Lessons Learned from a Year of Writing

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Last week marked the one year anniversary of my writing experiment. In December 2013, I challenged myself to try writing at least three hundreds words every single day for the next year. Some of those efforts have made it to this blog. Looking back on the year, I’ve jotted down some thoughts on the experience, what I’ve learned, and what I plan to do going forward.

  • I’m really proud and happy that I kept up with it. Even when I was dead tired or incredibly busy, I carved out time to write.
  • Most of my entries were over 400 words. Many were in the 500-700 range. Some were 1,000+ words long.
  • I’m not proud of the days when I felt like I took shortcuts. For example, I would some work-related writing such as company memos and policy drafts as part of my 300+ word exercise. This, even when I was doing it, felt like a cop out. It didn’t happen every week, but enough times to make me feel like I cheated a little. I’m going to avoid counting such writing as part of the exercise in 2015.
  • I wrote a good number of entries while commuting to work. I would open up Evernote on my iPhone and tap away furiously while waiting for and riding the subway. I’m going to curb the practice of writing entire entries during my commute because I always feel rushed to complete my writing before my stop. Instead, I’ll use the commute to jot down ideas and complete the entry when I’m sitting down and able to concentrate.
  • I found myself reflecting more often on my personal habits, behaviors, decisions, and desires. Because of the pressure to write something every day, I often looked inward for topics. Many of my entries are about things that I like or don’t like about myself, things I wish I could do, places I enjoyed or didn’t enjoy visiting, and even some concrete plans for how I can shift my habits. I also analyzed certain days in detail with a critical eye and pinpointed moments that I could’ve handled better.
  • When I wasn’t writing about personal topics, I wrote a lot about the business. I wrote about interacting with employees, generating new business, planning for the next six months, what interview questions to ask candidates, and more. I also wrote about ideas for potential service offerings and products. I think by writing them down, I was able to see that most of my ideas were fairly terrible. In writing about my business, I was able to organize my thoughts and ultimately be in a better position to articulate my position on various topics. There were times when I would share a link to an Evernote entry with people at work if I thought it did a good job of outlining relevant ideas.
  • I wrote a few pieces of fiction. One was continuing series that took up 16 days about a guy who leaves New York to live by himself in a cabin in Maine for a year. I think in 2015, I’ll write some more stories.
  • My favorite entries were about the things I’m grateful for. Whether it was personal or work-related, it feels great when I look back on past entries to read about the things, small and big, that made me feel lucky. These days, in addition to my 300+ words exercise, I’ve been doing the 5 Minute Journal, which helps me reflect daily on things I’m grateful for. It’s been an uplifting routine for me.
  • One thing I didn’t do enough of this year was to go back and re-read my entries more often. Sometimes, I’ll write about something that feels incredibly familiar only to find that I had already written extensively about it a few months ago. I’m hoping to put aside more time on weekends to re-read old entries and see if some of them can be turned into public blog posts.

I plan to keep up my daily writing exercise in 2015. And with a year’s worth of experience under my belt, I will be making tweaks that can push me to write more challenging and stronger entries. These tweaks include: a more deliberate editorial schedule (or at least a pre-planned list of subjects) to encourage me to write broadly about different topics rather than scrambling for new ideas every morning; more entries that reflect on books I’ve read; and more experimental entries on crafting better sentences. Happy new year, and here’s to at least another 109,500 words.

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