First outlines of a plan: thinking strategically about a modern tech and media business
Last year was a bit of a paradox, at least at first glance.
It was great for the newsletter but not great for my work or business. I kept a steady weekly pace on the newsletter and doubled the number of subscribers over the year.
But it was also unrewarding, in both a creative and financial sense. I ended the year drained and exhausted. And the newsletter – ostensibly a tool for growing my business – did no such thing.
As I wrote in Let’s pause for a moment, I need to think:
Back when I relaunched this site in 2010 – switching from a pair of named blogs, Loud for links and Another Quiet Day for essays, to a eponymous blog and site – the point was that it would be a more focused foundation for my career. Unlike the blogs I’d been running up until then, this site has always had a defined purpose. I might digress into topics that suit my fancy, after all you always bring your whole self into your career so expecting yourself to leave bits off is like leaving an arm at home and expecting to easily reattach it when you get back, but ultimately it should always return to form:
Work.
When your work is caught in an unproductive rhythm and pace, that means you’re stuck in a rut. I kept writing, but without a plan or strategy for how it would help me work and this site is explicitly for work. Instead of helping my career, the newsletter, the essay writing, and the blog felt like an anchor I was dragging along behind me. Or, worse, a potential distraction.
The newsletter and the ongoing commentary on the tech industry’s self-destruction had become a chore – a gruelling obligation with no reward.
It was time to pause and rethink things.
The Ideal #
Ideally, my sites should be a part of a cohesive strategy for furthering my work and my career. Otherwise I’d just be whatever comes to mind, just for myself.
My publishing needs to be a part of a process and be done with purpose.
- What I publish helps people solve their problems.
- Their interest directly feeds into my work.
- This gives me more time, space, and incentive to publish more and be more useful to the community.
- If something resonates with people and they find it useful, then that’s a signal that I should offer more to help with that kind of problem.
It should also make sense to an outside observer, because that’s what leads to the best outcomes for everybody.
Nobody blinks an eye if a professional landscape photographer offers prints or landscape photography courses for sale on their site.
If you browse to a site where an interior decorator writes expert advice on interior decoration, you’d be more surprised if they didn’t offer their services somehow on the site somewhere.
Their business is to provide us with access to their expertise in various ways and, done right, it will feel natural to everybody involved.
This creates incentives to publish in a way that is logical to the audience and to the publisher. The income gives you space to put some work into what you publish, which should then feed into the business.
Logical, no?
But how do you actually make it work?
The first outlines of a plan #
For this to work you need to be working in an industry or niche where people actually pay for products and services and that’s where plans tend to fall apart.
Students and academia, for example? Generally an awful target market. How well a niche works for you also depends on how well what you have to offer suits the audience. Hairdressing salons are, notoriously, a bad market for software products but I’m guessing that they’re a great market for goods and services that help their core business.
You also need to have a process:
- Research and discover the problems those in your chosen audience are dealing with, preferably the ones that are costing them time or money.
- Create and publish solutions that help solve those problems, building credibility, and creating an incentive for them to subscribe to your newsletter or feeds. This was helpful. The next one might be helpful too.
- Occasionally, you launch a product or service that’s helpful to the audience you’ve attracted where the investment seems likely to pay off for their own work.
If much of this like some of what Amy Hoy and Alex Hillman write on Stacking the Bricks and in their 30x500 course, that’s because I did the course a few years ago, at the start of COVID. I’ve never managed to follow their guidelines perfectly, but that’s on me. Their advice and ideas have generally worked well when I’ve put in the work.
My mistake – and I’m very much not alone in this – was that I’ve never managed to do a good job of picking an audience and sticking to it. I’ve gone from nitty-gritty web development topics, to commenting on software development at a pretty high level, to commenting on the AI Bubble, to writing about tech for people in publishing, and everything in-between.
So, during the break, I had a few tasks – questions about the sites and newsletter I needed to answer – and the most important two were:
What do I do?
