Years ago, on a once functional and enriching website known as Twitter, I befriended a journalist named Edward Ongweso Jr. Ed is a tech critic who writes a lot of incisive essays about AI and Silicon Valley, posts a lot of funny memes, and shares with me a lot of mutual friends. I remember always thinking he seemed like a very Cool Guy.

Since I first med Ed I’ve sobered up, moved to LA, and spent a lot of time trying to figure out how to find peace and fulfillment in a world that feels hostile to those ends. I’ve learned a lot in my little quest so far, and part of my goal in this Substack is sharing what I’ve learned with you. In my series Tomorrow I’ll Be Different, I promised to share “ideas, personal stories and inspiration from others, books, resources, practical tools, and step-by-step guides on How to Change Your Life.”

One of the simplest and most important ways to learn how to live a Good Life is to study the lives of other people you admire. Ed is easy to look up to. He’s a successful journalist in an era when those are a critically endangered species, and he writes about vital subjects with a passionate moral clarity and rigorous depth of knowledge. He co-hosts a popular podcast, publishes a very successful Substack, writes regularly for publications like the New Republic, the Guardian, and the Nation, has fabulous taste in art, and lives an exciting life in New York City, which I think is an accomplishment for anyone who pays rent in the 2020s. All in all I think he’s a swell guy who seems to really have his shit together.

People who Have Their Shit Together often make it look easy, but it rarely is. There’s almost always a method behind the sheen. I wanted to know how Ed gets it all done, so I interviewed him about his life: his background, his writing process, career, motivations, disappointments, and personal passions. I learned a lot, and I think you will too. Thanks to Ed for being my inaugural interviewee in this ongoing series, and make sure you subscribe to his Substack and follow him everywhere.

This interview has been edited for length and clarity.

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Who you are, and what you do?

My name is Edward Ongweso Jr, and I'm a writer, tech critic, and journalist. I write about labor, tech, and finance, how those intersect in Silicon Valley, and the ways in which technology affects labor conditions. I also write more broadly about surveillance, politics and the economy at large.

Tell me about your background and how you got to where you are.

In college I was really interested in geopolitics. I thought I was going to figure out a way to end up in DC at some think tank and work on a foreign policy for the left.

That was kind of my plan, hah.

I was dead set on that. I'd gone to [UMD] College Park, dropped out, and drifted around for a few years, and then I went to Hampshire College. They let you design your own major, and I took this class on learning how to be a grassroots organizer.

I got dropped into what was then the company union at Uber, but a bunch of Marxists and leftists were in it, and they were like, “we think we can leverage this into an opportunity to galvanize and militarize some vanguard of drivers to get some labor actions going and change working conditions in the industry.”

It didn’t up panning out, but the time that I spent with that group, the Independent Driver's Guild, really deeply radicalized me, because I realized how horrible the working conditions were. After that I became obsessed with Uber. That was around 2017.

After that, I shifted gears. I was learning more about venture capital and how Uber was able to stay alive, and the role that venture capital played in sustaining them. I ended up doing research into the history of the venture capital industry and its relationship to the military-industrial complex.

And that became the kind of stuff that structured most of my writing since then, which is basically: where's the money coming from? How's it being used to deploy this technology that should not exist? What harm is it doing to the public and workers, how is it wasting investors’ money, and how is it hacking laws and politics and grafting itself onto the economy so that we all have to accept it?

So that’s pretty much been my main track. Things come into my work that relate to that, like crypto and startups more generally, but it's all pretty much just a focus on how these guys are blood suckers, basically.

And you were at Vice, right, and then moved to freelancing?

The only place I ever got a proper newsroom gig was Vice, and that was a flash in the pan, [from 2019-2022]. I got there and I worked with Motherboard, an amazing, amazing team. The whole desk was focused on startups, labor and tech, and I would focus more on the financial angle.

And then I quit Vice in 2022, and I've been freelancing ever since then.

What does a typical day look like for you, work-wise, or a typical week? I’m interested particularly in how you structure your time, as a freelancer, and someone who has to design their own life and schedule completely.

Honestly, for me it’s about cycles. There are periods, maybe two or three month periods at a time, where I'm able to structure my day really well. I structure the week such that there's some days I have on or off. The goal is to try to have some writing time, and if you don't, you have time to let things gestate. And then there are also periods where my time isn’t structured and it's a mess, and I kind of just go by the flow and what I'm feeling.

