A Writing Report: Two Years In

My biggest articles, lessons learned, and plans for this year.

Photo by Elijah O’Donnell

I started a daily writing habit two years ago. If you look at my output since then, it’s a bit haphazard: Lots of advice to founders, discussion of venture capital and the blockchain, and a bit of telling my own story.

My own review of my writing is mixed. I think the writing is good, and in most cases I think the topics are important and my viewpoint adds something. But the writing style is painfully far from how I talk, and thus too far from how I think of myself. There’s little humor in it, as one example, which is counter to how I present, or even just talk with friends. I have found a voice, but not my voice, nor one I’m terribly fond of. Maybe I read too much fancy writing in college, and too many Serious Business Books since then, but not enough that didn’t take itself seriously.

I expect one of the main reasons I struggle to include humor is that my jokes tend to be self-deprecating, but I still don’t feel comfortable writing much about my failures and problems at Puppet. I’m still involved, but can’t claim to be a spokesperson or any such thing, so a lot of topics aren’t available. Yes, these are my stories, but I recognize how much of an impact I could have on the company, its employees, and its community if I were flippant about my failures of the past. This was manageable when I was running the company, but doesn’t really work in this state. That can’t be the whole explanation, though, and I plan to do more experimentation this year to begin to suss it out.

I have mostly chosen topics by focusing on beliefs I have that others don’t. Some of this is insight I think is special to me, such as one of my favorite essays, Where Does Your Work Live, and some is straight disagreement, as in No, You Don’t Learn More From Failure. I still run into this last one all the time, and I love having a well practiced argument for how silly this popular belief is.

My series on VC was very different: An attempt to share with a wider world what I’ve learned about how venture works from the inside. Of course, I’m not inside venture in the normal sense: I raised a bunch of money, and spent a ton of time with investors, but have never been an investor myself. But my own learning over those years didn’t seem to be represented anywhere, and based on how often this is brought up, it seems people found it valuable. A year later, it’s a bit unclear even to me how much this series is an explanation of venture capital or an indictment. I truly do believe venture is totally broken, and it seems much of the rest of the world has now come to agree, based on the conversations I’m seeing. Even so, it is actually a fit for some people, and they should know how it works internally. Hopefully the series helps them.

I did a series on the blockchain, too, and this was much more an exploration on my part than an explanation. I had plenty of education and opinions going in, but I didn’t really know what unique insights or beliefs I had until I started writing. This is probably my best example of learning by writing. I started with the knowledge that the blockchain was primarily full of fraud and black market sales, and that I was more interested in the crypto legacy of git and BitTorrent than Bitcoin, but I learned a heckuva lot more in the course of exploring this area in more depth. I’m not sure anyone else learned anything; I’ve never had anyone mention these posts to me, nor seen them reposted anywhere. I am not sure what to take away from that.

My most frequently shared piece is Strategy is Culture. Even after all this time it still gets shared roughly weekly, which is more than all of my other pieces combined. This article took me more than a year to write; every week I’d try to write it, give up, then dash off something simpler and less important. I had to figure out a lot to get to the point where I could successfully explain how closely linked I think strategy is to day to day execution, and how that, in the end, is your company’s culture. It still feels like a fundamental insight that most other people are missing, something so important that my struggles at Puppet all make sense suddenly.

Unquestionably my most popular piece was Why We Hate Working for Big Companies. It was the only one I wrote that got mainstream visibility (albeit just a reposting on a sub-brand of CNBC), and it got shared far more often and widely than I could have hoped, especially given its length. Weirdly, after a big splash it has almost completely dropped off.

In addition to it getting the most reach, it also had the biggest impact on me. It forced me to express my weird combination of beliefs. In doing so, I realized how rare they are, and how important they are to what I do. It took a lot more work, but I eventually realized this essay introduces the topics I need to focus on, both in my writing and in my company building.

My interests today are at the intersection of economics, technology, and the individual worker. I’m educated and opinionated on each of them, but only by considering them together does a complete picture of my opinions and drive start to emerge. This piece on why it sucks to work at big companies is the first time I brought it all together, and I think that’s why it worked so well.

It’s also a longer piece than just about everything else I’ve published. I’ve tended to write articles around 1200 words, mostly because that’s right about what people recommend you write on a daily basis. But the success of this one began to make me think I might do better with longer works, and my struggles to get hard topics out over the last six months has helped validate that for me. It’s really hard to bring together a bunch of ideas into one coherent whole — it’s much easier to instead just write one article on each concept — but it’s more valuable and better work to do it all in one.

After two years of writing, my goals for the next year are, in no particular order:

Come closer to my real voice. This means being more funny, but also more relaxed. I feel like my writing style is too stiff, too formal, which is hilarious given how informally I speak.

Write more about what I think about. I have written a lot of things I believe, but mostly not written much about what’s filling my brain. I hope to do better on that this year.

Write bigger pieces. I think I’d worked through the bite-sized ideas that were fighting to get out, and now any effort to produce something easily digestible seems to require compromising the work, rather than making it better. I think it’s holding me back, not being a helpful constraint. I’m going to be a bit more willing to go long, and pull a complete thread together, even if it means plenty of people will skip it because of length or complexity.

Thanks for reading so far this time. I hope to keep you entertained this year, too.

Several short sentences

I have plenty to share. I can even write it. I just can’t publish it.

