October 15th 2026, When Did Everything Become a Side Hustle?

Joshes and Joshettes, lately I've been wondering when we reached the point where everything we enjoy doing suddenly needs to become a way to make money. If you enjoy playing video games, someone will tell you to start streaming on Twitch or YouTube. If you like taking pictures, you should become a photographer and start selling your work. If you enjoy cooking, you should make TikTok videos, start a food blog or sell recipes. If you like writing, you should publish books on Amazon. There seems to be a business opportunity attached to almost everything we do now, and while I don't necessarily think that's a bad thing, I do wonder when we stopped being able to enjoy something simply because we enjoy it. When did having a hobby become an opportunity we're supposedly wasting if we aren't trying to make money from it?

This actually connects to something I talked about in Episode 111 of The Books By Josh Audio Immersion, where I discussed how having too many choices can make it harder to decide what we actually want. One of the things I brought up was how many different ways there are to make money now, and I think that deserves its own conversation because the internet has created an entire culture around the idea that everyone should have multiple sources of income. You can't scroll through YouTube or social media for very long without finding someone explaining how they make $10,000 a month from a business you've probably never heard of, or how you can start generating passive income with just a few hours of work every week. There's always another opportunity, another business model, another course and another person showing you the lifestyle you're supposedly missing out on. The strange thing is that we've reached a point where someone can work a regular job, pay their bills, enjoy their weekends and still feel like they aren't doing enough because they don't have a side hustle.

I think streaming is probably one of the easiest examples of how much things have changed. When I was younger, playing video games was something you did because you enjoyed playing video games. You might spend hours playing with your friends, trying to beat a difficult level or just enjoying whatever game happened to have your attention. Now you have people who see how much the biggest streamers make and immediately start thinking about how they can turn gaming into a career. I talked about Ludwig in the podcast because he's one of the biggest names in streaming, and he's publicly discussed the enormous amounts of revenue a successful creator at his level can generate. When someone hears those numbers, it's easy to imagine sitting at home playing video games and making more money in a month than most people make in years. What gets overlooked is that running a business at that level comes with employees, production costs, equipment, sponsorship obligations and plenty of other expenses. That's before considering the fact that we're talking about someone at the very top of an incredibly competitive industry. There are countless people streaming to almost nobody, and we rarely hear about them because nobody is making videos about how they streamed for six hours and earned absolutely nothing.

I've actually tried streaming myself. Back around 2014 or 2015, I was experimenting with it, and I've also made YouTube videos and tried different approaches to creating content over the years. Some of those things made money, and others didn't really go anywhere. There are YouTube channels I haven't uploaded to in a long time, not because I couldn't technically make another video, but because my heart isn't particularly in it anymore. I was interested in seeing whether those opportunities could become something profitable, and when that excitement disappeared, I didn't have much reason to keep forcing myself to do them. Writing has been different for me. I've been writing for most of my life, long before I was publishing books or earning anything from them. I enjoy coming up with characters, building worlds and telling stories, and that's something I would continue doing even if the financial results disappeared tomorrow. The same applies to blogging and podcasting. I enjoy sitting down and talking about things that interest me, which is why you're reading this article in the first place. Making money from something I already enjoy is great, but I think there's a big difference between that and convincing yourself to enjoy something because you believe there's money waiting at the end of it.

Of course, I don't think this entire obsession with side hustles came out of nowhere. Life has gotten expensive, and pretending everyone can comfortably survive on one income doesn't reflect the reality a lot of people are dealing with. Groceries cost money. Rent costs money. Electricity, internet, transportation, insurance and practically everything else we need to get through the month keep taking another piece of our paychecks. I mentioned in my previous article that a friend was looking at a one-bedroom apartment in Brooklyn that cost around $2,900 a month, and that's just somewhere to sleep. You still have to eat, get to work and pay for everything else that comes with being alive. So I understand why someone might get home after working eight hours and start looking for another way to earn money. For some people, having a side hustle isn't about becoming wealthy or buying a luxury car. It's about paying bills without constantly worrying about what happens if another unexpected expense shows up. The problem is that there's an entire industry waiting to take advantage of that financial pressure by convincing people that making additional income is considerably easier than it actually is.