I prefer the days it's structured, though. When I was at Vice, I really thrived where you had to write essentially three times a week, maybe two blogs and one longer thing, and that's the routine for each week. That was a rhythm I really liked, but it's been hard to replicate that without employment, without the threat of losing your job (laughs).

So it's more been just trying to figure out, okay, if I can't publish three times a week, maybe I just put out once every once in a while, but I work at it as if I'm doing the three times a week thing.

The days for me are about trying to get a sense of where I'm at in various pieces, figuring out if I need to do more research, or if I'm feeling ambivalent and not really inspired enough to write. I think by now I have a pretty good sense of like, okay, I need to do some more reading, or I need to abandon this and not really touch it for a little bit. Or maybe I’ll realize the problem is I just don't actually like how what I’m writing is coming off onto the page. That's a process that took a while to figure out.

Are you a morning routine person, or do you have certain times in the day that are best for you to get work done? Do you set daily goals? I have some friends that have goals for themselves like, “I’ll write X amount of words per day” or “I work X amount of hours.” Whereas some people just like to be more go with the flow.

I think it’s conditional. Sometimes I know all I need to do is get out 500 words, whether or not those are the 500 words, and then work with it. But there are other times where putting a word limit on myself or a word quota doesn't really do anything. If I want to just get a burst of writing done, early in the morning and later in the evening are best. In the morning, it's nice because if everything goes right, I like to go out for a walk and then come back home and write a little bit. And if I'm not able to go on a walk or if I don't really feel motivated to walk, then just getting a bit of sunlight helps. I'm not really someone who has a strict routine.

The only time I really have a routine is when I'm visiting my partner. I like to get up in the mornings and make coffee for them and breakfast, and that really helps structure my days earlier because then I usually wake up earlier, and I get a little bit of the morning to myself. But when it's just me, I have no interest in waking up that early.

Do you have a system that works for you? Do you go by routine and regimen?

I have really severe ADHD, and I no longer take Vyvanse, so I had to kind of learn how to regulate my energy levels throughout the day. I'm most productive when I have a set morning routine and I get everything that I want to do for the day done by like, 2:00 PM. But that’s hard to stick to. Generally, I do think in terms of daily and weekly goals, and I do try to keep to my routines, and get back to them whenever I fall off, which is often.

I feel you on that. With my ADHD, finding structure has been hard. It really comes down to trying to figure out what the rhythm of my own body is and going with that, or getting a sense where it's like, okay, if I feel like I have writer's block, if I feel like I'm malaised, then I know I need to abandon whatever it is. I'm not someone who’s like, just keep pushing and you'll break through. That's not going to happen for me.

What do you spend your non-working hours doing that you enjoy?

I really like dancing. I really like music. I like sharing music, listening to music. I've been increasingly trying to get into running. Hiking is really nice. I love cooking, for other people especially. I'd say those are my main hobbies. Reading is really nice, too. I've been also trying to learn some musical instruments, saxophone and piano. I grew up learning a little piano, but I haven't played it in so long. And of course, hanging out with people is really nice as well.

Do you have professional goals, and if so, how do you think about those? Do you measure them or track them, if you have them?

I have goals with the podcast and the newsletter we're starting. We're going to start a video series and some audio series, so I'm really interested in getting those off the ground.

For the Substack, when I started it last year, I told myself I wanted to get to the point where at least I have something once a week that's free and then once a week that's paid. So I think that's kind of a goal in terms of something I’m making.

Professionally, I'm thinking about grad school, but then again, I think everyone is, now that the economy is going to shit (laughs). I really, really, really would love to use a law degree to challenge some of the companies that I've been obsessed with over the past few years. But that's such a far off goal that it doesn't feel real because so much would have to happen. So I don't know.

I think short term, I want to hone down my independent writing process. I want to get out some fiction. I want to get a story or two out this year. I want to work on a few series of essays on artificial intelligence, on companies that model their business model after Uber, and finish those, and make real progress on this book that I've been interested in writing, that's just about Silicon Valley. I would say those are probably my immediate professional goals.

Other than that, my time at Vice was so special, I don't really have much interest in working in a newsroom again. I like freelancing, and I like the research I've been doing on the side with other places. So I think the professional stuff is more so, “how do I tap into doing my writing more consistently, and maybe how do I figure out if I can get more impact from the writing itself as well?”

Do you have any personal goals that you'd want to share? Things in your non-working life that you're striving towards, or thinking about?

