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Perspectives: Jailbreaking hustle culture
Freedom from worth defined by work and meaning defined by money
This week’s newsletter was written by Sarah Duran. Sarah and I met a few months ago — almost by accident — and instantly clicked.
Sarah quit the 9-5 because she was tired of people telling her what to do, how to do it, and what she was worth. Now she runs a successful freelance business, and she’s also a coach, blogger, author, and content creator who helps solopreneurs live up to their highest potential. Check out her Substack, The Hustler's Manifesto where she writes about manifesting a life you love and control, managing the next apocalypse like a boss, and turning uncertainty to your favor.
Sam finished her Ph.D. and realized that the job she wanted didn’t exist—so she created one. She’s building a freelance evaluation business that focuses on content she’s passionate about without navigating university bureaucracy.
Tom bounced from low-paying job to low-paying job, suffered under the control of terrible bosses, and hated what he did every day. Now he has three part-time hustles that pay the bills and give him work that has meaning. He also works when he wants, which means he has time to volunteer, spend time with his kids, and take care of himself.
Blanca was a young single mom who needed to support her family. She started marketing herself as a virtual assistant on Upwork. After years of refining her skill set, she now runs a six-figure freelancing business, has ten rental properties, a budding brick-and-mortar boutique, and still maintains a flexible schedule that allows her to take her kids on multiple vacations a year.
Eli loves his job as a high-level project manager in the tech world, and he also has a side hustle as a professional astrologer. He chooses to have a side hustle, not because he needs the money, but because it fulfills him in a way his 9-5 doesn’t.
Anne pulls weeds for a living. She loves being outside and working with her hands. She built a loyal following through Fiverr and now has a business that pays more per hour than most of her friends who work a “normal job” in a cubicle.
These are all hustlers but maybe not the ones that come to mind when you think about modern-day “Hustle Culture.”
“Hustle Culture” is branded as a work-all-the-time mentality that helps you climb the corporate ladder and succeed at all costs. Hustlers are portrayed as big shots, corporate CEOs, start-up dudes chasing venture capital, and celebrities who’ve turned their fortunes into brands.
That narrative stole “hustle culture” from the true hustlers.
Hustlers are not the powerful, the monied, the well-connected. Hustlers are the scrappy, the driven, the underdog. Hustlers take what’s been handed to them and turn it into something better—they design their ideal with the scraps that others have left behind.
So, where did the warped version of modern-day “Hustler Culture” come from?
Some say it grew out of a generation of millennials who graduated college during the great recession and Gen Zers who became adults in a world that had become much more expensive than the world of their parents. These generations had to “hustle harder” than previous generations to make ends meet. Data backs this up with price indexes indicating that while costs have dropped in some areas over the last decade, they are rising on the things that drive poverty and prevent people from escaping it. The price of a “middle-class life” has become unattainable on a middle-class salary.
Others point to CEOs like Elon Musk, motivational speakers like Tony Robbins, and countless others who push the narrative that hard work is the only way to find success and define success in purely material terms. This plays out every day in the workplace, with many employees associating long hours with the ability to climb the corporate ladder.
While all of these are factors that contributed to modern-day “Hustle Culture,” the truth is that the succeed-at-any-cost mentality is fundamental to the history of America. From colonization, to the Protestant work ethic, to manifest destiny, to the industrial revolution—the American narrative is based on “success” due to “hard work.”
Both “success” and “hard work” are problematic.
The concept of “hard work” is fraught with historical and cultural baggage, from how work is defined for different sectors of the population to the “equality” that supposedly allows people to succeed based on their own merits.
“Success” is defined narrowly as having money, prestige, and property.
Many of us are disillusioned by the simplistic narrative of worth defined by work and meaning defined by money. We are reclaiming “hustler” as a rallying cry against burnout and not in service of it— jailbreaking hustler culture from the limiting mindsets of colonization, capitalism, and corporatization.
So…what does that look like?
Personal Agency in Service of Interconnectedness
Hustlers chase fortune not for fortune’s sake but for the satisfaction it gives them to know that they’ve forged the path themselves instead of waiting for someone to do it for them. Instead of accepting the pre-defined definitions of work and success, hustlers define these things themselves.
Personal agency is a mindset that is not the norm. It is easier to fit into standard categories, roles, and systems than create your own. This conformist mentality robs us of control over our own lives and forces us to rely on top-down approaches instead of the intimate networks of people we are surrounded with every day.
