Looking Back, Forward, and Up
Three Lessons From the First Year, Three Goals for the Next
Welcome to the 128 new subscribers since last Thursday’s e-mail! If you’re reading this but you’re not subscribed, now’s the time to join our growing family of 1,294 Not Boring people.
Hi friends 👋🏻,
Normally, Not Boring analyzes the things other people and companies do. Since Tuesday marked Not Boring’s 1st Birthday, I want to pause to look at what I’ve learned over the past year of writing this, and set some goals for the next one. I may even keep this one short…
Let’s get to it.
I’ve gone deep down the newsletter rabbit hole recently, and in that rabbit hole, people offer a ton of advice on how to optimize your funnel, how to write content that people share, how to write subject lines that make people click, etc etc etc… In a bizarro meta way, people write those pieces to move people down their funnel, share, click, etc etc etc… That stuff grosses me out tbh. This is not that.
I just want to share three things I’ve learned writing Not Boring for the past year.
Pick a Lane but Keep it Fresh
Find your “Personal Monopoly.” I learned about this concept from the writing course that kicked off my journey towards writing this newsletter. A Personal Monopoly is that specific thing that you are uniquely qualified to write about, and it often comes at the intersection of a few topics you’re passionate about.
For example, Bill James combined baseball and statistics, coined the term Sabremetrics, and has written more than two dozen books on related topics since 1977.
I, like so many other beginner writers, dismissed the idea at first. “Personal Monopolies might make sense for some people, but I’m different. I have interesting things to say about a lot of topics!” I was wrong.
Since focusing in on business strategy + pop culture, I've gotten more positive feedback and attracted more new readers than in the first ten months of writing this combined.
But don’t do a schtick. People can get so focused on their schtick that it becomes formulaic and a little nauseating. It’s tempting, because Schticks can work. A lot of those people have tens or hundreds of thousands of subscribers, book deals, and courses. But not being able to deviate at all doesn’t seem authentic or fun. It comes off kind of corny. It seems… boring.
Pick a focus, but improvise.
Consistency is Hard But Worth It
When I set up this Substack, I thought it would be casual. Maybe some links every couple of weeks.
Since then, I’ve sent 57 editions of Per My Last E-mail / Not Boring for a total of 107,295 words. The only time I was more than a day late was when I had Coronavirus, and not having the energy to think or write was one the most frustrating part of the experience. I’m hooked.
After I sent the first edition and no one laughed at me, and then the second, and then the third, I decided to write every week. It was challenging at first, but it’s been great in two ways.
First, sticking to doing something every week has given me stability during a crazy year. Second, delivering predictably lets people know what to expect from me. Ben Thompson wrote on the value of regular delivery:
A subscriber does not need to depend on the random discovery of content; said content can be delivered to the subscriber directly, whether that be email, a bookmark, or an app.
I hope that you look forward to finding Not Boring in your inbox every Monday (and now Thursday) morning.
People Are Nice and Secretly More Curious Than They Let On
When I started writing this newsletter, I had an image in my head of a text chain among all of my friends making fun of everything I wrote.
As far as I know, that wasn’t the case. We all think we’re the center of the universe, but people have their own shit going on. If someone you know takes the time and energy to make fun of you for writing, it’s either because a) you reallllly deserved it, or b) they’re an asshole. But really, it doesn’t happen.
In fact, it’s been the opposite. Writing reignited conversations with people I haven’t spoken to in years, deepened and flavored relationships with good friends, and introduced me to new ones. In return for putting myself out there and writing, I’ve gotten to see peoples’ secret nerdy sides.
I’ve written a lot about community over the past year; writing is the best way to find and build a community of smart people people who are curious about the same things I am.
Two months ago, it became clear that Shelter-in-Place was going to be a feature of life for the foreseeable future. I decided to make the most of a weird situation by focusing on growing this newsletter. On March 23rd, I sent an e-mail announcing a name change to Not Boring, and asked for your help in growing from 473 subscribers to 1,000 by the end of quarantine. Two months later, quarantine is still going strong, and we have blown through the 1,000 subscriber goal. We’re currently at 1,294. 🚀
Setting a goal made writing this so much more fun and interesting. It focused me, forced me to up the quality and consistency of my writing, and got my competitive juices flowing. It also showed me that this newsletter could be a part of what I do professionally, and not just a weird side thing.