And…
Who do I do it for?
Because I write to think, I wrote a few interim notes to help gather my thoughts, most of them pretty unstructured. They did the job of helping me get a better sense of where I am and what kind of environment I’m working in.
- Interim note 1: tech. “Tech is about to enter a proper wealth extraction phase.” What is and isn’t safe and reliable in tech is changing.
- Interim note 2: business thoughts. The business environment is changing.
- Interim note 3: text-based media in the age of showmanship. “Video and truth comes from showmanship is the new norm with YouTube, Instagram, TikTok and other primarily visual media being the default for most people.” How people experience media is changing.
- Quick and only partially coherent review of 2024. “But I focused on maintaining a release pace for my newsletter because that was simpler than trying to answer a bunch of tough questions I really needed to be answering.”
- Interim note 4: time-based media. How video and podcasts have been changing.
- Interim note 5: web media and web dev employment. “My guess is that “big company web developer” as a target market will effectively dwindle into non-existence over the next few years. The only question is how fast. Whoever remains will be underfunded and underpaid.” The web dev job market is falling apart.
- The web is a creative industry and is facing the same decline and shattered economics as film, TV, or publishing. Like, really falling apart. And media in general isn’t doing so well, either.
What do I do? #
The what do I do? question turned out to be relatively straightforward:
- In my freelancing I’ve generally done specialised web development for companies on the fringes of the trade publishing industry. Web-based ebook reading. Annotation. That sort of thing. My website hasn’t meaningfully been feeding into my freelancing business for over a decade, or since the ebook bubble collapsed. My contacts in this space have slowly been dropping off, one by one, largely because their companies have been going broke, sold off and dismantled, or retooled completely to stave off bankruptcy. None of this is ideal.
- I used to also do education-oriented freelancing where I worked as a tech editor, tech writer, or consultant for larger organisations who were creating their own training material, but that disappeared overnight with the AI Bubble.
- But, finally, I started to see more clearly what it was that I do with my blog and newsletter: I explain technical issues by putting them in a context that’s comprehensible to non-experts but grounded in research and practice.
That last part warrants more explanation.
Out of the Software Crisis, for example, is an attempt to explain how software development works, at a high level, in a way that helps a manager avoid some of the biggest organisational and systemic landmines that sabotage software projects. It uses systems-theory as context to explain how to approach research, design, and planning of software development in productive ways, with one of the biggest messages being that too much variability is poison and leads to chaos, costs, and delays. You don’t need to understand code or to ever have coded to benefit from the book.
A complex topic recontextualised to be at least somewhat comprehensible to non-experts in that topic.
The Intelligence Illusion similarly explains how generative models work and what that means for any attempt to use them as a part of your business. (Short version: it’s bad, these tools are non-deterministic and error-prone, which leads to excessive and unpredictable variability in your processes and, as I pointed out above, that’s poison to a business system.) You don’t need to have studied Machine Learning or coding to understand it, but it might help you manage a team of coders, for example.
Even the newsletter archive bears this out. I may not have been thinking strategically as I published every week, but for the most part I’ve kept to a theme: I explain technical issues by putting them in a context that’s (mostly) comprehensible to non-experts.
Since it’s usually sensible if you’re building a business to try and build on what you have and your existing resources, a good starting point for my search for a strategy is to look at the bricks I’ve already stacked, so to speak.
Who do I do it for? #
Who could benefit from how I write, my focus, and the resources I’ve built up over the years?
The obvious target audience would be managers who need to work with and understand tech but don’t come from a software development background themselves, like project and product managers, for example.
This has always been the obvious target audience for my books and my newsletter, but I’ve generally resisted the idea because I’ve never worked as a project or product manager. I’ve been a lead developer who gives advice or helps guide a product manager through complex technical issues, but the management side itself hasn’t been my beat.
I’m not in a position to give advice on project management so this always felt like a non-starter.
