Indentured & Independent: Freedom and Fatigue in Gig Life

In this episode of Deep Dives in the Shallow End, we put hustle culture on blast and offers a heartfelt “thank you” to the gig economy…for our daily existential crisis. From recording in his hatchback en route to sell plasma (for the rent), Donovan navigates the wild, soul-crushing world of modern side hustles. Think freelancing is freedom? Think again. We’re talking endless rideshare shifts, grocery gigs, and desperately avoiding that feet-pic hustle—for now.

With dark humor, painfully relatable anecdotes, and some brutal truths, we break down what it’s really like to be an “independent contractor” in a world where burnout is a badge of honor, “self-employment” means zero benefits, and sleep is for the weak. Tune in for a laugh, a reality check, and maybe a light cry as we explore if the dream of “being your own boss” is just another way to clock in...forever.

Transcript

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["The Hyundai hatchback on the way to sell plasma. It's your host, Donovan. Hey folks, welcome back to Deep Dives in the Shallow End, where we examine the overlooked corners of modern drudgery, the overhyped illusions of freedom, and the rat race to which we are all enslaved. And then have a good cry about it during the daily existential crisis we have on our chaotic drive between gigs. I'm your not so expert host Donovan, back again like a herpetic lesion that just won't seem to go away. Today, we're diving into something that defines modern life. or perhaps better stated, modern suffering. Yes, it's the gig economy and the modern hustle culture. So strap in, or should I say clock in, because it's about to get soul crushing. Alright, let's start with the basics. What exactly is the gig economy? Well, imagine a magical place where employment stability is a distant myth, healthcare is a foreign concept, and you're juggling five different jobs to barely afford running water. Yeah, it's that wonderful place where our ancestors' dream of a stable nine-to-five has been traded in for a scattershot mix of freelancing, side hustling, and desperately hoping you can avoid selling feet pics for one more day just to keep the baby fed. and there's absolutely no judgment there. It's a lifestyle, folks, or rather the lack thereof. A glorious existence where you're no longer an employee with the rights and benefits, you're an independent contractor. This means that instead of working for someone else, you work with someone else. Like how that tapeworm is working with me to deprive me of essential nutrients. Except in this case, you don't get to grow bigger, you just get the satisfaction of paying self-employment taxes and all your own overhead. and you have the freedom to work for multiple companies, all of which treat you little better than an indentured servant. But hey, if you don't like it, at least you can leave. If you can afford to, which you can't. So quit lollygagging and get to dancing clown. It's a revolutionary system where you're empowered to hustle harder and harder just to stand still. Now, don't get me wrong. Hustle culture has convinced us all that working nonstop is not only normal, but cool. Somewhere along the line, some genius figured out how to convince everyone that weeping over the sink while you question every life decision that led you to this point out of sheer desperation is a badge of honor. We're not burning out people, we are thriving. Who needs sleep when you could spend that time turning a $15 procrastination journal you bought from Instagram into a business empire? You've got dreams after all. Dreams that will only be achieved by working three part-time jobs. running an Etsy shop hawking secondhand jade eggs, and driving for rideshare apps until your spine fuses and the backs of your thighs have weeping pressure sores. And let's be real, this illusion of freedom is just that, an illusion. Gig work and hustle culture are a lot like a horror movie without a happy ending. We start off with a full heart and pocketful of dreams only to find ourselves 90 minutes later thoroughly terrified and gasping for air having to seriously contemplate death or cutting off our own foot that has been cuffed to a pipe on the wall. Be your own boss, they said. I hate to break it to you folks, but being your own boss means you now have some jerk breathing down your neck 24 seven who expects you to answer their email at 2 a.m. and thank them for the opportunity. Being your own boss in this context sounds about as enticing as bamboo shoots under the fingernails. And since you're an independent contractor, you can take all the time off you want because you won't have a job when you get back. There are a hundred people behind you just waiting to snatch up that opportunity despite the fact that they know misery is the only path forward. Like, waiting in a drive-thru at Taco Bell. And if that's not enough, think about the beautiful benefit structure of being your own boss. No healthcare, no paid time off, and no casual Friday where you can wear a knit top and chinos for having hit your quarterly sales goals. If you're lucky, maybe you can afford a high deductible health insurance plan that will allow you to declare bankruptcy after having to go to the ER when some nut job assaults you during an Uber ride. On second thought, you may want to forego that MRI because the rent's already two weeks late and time is money. Retirement? Well, forget about