Marketing Monday Written by Jon for March 16th

I switched away from Gmail last week.

I've used Google's professional email product (along with the rest of their workspace) for the past decade. But as of this morning: I'm off.

The switch was, as expected, a bit of a hassle. I had to swap DNS records, get new user accounts for my team, and copy over a bunch of email filtering rules that I'd set up as part of my ongoing (losing) battle against inbox bloat. All told, the move took me about four hours, and I'm sure I'll spend more time this week tying up lose threads.

But the bulk of it is done.

I'm now using a German email platform called Tuta, which claims to be the world's most secure email provider. I take this to be a good thing, although I'd rather you didn't ask me to explain the details. My understanding of "quantum-safe encryption" is limited to the observation that it sure sounds cool. I think they made an Ant Man movie about it.

But honestly, I didn't switch for the security. I switched to escape Google Gemini.

My goal in life, increasingly, is to get away from all things AI. This may be unwise, and in the long run it'll undoubtedly be unsuccessful. AI is in everything now. My new email service might introduce their own "quantum-safe AI" next week, in which case I'll be right back to square one (and Gmail).

But I've been thinking about my relationship with technology a lot lately, as you've probably gathered from my emails. So I wanted to take today's email to give this line of thought one last run-through.

Sorry to beat a dead horse, and this isn't meant to be an anti-AI screed. There are enough of those already, and anyway I've said my bit on that before. Today's email is at a broader, higher level: I'm just trying to explain a little, for your sake and mine, where I'm at with technology and life.

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I used to be much more optimistic about technology.

I'm a millennial, so I grew up on the edge of the internet. I'm old enough to remember a world before iPhones, but young enough that my entire professional life has been spent helping older people figure out what's wrong with their computers.

The digital revolution rolled over my generation like a wave.

And for my first couple of decades, I liked the water I was swimming in. Generally I just thought digital stuff was cool. I was a freshman in college the first time I saw a friend use Spotify, for instance, and my first thought was not to critique its impact on creativity or analyze its capacity for societal good – it was to ask whether it was really free and if it ran on Windows. It was and it did, and I've been using it ever since. Unlike Tom, I've got no plans to stop.

I'm 33 now. It's really only in the last decade that I've started to sour on tech trends: to feel, upon hearing of something new, fatigue rather than excitement, wariness rather than wonder.

Maybe this is just a normal individual trajectory. Maybe to get older is to get grumpier.

But I don't think my individual arc is the only story. I think there's pretty clearly been a societal-level shift, too – a cultural movement from wide-eyed tech optimism to guarded cynicism.

(As an aside, you can see this movement really clearly in the tone of online content: It's impressive how much more sarcastic internet humor has become in my two decades online. We are in an infinite, ironic, self-referential loop, and at the center of it we've elevated self-consciousness to core virtue. Nobody would make "Chocolate Rain" today, because we're all too afraid of making "Chocolate Rain." Except Tay Zonday still isn't, apparently, God bless him.)

All waves have their backwash. As the initial waters of the digital rush have receded, we've gotten counter currents: digital minimalism, The Anxious Generation, mindfulness apps. The dissatisfaction has been strong enough to be almost mainstream. But the tide keeps coming in, anyway, and the undertow only gets sucked into the next wave, which promises to be even bigger. Get ready for AI, or at least put your floaties on. We're out at sea now, carried farther from the shore of the pre-internet world each year, and we can never go back. All we can do is be sarcastic.

I run a digital marketing agency.

It's a good business. It makes good money, and it could probably make better money if I squeezed it harder. I work with my brother and my friends. I have wonderful clients – seriously, some of the best people I know. And all of this is in the name of supporting music, which is about as high a Good as I can think of.

I ought to be grateful. Very. I am.

But there is also a large part of me that would like to turn off this computer and walk away from it forever – to stop making marketing content and YouTube videos and go do something with my hands, like plumbing or electric work or carpentry or guitar. In the depths of my deluded idealism, I imagine moving to the country and starting a farm in some lonely place, raising chickens and cows and corn.

(The problem with this dream – or one of many problems – is that I'm even less informed about farming than I am about "quantum-safe security." My chickens would die faster than you could say Wendell Berry.)

If I'm honest, the main question I've been wrestling with these days isn't how to crack the Spotify algorithm, or what the ideal number of videos in a dynamic Meta ad is, or whether first-click attribution makes a difference in efficiency. My main question is so much further back from all that as to make the weeds of my daily work feel irrelevant.

How can I live well?

It's cliché to even ask this, I know. Doesn't make it easy to answer, though.

It seems to me that there is one right way to live, but no one right life. Meaning: You should love people all the time, but what that looks like in practice will vary as much as the people and the times. And we're living in strange times with strange people.

Maybe we always have been:

Dickens wrote that perfect sentence in 1859 to describe 1789, and damned if it doesn't fit 2026 like a glove, too. There's a degree to which we've always overestimated the particularity of our present moment.