But, I was thinking about the audience from entirely the wrong perspective. A project manager, for example, will generally know a lot about the nuances of their own job. They aren’t going to be needing much outside help on their own expertise and when they do, sure, they’ll look to people with deep expertise in management. But, whenever they have a task that takes them out of their comfort zone and into mine, that’s when I can step in and help.
That gives me a more focused lens for research. Instead of blindly researching all sorts of management issues, I can focus on looking for common problems managers have with understanding or dealing with complex tech and then figure out how to explain it by putting into a context they understand. I could focus primarily on covering the expensive trends and overhyped tech that the software industry keeps pushing on businesses and help managers weed out the ones that increase costs and focus on what lowers them instead, hopefully while improving other outcomes at the same time.
An upside to this is that explanations like these also benefit people outside the core target audience even though they wouldn’t be the group that directs my research.
If my sense of what do I do? and who do I do it for? is in the right ballpark, then that makes the overall strategy clearer.
But you can’t strategise in a vacuum. The world is… in a bit of a state.
A lot has changed since I first launched my blog and newsletter. Any plan needs to take the current situation into account.
The current situation #
Even if the newsletter hadn’t been stuck in a rut over the past year or so, I would still have to rethink and retool my overall approach and plan. Even though these changes have been a long time coming, recent events have surfaced a variety of structural and systemic issues in ways that need to be addressed.
I went into some of these issues in the notes above.
The short version for why I’m hesitant to pivot directly into web dev education or training, at least in the short term:
- Web dev overall is in a very bad place in terms of standard practice and overall quality of the work delivered by the industry (websites and web apps).
- Employment is down substantially due to a combination of ongoing lay-offs in the tech industry and web media getting hit hard by sharp drops in the traffic generated by search engines and big social media.
- “Standard practice” is likely to be unstable and chaotic in the near term as organisations don’t have teams that are big enough to sustain the bloat and nonsense that is the norm any more. Regular lay-offs also cause chaos in and of themselves.
- This means that the usual market for anything related to web dev training and education is probably shrinking fast.
- My guess is that the corners of that market that will survive or even thrive are those that help people address the problems of modern web dev using cost-effective approaches that delivering fast websites with less effort.
- Basically, CSS, maybe HTML, and server-side or static rendering would be my bet if I were in that game. (Andy Bell’s Complete CSS looks amazing!)
I’m still interested in writing about my own web dev, especially when it comes to implementing some of the ideas I have for this year, but not as a part of an overall strategy.
Another factor is the decline of tech, which is looking more and more obvious to many of us.
- Software quality at major tech companies is declining and has been in a decline for a long while.
- Platforms that aren’t declining are changing constantly and aren’t a reliable foundation for many businesses to build on. (What framework is Microsoft telling people to use to write native Windows software this week? What APIs did Apple break in their latest OS update?)
- Big tech companies are opting to use political leverage to avoid scrutiny and reduce transparency, which inherently makes these platforms less reliable and predictable. That is if you are naive enough to believe that active avoidance of regulatory scrutiny doesn’t strongly imply that there’s malpractice and misbehaviour going on behind the scenes.
- This both means that many of the platforms we software developers build on are inherently unstable and that instability threatens our businesses and livelihoods.
- And that’s without getting into surveillance, propaganda, political and economic manipulation, and hostility to labour movements and all of the other double-plus ungood nonsense that’s going on in tech.
The third and possibly most important factor is the increased political instability of the US and, with it, most of Europe and North America.
- The odds of a trade war seem quite high.
- The US executive, legislative, and judicial branches look increasingly arbitrary, authoritarian, and partial to insular and bigoted ideologies.
- The new political environment also provides cover for corporate misbehaviour. If a payment processor, for example, bans you from their platform because they think you’re gay or black and find your very existence offensive, you’re going to have fewer options for recourse than before.
