Khe Hy, ex-Wall Streeter and author of Rad Reads joins Stew Fortier to discuss the benefits of shipping quickly, creating your own deadlines, and the challenges and fulfillment of leaving his job and never looking back.
The interview summary below was prepared for Compound Writing, a paid invite-only community of online writers. Apply here
1. Ship quickly and often.
There are a few reasons you should try and get your work out quickly.
First, you’re more likely to hit the zeitgeist.
Khe is a strong believer in the power of connecting whatever you’re writing about to the current cultural conversation. Publishing regularly is critical if you want to do this.
“If this week everyone's talking about a movie, there's no need to create a Roam document, grab your quotes, etc. By the time you do all of that, no one's talking about the movie anymore. Just write the post the next morning. Sit down for 25 minutes, give yourself a limit. It's really important as a writer to always try to hit the zeitgeist, even if you're writing about something totally different. If you can peg what you're writing about to the thing people are talking about, people are more compelled to read it. It's just more interesting”
Next, you’ll benefit from quick feedback loops.
“Because it’s digital, you get these really fast feedback loops,” Khe explains. The more frequently you write and ship, the more feedback you will receive on a consistent basis. This continuous feedback will generate improvements in your writing that you just won’t get if you’re only publishing every month or two.”
Finally, the pieces that work will serve as the foundation for whatever you write next.
If you’re struggling to hit “publish,” Khe reminds fellow writers that each post is really just a building block of ideas for future writing, and that you can’t expect it to be perfect. Reframing your piece as a starting point rather than the end-product can relieve some of the pressure and ease anxiety.
“There are so many posts that I've written like three, four, or five times over a multi year period. What you see now is SEO-worthy, high-volume traffic, beautifully optimized posts. But originally, it was an email that a few people responded to positively. Then I’d paste the email into a blog post, add two quotes to it and format it a little bit better. Then, some people start sharing it on Twitter, so you blow it out into a 2000 word piece, add some research, and interview some more people.
That’s the creative process, but it’s all in the wild. There's that public accountability and a public feedback loop. You get the pulse of what people are thinking because people tell you. they're like, I discovered that quickly, and once I discovered it, I couldn’t unsee it. I could never go back to just sitting in isolation, trying to crank out a 3000 word essay. It just wouldn't work for me.
2. No seriously, don’t overthink your first few posts. Just ship.
When asked what common mistakes he sees in writers that are just starting out, Khe reinforced his belief that they’d be better off starting with short-form pieces, shipped more frequently.
“I would say the mistake that I constantly see first-time writers doing is spending two months writing a post. And it's 5000 words. And it's bad, just by virtue of it being their first post. Then they get so disheartened because no one reads it and they have to beg people to share it. I've just seen this so many times. Don’t do that.”
3. To find inspiration, look for shared signals across the work of other writers.
When looking for inspiration for his writing, Khe keeps tabs on other writers and newsletters.
“I subscribe to probably 50 or 60 newsletters. I skim them and if there's something that shows up in two or three newsletters, I like finding a way that I can insert one of my ideas into that.”
4. Set tight creative constraints.
Khe finds that time budgeting is a great tool for turning your writing around quickly.
“I also think it’s quite helpful to give yourself time budgets, especially if you're going to ship quickly. For my Saturday posts, which is normally 800 words, I don't let myself start it until Saturday morning. So I wake up at 6 AM and I try to send it by 8 AM. I basically have two hours to send it. Otherwise you just get in this rigamarole with editing and re-editing and re-tweaking.”
5. Don’t dilute yourself by trying to be on too many channels.
When you produce content you’re proud of, it’s tempting to want to leverage every channel you can get your hands on to promote it. Khe warns that this probably isn’t the best strategy.
“I learned very quickly that email and blogging were my best channels. If you're just spraying and praying across mediums, you're just going to dilute yourself. You're going to burn yourself out, and you're going to lose touch with the feedback loops. These things are very precise. What works on YouTube does not work on Twitter does not work in email. You need to really understand the texture of each channel, and you can't do that by being on five mediums at the same time.”
6. Expand your perspective with the help of an editor.
If there’s one thing Khe regrets in his transition to writing full-time, it’s that he didn’t work with an editor sooner.
“I wish I had started working with editors earlier because I think that editors make your work so much better. Not only do they make your work better from a copywriting tightness perspective, but they take you out of the semi-myopic lens of your very narrow worldview that you think everyone relates to. A good editor will quickly shatter that impression.”