Oh, yes. I really want to learn the saxophone. I've been talking with a bunch of my friends for years about doing a quartet, and it would be so cool to do something like that. So I’m working towards that, and I want to learn how to paint and draw, do a little bit more art. I had my first art showing in New York a few months ago, and it was really fun.

Wow, that's so cool.

Yeah! I want to explore that more. That was a bit terrifying. I'm incredibly intimidated by pretty much every other art form, but I would love to explore that more.

I feel like [something] you were saying [earlier] is a great reminder of how interconnected so many creative outlets are. Some of my favorite essays have come out of me vegging out and watching three movies a day for a while, and then something hitting. The art piece I did kind of came out of a period like that.

I love that. It reminds me of an interview that I watched with Robert Pattinson once, where he was talking about being really stuck on this performance, trying to figure out what to do with it before they started filming, and then saying he went some gallery and saw a sculpture and felt like, “that sculpture is what I'm trying to do with this performance.” I think about that a lot, in terms of how important it is to expose yourself to all the creative mediums.

I think that's also part of why it's so fun to procrastinate sometimes with other work. Sometimes you do just come across something that makes you realize, “oh, I'm going about this completely wrong,” or makes you feel a fragment or a sliver of or the whole thing of whatever it is that you're trying to grab onto, and that's always magical.

Totally.

Do you have any specific tools that you use to keep yourself organized or motivated?

Yeah, none of these fucking [productivity] apps work for me.

I need to literally have a thing physically next to me, not a phone, but paper, sticky notes. I try to write notes to myself, like, “you need to do this, remember to do that,” or else I will forget.

Also, I usually have two drafts done before I start writing [on my computer], because I either start by recording myself talk, after I've gotten all my stuff together and it's gestated for a bit, or I write and then I record myself reading it. And that serves as a way to edit, either reading to myself what I wrote on paper, and then kind of talking through the edits out loud or writing down what I wrote, and pausing and editing as I write it down.

From there, I usually take it onto a computer. There are some times where I can just straight up bang it out, but usually when I'm writing without any sort of draft, I get much more hung up.

That's fascinating, reading out loud what you’ve written as a way to get to a first draft. Is that something you just kind of figured out on your own, that process?

[It came from my interest in] the saxophone, because I like listening to music and then thinking about what I would like to add to it. Part of the motivation to start learning the saxophone is thinking about how I would like to remix a bunch of pieces. So I like to record myself playing and listen back to it as a way to capture what I want to add or remove.

So figuring out that I could do something like that with writing has been very helpful, because I like to think that my writing sounds like me, like a rant of mine kind of intermixed into written format. So speaking it out loud and having some sort of oral component to it, it's very important.

What motivates you, or inspires you to keep going?

What inspires me to keep going is my hatred of everything that I write about (laughs). It really is. I have pure hatred.

And that really does keep me going. People underrate it. And it's not corrosive! It's actually fulfilling, because most of my entire life is full of love for other things, and the hate comes out of how much I hate how the things that I hate affect [the things that I love].

Totally. It's funny, I feel like anger is a very toxic, unhelpful emotion, but I think righteous anger is very much a separate thing that is valuable and can be powerfully motivating, and should be.

Are there any mistakes in your career or life that you've made, or rough patches you've been through, and things that you’ve learned from them?

Hmm. I wish I worked a bit harder after I quit Vice to freelance at more places. But I think I didn't realize how burnt out I was, and how much time I needed to relax and fuck around. I got this fellowship that was really helpful. Part of me wishes I was a little bit more serious about it, but also that's exactly what I needed, a period to kind of just relax, think, read, learn more.

Part of me is maybe I shouldn't have gotten it into writing at the time I did—

I think every professional writer these days has probably felt that at some point or another.

It is what it is, and I'm happy I did it. I would've been miserable in my other life. For most of my life, I wanted to be a neurosurgeon, and I was in pre-med, and convinced I was going to go into med school. Everyone around me was like, “I don't really understand why you want to do that when all you talk about his politics.” And at the time, I was like, “yeah, that’s a side thing!”

That's so funny.

So I don't know. I'm happy with how everything has fallen out. I wish I pushed a little bit more, but also I'm just not sure how much I should have even in the first place. I think those periods [where I had more down time] were good resting periods.

Something I talk about a lot is how toxic and unhelpful it is to be really hard on yourself, which I think is very common in creative minds. And I’m hearing you say, “well, maybe I could have taken this thing more seriously, or worked harder at that, but at the same time, maybe I just did what I needed to do for me.”