- This goes beyond pre-emptive compliance. The risk is also over-enthusiastic compliance with implied bigotries. You might lose access to a platform, not because you broke a rule set by the authorities but because managers or executives see themselves in the new regime and believe that acting on their own prejudice and aggression is not only allowed, but implicitly endorsed.
- Actively protectionist policies and attempts to stifle speech in the US also represent direct threats to non-US businesses who use US-based platforms, cloud storage, or hosting. This isn’t limited to actions taken by the authorities as pre-emptive censorship by US-based platforms is likely to have a much wider impact than government action. It’s clear that many of us are to be considered economic, if not political, adversaries.
- The best case scenario for the US in the near term is a chaotic environment that’s hostile to foreign businesses.
Continuing to pretend that the US and big tech companies are stable and predictable environments is untenable, which means we need to adjust our strategy and figure out something more robust.
The media environment is also shifting.
- Video and other time-based media are taking over from the last bastions of text.
- The epistemology of video is that of showmanship, as in good showmanship makes the audience more likely to accept what’s said as the truth. This bleeds into textual media, leading to an environment where “loud” or “showy” writing attracts the most attention. We are no longer operating as a society under the epistemology of print, which is that of exposition, where well-constructed explanations and exposition make readers more likely to accept what’s written as the truth.
- Time-based media today is much more fluid than the video or TV of a few years ago. Podcasts are recorded with video. Videos are broken up into clips for TikTok or shorts. A single production gets shifted into multiple different audio and visual formats. Captions and transcripts are getting more and more common, if not the norm, albeit of a wildly varying quality.
- Video is even more dominated by silos and closed platforms than text or audio (both of which still have a bit of a feed-based ecosystem, even though they’re arguably in decline).
- Time-based media is where the masses are and it’s increasingly likely that anybody who wants to reach an audience will have to rely more and more on video.
- Video-oriented social media platforms have become focal points for multiple political crises around the world.
Text-based media is still important, just less so.
- The book and the ebook especially remains a good deal for both the publisher and the reader.
- Text has a kind of authority that video does not – due to still being at least partly based in the epistemology of print. If you need to convince your manager or your co-workers on a technical issue, a white paper will carry more authority than a video course.
- Text is an economical way of testing out arguments and ideas before investing the time and money necessary for a video or audio production.
- Writing is an essential part of video and audio production. Only fools start production without something written down.
- Text is important for accessibility and reach.
The first outlines of a plan #
It’s easy to overwhelmed by all of this. (This is why a break with lots of sleep was helpful.)
But I think it’s possible to put together a sensible plan without overthinking it. (Too late! Hah!)
Since I have a clearer idea of the audience, I can restart the newsletter with episodes that should still be useful to the existing audience. The difference would be that the topics I choose should be more based on research into what people are dealing with and not simply my reactions to shit that’s happening.
So, Out of the Software Crisis – the newsletter – continues.
But, I also need to, well, pivot to video. (Ugh.)
The idea is to start small and simple. Straightforward audio-oriented videos of the pain-dream-fix format that can be distributed as either portrait- or landscape-oriented video as well as audio for podcasts and transcripts or text versions for the web and the newsletter.
The problem is that every single major video platform is a combative and unstable environment, which means that my video efforts need to be built around a hub that I control.
This is why the softwarecrisis.dev website should be the core home for the videos and the podcast while this site would be the home for the newsletter essay archives. The first and primary home for the videos I make should be a site of my own.
I would distribute the videos and audio to a number of different platforms – Mastodon, Bluesky, TikTok, YouTube, podcast aggregators, LinkedIn, etc – effectively the IndieWeb POSSE strategy except applied to video. Post to every site available, but link to the original in the description or comments.
This would require another important change from the usual way people post and promote their video on YouTube, for example.
No more “please like, share, and subscribe” taglines.
Even though it might harm distribution (algorithms!) every video and audio should end with a pointer that the best way to keep up with new releases would be to go to softwarecrisis.dev and subscribe to the newsletter, viewers would not be prompted to follow, like, or subscribe on the platform in question.