Personal agency is not self-reliance—hustlers also don’t succeed in isolation. Even though I’m a “solopreneur,” I don’t work alone. I have a network of other solopreneurs, clients, and collaborators who make what I do not only possible but gratifying…and that relationship is reciprocal. Not to mention my family, friends, and neighbors who contribute to this reciprocal web of value—gifts, favors, legs up, and handouts.
“The community of the future will arise from the needs that money inherently cannot meet.”
― Charles Eisenstein
The control, flexibility, and prosperity I’ve carved out for myself allow me to serve those around me better. When I’m doing my Work in the world, I can contribute to a regenerative community where success isn’t seen as a zero-sum game.
Getting Shit Done and Knowing When It’s Enough
Hustlers don’t stand on the sidelines or wait for life to deliver—they find solutions, not because they have money or power, but because they have no other choice. Hustlers don’t waste even a moment wishing something was different; they act. This “go-getter” mentality often means pushing toward something that may never come to fruition, seeing the horizon and moving toward it until you find the destination shifting under your feet and adjusting accordingly.
The key to a jailbroken hustler mentality is harnessing the obsession with getting shit done to solve problems and knowing when enough is enough.
Standard definitions of productivity, work, and rest trap us in a hamster wheel where we constantly strive for some idealized finish line. Success is always around the corner and never entirely within reach.
At an individual level, we’re trapped in a Hedonic Treadmill where we’re constantly chasing happiness but never actually achieving it. If I can just check off that last thing on my list, put that last $10K in my retirement account, get that last promotion…then I can rest.
At a societal level, we’re constantly chasing efficiency so that we can work less and consume less. The catch is that increased efficiency doesn’t create space; it raises the bar for “productivity.” The time we save with automation isn’t filled with rest; it is filled with more work. We’re always pursuing fulfillment, which means we can’t see it when it’s actually here.
A jail-broken hustler mentality gets shit done and worships rest, elevates it, praises it, and doesn’t make it contingent upon goals achieved, money saved, or missions accomplished. Hustlers have decoupled success from externalized metrics so they can recognize it when it happens and bask in it, instead of chasing the next best thing.
Money as a Means, Not an End
Money isn’t everything…says people who have money. We live in a world where money matters and is a form of power that is not equally accessible to everyone. Hustlers define their relationship with money for themselves. That definition process is highly personal, but the common denominator is that hustlers leverage money to create prosperity—they see money as the vehicle, not the destination.
“Wealth does not mean a person who owns a lot, but refers to someone who has enough time to enjoy what nature and human collaboration place within everyone’s reach.”
― Franco Bifo Berardi
Defining wealth outside of conceptions of money and property is hard work in a society that values little else. The world wants us to define our worth by money but not actually talk about money explicitly. Jailbreaking the relationship with money means owning and being explicit about money's power while not letting money control you.
Top-down solutions, rarely successful to begin with, are no longer serving us. The complexity of the problems that surround us must be addressed from the bottom up — by those of us who have skin in the game, have everything to lose. As we face an increasingly uncertain future, the hustlers will rethink the systems and structures that have proven defective.
“We must become builders again. We live in a decentralized economy, and the next safety net will be no less decentralized. Traditional business and big government no longer apply.”
― Sara Horowitz
The way work has been done is no longer working. Let’s be honest; it hasn’t been working for many of us for a long time. And work is just a symptom of the larger structural problems we’re facing on so many levels.
I don’t work for myself so I can ride off into the sunset on a Lambo; I do it so that I have control over my time and resources, which allows me to be a better human, raise a better human, and support others in getting what they need to be better humans.
I’m not saying that everyone needs to work for themselves; I’m saying that if we can embrace a jail-broken hustler mentality, we can be more in control of our own lives, which gives us greater capacity to help others do the same and ultimately build a more connected, sustainable, meaningful world.
A roundup of stuff from around The Interwebs. Some to make you smile, some to make you roll your eyes. And some stuff that I wrote on other platforms.
When — and How — to Say No to Extra Work | Harvard Business Review
An Introduction to Vertical Social Networks | Tamilore Oladipo
You can also follow me on LinkedIn for more insights about work, or on Twitter for spicier takes, and Medium where I write about fun stuff like productivity and creativity. Or catch up on the personal side of my life on my blog.
This publication is free because I love sharing ideas and connecting with others about the future of work. If you want to support me as a writer, you can buy me a coffee.