My Super Secret Anniversary

Reflections on Having Done This for Seven Months

I’ve now been writing this newsletter for over half a year, so I thought I’d take a moment to share some reflections on having done this for the past seven months. I originally intended to write this piece after six months, but my sixth-month anniversary slipped by without my even noticing. This is either a testament to the degree to which this newsletter has become integrated into the fabric of my life, or it just means I need to pay more attention to what’s going on around me.

Anyway, here are a few things I’ve learned from having written and published this thing 31 weeks in a row. 

Ideas are everywhere once you train yourself to look.

Before I’d ever started a company, coming up with startup ideas seemed impossible. In fact, when I did start a company, our idea wasn’t even mine—it was my cofounder’s. But then, after a few years of being an entrepreneur, I started to see startup ideas everywhere.

The secret was lowering my standards for what counted as a “startup idea.” It didn’t have to be a fully-formed business concept. Instead, it could be just a germ of something, a thread to pull on—“what happens if I look over here?” Once you’ve trained your brain to think this way, it’s hard to turn off.

A similar pattern emerged when I started this newsletter. At first, I had no idea how I’d come up with something interesting to write about every week, but here I am, 31 unbroken weeks later. Again, the trick is, in effect, lowering your standards. I usually start writing with the tiniest version of what could possibly even be considered an idea—sometimes, it’s just a single sentence. It’s not even that accurate to say that I come up with a newsletter idea and then start writing. It’s more that I discover the idea through writing.

Skeptics may point out that not every installment of this newsletter has actually been all that interesting—which, you know, fair. But I usually don’t know what topics will be the most interesting in advance. All I can do is pull on the thread and see where it goes.

Inspiration and routine are synergistic, not opposites.

Perhaps another way of phrasing the above is that there’s no trade-off between inspiration and routine. It’s not a matter of either waiting for inspiration or writing on a regular schedule: instead, writing consistently creates the conditions to be inspired more often.

Knowing that I have to write this every week means my brain is constantly on alert for subject matter, and that means I end up feeling inspired far more often than I would if I just sat around waiting to be touched by the gods.

It’s okay to repeat yourself.

Every writer I know is worried about repeating themselves. But it’s impossible to write every week and not repeat yourself at least a little bit. And I don’t think it’s a big deal.

Mary Karr and Elizabeth Wurtzel plumbed their lives for similar memoirs over and over. Philip Roth wrote 28 novels about being Jewish and masturbating. (I can relate.) Malcolm Gladwell has basically just kept coming out with the same book over and over for the past two decades, and it hasn’t made him any less famous.

Besides, most readers aren’t paying as much attention to your writing as you are, so it won’t be as obvious to them when you revisit topics you’ve already covered. They might even be grateful for the refresher. I even practiced what I preach and repeated myself with my first two points above, and I bet it didn’t bother you.

If you write good stuff consistently, growth will follow.

Here’s what this newsletter’s growth has looked like since I started writing last October:

Other than occasionally posting on social media, I don’t do anything to promote this newsletter—I don’t even ask my readers to share it! I’m aware that my writing here is, shall we say, an acquired taste, and as I’ve written before, audience growth isn’t a priority for me.

And yet, somehow, it’s growing. I don’t really know how or why, and frankly I’m still kind of shocked that hundreds of people want to read this, but from talking to other writers I know that I’m not alone in finding that consistency creates growth.

In this sense newsletters are the opposite of startups, where an “if you build it, they will come” attitude usually results in no one using your product. But here, if you write good stuff regularly, at least some people will read it.

Yours in half-expecting my growth to start falling off a cliff now that I publicly called it out,