I think that's a really healthy attitude, and in my experience it’s sort of a rare one. Have you always had the ability to be kind to yourself when you look back on your life, even if you think there are things you might have done differently?

That's a good question. I think I wasn't for a while, but a few things helped. One thing that helped is having friends who are constantly reminding me to do that, or why I should do that. Having a lot of people, people who are either familiar with my work or familiar with the course of my work broadly, being on the outside looking in, or as someone who also does this same sort of work, telling me “you're fine. You're doing okay. You don't need to be so hard on yourself.”

And then I think also something that has been healthy, we're talking about healthy kind anger and rage, is finding someone you really admire and want to emulate as a way to not be so hard on yourself.

And also finding someone who you hate (laughs).

I would love to know who’s on your hate list. We can keep it off the record (laughs). Who's that person on the positive side?

Intellectually, my [podcast] co-host, Jathan Sadowski is a big inspiration. There are people who are inspirations in terms of moral and ethical foundations, like Veena Dubal, whose work is actually what helped me hone my focus on Uber.

I also have broader, more historical inspirations in terms of thinking through, with tech specifically, how bad things are getting but how much can be changed with organizing, and those are helpful, and relate more broadly to other social struggles and movements [and thinking about the role of writers within in social movements]. [James] Baldwin's writing is always very inspirational on that front.

I think there are lots of wellsprings to pull from. Some people tell you about how you should hold to your morals no matter what, and some people teach you to think about what the role of writing is, some people teach you to think about the ideas in and of themselves, and how long it takes to build them.

Okay, last few questions here: any professional and or personal accomplishments that you're really proud of?

My favorite is when someone listens to our podcast, or reads my writing, and says something like “this helped me convince someone that maybe we shouldn’t use AI in the workplace. Or maybe we should unionize the workplace.” Those things matter to me much more than the accolades.

I’ve gotten some awards for writing, but when workers are interested in using things I’ve written, or when you radicalize people, that’s always inspiring to me.

And alongside workers, getting people who work in the parasitic industries, like finance, like venture capital, fintech, etc, having those people reach out and talk about how this essay I wrote or that podcast episode convinced them they should leave their job, and try to do something more helpful to people, I really enjoy that.

What’s something you’re excited about in your future?

I haven’t co-written that many things, but me and my partner are working on a bunch of essays, and that’s really exciting. It’s been a really deep and intimate but also very exciting process. We’ve been friends for a very long time, and their ideas have been an influence on my thinking about technology, specifically the way toxic products get repackaged as tech products. We wrote an essay together on insulin and why it’s been so expensive, and we’re working on some pieces about medical devices being used for people who aren’t diabetic.

So that’s something I’m really excited for, because it’s really fun having a co-writer, and it’s been really fun influencing each other's thinking on these things.

To close out here, I have three rapid fire questions.

One: what’s one favorite anything? Could be a band, a city, a type of cheese…

My favorite song I’ve been listening to a lot lately is a song by Masayoshi Takanaka called Beleza Pula. Really, really fun. He’s a Japanese Brazilian-infused jazz musician. I love a long song, I love a beat change, I love really maximalist sounds bleeding in on every level. So I’ve been obsessed with this song for so long. The thing that comes to mind when I listen to this song is the scene in The Master, when Freddy rides off into the horizon when they’re playing that game on the motorcycle. I use that song a lot when I write and when I’m trying to channel a specific emotion for writing.

Is there one smart person you wish more people knew about?

My favorite right-wing nut author is this Catholic neck beard, John C. Wright, who I want people to know about because his books are so ridiculous. They’re in conversation with my favorite sci-fi writer, and at times they’re much more imaginative, but they’re also so much more misogynistic and racist and bigoted.

So it’s funny, to see an author who’s capable of imaging alien species in ways you don’t really see in other books, and creating different worlds thousands or trillions of years into the future, who then also says like, “our Western civilization is the most important form of life in the world and marriage is the foundation of any healthy civilization, and the church has to be in the room,” etc.

It’s interesting to read right-wingers in sci-fi, because it’s fun to see how imaginative and experimental and post-human they can be, but how they keep glomming onto like, a nuclear family, even when that doesn’t make sense, three million years from now.

What’s that favorite sci-fi author you mentioned?

Olaf Stapeton. he wrote Star Maker and Last and First Men.

Well I’ll have to put those on the list. Thanks so much Ed, great chatting with you.

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The interviewer has since ordered Last and First Men, and looks forward to reading it soon.