How Writing a Weekly Newsletter Has Helped Me Become a Better Writer, a Better Reader, and Care More About Adding Value.
A few months ago, I launched Woolgathering, a weekly newsletter in which I provide 4 main things:
- links to stuff I’ve written (almost exclusively on Medium) in the past week
- a brief meditation on an idea that I’ve found interesting
- 3 or so pieces that I’ve read online that piqued my interest, and
- a thought-provoking quote.
Eventually, I hope that this newsletter could be a small source of income for me — though never at the cost of the integrity of my writing or the sanctity of my subscribers’ inboxes.
In the short-run, however, writing a weekly newsletter has proven to be a positive constraint for me. It has forced me to write more and write better. It has also forced me to read more and better stuff.
To me, hitting “subscribe” on an email newsletter is no small thing. I see the email inbox as a sacred thing. When someone invites my work into their email inbox — like inviting me as a guest in their home — they are trusting that I’ll respect the sanctity of their inbox. That means not flooding them with a bunch of emails, and providing them with something that they’ll (mostly) look forward to reading each week. It means providing them with what they signed up for: something that will benefit them.I take that very seriously.
But beyond the benefit I hope to bring to others, a weekly newsletter has brought benefits to me as well. Here’s a few ways that has happened.
I’m Forced to be Accountable
There is hardly a more effective way to force yourself to stay on track with something than making an external commitment. Once you tell a person — or even better — 100+ people that you’re going to do something, you’ve got some skin in the game. So as my newsletter grows, I’m forced to stay on track. I have a motivation to keep writing, and to write stuff that people really want to read. I’m forced, in essence, to add value — as they say.
Now don’t get me wrong, if the pressure ever causes a conflict with other more important commitments, the choice will be clear to me. But that external commitment that I’ve made keeps me rearranging the stuff that I do every day to make room for this thing — the newsletter that I’ve promised.
Will any of my readers be heartbroken if I don’t push out this week’s newsletter by Wednesday? Maybe, but probably not. Everyone’s busy, and few are monitoring their inboxes for each and every newsletter they’ve signed up for. But the minute I start missing the promised deadline is the minute that I start slowly shedding credibility. I’d like to avoid that as much as possible.
I’m Forced to Find Interesting Things to Read
There is so much stuff published online each day. A lot of it is clickbait, or listicles with really no attempt at originality or provoking thought. But there is still so much written every day that moves thinking forward — stuff that really challenges us or reveals new ideas and mental frameworks to us. That’s the stuff that I try to find — but it’s not easy.
Having to find quality stuff to link to in my newsletter forces me to spend more time actively, rather than passively reading things. It has also forced me to look at more and different channels of information. After all, the last thing I want to do is to send a link to the same HBR or Inc.com article that every other newsletter is featuring.
So I am forced to keep casting my net as wide as possible, in an attempt to bring really writing, and really interesting ideas to the people who have taken the leap to subscribe to my newsletter.
I’m Forced to Stay Honest
Nearly every link I’ve included to sign up for Woolgathering includes a promise that I’ll only be sending one e-mail per week, and that I won’t spam or use my subscriber list as a list of leads for selling random stuff that I’m trying peddle.
As my list of subscribers grows, it would be easier for me to try all sorts of ways to make money off of it — there are courses and books about how to do just that. But doing that would betray the trust of my subscribers. The promise I have made ensures that I always ask myself the question “is the email I’m sending in line with why people initially signed up for my e-mails?”
I’m Forced to Be Helpful
There is only one truly effective business model — only one way to go to market with your thing that is sustainable and doesn’t require all sorts of unnatural maneuvers, pivots, and re-brands: offer something that really helps people.
On that note, each weekly e-mail I send is aimed at helping those who receive it think a little differently and think a little better than they were before they received it. I’m not promising disruption, life-hacking, or miraculous changes — by my estimation, those promises aren’t sustainable, and rarely ever meet expectations anyway.
I just want to provide a slightly different take on things, and some interesting material to read and think about. When done 52(ish) times per year, I think that adds up to something valuable.
I’m Forced to Find Better Tools
I love finding new and better tools to help me do the things that I do often. So now that I’m writing a weekly newsletter, I’ve been forced find the best tools to aid in making that process go as smoothly as possible. A few tools that this process helped me find are:
- Workflowy. I’ve actually been using this for a long time as my main organizational and productivity tool. I track every project and related next action in my Workflowy document. It helps me to be more structured in my thinking and in my organization.
- Tiny Letter. This is MailChimp’s little sibling — a stripped-down version of it that offers a simple newsletter writing interface and the ability to send emails to up to 5,000 subscribers. I love it.
- Upscribe (beta). I recently found this tool, and have begun to love it. It allows you to embed a subscribe form right into a Medium article, so that people don’t have to leave Medium to sign up for a newsletter. It offers integration with other large newsletter apps (like MailChimp), but it also provides a very simple interface for sending out your own newsletter. I’ve been communicating with Josh, one of its main developers, and he has some cool plans for it going forward.
I think this model could work for anyone who is already writing online, and is looking for a way to force themselves to get better. It’s not for everyone, but for me, at least, it’s proven invaluable.
Hey, speaking of my newsletter, consider subscribing. One email per week, no spamming, no selling.