*a quick promise to you: our newsletter will always only ever be written by humans and never by robots. we wish we could say that this is out of love & respect for writing & the environment, and while those are both true, it’s mostly that we really tried a couple years ago for months on end to get the robots to write in this very weird (but always hilarious, obvi) tone and it just…has not delivered. easier AND funnier to keep it highly manual and we are very okay with that. thank you for your understanding.

while normally how a mansplainer gets his water, “well, actually” will explore the different angles of an argument or conversation & favor celebrating nuance & complexity over the short-term satisfaction of “hot take culture”.

This week’s Well, Actually is going to be a response to a reader question that came in this week:

I’ve been thinking a lot lately about starting my own newsletter, specifically about switches that people can make to be more analog in their lives. I see a lot of content being made on social about this, people sharing how they are making swaps to be less online, and I think about the ways I’ve successfully built in more analog time in my own life; I think I could provide some good recommendations and education on it. I also just really feel a strong urge to write more lately, and about something like this. Does that sound like a good idea? How do you do your newsletter? Is it even worth it?

Well, first of all, this newsletter sounds amazing and I hope you DO write it and I will absolutely be subscribing. I’ve gone down the rabbit hole with content like this, and I would love to read it.

But the bigger question here, it seems, is: Is it worth it?

Let me start by saying that, without question, I think you should write if your body and your brain want you to write. We are beings that have instinct and compulsion to create, so we should create. For wayyyyyy too long, I only did things I was really good at immediately–I got instant validation from it, I never had to struggle through it, “practice” and “improvement” became relative terms, and the stench of failure was something I never wanted to smell like. 

And that was a really dumb way to live.

I’ve realized as life has gone on that you should do the things you want and try the things you wanna try because you WANT to do them and not only if they will be an overnight success. Learn how to be bad at things and to not care about it. I’m not even talking about, “learn how to be bad at things knowing that that’s the worst you’ll ever be and you can only go up from here as you practice and improve,” even though that is also accurate and true. I’m saying, “who gives a shit about improving, do it because you fuckin want to.” Who gives a shit if it’s “good” or not to someone’s standards? A lot of people think Jackson fucking Pollock was a hack. If you want to create, then create. The act of creating can be the goal…not just what happens post-creation.

That said, it’s also really important to be realistic with yourself about what you want out of this and the type of person you are (the self-awareness piece is actually so critical).

Now, that might sound contradictory, since I just told you that there doesn’t need to be a goal beyond the act of creating, but you DO need to understand what you’re aiming for or trying to accomplish before you start. It could be that simply the act of writing, or of practicing, or of building something…that’s the goal. But newsletters are a very specific type of writing, and with an audience in mind, so why this specific medium for yourself?

I write this newsletter for a few reasons:

I do NOT write this newsletter to:

Before you commit to starting a newsletter (or podcast, or blog), understand what you ultimately WANT to happen from the whole endeavor. It’s critical to establish this BEFORE you start, because there WILL be times you want to stop, where you just don’t want to do it, where you wonder why you started in the first place, where you can’t believe anyone still allows you access to written language because you’re the least worthy person on earth to use it, and you’re gonna need to come back to that “why.” It will help you define what “success” looks and feels like and will help you avoid setting unreasonable expectations for yourself and your work. It will also be the solid railing you can cling to when you’re feeling like an absolute failure next to all the hyper-capitalist-success-hustle-grind-be-your-own-boss-financial-freedom-make-money-off- your-course-with-these-10-easy-tips content you are fed every day.

Next, you need to understand what you’re trying to say and who wants to hear it. This newsletter originally started years ago as The Weekly BROADCast for my then-business, built with a whole team. The audience was built over time, and it was more marketing-specific. While it eventually lapsed, I always knew I wanted to come back to it. We built that audience over two years to 600-some subscribers, so I had the benefit of that list when I relaunched it as something completely different.

Even now, I have known what I want to say, how I want to say it, even who I want to say it to, but the hardest part has been figuring out how to properly articulate all of that to anyone else. It’s NOT a marketing newsletter or a tech newsletter or a trade newsletter or even a wu-wu morality newsletter. You have to know what your newsletter both IS and ISN’T or you won’t really have an audience to speak to. (And full disclosure: I’m actually still figuring out the “what it IS” part, which is why I haven’t spent more time building my audience - I need clearer messaging first. See how it’s all a building exercise in every phase?)