Still. Doesn't this decade just feel different?

Don't things seem harsher, harder, more cynical, more upsetting, more confusing? Isn't the world louder? In 30,000 years of humanity, ours is the first age in which no parent on earth can imagine what their grandkids' lives will look like. Doesn't it seem like we really are coming to some kind of edge?

I don't know. But I do get a couple hundred emails each day telling me it's a brave new world, and I should register for an AI-product-feature webinar to figure it out. Every YouTube ad I skip is for some AI-Super-Thing that promises it'll change my life if it doesn't kill me first.

I want to live well. I'm not sure what exactly that means, today, but here are a few small things I'm moving toward.

1) I'm opting for more single-use technologies. I find I'm less distracted by my tools when their intended purpose is clear. To give some examples: I prefer to use an actual calculator rather than my phone calculator. I prefer to read physical books rather than using the Kindle app on my phone. I've switched from Google Workspace to Tuta and Dropbox.

2) I'm opting for local things wherever I can. I try to buy produce from the farmers' market down the street. I just subscribed to the print version of our local newspaper, and I'm trying to avoid all online news. I gave up Amazon Prime for Lent; I know that's laughably lame, but I find myself wanting to order something like twice a day, so the addiction is real.

3) I'm trying to spend as little time as possible looking at screens. I keep my phone in black-and-white mode, I don't take it to restaurants, and I turn it off on Sundays. Alli and I are replacing our TV with a projector so we can clear screens out of our house when we aren't watching. (I briefly considered getting rid of TV entirely, but I'm rooted to Pittsburgh sports.)

4) I'm focusing on doing good work. One of the most fulfilling things in life is to lose yourself in doing a job well, so I'm chasing the kind of work I can lose myself in. This is part of the rationale behind my recent offer to help one artist get 1m streams. I would rather spend a full day writing one good email than answer 200 emails in 10 minutes with ChatGPT.

5) I'm trying to work with people as much as I can. I'm focusing on growing my marketing membership and hosting live events. When I can, I'm hiring people to do business tasks – making videos, handling customer support – rather than automating everything with AI. Speaking of which...

5) I'm avoiding AI as much as I can. It's an incredible tool, horribly useful. It's frighteningly close to magic as us humans have gotten, and I hope it makes medical advances and saves lives and ushers in utopia. But every time I use it, even when it's undeniably helpful, I feel like less of a person. So I try not to use it.

None of this is meant to be a moral stance, really. It's a feeling rather than a formula. But I feel it pretty hard.

Hence the move off of Google.

And most of this is the direct opposite of what every worried LinkedIn post tells me I should do.

I should, they explain, automate. I should go for scale: Get more clients, and also bigger clients, and service all of them with swarms of AI agents. I should use AI to its towering potential. One person can run a billion-dollar company. I should fire everyone. Sorry, Tom. I should use AI to amplify my thinking and my content, make myself more human, make my AI-cloned voice so loud you could hear my stupid emails being read by a genius robot from outer space. There's a moral imperative. It's dangerous not to use Microsoft Copilot. If I slack off for a year, everyone will migrate to the cloud and I'll be left behind like after the rapture.

Maybe I'd rather be left behind. I don't know.

I had someone respond to last week's email and tell me I ought to be grateful. I'm lucky to have Spotify, they said. It's a great business just trying to get by in this great capitalistic nation. You think a phone isn't incredible? You think it's all bad? Stop complaining, and if you don't like it, go live in the woods or move to Canada or something. You won't.

There's wisdom to this. I agree.

I'm not sure how my simmering tech antipathy fits with Two Story Media as a company. Maybe that person was right and it doesn't, and the two things are at odds, so neither can live while the other survives. Maybe one day I really will take a hammer to this laptop and go live in the woods. Maybe the only reason I won't is because I'm a coward.

But for now, I feel a weird sort of peace in this tension.

I'm a tech cynic, more each day. But I'm a person optimist, still, and people use tech, more each day.

So I don't know, but I think living well means living well here: in the small city of Frederick, Maryland, in 2026, in this world where everyone I love checks the news on their phones the first thing in the morning and the news is always bad, in this job that's basically massaging algorithms and making 15-second videos and clacking a keyboard into the yawning abyss of the internet.

Here. It might be cowardice. It might not last. It might be the only place I can do good work.

There's tension in this, all right, sharp tension, stretched tight as a guitar string. One day it'll snap, maybe, who knows. But you need tension. You can't make music without it.

– Jon

Jon Anderson Founder @ Two Story Media Surprisingly Bad @ Scrabble

🫆 100% Human Guarantee I wrote this, not AI. Lol do we even need this section today? But here's a picture of us and some friends after Alli and I absolutely dominated everyone at pickleball this past weekend.

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P.P.S. – I can't speak for Tom, but this will be my last anti-tech rant for a little while. Time to move toward the other end of the line; I owe you guys some good ol' fashioned marketing content.