it. Unless by retirement, you mean collapsing from exhaustion in your 60s while trying to assemble Ikea's flug-flurbed and canopy bed for some ungrateful teen in the suburbs who will never have to play hide and go seek with the ever-looming darkness of mortality constantly nipping at their heels. Or, on a more hopeful note, perhaps societal collapse will mercifully take care of the problem and your golden years will be spent scouring empty stores for stale scraps while keeping that leg infection at bay. And if it's not enough that you're on the edge of a nervous breakdown trying to balance gigs and side hustle There's also the social media hustle brigade. The influencers and vapid, nothing behind the eyes thought leaders who have turned rise and grind into a supposed personality trait like lost souls clawing at the gates of digital hell, praying for recognition from their mercurial algorithm god whose favor is as fleeting as their sanity. While the machine churns on unmoved by their motivational cries which echo as hollow affirmations to some, but sound to those who truly listen like the desperate screams of the dam. They post videos that go something like this. I wake up at 4 a.m., meditate for three hours, drink organic Himalayan stream water, close a $15,000 sale on my lunch break, and by 10 p.m. I'm dancing under the stars while the universe rains abundance upon me. Meanwhile, the rest of us are just trying to remember if we've yet stopped for our daily three-for-three cheese and steak taquitos and super big gulp of Mountain Dew at 7-Eleven, or if we've just been fueled by terror and tepid gas station coffee. Are we feeling motivated yet? It's exhausting. And it's everywhere. The relentless pressure to hustle, monetize, and grind bleeds into everything we do. Got a hobby? Great. Better start an Etsy shop or a YouTube channel and monetize it. Got a talent? Well, don't keep it to yourself. Turn it into a course, create exclusive content, and brand yourself. Got nice toes? Grab the Polaroid and hit up Feet Finders. Everything must be commodified, because if you're not squeezing every last drop of productivity out of yourself, Are you even trying? It's a hamster wheel and we're sprinting, hoping one day to be rewarded with stuff we don't really want and certainly don't need. But at least it will look great on social so we can keep working. At that point, do we own the stuff or does the stuff own us? Oh yes, the hustle lifestyle is freedom in the ironic illusory sense of work shall set you free. Freedom to work whenever you want, wherever you want, as long as... whenever means always and wherever is your shared studio apartment in the Tenderloin district. It's true, you really can work anywhere. You can send your gig invoices from a beach, but it's more likely you'll be sending them from the local Planet Fitness where you stop to bathe and BM because the shared bathroom at your place is on the fritz. Hey, the Wi-Fi may be slow, but at least it's free. And let's talk about opportunity. Hustle Culture likes to talk about endless opportunity. Sure, there's endless opportunity. to compete with the millions of all the other people who find themselves in the same cycle of despair as you, all desperately trying to scrape by on jobs that pay less per hour than maintaining your sanity, all while convincing themselves that it's only temporary, as if hope can pay the bills. Remember when you could just go to work, do your job, and come home to enjoy your life? No, me neither, because now we're all too busy building brands to be able to go to Timmy's soccer game. But don't worry. These experiences build character, and one day your little guy will grow up to be the next Harry Chapman, and hopefully not the next Mark David Chapman. But today, nothing says success in the lower and middle classes quite like converting your very existence into a commodifiable concept that's palatable to the masses. But you know what? I can't blame someone who needs the money for having to miss out on their children's milestones for the sake of survival, and I am not judging them. Parents have long had to make regrettable decisions in the name of parenthood, and for that I commend them. They didn't ask for the system to be created in a way that grinds the human soul into dust like so much wheat beneath a relentless millstone. It's all part of the great modern illusion. Work hard and you'll succeed. Go to school and you'll get an education. That's how you get a great job. We're being fed the same old recycled myths that may have held true in the past, but have now worn thin. Like when my mom tells me I look handsome. Well, there's a few problems with that. I have a mirror. I'm having to hustle to make podcasts in my early 40s. and your filmy cataractus eyes led me to believe you aren't the reliable source you once were, but I guess it's still nice to hear. And let's not forget the ultimate slap in the face, the Gig Economy Star Rating. The only feedback you get in your job is a five-star rating system where people judge your ability to deliver groceries or drive them around. It's truly one of the most dehumanizing and condescending situations one can find themselves in. Having to grin and bear the criticisms of the middle class because they think sinking $12 to be driven to their Friday night date at the Red Lobster makes me, their cow-towing chauffeur, eager to hear how my 2004 Honda Civic with 250,000 miles and the smell of 1,000 butts ground