Silicon Valley killed my dream job

Lessons from the .com era (RIP)

an obituary, via LinkedIn

Welcome to Ordinary Delusions, a newsletter searching for answers in the chaos of late capitalism. I rebranded last week (just my name in caps lock was kinda boring, I like this much more). I will still be writing about fashion, but I am exploring new directions as well. Read more about my new direction here. If you find my work meaningful, please consider becoming a paid subscriber.

I am opening this new chapter with a trilogy of stories (or a triptych?) about how disruption in technology and the economy shaped my 20s and 30s.

The word “downstream” has been knocking about in my mind for the past few weeks. It’s business/corporate lingo that means a lack of power compared to something else. We are downstream from the economy, downstream from Big Tech, downstream from the laws of physics. We can’t stop the climate emergency or democratic erosion or the insane billionaires, but we can shape our reaction to them, and maybe make the world 0.000000001% better while we do it.

There is a lot of talk about AI right now, and how LLMs and data centers and Sam Altman are going to make us all unemployed — or how they’re not. Is AI going to make us slaves to Silicon Valley like in the Matrix, but with Marc Andreesen as Agent Smith? Will it make everyone more efficient, so that we all get universal basic income and work two days a week? Or is it just going to make it easier to find recipes? Clearly, none of us have an answer to that, but what I want to do here is show how a previous technical revolution upended my own career path a few years after I started on it, and how it’s left me better prepared for the future. Writing this makes me feel old, but it wasn’t even ten years ago. (How much disruption does one person have to live through? IDK, I get tired just thinking about it.)

2014 was a good year for streetwear, and 25 was a good age to be working at Highsnobiety. Supreme was just a handful of stores with a small army of kids queuing outside, Raf Simons had just done his first Sterling Ruby collaboration, Long Live A$AP had just dropped and Virgil Abloh was just about to debut Off-White. Highsnob was just a little blog back then, 10 or so people plugging away in a tiny office in Berlin with a few freelancers scattered across the globe.

On my first day in the office I was posting about motorbikes and one of those computer generated architecture concepts of a glass house nestled in the side of a cliff. Probably a bunch of Nikes as well. I was writing about stuff I hardly knew about, but it looked cool on the homepage. From then on, I would bang out 10+ posts a day. I was blogging.

As streetwear got bigger, Highsnobiety got bigger. More money was coming in from ads and sponsored content, and marketing execs were realizing that this streetwear thing was going to be huge. I ended up being the guy in charge of the fashion content. I went to a lot of fashion weeks. It was awesome.

I was traveling non-stop, meeting interesting people all the time, plugged into one of the world’s biggest cultural spaces and seeing how it all worked. And in the office, I felt like a valuable part of a company with a bright future ahead of it. I loved writing and I was good at it. My life was a total blur at the time, but I remember a few distinct moments of clarity where I was like, this is my dream job. I wasn’t making a lot but I was in my 20s, happy with not much, and figured my salary would grow much bigger down the line.

I assumed I’d follow in the footsteps of the previous generation of fashion editors. I’d make good money working at a company where the business model stayed the same for decades. I’d go to lots of parties and hang out with interesting people. I wasn’t expecting Conde Nast levels of luxury, with a driver and a clothing allowance, but it seemed like the future was bright.

Like all digital publishers, Highsnobiety made money from people looking at its website. The Nikes and Adidases of the world need to reach young men with money to spend, and putting ads on highsnobiety.com was a very good way of doing that. My job was to make sure the fashion content was really good, so that guys would keep coming back to the website, while also making sure Highsnob was the kind of space brands would want to advertise on. The content was the product.

This was the late 2010s, what media people now call the .com era. Publishers made money from traffic going to their websites. Social media was not the center of the information space at this point. Influencers were an annoying trend, not a built-in feature of capitalism. But Facebook was a goldmine. The early news feed gave a lot of weight to online publishers, and we’d get consistently crazy numbers for anything with Kanye/Supreme/Rocky/Kim Kardashian.

That started to change once Trump got elected the first time around and Facebook got the blame for platforming Russian misinformation. Facebook responded to all the heat it was getting by pivoting the algorithm away from external sites and prioritizing users’ own content. Traffic fell off a cliff for the entire media industry.

Meanwhile, social platforms were slowly creeping into everyday life, and before long they’d taken over the information space. The audience got their news from Facebook or Twitter or Instagram rather than typing a url into a browser or pulling up a bookmark. And the platforms built advertising technology so that brands could reach audiences themselves without having to buy ads on somebody else’s homepage.

The smart publishers quickly pivoted into doing agency work, and Highsnob did a very good job of it. They went from serving ads to making ads. If you were a major brand wanting to get young men interested in what you do, then you could go straight to Highsnob for the strategy, creative, research, events, everything.