One of the things that bothers me about the side-hustle industry is how casually people throw around the idea of passive income. Someone will tell you that you can make money while you sleep, and technically they're not always wrong, but they usually leave out everything that needs to happen before the money starts showing up. I earn money from the books I've published, and there are days when someone can buy one of my books while I'm doing something completely unrelated to writing. That sounds pretty passive until you consider the years I spent writing, the books that barely sold anything, and the work that still goes into keeping my catalog competitive. Keywords change, descriptions need adjustments, sales fluctuate and something that was performing well a few months ago might suddenly need attention. My first book was published in 2017, and there were stretches when I could go months without selling a copy. If I had started writing solely because someone promised me passive income, I probably would have stopped a long time ago. Instead, I kept writing because I enjoyed it, and eventually the financial side started becoming something meaningful.

Investing is another example because I have dividend-paying stocks that generate income, but that money didn't magically appear because I discovered some secret strategy. I had to invest actual money, continue building my portfolio and give those investments time to grow. I've invested six figures over the years, and while the income is nice, it isn't some magical amount that allows me to retire tomorrow and spend the rest of my life sitting on a beach. There are people online who make it sound like you can put a thousand dollars into the market and immediately start collecting enough dividends to pay your rent. That's not how it works for most people. The same thing applies to real estate. Someone might tell you to buy a property, rent it out and collect a check every month, but what happens when the roof needs replacing? What happens when a tenant calls because the toilet stopped working or something breaks in the middle of the night? Those responsibilities don't disappear simply because someone decided to call the income passive. You can absolutely build wealth through investing or owning property, but there are costs, risks and responsibilities involved that don't make for particularly exciting social media videos.

I also think people underestimate how different enjoying something is from actually running a business around it. I've worked in small businesses and had opportunities to work closely with owners in different industries, including retail and construction. I've seen some of what happens behind the scenes, and it's considerably less glamorous than people imagine. In the podcast, I mentioned someone who was running a business cleaning and restoring headlights. The actual service wasn't the problem. The problem was how the business was being operated. Someone would reach out asking about the service, and the response might not come until twelve or fourteen hours later. If a potential customer messages you at eight in the morning and you don't respond until eight that night, there's a good chance they've already found someone else. That's one of those things people don't necessarily think about when they're excited to turn a skill into a business. You have to answer customers, advertise, manage expenses, figure out whether your prices are competitive and give people a reason to choose you. You can't just be good at something and assume the business side will magically take care of itself. Sometimes the work you originally enjoyed becomes the smallest part of what you actually spend your time doing.

Social media makes all of this worse because we spend so much time looking at the results people want us to see instead of the reality behind them. Someone posts a picture standing next to an expensive Lamborghini, and we assume they own it. Someone takes pictures inside a private jet, and we assume they're flying around the world living some incredible lifestyle. There are businesses where people can rent luxury cars, and there have even been sets designed to look like private jet interiors for photo shoots. I'm not saying everyone showing off an expensive lifestyle is pretending, because plenty of people genuinely have the money to enjoy those things. I'm saying a picture on Instagram doesn't tell you very much about someone's actual financial situation. Yet people look at those pictures, compare them to their own lives and start feeling like they're falling behind. Suddenly having a decent car isn't enough because someone else has a Lamborghini. Having a working phone isn't enough because the newest iPhone just came out. We're constantly being shown things we're supposed to want, and then we're shown all these supposedly easy ways to make enough money to buy them. It's a pretty convenient arrangement for the people selling us the dream.

And now artificial intelligence has created an entirely new version of the same problem. Every time I open YouTube, it seems like there's another person explaining how to make thousands of dollars selling AI-generated books, building apps, creating digital products or starting an AI agency. Apparently all you need to do is open ChatGPT, type a few prompts and start collecting money. I use AI myself, and I've been experimenting with building applications and games using these tools, so I'm definitely not someone who believes we should ignore the technology. I think it's incredible that people can now create things they might not have had the technical knowledge or resources to build a few years ago. The problem is that creating something and creating something worth buying are two completely different things. You can ask AI to build you a to-do list app, but why should anyone download yours instead of the countless other applications that already exist? You can generate a book and publish it on Amazon, but why should someone spend their money reading it if you couldn't even be bothered to read it yourself? Just because a tool makes it possible to create a product doesn't automatically mean you've created a good product.

That last example bothers me particularly because I write books myself. I have no problem with people using AI to help them develop ideas, improve their writing, edit their work or handle parts of the publishing process. Technology changes, and I don't think pretending those tools don't exist accomplishes anything. What I have a problem with is someone generating an entire book with a single prompt, barely looking at the result and uploading it because a YouTube video told them they could make money selling books on Amazon. Then you end up with stories full of inconsistencies, repeated passages, characters changing names and books that clearly haven't been reviewed by anyone who cares about the finished product. Those books are competing for attention with work created by people who actually enjoy writing and spend time trying to make their stories better. The same thing can happen with apps. You can ask AI to build something that looks impressive, but if you haven't tested it, don't understand how it works and can't fix it when something breaks, what exactly are you selling people? I'm all for making technology more accessible, but I don't think easier access to creation should mean we stop caring about what we're creating.

