20 Years of Blogging: What I’ve Learned

This week marks the 20th anniversary of this blog.

I thought the best way to observe the milestone, and to try to pass along some of the benefits I’ve gained from keeping a presence online all these years, would be to share some of the most important things I’ve learned since I started this site.


It’s almost impossible for me to remember my life when I started this site, or to really understand how much it’s changed after tens of thousands of hours spent on social media in the decades since. More than anything, my response to twenty years of writing and sharing things on this site is an overwhelming gratitude for all the opportunities it’s opened up, and a deep appreciation for the relationships and connections that it’s made possible.

Now, I’m hardly an expert on major aspects of life. But If you have enough of a high profile, or spend enough time who are at a different stage of life, you’ll regularly end up being asked for advice. So, while I may not have any particularly unique insights, I hope that simply sharing my most responses to the types of questions I’m asked most frequently may have value to people. And of course, if you disagree or have any corrections for things I’ve gotten wrong, please don’t hesitate to write about such things on your own site and let me know that you did!

Understanding Technology in Society

As is probably appropriate to observing an anniversary of this blog, the first set of lessons I’d share are about technology and social media itself. Some of the most fundamental lessons were summarized in a piece I wrote last year, "12 Things Everyone Should Understand About Tech". I go into more detail there, but some of the key points are pretty easy to understand:

  • Tech is not neutral, and not inevitable.
  • Most people in tech want to do good, but tech history is poorly understood. As a result, many in tech don't understand how tech can have negative impacts when they think of themselves as good people.
  • A lot of tech is created without much explicit knowledge about users or ethics.
  • Tech is never created by one single genius, and is mostly not made by startups.
  • Most tech companies make money in a few ways that usually aren't about selling tech itself, and those business models skew all of tech. (One of the worst effects of those business models are the creation of fake markets.)
  • Tech is as much about culture as it is about innovation, and thus no one institution can fix tech's problems — it will take a broad effort. And that effort will have to go far past traditional tactics like boycotts and regulation to truly have an effect in reforming tech.

All of these observations about how tech works are grounded in a broader, more important perspective that I wrote about a few years earlier: there is no "technology industry". Every industry, and every social institution is both shaped by, and responsible for creating, technology, and so trying to understand tech as if it were a conventional corporate industry isn't a useful perspective.

After years of thinking about the place of technology in society, I'm increasingly asked to summarize the challenge facing society today as we reckon with how tech is changing our world. Perhaps the most cogent articulation of that challenge happened a few years ago in this conversation with Krista Tippett for On Being, where we talked about tech's moral reckoning.

How Social Media Works

In addition to broad observations about tech, I've tried to articulate some of the specific lessons I've learned in 20 years of creating, and living in, social networks online.

One of the most popular things I've written about my lessons in social media was actually on the fifteenth anniversary of this blog, when I shared 15 lessons from 15 years of blogging. Maybe one of the most important points outlined there is to always write with the idea that what you’re sharing will live for months and years and decades. I also do still strongly believe that someone who really has a strong point of view, and substantive insights into their area of interest, can have huge impact just by consistently blogging about that topic. It's not currently the fashionable way to participate in social media, but the opportunity is still wide open. (I also published a far sillier list of 10 rules of Internet, which still kinda holds up.)

Then, there's the evergreen truth: If your website's full of assholes, it's your fault. Of everything I've written over the years, this piece from 2011 gets cited more than almost any other. When I first started talking about the idea a decade ago, it was often seen as heretical, and the concept of holding online platform owners accountable for the worst social impacts that they enable was commonly seen as absurd. When I warned that Facebook was gaslighting the web, I was called alarmist. When I said, a decade ago, that Facebook was due for a reckoning for what it was doing with users' data without their consent, I was warned that I was ending my own career.

I wish I could find some validation in the fact that culture has shifted so much in this regard, but the truth is that people only clamor for accountability now that such an egregious amount of damage has happened. And that harm was exactly what I had been hoping this kind of writing would help prevent. I failed.

My presence on social media is an odd one. I've been around longer than most, which gives me some perspective. I have a social network that sort of resembles that of a famous person, despite not actually being famous, and it yields glimpses into phenomena like what it's like being verified on Twitter. This was all forseeable; back in 2002, I wrote about how we'd have to own, and control, our identities online:

We’re all celebrities now, in a sense. Everything that we say or do is on the record. And everything that’s on the record is recorded for posterity, and indexed far better than any file photo or PR bio ever was.

But I still have some hope for how social media might evolve. By doing things like looking at the history of what's worked for social media in the past, we can predict what sorts of things we might want for the future. And to be clear, I'm not someone who thinks there was a "good old days"; social media has always been too exclusionary, and too dependent on systems and infrastructures that replicate the injustices of society as a whole. It is possible, though, to make new systems that are a little more equitable, and I still haven't given up on that hope at all.

Ultimately, it's my belief that social networks are systems that can be intentionally designed, and intelligently managed, to ensure that their primary impact is a positive one for the people who use them, and for the world. This is an optimistic idea that was the original spark for the creation of platforms, and a promise that's been painfully abandoned in the years since. But I think we have learned enough lessons for it to still be worth trying to make something that works for the world.