My guest on the show today is Chris Cillizza. You may know from his many years writing for the Washington Post, his many years on-air for CNN, or his recent third act on Substack, but I know Chris from way back when, as a friend and classmate in the Loomis Chaffee class of 1994. We didn't stay in close touch after we graduated, but we’ve stayed friendly and have crossed paths occasionally in the 30 years since. When Chris agreed to do this, I'd intended to focus on his long and successful career in journalism, concluding with a discussion of his unexpected lay-off from CNN, in 2022, and his subsequent re-invention on Substack. We do some of that, but the overall vibe is less professional than it is mid-life existential. We talk about the arcs of our lives over the last few decades — how we've balanced ambition and responsibility, what we're thinking about now that life has beaten the shit out of us a fair amount and we have a little bit of wisdom about things, and what comes next.To give you a taste, here's a lightly edited passage from the conversation where Chris and I are talking about how ambition sometimes got the better of him when he was working at CNN:

Cillizza: There's this great quote from a German philosopher [Arthur Schopenhauer] that I think about all the time: “Wealth is like sea water; the more we drink, the thirstier we become. And the same is true of fame.”

So when I got to CNN from the Post, I was bigger than before. More people knew me. More people read me. I made more money. And you know what I spent most of my time thinking? ‘Why am I not anchoring? Why am I not on the 7:00 to 11:00 PM election night coverage? Why am I on the midnight to 4:00 AM election coverage?' Oppenheimer: Do you worry about falling back into that? Up until three years ago, you were on that train and were being driven by those incentives. Then you had this massive shock to the system. Since then you've done a lot of introspection. You’ve grown. But look, you're a talented guy. You're still a hardworking guy. You could go back up again, right? That could happen, whether it’s growing to 5 million subscribers on Substack and you're making a shit ton of money, or CNN calls, or MSNBC calls, or the next Democratic administration calls and says, ‘Hey, we need a press secretary.’It's not implausible that you could be back up, or even get to greater levels of fame and influence. Do you worry that you could get sucked back into it? Do you feel like you have enough guardrails in place or you've done enough introspection? I just think about it with you because while the sudden epiphany is great, it can also be very evanescent, right?Cillizza: Totally, and certainly in the first 18 months after CNN laid me off, if NBC had called and been like, ‘Hey, you wanna come work here?’ I would have said, 'Absolutely.' The reason that I am on this path now is partly because I chose it, but also partly because no one else asked.So I don't think it’s likely that someone will ask, but yes, of course, if you've gone down a road before, it makes it more likely that you’ll go down it again.I think two things are true. One is that it’s almost impossible that one of those places would call and say, ‘Chris, we want you back.’ And I think it is equally unlikely that I would say yes, for a number of reasons. The first is that this is where I’ve been most my true self. It's a better space to be in. But also it is unlikely they would pay me enough to make it worth it.I think you always have to be mindful of it, and yes I have put guardrails in place, but you hit a guardrail hard enough and it breaks. It's not a guarantor.Oppenheimer: So maybe it's not a news network. What if it's this scenario? What if you write a memoir? You write a memoir about your midlife crisis, and most books don't do much of anything, but let's say it hits. Your book is a bestseller. It's not a Tuesdays with Morrie bestseller, but it's a solid bestseller. You're already on the speaking circuit, but its success vaults you up to the next level of the speaking circuit.Now there's more that you're being asked to do than you can do while also maintaining a healthy life and spending enough time with your wife and kids and working on yourself to make more close friends. That’s a plausible trajectory. Maybe it won't happen, but it's plausible. And so you would have to be very strong to be able to say, ‘You are offering me $50,000 to go for the weekend to give this talk, and I just can't. I can't do it. My son has a baseball game.'

It’s a really good, wide-ranging conversation. You should listen.

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