Then there's the entire business of selling people information about how to start businesses. I've seen videos promising incredible investment returns, courses explaining how anyone can make thousands of dollars selling products online, and people offering to teach you how to generate income with practically no effort. Some of those people undoubtedly have legitimate experience and useful information to share, but I think we should be considerably more skeptical about the promises being made. If someone tells you they can consistently generate extraordinary returns on their investments, why are they spending so much time trying to convince strangers to buy their course? If someone claims a particular business model practically guarantees thousands of dollars every month, what are they leaving out of that explanation? I'm not saying successful people can't teach others what they've learned. I'm saying we should probably ask more questions before handing over our money to someone whose business might primarily consist of convincing other people that they know how to make money. At some point, the side-hustle industry became a side hustle of its own, and I sometimes wonder how many people are making more money selling the idea of financial freedom than they ever made from the businesses they're promoting.

The other thing I've been thinking about is how much we've started confusing being busy with being successful. There's almost a competition over who works the most hours, who has the most businesses and who manages to squeeze the greatest amount of productivity out of every day. Someone says they work eighty hours a week, and we're supposed to be impressed without asking what they're actually accomplishing during those eighty hours. I've worked jobs where I was physically at work for an entire shift, but the amount of time spent doing actual work was considerably smaller because that's simply how the job operated. Being present somewhere for eight hours doesn't automatically mean you've accomplished eight hours of meaningful work. I think the same thing applies to side hustles. You can spend every evening watching videos about business ideas, creating products nobody asked for and making plans for another source of income without actually building anything sustainable. Meanwhile, someone else might work a regular job, enjoy their evenings and spend their weekends with family or playing video games. I don't think the first person is automatically more successful simply because they're constantly busy.

I also don't want this to sound like I'm against ambition because that would be pretty hypocritical coming from me. I have different business interests, I write books, I invest, I experiment with technology and I enjoy learning how things work. I'm not planning to stop doing those things, and I don't think anyone else should abandon their ambitions simply because there are people online making unrealistic promises. If you love working on cars and want to become a mobile mechanic, go for it. If you're passionate about fitness and want to become a personal trainer, there's nothing wrong with trying to build a business around that. If you enjoy writing and want to publish your stories, I certainly wouldn't be the person telling you not to. Just understand that being passionate about something doesn't eliminate the responsibilities that come with turning it into a business. You still need customers, you still need to understand your market and you still need to put in the work. And if you discover that turning your hobby into a business takes away the enjoyment you originally got from it, there's nothing wrong with deciding that particular hobby doesn't need to generate income.

I think that's what bothers me most about the culture we've created around making money. There are already enough things in life that we have to do whether we enjoy them or not. We have bills to pay, responsibilities to manage and obligations that don't disappear simply because we'd rather spend the afternoon doing something else. Our free time used to be the opportunity to step away from those things, relax and enjoy ourselves without worrying about whether every minute was productive. Now even that time comes with someone telling us we could be building a business, learning another skill, generating content or working toward another source of income. I understand that some people don't have much of a choice because they genuinely need the extra money, and I respect anyone putting in that work to improve their situation. But I also think we need to be careful about creating a world where people who are financially comfortable enough to enjoy their free time still feel guilty for doing so. If you spend Saturday playing video games, reading a book or watching television, that doesn't automatically mean you've wasted your day. Maybe enjoying yourself was exactly what you needed to accomplish.

Maybe the bigger question isn't when everything became a side hustle, but why we've started treating everything that doesn't make money as though it has less value. I write because I enjoy writing. I podcast because I enjoy talking about things that interest me. I have other hobbies that I don't particularly want to turn into businesses, and I don't think I need to justify that decision to anyone. If something I enjoy eventually creates another source of income, great. If it doesn't, that doesn't automatically make the time I spent doing it worthless. There will always be another opportunity to make money, another business someone claims is taking off and another person showing you how successful they've supposedly become. You can spend your entire life chasing those things and still feel like you're missing out on something. I would rather spend my time building things I actually care about, learning things that interest me and giving myself permission to enjoy the parts of life that don't come with a paycheck. Not everything needs to be a business, and not every hobby needs to become another responsibility. Sometimes it's perfectly fine to do something simply because it makes you happy.

Thanks,

Josh