Where we've been (and where we're going)

Looking back -- and forward.

On January 18, 2023, I wrote the first real post for this newsletter. It was headlined “A New Theory of News” and it laid out, in broad strokes, what I was hoping to do in this space.

The theory was (and is) pretty simple: Most media outlets spent (and spend) their time on the “what” of a news story — the basic details of what happened. I wanted to put all of my time and energy into the “so what” — why the “what” matters and, as importantly, what (ahem) to look for next.

It’s been 347 days since that first post. In that time, I’ve written 586 pieces — or about 1.6 posts a day since that first one.

We’ve gone from zero subscribers to over 9,000(!). We now have almost 2,000(!!!) people who invest — with their own hard-earned money! — in this newsletter.

With the end of the year now just hours away, I have been thinking a lot about these numbers — and what they mean about where we’ve been and where we’re going.

So, a few thoughts on [gestures around wildly] all of that.

Let’s start with what’s worked.

I think my general conceit of what this newsletter could and can be has been (mostly) proven out. I think the response from you all — to individual posts and to the broader ideas underpinning what I am doing — suggests that there is a real appetite out there for this sort of content.

You guys really want to understand why our politicians say (and do) what they do. The strategy (or lack thereof) behind it. Where we are headed and who will lead us (gulp!).

So, there’s that. But there’s also this. When I started writing “So What” my plan was to make it 99.9% about politics. It’s what I know best and what people know me best for. It’s what I have always done.

But, at some point relatively early on in all of this, I was really struggling with being laid off by CNN. So I decided to write about it — sharing a part of myself publicly that I had never really done before.

I was, quite frankly, stunned with the response. People were empathetic and understanding. Some shared their own stories of similar struggles. It was, in a word, uplifting.

So, I did more of it. When my father-in-law passed away suddenly in March, I wrote about it. (It’s still the most read post I have ever done.) When I realized I was struggling to make and keep male friendships, I wrote about it. When I debating whether or not to take a role teaching journalism (I did!), I wrote about it.

And, yes, I wrote a lot (maybe too much for some of you!) about my professional journey — going from a major media outlet to a media entrepreneur. For people who have been with me since I started this newsletter, you know that journey has been a rocky one. There are days (today is one, actually) where I feel overwhelmed by the uncertainty of what the future holds for me. (More on that below.) There are other days where it feels like I have never written better or more clearly — or more honestly — than I am right now.

But, feeling as though I can share what I am thinking (and why) has been a massive blessing for me. Because I know there is a community out there — you all! — who have sought out the sort of work I am doing (on politics and, well, not).

And THAT has been the thing I think we’ve gotten the most right this first year: The community.

I will admit that coming off of my experience with CNN, I was mostly convinced that civil conversation about politics was impossible. That all we had left was name-calling and vilifying — and purposely misunderstanding or choosing to ignore where people who disagreed with us were coming from.

Building this community has helped me reclaim some faith in people (and our politics). Yes, I know our community tends to lean left — and to be anti-Trump — but I want to make clear that I welcome ANYONE to it who is willing to engage in ideas with a civil tone. (In fact, I would love to have more people who disagree with the leftish lean of our community — so that we can have more varied (but thoughtful) opinions in the comments.)

This community has been sustaining for me in hard times. It has challenged me to think through some of my long-held beliefs — and better explain why I believe the way I do. It has led me to reconsider what I believe is possible for myself — and for this endeavor.

So, thank you.

I’ve also been thinking about what didn’t work this year. I wanted to write more about culture more broadly — sports, entertainment etc. — than I did. I wanted to do more Q and A’s with interesting people than I did. I wanted to launch more special features for paying subscribers than I did.

I suppose any time you start something from scratch — and sort of make it up as you go along — there are going to be some regrets when you look back. I don’t feel like I failed forever on any of these fronts. But I do want to do better — on each and every one of them.

Which leads me, somewhat naturally, to what the next year holds — for me and for this project.

Short answer: I don’t totally know.

Let me be frank: When I started this Substack 347 days ago, I didn’t think it was going to be a long-term solution, job-wise. It was something to do — to keep writing until I could find the next thing.

But, over the past year — and especially the last 3-4 months — I’ve started to see a path where this newsletter can be the central piece in what my professional life looks like going forward.

That said, we are not there yet. While the growth we’ve had is amazing (at least to me!), it’s not enough to ensure that I can make this newsletter my main job going forward. The next year will (likely) determine that. Can we build on the growth of this first year? Can we go from 9,000 followers to, say, 20,000 followers? Can I expand the number of people willing to invest in me from 2,000 to 5,000?

I think it’s possible! (Anything is possible!) But, I would be lying if I told you I had some secret plan to get there. I don’t.

I have ideas. I am going to start doing a monthly Zoom call with paid subscribers in January. (If people like this, I may do it more than once a month.) I am going to dabble in the podcast space (likely via Substack). I am going to do more video posts (most of these will be for paid subscribers only). I am considering doing an in-person meet up with me for paid subscribers. (Would people be into that?) I may do an open thread post every week — where you guys can talk about whatever is on your mind (and I will weigh in too!).

The truth, though, is that my future — in this space and more generally — is uncertain. I don’t know where I will be on December 31, 2024. Or where we as a community will be.

But, if there’s one big revelation I have had this year it’s this: Uncertainty doesn’t have to be a bad thing. After all, an uncertain future means that things can go in a LOT of different directions. Sure, it could mean that things take a bad turn. But it could also mean that things wind up surprisingly great.

Guessing at which way things will go is a fool’s errand. My last 15 months have taught me that. All I can do it continue to write and think and share and reflect. And that is what I am absolutely committed to doing. Thanks for coming along on this journey with me. I am excited for what the future might hold.