Picture courtesy of Cliff Johnson

Last year I decided to write more. Daily, in fact. One of my first actions was to ask Om Malik for advice. I had been following him since he was writing for Business 2.0, which was an actually valuable business magazine in the tech bubble. I am now lucky enough to know him through True Ventures.

When we talked, he shared a story about his first published piece. I did not find it helpful.

The magazine he was writing for (Fortune, I think) said his article was too long. He shortened it. A lot. It was still rejected. He compressed it more. Again. And again. I believe the original 1500 word piece became 300. Om’s punch line was that they told him it was their best-ever first contribution by an author.

I don’t think I’m cut out for writing 300 word articles. It’s not just that that kind of compressed writing is hard. It’s also about the missed opportunity: If you’re reading one of my articles, I want to take full advantage.

But my lack of desire to write short pieces is not why his story wasn’t helpful.

It’s one thing to say: “Write shorter”. Ok. I can see how that makes sense. Everyone knows the line, “I’m sorry this is so long, I didn’t have time to make it shorter.” It’s intuitive, implying that investing in the quality of writing somehow intrinsically shortens it.

But more than a year after this story from Om, I had still not found a way to put this principle into practice.

I could compress writing a bit. Programming taught me that shorter code is often simpler and clearer. Of course, it still took years to be good at it.

Stephen King had taught me that adverbs often indicate a problem. If you can get rid of them without losing meaning, your work is almost always better. One way to do this is to choose more expansive verbs.

I was able to translate my speaking coach’s advice into writing, too: She helped rid my talks of filler words. You might not think this is useful in writing — I never find myself typing out ‘um’1 — but I am over-fond of long phrases that can be easily replaced with a single word.

I tend to over-qualify. This is an opinion piece. You know that. I can skip all the incidences of “I think”. One “maybe” is enough, I don’t need “should maybe”. Two examples suffice; I don’t need three and an “etc”.

For example, in this piece, I replaced the phrase “was still not able to learn” with “had not learned”. “I had learned as a programmer” became “programming taught me”. Both of them are clearer, simpler, just… better. In particular, the verbs are much stronger.

Again, it’s not that I had learned nothing over the last year. I just… I knew I was using tactics. Simple rules. My writing was shorter, but… not short. The Hemingway app was still harshly judging all my failures.

Then I got lucky. I ran into Lucy Bellwood — a fellow Reedie! — at an Indie.vc event, and we traded book recommendations while her partner patiently slept on his feet. She recommended a new book to me: Several Short Sentences About Writing, by Verlyn Klinkenborg.

It’s amazing.

Of course, I doubt I’ll ever finish it.

It reads more like poetry than prose. I do not like poetry. Nearly every paragraph is a single sentence. Almost none grow to more than one line.

Many books on writing can be summarized as: Sit down and write. Seriously. Now. Keep doing that.

Not this one.

I can’t summarize it for you. It’s, it’s… dense. But I can share a little I have learned. And how it has cursed me.

I received a new term from it: Transitions. I knew what adverbs were long before Stephen King taught me that they’re suspect. Not to be entirely avoided, but hold your nose when you use them.

I already knew my sentences were too long. Even when I broke them up, I knew I relied too heavily on words that connect them (like the phrase at the beginning of this one). This knowledge wasn’t useful, because I wasn’t able to translate it into methods of fixing them.

The first thing Klinkenborg gave me was a name for these words: Transitions.

Like adverbs, they’re usually a sign that you’ve failed somewhere. That you were lazy.

This labeling did not magically fix my writing, but it gave me something to track. An easy measure for how I was doing.

Then he delivered the kicker: Simple guidance on how to eliminate them. Or at least, reduce them.

Knowing sentences should be shorter is not useful if you don’t know how to get there. What makes a great short sentence, vs a crappy long one?

His answer is incredibly dense. I have to slow down when reading it: You should minimize the distance between the period of your previous sentence and the point of this one.

Those long, complex sentences I like to write aren’t bad because they’re long, or because they have too many phrases. They’re bad because their point is so far away from their start. The reader is left to wander through it, holding out hope for a conclusion.

What are you trying to say? Say that. Immediately. Did you leave something important out? Say that. Now. Keep it up until you’re done.

Your old, complex sentence is now a series of short sentences, in order of importance, each getting right to the point.

Of course, that’s not how the book describes it. My description would likely horrify its author. There’s far more to it than this. But it’s a start. And a huge departure from what I was doing.

It’s also why I can’t write any more.

The topics I’m working on now are incredibly important to me. They’re hard to reason about, to capture. And while I’m sitting here struggling with the content, the writing itself keeps getting in the way. The form. The structure of the sentences. The line breaks.

Where I put paragraphs.

It’s not that I’m embarrassed. It’s that the process of writing is distracting me from what I am trying to write.

So please. Forgive me a little writer’s block. I promise I’ll get better.

When I do, I hope you’ll also tolerate experimentation and failure in how to put all this to work. Expect wild oscillations in sentence length. Inconsistency between sentences and paragraphs. Confusion across pieces. I’m in that ’conscious incompetence’ phase of short sentences, and it’s going to be a rough path for a little while.

I’ll come out a better writer, though. And hopefully you’ll gain something from witnessing the process.

I recently updated Om on my progress, sharing how much his story confused me and these tactical lessons I’d just received. Thankfully he appreciated the note, and was happy to see I took his story as a challenge, rather than a judgement. And he didn’t seem fazed in the slightest that it took more than a year to make anything of his help.

  1. Except, obviously, in this case. Not never. Just not usually.