How to Write More—One Step at a Time

Of all the advice I’ve gotten in my career, the one I wish I’d gotten (and heeded) earlier was to just write more.

Up until two years ago, I had barely written much at all. In the past two years, I went from writing answers on Quora, to writing several articles featured on the front page on HackerNews (even making the top spot), to writing a book on recruiting. I don’t consider myself a talented writer (or even a writer at all), but I feel like I’ve come a long way, and I wanted to share why I did this and how I accomplished it.

Writing has vastly improved my communication skills. It has forced me to improve the clarity of my thinking. It has helped me connect with other people. And hopefully, it has helped me share ideas with people who found them useful (or at least, thought-provoking).

How to write more

If you’re anything like me, actually sitting down and writing something is tremendously difficult. There are a whole host of excuses you can come up to avoid writing; everything from “I have nothing interesting to say” to “I have no time”.

Here’s how I overcame those barriers.

Start small

The easiest way to overcome any procrastination-prone task is just to break it up into the tiniest, easiest of pieces, and just get started.

Specifically, for writing, I learned a bunch of “start small” tricks when I was working at Quora from the Writer Relations team. I had been trying to push some of my colleagues to write more so they can experience different angles of the product, and in turn, better understand how it works and how we can improve it. It was also a chance to get my colleagues to show off some of the cool work they were doing. But I found it really difficult to convince my colleagues to write about their work.

My requests were usually something like: “Hey Y, you should write about that cool feature you just built” and were ineffective. But the Writer Relations team had a little trick. Their conversations would go something like this:

WR: Hey, Y, you should write more on Quora.
Y: Uhh, maybe I will at some point. I don’t have anything I’m ready to write about now.
WR: You were just talking about [some topic like powerlifting/sushi-making/Pokemon Go/growing up in ___/going to school at ___]. That was interesting. Here, I’ll ask a question about that on Quora right now, and send you a link. Just write an answer there.
Y: Ummm…
WR: Just write what you were saying earlier, it was cool. Don’t overthink it.

And lo and behold, Y would write an answer about that topic. But something amazing would happen. Within a few weeks, Y would be writing more, and they would write more confidently. Because they didn’t overthink it.

Often, people hesitate to write because they think they must write really well, with masterpieces just flowing out of them. But it’s better to start small, and work your way up.

Write for yourself first

In addition to starting small, another tip is to write for yourself. There are a lot of benefits to writing. For one, it improves your communication skills. But more importantly, it forces you to think about things more deeply, to make your thinking more structured and concrete. So writing is helpful even if no one is going to read what you write.

Some of my favorite pieces were written on this blog before I put my name on it. It was just a domain called “somehowmanage.com”. No one knew about it, no one was reading it, and even if they were, they had no way of connecting it to me. So when I wrote here, I didn’t worry about whether someone would judge my ideas. I just wrote.

Now, I have since added my name on this blog now because I’ve found it incredibly fulfilling to connect with people who stumble across it. But when I write, I still try to write primarily for myself, and maybe a close circle of people I might send each article to because it’s relevant to something we’ve talked about. If other people read and find it useful, that’s just icing on the cake. So write like nobody is watching.

Find a steady source of prompts

A good writing prompt can make a world of difference. Prompts give you a starting point, a thread you can pull at to unravel the spool. Good prompts don’t just give you a starting point, they give you an indication that at least one other person (or group of people) in the world care about this topic.

I have a few steady sources of prompts for myself:

  • One-on-ones with my team. Sometimes, a colleague on my team will ask me a question like “how do I improve my product intuition?” or “can you tell me a bit more about window functions?”. Often, I don’t have a fully thought-out and coherent answer right then and there, so I’ll say: “Great question. I’m going to sit down for an hour this weekend and write an answer to that question as an internal company doc, or a blog post, or a Quora answer, then I’ll share it with you and we can discuss and iterate on it together.” My best prompts have come from my team asking me questions that I assumed I knew the answer to, but not well enough to write about yet.
  • Conversations with smart friends. There are some people who will spit out gems while you’re talking to them and asking them questions, or will ask you really insightful questions when you’re just engaged in random chatter. For instance, I was talking to my friend Josh Levy a few weeks ago about how I prefer pull-based urgency to push-based urgency, and he asked me what I meant. Turns out, what I meant was really fuzzy and ambiguous, but we explored the idea together and it became a pretty long discussion/debate that I then turned into a blog post and he turned into a Twitter thread.
  • Quora questions or Ask HackerNews questions.
Keep a list of prompts and drafts

I keep a Google Doc with prompts I want to write about at some point, and will often sit down and write out a few paragraphs for each prompt. These paragraphs might turn into drafts that then turn into blog posts, or they might never see the light of day. But, keeping them in an accessible Google Doc has a few benefits.

First, let’s say I’ve got a fuzzy idea I want to write about. In my mind, it’s probably at around 25% clarity. I jot down a few ideas and sentences, and now that I’m forced to think about it, it gets to 50%. But now I’m stuck at 50% clarity. A few weeks later, I have a conversation with someone or read something somewhere, and now, I can take that idea to 75 or even 100%. If I hadn’t written anything down, I’d still be stuck at 25%.

Structure Your Time

Writing won’t happen unless you make time for it. But different schedules work for different people. For instance, my friend Alex Allain wrote a book by forcing himself to write for ten minutes “every day, no excuses, ever”. Other people I know block off some time on a weekend morning. I write sporadically, but try to publish something (even if it’s really light/silly) once a week. The point is, since writing is a little uncomfortable, you need some forcing function to get yourself to do it.

I purposely kept this point last. A lot of advice around writing starts by asking you to find a forcing function and block off time. But I’ve found that that only works after you’ve reduced the friction of writing and convinced yourself of its benefits.

Find Support

When working on my book, I partnered with an awesome editor, Rachel Jepsen. Rachel not only worked closely with me to edit what I wrote, she also gave me feedback on my overall writing style and voice. However, equally as important, she provided much-needed moral support. When I was stuck on a thought or wording, or when I was feeling lack of confidence, she was always there to encourage me. That helped overcome a lot of writing friction. And in addition to the help I got from Rachel, my publisher Holloway provided a lot of other support.

Unfortunately, apart from book-writing, I don’t have a dedicated editor and publisher supporting me when I write. But I’ve tried to recreate that support whenever I’m feeling stuck. I’ll reach out to friends or colleagues to ask them to brainstorm or proof-read something I’m writing. Sometimes, just finding someone to bond with over how difficult writing is is encouraging enough to get me over a hump.

Conclusion

I hope this helps you write more. I’ve met and been inspired by so many incredible people with amazing thoughts and ideas. I always urge them to write more. Not only would it probably benefit them, but it would amplify their ability to benefit others.

I wouldn’t feel comfortable publishing this piece without thanking the people who helped me build my writing confidence and find my voice. You know who you are.

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