Content wasn’t how media companies made money anymore. And my job was content.

The editorial team was slowly sidelined, under increasing pressure to do more with less while the agency made all the money. This was not a happy time. There were lots of Slack arguments and passive aggressive meetings and unanswered questions lingering over everyone’s heads. After a while, it became pretty clear that content was not the future anymore. The business model had changed. I left.

I didn’t go to another magazine because I knew from talking to editors at other titles that everyone was going through the same shit. Nobody else felt like they had a bright future ahead of them either. The writing was on the wall by that point. Silicon Valley had changed how the world got its information. The era of .com content was over, and it wasn’t going to come back.

Honestly, the transition into freelancing was kinda like starting again. I crashed through it blindly, and ended up making some pretty significant mistakes. And this is where all this ancient history becomes relevant again, because when the next round of career-changing disruption comes, I’m not going into it blind.

Learn from my mistakes:

— I was telling myself stories. I was living in a fantasy world where everything was going to stay good forever. I didn’t seriously consider that something bad might happen to my line of work like, you know, Big Tech destroying its value.

— I did not lean into any of the side hustles that I could have gotten into. Online editorial teaches you a ton of stuff that you can turn into something valuable later down the line. I saw my job as a steady path where success was laid out in front of me, rather than a place to learn skills I might need to take somewhere else. I hardly posted on Instagram, let alone got into consulting or speaking.

— I did not understand the value of having my own platform. When you work on the front end of media, there is an expectation that you are going to be part of the conversation. That doesn’t mean you need to become a micro-celebrity, but there is a level of commitment that you need to give to social media if you want your work to resonate. The same goes for networking in other jobs. You need people to know you exist. I didn’t take this seriously until I was freelancing, and I wish I’d started earlier.

— Probably the biggest one: I was not keeping track of what was going on in my industry more broadly. I knew the situation in online media was bad, but I was so caught up in my own experience of it all that I did not see that there were also opportunities ahead of me. The bigger picture is so, so important, because that’s what’s going to change your life, for good and for bad. We’re all downstream of something.

This all comes down to being more responsible for yourself, which is a pretty unimaginative piece of advice to give when you’re 36, but also, it’s the truth. Something freelance life teaches you very quickly is that the biggest obstacle between success and failure is yourself. If you do not keep your mind open to new opportunities, if you do not have the confidence to try new things, you’ll sleepwalk into a dead end. If you do not have the discipline to show up for yourself every day, you’ll drift into a slump and not realize until you’re already there.

Brian Morrissey likes to say that media is “an execution business” — it’s about getting shit done and rolling with the punches much more than it is about having the perfect strategy. Another way of putting it is “fail fast, fail often”.

These are lessons that freelance life teaches you, often brutally. And media was one of the first casualties of the social media age. But the world is in the midst of so much disruption (aka the polycrisis) that these are lessons that I expect people in all lines of work will soon have to learn.

As a survivor of the media apocalypse of the late 2010s, it’s easy to hate Google and Facebook for eating up the ad dollars that used to pay my bills, but even those guys aren’t safe. There is a very real possibility that AI chat bots make search engines and social platforms irrelevant. Instead of hitting up Instagram to see what’s up or typing a question into Google, you could just get your AI to update you instead.

The same goes for the businesses parallel to fashion media: the creative agencies, the multi-brand retailers, the brands themselves. They are all under pressures of their own, forced into new directions by the disruption around them.

I still miss the Highsnobiety days. It was a really special time for me, but also for fashion. There was so much energy in streetwear that it felt like I was really in the middle of something. And I loved being part of a team. I’m sad that it’s gone, and I never really allowed myself to feel it because my life got so chaotic in the years afterwards. But I could not get that part of my life back if I tried. The job I had barely even exists anymore and fashion itself is in a really weird place.

I have decided that building a voice around the things I think are important is the best way ahead for me. I do not consider myself a Substack writer or a book writer or a content creator. My message is the product. I do not want to marry myself to a single way of working, let alone a specific platform. I do not feel great about spending decades in front of a laptop, but if I’m very good at anything, it’s writing.

We are all going to have to internalize the brutal truth that there are very few steady career paths ahead of us, that almost any industry you can make your money in is vulnerable to changes in technology / politics / the economy. Can you think of a more stable career than accounting? Well, what happens when you can get a chat bot to file your tax return for you?

This will be a storyline I’ll be returning to again and again — how these huge changes in the world shape our lives, and how we can thrive in spite of them.

Next week I’ll be looking at how my experience in sustainable fashion has been impacted by the global economy. The week after, I’m going to talk about how the political situation in the UK shaped my life in Berlin.