Packy McCormick

Packy McCormick is the founder of Not Boring, a semi-weekly newsletter breaking down companies, business events, and trends via strategy, economics, and pop culture. Before that, he worked in finance and turned down business school to work with Breather, where he was hired as the first US employee. After six great years there, he left to pursue his own thing. He's leaned into writing now and is building something really interesting with Not Boring.

Tell us about how writing is an important piece of the work you do today.

At this very early stage with Not Boring, nothing has been more valuable to me than writing. When I began thinking about what was next, I started by writing about the areas in which I was considering building a company: education and IRL Member Communities.

Writing is a great way to shape and strengthen my ideas, but it's also been really helpful in attracting like-minded people. By learning in public about the things topics I was exploring, I've been able to have conversations with experts, investors, and other people who are fascinated by the same things I am, and I'm able to come into those conversations with a well-formed point of view. 

Figuring out my business plan has been like writing a constantly-evolving essay, informed by research, conversations, and intuition, and I suspect that that will continue to be the case. Now that we're actually launching Not Boring, writing is probably more important than ever. 

At the beginning, since I'm not an engineer, words are my code. They're all I have at this point. From the blog post I wrote to announce that we were opening up application and writing copy for the website, to sending welcome emails and drafting our Code of Conduct, writing is integral to everything I'm doing. 

Most importantly, writing has helped me attract people to the cause and sign up our earliest members. A meaningful amount of the people who have applied to Not Boring did so because they've been able to see what I want to build by reading my newsletter every week or reading longer blog posts when I publish them. 

They know that building community around learning is something that I care deeply about, and I've been able to convince them of its importance over time. For me, writing is a better and more natural way to find those invaluable first “100 True Fans.”

Writing probably wasn't a huge focus for you in your early career, yes? Was confidence an issue you struggled with when it came to writing? And if so, how have you overcome it?

Confidence was a huge issue I struggled with. It's the #1 issue that other people I speak to who are just starting out struggle with. It's hard to convince yourself that you have something unique to say, that people will care about what you have to say, and that there's not someone out there who's already said it better.

In fact, the first twenty or so times I sent my newsletter, I imagined a group chat happening somewhere on which all of my friends are making fun of what I wrote and of the fact that I was presumptuous enough to write in the first place.

I still imagine that group chat sometimes. But the truth is, people don't think about you as much as you think they do. If someone doesn't like your writing, they just won't read it. Over time though, you'll find people who do resonate with what you write, and those are the ones who you should focus on. I haven't found a magic bullet to getting more confident in my writing.

I just write every week, and over time, I've gotten more confident, or at least secure, in my writing.

I saw you took the Write of Passage course. What did you think of that experience, and how did it help you become a better writer?

I wouldn't be writing if it weren't for Write of Passage. I've always liked writing, but kept it to internal company memos, the occasional draft I never published, and some e-mails with friends.

One day, I saw David Perell tweet about a writing course he was teaching, and decided to give it a try. The course wasn't like anything I'd taken in school. Instead of focusing on grammar and sentence structure, David and Tiago Forte pushed us to find our personal monopoly (the intersection of our personal interests and experiences that creates a unique niche), taught us how to build a compelling and surprising story, and forced us to just keep writing.

Every week, we had to publish an essay or a newsletter, and the fact that we had to discuss and get feedback on what we wrote in small breakout groups provided the accountability to publish. It was the perfect blend of education and community. I enjoyed it so much that I'm now doing the Write of Passage Fellowship, writing a 15,000 word essay alongside 10 people who are much better writers than I am, which is great motivation to keep working to get better.

What advice do you have for other people who are transitioning into a writing-focused role (that come from a different discipline/background)?

The number one thing is to start writing and just keep doing it. Your writing will naturally get better over time as you learn what works well and what doesn't and as writing transitions from something scary to something you just do.

This is the advice that everyone gives for good reason. Aside from just writing, there's nothing better than finding people who love you enough that they're willing to read and give honest feedback on your terrible first drafts. I'm lucky that my brother and sister are happy to tell me when what I've written is corny, bad, or just needs some tightening.

If possible, find a few other people who are at the same place as you and start a feedback group. If you're writing for work, find a co-worker you respect and ask them to be your informal editor. The person giving you feedback doesn't need to be a writer; just having a second set of eyes is really helpful in making sure that you're translating the jumble of ideas in your head to the page in a way that resonates with people.

Any writing resources you highly recommend?

I find myself going back to Julian Shapiro's "Writing Well" guide often. I also devour books, essays, and newsletters by people whose writing I respect.

When I write, I go back and read some of my favorite pieces of theirs to steal tricks. Anne Lamott's Bird by Bird is a classic and well worth a read.