“My dad's generation had the same company for 40 years and a pension and a gold watch on the way out. My generation was more about finding the right company to get into, and if you got the right one, like I got in with Apple, you could still make it. It feels like we're now in version 3.0, where you don't have that anymore. Even if you're at Microsoft or Facebook, it's not a safe job anymore. Everyone is their own free agent.”
Data Engineering Central · Software Engineering & Infra · November 2026
Context
The host said the era of long, stable careers feels over as tech companies cut staff. Kevin lays out three generations of job security.
Transcript
…people do without even realizing. And it's just, it's been super interesting for me to be on the outside and look in and kind of like I'm on the outside of a fish tank looking at what people are doing. And a lot of it's self-induced and then a lot of it is the just the crazy world that we live in.
…really like forefront now that the financial expectations of, you know, maybe we should approach things a little bit differently. You know, people who've never heard of emergency funds are probably like Googling it. It's probably like the number one Google thing probably in the last, you know.
I was actually thinking about this the other day. So like my dad's generation, same as yours, you know, he had the same company for 40 years and he gets a pension and a gold watch his way out. And then my generation, I feel like it was in the same with you. It's like, I feel like it was more about finding the right company that you could get in. And if you got the right Right company, like I got in with Apple, like you could make it still. And it feels like we're now in like version 3.0 where you don't have that anymore. And even if you are at the Microsoft or Facebook or whatever, like it's not a safe job anymore. And it's kind of like we're seeing this movement to everyone is their own free agent. And at any time, you might need to deploy that free agency, whether it's your choice or not.
Yeah, it almost seems like some of those big tech companies now are almost more unit, almost feels like they're more unsafe than like the maybe a little star. I don't know if that's true or not, but it almost seems like it flops so much that like I would be surprised if someone like wanted to work…
And the craziest thing now, and I had the light bulb moment. I don't know if you remember this, but Square, Jack Dorsey's company, they laid off like 25% of their staff. He mentioned it was because of AI and all that. And the stock went up 25% after hours. So I feel like what's actually happening…
Sure. Yeah. I totally agree. It's a weird world and strange world. And yeah, it's definitely changed. I think
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