The videos should have the singular purpose of driving people to follow the newsletter.
On the technical side, updating softwarecrisis.dev to be a video hub is going to involve migrating it over from deno to node and eleventy (mostly because I’m done with Deno except where I have to use it). And it means I have to figure out how best to integrate an affordable video CDN such as Bunny CDN (which has the added advantage of being a company that’s headquartered in the EU) so that the site itself isn’t reliant on video playback hosted by US-based social media platforms. At the levels of traffic that specialised videos are likely to get, the costs shouldn’t be prohibitive.
Web media has lagged quite a bit behind social media sites in terms of formats, such as portrait-oriented short video, ebook-styled long-form reading, and playback experiences. It might be fun to experiment a bit with how to accomplish some of those ideas with a static eleventy site.
I’m still noodling around with ideas for how to structure the videos themselves, but I’m leaning towards starting with a series of themed audio-oriented videos, shot with the cameras and microphones I already own, in the 5-20 minute range, initially drawing from the newsletter entries and blog posts that I know have resonated with people. The base video should work for the most part without the video so I could offer a podcast version of them all. Ideally, it should be possible to break the video into shorter stand-alone segments for short form video platforms.
Some of the ideas I’m considering in terms of overall topics or series:
- We keep making bad software. How do we stop? Each focuses on a single thing that causes us to make bad software and how to avoid it. Based on ideas and writing surrounding the Out of the Software Crisis book and newsletter.
- The collapse of complex software. About how complex software platforms expose us to risks and political instability, which directly harms our businesses and projects. How to make our software simpler and more robust.
- Why generative models are bad for business. Video versions of many of the arguments I’ve made on generative models in the past.
- Keep calm: a disaster doesn’t have to be a crisis. How to react when tech shit hits the fan.
I have quite a few more ideas for videos and podcasts, but there’s no point in getting into more ambitious productions if I can’t get the basic stuff working.
Something’s gotta give and in my case it’s the link posts #
For this to be sustainable, I need to adjust what I’ve been doing. The essays won’t be weekly any more. I’ll still be doing them, but only when I have a good subject for one. I’m hoping that text versions of the videos (probably based on the script directly as there’s no way in hell I’m going to be ad-libbing them) will work for the regular newsletter schedule. I haven’t decided on the format exactly, but I will adjust it based on feedback as I go.
However, I’m pausing the weekly link posts, where I collect and curate lists of links, until further notice. Instead of the curated list where I boil down the best links I’ve found over the week into a single list, I’ll only post link sections if I’ve found something I think people should absolutely read.
I’ll still be posting links on social media (mastodon and bluesky), just not curating them into link posts afterwards.
And I’ll still be posting photos at the end of each newsletter because I find that personally uplifting.
This is just the first plan and it might fail #
If none of this makes any sort of headway towards turning things around for my work or career, then obviously I’ll end up looking for a full-time job somewhere here in Iceland and put the newsletter and blog on a hiatus.
That’d be fine. Not fun, but also not a disaster. I’d rather preserve my independence, but keeping a roof over my head is more important.
Part of my promise to myself this year is that I will give myself the time and space to try a few new (and old) things as well. I don’t know what that will look like, but if that changes things, then it changes things. (Obviously.)
Do let me know what you think about this overall (and only partially formed) idea and I’m still open for suggestions. I think it might work. At least it should be fun to try.
I’m not ruling out the unexpected. If a side activity or something off-topic suddenly gets more traction than the main newsletter, then I will absolutely pursue that instead. I don’t expect anything like that will happen but building a sustainable business is more important that building a specific business. Those are two very different tasks.
If you define success as attaining a singular and specific thing, then success will almost always remain out of your grasp.
But if success is I’d like things to improve somewhat and I don’t particularly care how it happens then that’s an open-ended search which is much more likely to succeed.