so I was posting something every week inside my firm.

The struggle

Writing did not come naturally. I would procrastinate. I would stare at a blank screen not knowing what to write. I would hate my early attempts at a post as I kept failing to make a concise point.

I was mindful too that I was often spoiling Saturday mornings with my brooding over a laptop, testing my wife’s patience. And for what?

I thought of stopping, but I remember reading Seth Godin’s daily blogs at the time, and they provided me with much-needed encouragement. Here’s one of them:

“Where, precisely, do you go in order to get permission to make a dent in the universe? …

If you think there's a chance you can make a dent, GO. Now. Hurry. You have my permission. Not that you needed it.”

And another:

“Are you making a dent in the universe?

Hint: lots of random pokes in many different spots are unlikely to leave much of an impact. And hiding out is surely not going to work at all.”

I always thought I could make a dent, but I was increasingly aware that time was running out. I became more purposeful. At a low point in my career, I saw what it was like not to have many options, and I saw writing as a way to take some control over my learning and access to possibilities. I refused to give up.

In June 2011, after writing for a few years at work, I was going to give a talk at a conference and I wanted people there to be able to find my work online. So I bought a domain name, picked a Wordpress theme, and anguished over my first public post.

I think only 16 people read it, and despite all that writing at work, I still hadn't found my voice - what I wanted to say and how I wanted to say it. But that is now 200 weeks ago. The more I wrote, the more comfortable I became. Over time, a gradually growing audience would tell me how they came to expect my posts every Saturday morning. Not wanting to let them down motivated me to ship each week.

Making it a habit

As the weeks went on, I gradually got smarter. I kept a list of topics so I wouldn’t ever panic in front of a blank screen. I started drafting posts earlier in the week so my subconscious could work on the post for a few days. And I stuck to a schedule. Everything I had read about authors I admired said they treated writing like a job. You sit down and write, and you meet your deadline no matter what.

After perhaps 100 public posts the writing started to get easier or, more precisely, I didn’t worry about it as much. The regimen relieved me of much of the stress. The difficulty of writing a good first draft is now familiar and my anxiety quickly turns into recognition. “It’s okay,” I tell myself, “it’s just part of the process.” I also know that each post is another small step towards getting better.

While I still don’t recognize myself as a disciplined person, I have become a disciplined writer, posting twice a week now and having just finished a book. Writing is now something I enjoy doing, and I can see applying that process, that discipline, to other parts of my life.

I’m looking forward to it.