The Pivots newsletter has been a success, and I am figuring out what to do about that.

I just sent out the latest issue – 29 subscribers. To put that in perspective: This list has about 40, and my biggest list that I’ve been writing for since 2021 has about 230. So in a month I’ve gotten about as many readers as writing on my “regular” newsletters has gotten in three years.

Some of this is that it’s a pop-up newsletter — because people won’t need to unsubscribe they’re a little more willing to put up an e-mail address, and “limited time only” is a staple of marketing because it works. But some of it is the topic, too — people really want to read about Pivotal.

The best thing about the project is that I now have a much better understanding of why people like to read about Pivotal so much — about the “job” that people are “hiring” my writing on the topic to do.

  • People who worked at Pivotal read what I write about it to help them “make sense of” what was often one of the most significant experiences of their (professional?) lives.
  • People who didn’t work at Pivotal but work with people who did read what I write to help them understand the former Pivots they work with, and why they do and believe all these strange things.
  • People who didn’t work at Pivotal but wish they had read what I write to understand this experience and how and where they might have it now.

People in all three categories also read what I write about Pivotal for inspiration and for motivation to “keep doing the thing.”


The amount of writing that I have been doing for this project is somewhere below “the amount of writing I could do if I was 100% on writing” but somewhere above “the amount of writing I can do while also working a full time job.”

Incidentally — I am looking for a job right now — or contracting or consulting engagements. One of the main problems with “looking for a job” is that I don’t know exactly what kind of job I want, really, but if you know anyone who is looking for Elixir developers, or for polyglot subcontractors with Extreme Programming experience, you should point them my way. I’m also interested in talking with anyone who’s in the market for custom software — that’s a world that I’m vaguely familiar with but would like to understand better.

Anyway — like I said, the big problem with “looking for a job” is that I don’t know what kind of job I really want. Lots of things seem potentially interesting. XP consulting? Sure, if I can get it.

Straightforward delivery work? Sure — if there’s pairing and TDD.

I’d like to work as a contractor and/or 4 days a week, so I have time to write — but I really like writing Elixir, so maybe a full time job would be okay if I was doing that and the environment was good.

I don’t necessarily love infrastructure and writing Terraform — but doing that part time for a company that doesn’t quite need a full time DevOps hire yet might be perfect.

I’d probably get the best time-to-money ratio if I picked something to specialize in as a consultant — but the sales process there seems really intimidating, there are so many different things that I technically can do that I have a hard time picking just one to work up into a distinct “offering.”

I’ve had some success selling digital products on Gumroad and would like to explore that more — but I’m pretty far from being able to pay all my bills that way, so in the meantime I probably need to be doing something else, too.

There’s a SaaS that I want to build — and have started exploring with some friends — but, again, even in the best-case-scenario that’s like six months out from being able to pay for my time.

More than anything, I keep circling back to the question: Do I want to start a membership business?


A membership business let me make some money from what I’m doing right now — this “writing about Pivotal.” The pitch would be something like “$10 a month to support Nat writing about this thing you care about.” There’d be some members-only perks — a discount code for everything I’ve got up on Gumroad, access to the drafts of some newsletters that have never been publicly available, maybe a private Discord or Slack — but the core of the thing would be about funding the creation of publicly-facing work. More newsletters— and books.

I think the Pivots newsletter wants to be a book. I think maybe it wants to be several books.

Craig Mod writes: 

Putting edges around an experience, paradoxically, amplifies it. Allows it to continue to grow in the world after you’ve completed it. You could call this the classic superpower of books — you die, you disappear, vanish, but the transmutation of whatever led to that book lives on in that world.

I want to do that for this experience that we had at Pivotal. I don’t want to only do that for Pivotal — I am vast, I contain multitudes — but I want to do it for Pivotal. For the people who were with me at Pivotal.

I want to write books. Writing that — sharing that “out loud” with the world — scares me a little bit. What if I’ve cursed myself? Drained out all my ability to write books, by saying so? What if I was never able to make books, anyway? I’ve been thinking about writing books in some form or another for thirty years now.