And we’re just getting started. Here are three goals for the next year.
Grow to 5,000 Subscribers by Labor Day and 10,000 by May 21, 2021
I spend a lot of time writing this newsletter and working to make it entertaining, educational, and worth your time. Up to 20 hours some weeks. Currently, that means that I spend just under 1 minute for every person who receives the e-mail. I want to amortize the time I spend over more readers, so that every minute I spend packs more punch, and because every conversation that comes from one of these e-mails makes the content in the next one better.
It took ten months to get to 500, but less than two to get from there to 1,294. I’ll be testing a bunch of tactics over the next few months to get to 5,000, but the most important will be continuing to improve the content and provide more value so that you want to share it with your smartest friends. Speaking of which…
Make Enough Money From the Newsletter to Cover Rent
The ultimate test of whether I’m providing value is whether I’m able to charge for Not Boring. In the same Ben Thompson article, he said:
It is very important to clearly define what a subscriptions means. First, it’s not a donation: it is asking a customer to pay money for a product.
Within the next 6 months, I want to launch a paid version of the newsletter. By this time next year, I want to be making enough from it to cover rent or mortgage payments.
The Passion Economy is taking off, enabling thousands to make a living off of what they create. Personally, I love the idea that covering the basics doing something that I love will allow me to take bigger swings elsewhere.
Plus, having people pay me is a surefire way to ensure that I bring it every week.
I would love to hear your thoughts on this. Would you be willing to pay for Not Boring? If not, what could I add that would convince you to pay? Community, case studies, interviews, videos, Not Boring merch - no idea is too crazy.
Build an Ecosystem of Smart, Talented People Participating in Various Ways
I've recently introduced guest writers to Not Boring. Jeremy wrote about Cloud Kitchens and Ali wrote about Kim and Kanye. Others submitted their favorite Worldbuilders and Shotcallers. The comments section is heating up.
I want to continue to bring your insights and perspectives front and center. If you have ideas for guest posts or collaborations that you think other Not Boring readers would appreciate, send them my way! And if there are other ways that you think we can get to know each other better, I’m all ears! I have a few ideas, but all of our ideas will be better than mine alone.
I have always loved words.
My parents and their friends tell me that when I was a baby, they couldn’t get me to shut up. One of my earliest memories is spelling “refrigerator” correctly in Pre-K. In Mrs. Sweeney’s second grade class, I tore through the year’s extra credit vocabulary book in the first month.
Eighth grade is when I started to love stringing those words together.
My eighth grade teacher, Mr. Algeo, assigned “Comps” for classroom misbehavior. Comps were 1,000+ word compositions on a particular topic; Mr. A taught Latin, so the topics were usually Caesar-related. Comps were part of school folklore, passed down from generation to generation (Mr. A taught my mom 8th grade, too). Everyone dreaded Comps. I fucking loved them.
I acted out just so Mr. A would assign me Comps. In them, I would lightly touch on the assigned subject before going off on comical tangents about the school, my classmates, current events, whatever. When they were really good, Mr. A would even let me read them in front of the class. They were my first taste of the idea that if you combined words in the right way, mixing smart and funny, even serious teachers would have no choice but to laugh.
And here we are, twenty years later.
It's been so much fun combining smart and funny (I hope) in this newsletter over the past year. It has been incredible to get to flex that muscle again, more incredible to see so many of you join in, and most incredible to get to have interesting conversations with so many of you, some of whom I’ve known for a long time and most of whom I’ve met through writing this newsletter.
I’m excited for the next year of writing, growth, and conversations. Thanks for being a part of it!
🕰 Counting Time - May 21st, 6pm
We have over 200 people signed up for our discussion on Counting Time on Thursday! Join us here.
We passed 1,000 responses - thanks for taking the survey and spreading the word. We’re closing the survey tomorrow, so today is the last chance to make your mark on our snapshot of this wild time.
Thanks for reading,