Never jump into an overcrowded pool

Public pools are disgusting. When I grew up in the suburbs of Pittsburgh (I’m really selling my first point!), we would go to Mineral Beach. It was a concrete slab that sunk into the earth to — I guess? — mimic how the ocean gets deeper the farther you walk in. It was incredibly popular and there were always a few coupons for entry in the Entertainment Book (Mom, we are leaving money on the table if we do not go to Mineral Beach.)

Loads of little yinzers would jam into the pool each summer. There was a diving pool at the deep end and mildew-y changing rooms. We’d slop over to the concession stand in jelly sandals for a single bag of Cheetos to share with our best friends. It was disgusting, it was overcrowded, and it was a fucking blast.

This is all a convoluted way to introduce Why I’m Starting a Newsletter Now. Everyone is about to have a newsletter in the same way that everyone has a podcast. You will or maybe already have too many newsletters. Your inbox is groaning and keeping up is a fool’s errand. Yet here I am: the next jester begging for your attention!

I’m jumping in now because I’ve watched everyone else backflipping into the deep end and gossiping at the pool’s edge and it looks fun as hell. I am paying my entry fee, wiggling into a swimsuit, and I am asking that you watch me do an underwater handstand over and over and over again (1-2 times a week, probably).

I will readily admit that there’s an entrepreneurial undertone to launching Hater’s Guide (I have 2.5 more years to make a 40 Under 40 list!): I am very tired of thinking that another opportunity to write like this (freely insane) is going to present itself. You do not have to be a labor market expert to know that good, paid writing gigs are few and far between. And I probably made enough mistakes early in my career (not being born rich, for example) to still not have just the right portfolio to find the type of success I want. 

I started poking around at this feeling of “I’ll make it myself, then!” and came upon Make Your Own Job. The book’s author, Harvard University lecturer Erik Baker, explores the history of the entrepreneurial work ethic and argues that, while there are plenty of valid reasons to exit the conventional workforce, the hope that entrepreneurialism offers is frequently and historically illusory. Basically: We’re fooling ourselves if we believe that starting our own venture is going to throw off the chains of the capitalist forces that govern us.

“The consequences of what I call the entrepreneurial work ethic have been quite pernicious for our culture and our society overall,” Baker told me.

We’re sold this idea that doing work “our way” gives us full control of the situation, but it really doesn’t — because it’s still work that happens within our current economic system. (Just because you’re wearing Converse high tops with a wedding dress and calling yourself a “nontraditional bride” doesn’t mean you’re exempt from the inevitable divisions of labor thereafter.)

“The idea of entrepreneurialism has been linked for a very long time with the sense of putting yourself into your own work, pursuing your own projects that really matter to you,” Baker said. “It turns out that it's not just the hypothetical boss who doesn't care about what matters to you, but the conditions for success in the capitalist marketplace don't care about what matters to you either, and you can find yourself becoming — ironically — the very kind of abusive or exploitative boss that you know you were trying to to escape from in the first place.”

Is there a solution if we’re all still cogs in the machine? Even if some of us are different and unique cogs? I liked the suggestion The Washington Post gave in its review of Make Your Own Job: “does our salvation lie in leaning out for once?” A relief! My almost 40 Over 40 back cannot take all the leaning in.

I asked Baker whether he thought it might be helpful to detangle our identities from our jobs (my job is email, to be clear). He said he couldn’t quite prescribe a mindset shift, but emphasized the deeper conflict between the material structures that govern our lives and our hopes and aspirations. In other words, when we’re not reaching our success metrics, maybe we shouldn’t blame ourselves for not working hard enough/wanting it enough/rise-and-grinding enough when we’re really up against much larger outside forces (the marketplace/the devil/the TARIFFS).

It made me think a lot about the idea of “if you really want it, you can make it happen.” It’s such a LinkedIn/fitspo mindset that places the blame on the person, never external forces. And with the internet at our fingertips? Obviously you just didn’t network enough or download the right app or run the right social media campaign! 

In his book, Baker describes the opportunities that a new internet era promised workers: freedom from the office, streamlined processes, shooting off emails from the beach. Instead, we’re more handcuffed to our jobs than ever, responding to Slack messages on the toilet when we should be solving Wordle puzzles.

“It’s not the only iteration of a new kind of entrepreneurial horizon, a new sort of liberated future, and then this kind of calcifying into a new order that feels repressive and unfulfilling in its own right,” Baker said.

Knowing that Baker has engaged in a variety of gigs himself, I asked if writing Make Your Own Job changed his own approach to labor.

“I'd like to think that there was perhaps a bit of a therapeutic function in writing this book,” he said. “It definitely helped me to recognize and — hopefully — to check some of my own impulses toward overwork, toward this sense that you need to constantly be scrounging up new opportunities. At the same time, it also helped me to understand better where those impulses were coming from.”

I found this deeply relatable, considering I’ve become a hustle queen over the four years I’ve freelanced full time. At first I loved the supposed freedom of it: scheduling meetings based on the weather, waking up at whatever time each morning and slowly making my way to the computer. Now I’m a drill sergeant for one: Time is money and money is NEVER GUARANTEED.

I would hate for this newsletter to become another stress point, or like I’m “doing it wrong” in some way if it doesn’t take off. As Baker so deftly explained the power we can have to self-destruct: “You initially feel like you're liberating yourself, and then you wind up being an authoritarian, lording over someone else.” (I.e., I become my own asshole boss/newsletter bridezilla.)

So how do I avoid stretching myself too thin with the Hater’s Guider? How do I get over the fact that it is, in fact, a super-crowded space? By thinking of it as a place to play, but with some amount of intention. It’ll be like busking: I’ll play my little songs for you, and you can toss me a few bucks if you like my tune (or if you just feel bad for me! Pity money spends the same.). Maybe I’ll go viral. Maybe you’ll get your aunt/neighbor/petsitter/priest to become a fan. Or maybe I’ll live happily ever after just playing on the street. Who cares?

The point being: I think there’s actually a sweet spot between going it alone and elbowing into the crowd that I can really enjoy. I can lean out on my pool float. In fact, there’s something about getting into the crowded pool that actually makes this newsletter more appealing to me, not less. There’s a party spirit to it: I get to pop up and bother you a couple times a week, you guys can chat with me directly, I’ll get to know some other newsletter authors (god, I love making new friends), and maybe, one day, we’ll even have an in-person event??

This is going to be fun. Thanks for letting me splash around in your inbox.