On Shame, Self-Reflection, and Taking a Break


No matter how long you’ve been at it, publishing a weekly blog never gets easier. Eventually, you’ll grow accustomed to the timeline and inadvertently find your rhythm, but producing high-quality work on a short timeline is always difficult.

Many of you are creative folks with big ideas – with your own writing, video projects, comedy shows, and careers. You know how challenging it is to practice creativity consistently. It’s why so many URLs point to barren blogs with just two or three posts from 2009.

Good intentions often crumble under imperfect conditions.

At the risk of sounding pompous, that’s why I consider this blog to be one of my greatest achievements. Every Monday, for 139 weeks, I’ve published a new essay, no matter what. But this prolificacy, while fulfilling, is ultimately exhausting. I feel a bit like Alice in Through the Looking Glass, running just to stay in place.

“Now, here, you see, it takes all the running you can do, to keep in the same place. If you want to get somewhere else, you must run at least twice as fast as that!”

The minute I hit “publish” on Monday morning, I am already falling behind on the following week’s essay. And on the off chance I do manage to get a week or two ahead in my writing, there’s no time to relax or take a break. That would only eat away at the buffer I’ve worked double to create.

The end result is that when I press “publish,” rather than a feeling of excitement, I feel a sense of shame. I know I could write something deeper, more meaningful, better researched…if only I had more time. Some of my favorite articles from the past year have been those that required me to push myself – like my essay about automation, or the one about digital advertising. But those are the exception not the norm.

This aggressive publishing schedule biases my writing towards articles that are easy rather than those that are interesting.

Of course, I am not alone in that. It’s the premise upon which the entire blogosphere is built. Aside from Seth Godin, very few people who write a daily blog can publish anything outside of regurgitated listacles or soft opinion pieces with any frequency.

I don’t have research assistants or full days where I can just read and write. I have to fit it in where I can. That means the 1000-word think-piece about hard work gets written while the grand theory connecting luddites, free-style chess, and Trump’s immigration order becomes nothing more than a random thought, lost in some chaotic word doc. Connecting the dots between history, science, literature, culture, and current events is hard. Producing new ideas and new knowledge is demanding. But writing another article about the importance of teamwork takes an hour.

It’s finally occurred to me why I feel trapped in a cycle where I want to write something else but generally end up back to the same place – it’s because I’ve never questioned my assumptions. I’ve spent plenty of time thinking about the specific content of my essays, but rarely do I focus on the bigger picture of why I write each week. Never have I stopped to consider what I would write about if I had infinite time and resources. I’ve always blindly assumed that this blog must continue to operate as it always has – a ~1000 word article published every Monday morning, without pause.

Now that’s not to say anything is going to change (it might, it might not), but I owe myself the time to at least consider the question, without the pressure of having to immediately turn around and publish something else 168 hours from now. That would ultimately distract me from this bigger goal of self-reflection.

So now, the announcement this entire essay has been building towards: the Monday Memo is taking a brief, four-week break and will return Monday, March 6th. I intend to take some time off the hamster wheel to reflect on where the blog has been and where it’s going in 2017, as part of my focus on writing articles that feel more significant.

Each week, I write a new article helping busy people find meaning and fulfillment through sustainable creative habits. If you enjoyed this week’s letter, you can sign up to get them delivered to your inbox each week by digital carrier pigeon.