15 Lessons from 15 Years of Blogging

This summer marked 15 years since I first started blogging here, and I'm happier than ever that I've chosen to live so much of my life in this place, with all of you.

Nearly everything has changed for me since I began this blog, from major milestones like getting married and having a kid to thousands and thousands of smaller moments. Along the way, the connections I've made here helped me turn "having a job" into a career that is deeply fulfilling and challenging, and opened doors to opportunities I couldn't have imagined.

But what have I learned? A lot. Some of these things may be obvious, and some may be slightly corny platitudes. But I hope a few will be useful to you. I'm far from an expert on this stuff, even after all these years, so I hope documenting my mindset when writing here might at least serve as a good reference for myself in the future.

  1. Typos in posts don't reveal themselves until you've published. If you schedule a post to publish in the future, the typos will be revealed then. This is an absolute, inviolable rule of blogging. This may be some sort of subtle lesson from the universe about our hubris in the face of fundamental impermanence.
  2. Link to everything you create elsewhere on the web. And if possible, save a copy of it on your own blog. Things disappear so quickly, and even important work can slip your mind months or years later when you want to recall it. If it's in one, definitive place, you'll be glad for it.
  3. Always write with the idea that what you're sharing will live for months and years and decades. Having a long-term perspective in mind is an incredibly effective tool for figuring out whether a topic is meaningful or not, and for encouraging a kinder, more thoughtful perspective.
  4. Always write for the moment you're in. Being true to how you feel and what you're experiencing is both more effective in connecting with a reader and more personally useful for when you revisit your work, serving as a reminder of exactly where you were at the time.
  5. The scroll is your friend. If you write a bad post or something you don't like, just post again. If you write something great that you're really proud of and nobody notices, just post again. One foot in front of the other, one word after another, is the only path I've found to an overall body of work that I'm proud of. Push posts down the page, and the good and the bad will just scroll away.
  6. Your blog can change your life in a month. If you want to understand an idea, or become a meaningful voice on a topic, or change your own thinking about a concept, write a little bit about it every day for a month. The first posts might suck, but invariably the exercise and the discipline of doing the writing are transformative. Sometimes the rest of the world even notices it.
  7. There is absolutely no pattern to which blog posts people will like. I've had pieces that I worked on for years that landed with a thud, ignored by even my close friends, and I've had dashed-off rants explode into huge conversations on the web. I've had short pieces or silly lists that people found meaningful, and lengthy, researched work that mostly earned a shrug. And of course, I've had pieces that I put my heart and soul into that did connect with people. If there's a way to predict what response will be online, I sure don't know it.
  8. The personal blog is an important, under-respected art form. While blogs as a medium are basically just the default format for sharing timely information or doing simple publishing online, the personal blog is every bit as important an expressive medium as the novel or the zine or any visual arts medium. As a culture, we don't afford them the same respect, but it's an art form that has meant as much to me, and revealed as many truths to me, as the films I have seen and the books I have read, and I'm so thankful for that.
  9. Meta-writing about a blog is generally super boring. (That probably includes this post.) Any housekeeping writing about how it's been a while since you've written, or how you changed some obscure part of your blog, doesn't tend to age very well and is seldom particularly compelling in retrospect. The exception are genres like technical or design blogs, where the meta is part of the message. But certainly the world doesn't need any more "sorry I haven't written in a while" posts.
  10. The tools for blogging have been extraordinarily stagnant. One of the reasons the art form of blogging isn't particularly respected lately is because the tools essentially stopped evolving a decade ago. The experience of writing, for most people, isn't even substantially different than it was when I started 15 years ago, despite the rise of the social web and mobile apps taking over during that timeframe. This matters because tools deeply influence content. And this stagnation is particularly egregious when we consider that almost every common behavior on the big social networks is a subset of what we originally thought blogging might be.
  11. If your comments are full of assholes, it's your fault. I've already written about this a lot, but it's still true. If you're not willing to invest in managing a community of commenters, then you're not ready to have comments.
  12. The most meaningful feedback happens on a very slow timeframe. It's easy to get distracted in the immediacy of people tweeting replies in realtime, but the reason I write is for those rare times, years later, when I get an email from someone I might only barely know, saying that something I wrote meant something to them. Sometimes they email years later to say they thought I was wrong, or that they've changed their mind, but invariably it feels like a profound and personal connection, often around the least expected and least obvious ideas.
  13. It's still early. Anyone who's ever heard me talk about blogging has heard me say how, when I started, I thought "There are already 50 or 100 blogs! I'm too late! Everything's been done!" And then, of course, the next 50 or 100 million blogs showed up and I realized that maybe I was early. Particularly as the idea of personal blogging has fallen out of fashion or even come to seem sort of old-fashioned online, there's never been a better time to start.
  14. Leave them wanting more. One sure way to trigger writer's block when blogging is to think, "I have to capture all my thoughts on this idea and write it about it definitively once and for all." If you assume that folks are smart and curious and will return, you can work around the edges of an idea over days and weeks and months and really come to understand it. It's this process that blogging does better than pretty much any other medium, and it's sharing that process with you that's been the greatest privilege of writing here for the last decade and a half.

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