You WILL need to find that audience, speaking of that part. And it’s really challenging to both find and build an audience, then to keep them engaged or know how many of them even give a shit. You have to decide if your ego can handle writing to maybe 12 engaged people every week (my ego and I have been through a lot over the last few years). What if only five people read your newsletter? Can you be okay with that? Can you be okay with the work that goes into it?

Over the course of (now) 15 issues, I’ve lost more subscribers than I’ve gained. I’ve had probably 100 new subscribers to add on to that initial audience I had, but I’ve lost even more, through bouncebacks or active unsubscribes. No one tells you how bruising THAT is to your ego–I feel EVERY SINGLE ONE of those unsubscribes. I even put it at the top of this newsletter as a funny-ha-ha but DAMN I feel it, ESPECIALLY when I know them personally. It’s REALLY hard to see the metrics move in ways that don’t validate you, where you move two subscribers forward, but then five back and you don’t know WHY and you try not to get spooked that you’re doing the wrong thing or no one cares about what you have to say or you’re incendiary or (worse) boring.

But it’s also really fucking rewarding when people reach out to you personally to tell you what they loved or engage with an idea of yours. 

Are you okay writing to a small audience? Are you okay knowing that only 50% of your audience is even opening your emails, but you only know for sure that 5% read it and liked it? Are you okay writing for a list of people who will regularly forget you exist because their inboxes are already too full with everything else and who might only read every third issue? Is that going to be enough for you?

On some level, all art wants an audience–that is to say, all artists want an audience. Even if they don’t care what their audience thinks or they love or hate their audience, the audience is a pivotal character in the performance (take it up with Sartre). And building that audience is not easy or fast. 

Also? This is not necessarily going to make you a lot of money. I started running ads about 4 issues in and, in transparency, I’ve made about $116 from reader clicks over 10 issues. Could I make more if I had a larger audience? Sure–see above. Could I make more if I charged subscribers? Absolutely, even if only 12 people pay me. Maybe I WILL go that route one day (it’s always an option for you, too), but for now I’m happy experimenting and seeing how things feel.

Finally, it’s work. It’s work you’re doing because you love it and not because you get paid for it. But it IS work, and it’s creative work, so it’s definitely taking energy to do well. Do you want to do that regularly? Do you know what you want to say? Do you know what you want to say EVERY WEEK?

You don’t necessarily have to make it weekly or biweekly or even monthly. Some writers I know publish when they feel like it…they also have MUCH larger audiences and are MUCH more well-known than I am, so they can get away with it because people recognize their names and don’t unsubscribe to them and report them as spam even after opening 13 weeks’ worth of emails just because the newsletter didn’t go out two weeks in a row and now the audience forgot their existence entirely (totally not a real thing that has happened, what gave you that impression). I will say that, when I am consistent, I get fewer unsubscribes (because people remember who I am), so consistency can be good for both you and your audience. Figure out first what you want to say and how much you have to say and how many ways you can say it. Make a list of topics and add to it every time you have a new idea. Maybe even write some rough drafts of a few, to get a feel for it. This is not because you need to be perfect before you start. It’s to build confidence that you KNOW where to start and gives you an easy springboard when you do (and it will come in handy on the weeks where you’re almost past deadline thinking WHAT THE FUCK DO I EVEN TALK ABOUT I HAVE NEVER HAD A GOOD OR ORIGINAL THOUGHT IN MY ENTIRE FUCKING LIFE).

In all, I err toward writing it AND being realistic about it. Yeah, the market is flooded right now. Who gives a shit? It’s a NEWSLETTER, for god’s sake, you’re not overhauling your entire life to write it. Try it, see if you like it, keep going if you are loving it, stop when you hate it. Do it because you have things to say and you want to say them and you feel good writing them. I’ll be the first to read it.

we like to highlight tools, places, services, methods, or other things that make work suck less. these are some of those things.

no need to buy anything. this newsletter is free, and i appreciate your readership AND if you just click this ad, you can help me get paid just a lil bit with someone else’s cash.

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some events we think are worthwhile to attend, both virtually & in-person.

if you’re looking for grants or funding, we’re sharing some of our favorite opportunities here.

each week, we’ll end our newsletter with action item(s), or “what TF are you supposed to do about all this now?” we hope they help. 🤞🏻

XOXO,