So, the membership program: The reason I want to do it is also the reason I’m scared of doing it. A membership program would be a way to draw a line around this ambition, to make it something I have committed to. To change myself from “a person who wants to write a book” to “a person who is being paid to finish this book.” Whatever other work I do would need to happen around the so-many-hours-per-month I have committed to writing for the membership program.

My big hesitation here is that it’s unlikely that the membership program would be able to pay me enough to really “earn” the time that I’d have to commit to it, at this point. While this is thoroughly in “good problems to have” territory, it’s hard for anything to compete, in terms of dollars-per-hour, with making software for hire. So I’ve always told myself that I wouldn’t try to get anyone to subscribe to my writing until I could be confident that I’d be able to get about 100 subscribers — $1000 a month. That number is a little bit arbitrary but it feels like enough to “justify” a significant commitment of time, even on top of a full-time job.

I’m nowhere near being able to hit that number. The conventional rule of thumb is that a 10% conversion rate from free to paid newsletter subscribers is very good. So, rough napkin math says if I set up a subscription tomorrow, I’d be doing well to get $250 MRR.

One of the things Craig Mod emphasizes is how much work running a membership program is. I’d feel better about asking for money for writing if I felt like I could commit to substantially more output than I can with the need to fit it in around other work. Asking for money for the “a few hours a week, when I don’t have too much else going on” seems a bit ridiculous. Committing to even a few hours a week, no matter what, maybe on top of a full time job, seems like it’s asking for burnout.

But I keep coming back to the idea. Even at the $250 level. Because one of the things that I have learned from putting a few things up for sale on Gumroad is that people paying me for things I’m writing is very motivating. I made almost $90 this month, and I keep looking at that number and thinking, “Hm, I bet I could make that number a little bit bigger next month…” I want to get that thought process hooked up to writing.

Maybe that’s the answer, to where I am right now — put more things up on Gumroad — or other platforms — as one-off purchases. Maybe the only reason that I’m thinking about a membership business is all the business advice about subscriptions — you know, not having to start over with the sales process from zero every month. Maybe that’s just not where I’m at right now.

And I am thinking about more things I could put up on Gumroad. There’s a good chance, too, that what I will end up doing is writing the book and then using the book launch to launch a membership business, too — make the pitch “help me make more stuff like this.” Maybe I will feel a bit less silly about it once I actually have the physical object.

Anyway — I am writing this here, to you, mostly to help me think about it — there’s nothing quite like writing for an audience to focus the mind, I think — but also because I want to ask. Would you pay $10 a month to get me to commit to writing a book about Pivotal, however long that takes?


I do not understand how much I like something that plays unstoppable ads for NCIS: Hawaii before it starts, but, here it is: I love the Halo TV show. After every one Jesse and I turn to each other confused, and say something like, “Was that… good?”

It is possible that I have just been ensorcelled by gigantic, shirtless Pablo Schreiber. (Remember Reacher? We did not finish the second season of Reacher. We got to the second-to-last episode and were just like… this isn’t fun. It’s just Reacher killing people in nasty ways. And we just stopped.) There are absolutely parts of this TV show that are bad. Basically anything in the B-plot somehow manages to be both weird and boring.

But the Master Chief himself? The people making this TV show said, “Okay so Halo is a story about a gigantic cyborg child soldier. Let’s take that concept really seriously. What would being the Master Chief really be like?”

Also? Surprisingly good fight scenes. I normally kind of tune out fight scenes in this sort of thing — they’re just grey shaky-cam blurs. But “Master Chief fighting elites” is a thing that’s consistently paced well, and the camera work is clear enough that I can understand what’s going on.


Anyway– if you have some software problems that need solving, get in touch.

And if you didn't subscribe to the Pivots newsletter, and feel like you're missing out? The back issues are available on Gumroad for $9.

The basic plan for this month is to figure out the work thing – whether that's a contract or a full-time job, or if other things in my life will line up such that I can work full-time on something that doesn't quite make money yet. I also anticipate getting back on a weekly schedule for some newsletter or another.

Then, get enough of a break from Pivots to be able to come back with "fresh eyes" and start thinking about what book it wants to be.

- Nat

Mere Being 010 - February

Thinking about membership programs & books