into the seats wasn't quite up to their expectations. Well, I've got news for you, Your Highness. You're eating at a place that offers all-you-can-eat shrimp and encourages wearing a bib to avoid butter stains on your Kirkland Oxford. You're not exactly Rockefellers yourself. But we take it and assure them they're absolutely right and hope they have a great evening because we just wanna see an extra three bucks come through on the app later and hope that we don't fall short of being considered humans with a value of less than 4.2 stars for the fear of losing the honor of driving Austin to the vape shop. I'm starting to think that tapeworm has the right idea, just relaxing in the quiet, warm, and stress-free embrace of my small intestine. E.C.E. in the shallow end. But let's be real. We've got to call it what it is, exploitation with a modern filter. They took the concept of indentured servitude, slapped some emojis and a kitty ears filter on it and called it a lifestyle. They convinced us that instead of demanding fair wages, benefits and work-life balance, we should be grateful for the opportunity. It's the only economy I know where your boss can be an app that entices you to complete another 12 rides tonight for a $50 bonus because the last 12 hours of driving the sandals wearing southwest flying slobs from the airport to the local Red Roof Inn is only putting Lunchables on the table tonight. And the only feedback you get is a star rating from Carol Brady, 30 minutes outside of the city, who thinks two stars is appropriate because the 16-year-old Del Taco drive-through attendant who was playing on her phone forgot to staple an extra two sauces inside the bag. And by the way, I am very much one of the sandals wearing southwest flying slobs for the record. And fun fact, I've also been their driver. What's particularly galling, however, is how hustle culture romanticizes poverty. Sleep is for the weak, rest is for the lazy, and comfort is for those who aren't ambitious enough. It's become a culture where burnout is the norm and if you're not willing to sacrifice everything, your health, your time, your relationships, then you must not want success badly enough. The hustle culture is a relentless pursuit of productivity at the cost of humanity. It's a culture where having a full-time job isn't enough, and there's nothing quite like knowing that there are teachers with master's degrees grading papers on their break while working the swing shift on the janitorial staff at Alakinta. And no shade to janitorial staff, all work is honorable. The system, however, is a lie. It's an endless cycle of more, more work, more hustle, more exhaustion, all in the hopes of maybe, just maybe. reaching a place where we can afford to rest. But of course, the irony is that rest is for the unworthy in the hustle paradigm. So where do we go from here? I'd like to say there's a solution, but in a world where the term anti-work is considered a radical terrorist agenda, I'm not optimistic. I'm not advocating for another October Revolution, an ousting of the Bourbon dynasty, or the defenestration of Silicon Valley. And I'm not a radical communist, but people will only take so much. The people may take a cue from history, One day the growing poverty class will just get tired, stand up together and overthrow our corporate overlords in favor of a society where humans matter more than productivity metrics. Maybe we'll finally realize that we deserve better, that life isn't just about grinding until there's nothing left of us but a hollow shell. Maybe we'll start demanding things like fair wages, healthcare and actual meaningful rest. But until then, we'll keep hustling, side gigging and living that rise and grind lifestyle. until the hustle leaves nothing but hollow hopes and empty ambition. There will continue to be plenty of people glorifying the grind, posting motivational quotes on social media and trying to convince us that this is just how life is supposed to be. It's our job to fight against these norms and demand better. So support workers' rights, advocate for fair wages, and don't be afraid to push back on unrealistic expectations to the extent that you're able. It's something I am working on myself as well. Join or support a labor union? Vote for candidates who prioritize workers' rights, and spread awareness about worker exploitation through social media or community events. Share your stories, connect with others who are struggling, and let's work together to redefine what a dignified life looks like, one where rest, respect, and humanity come before profit. And that's our show, folks. Thanks for tuning in to Deep Dives in the Shallow End. Remember, while you're hustling your way to your next paycheck, don't forget to breathe, take a break, and maybe even question why we're all here in the first place. Who knows? maybe one day we'll be able to clock out, and hopefully soon enough to enjoy life a bit more, at least for a few years before the long nap. Many of us may be up against a lot, but if there's one thing I know, it's that change begins with us. One small act, one shared story, one moment of standing up for what's right. Let's make those moments count. Until next time, thank you so much for listening. It means the world to me. So take care of yourselves, your family and friends, be kind and understanding of strangers. We never know what others are going through. I do hope you'll join me on the next episode. She lives in the shower