Jon Stojan
Image Credit: TruWorth
In a city built on dreams, the promise of freedom can become a cage.
You moved to LA because you wanted to bet on yourself. You took a chance to build something on your own terms. You’ve got no boss, no cubicle, and no ceiling on your potential.
You’re a content creator, a freelance designer, a gig economy warrior with three income streams while manifesting your future empire from your laptop and a coworking space in Silver Lake.
When you describe your life to your old high school friends, they think you’re living the dream. Your social media feed makes most people jealous, with your expertly curated and filtered photos at all the right restaurants, wearing the right clothes, with the right people. You’re the very image of success.
When you take a glance at your bank account, however, the numbers tell a different story.
You’re constantly in motion, constantly creating, constantly hustling. And somehow you’re still not getting ahead.
Welcome to the freedom trap. And in Los Angeles, it’s everywhere.
LA Sold You a Dream. Here’s What It Left Out.
LA is ground zero for the independent worker revolution. Freelancers, influencers, entrepreneurs, and creatives flock here chasing the promise of autonomy. The weather is perfect for outdoor content. The networking opportunities are endless. The culture celebrates those who bet on themselves, even if it means you’re faking it till you make it.
But beneath the glossy surface lies an uncomfortable truth.
Freedom without direction isn’t freedom at all. It’s chaos, with better lighting.
Johann Berlin and Uma Viswanathan, founders of behavioral finance startup TruWorth, explore this paradox in their upcoming book Wealth and Why We Seek It. They describe the allure of independence: “Your freedom, your time, your genius… You’re blazing non-traditional career paths and that’s amazing.”
Then comes the reality check: “Yet, the uncertainty of whether it’s going to even pick up, whether you’ll ever have a steady income is starting to creep in. You’ve got no healthcare, and no safety net.”
Sound familiar?
No Benefits, No Safety Net, No Problem?
The gig economy promised liberation from traditional employment. What it delivered was a transfer of risk. You’re not just your own boss. You’re also your own HR department, benefits administrator, and retirement planner. And most freelancers are winging all three.
No employer-sponsored health insurance. No 401(k) match. No paid sick days. When you don’t work, you don’t eat. The freedom to set your own schedule becomes the obligation to never stop working.
Then there’s the debt that accumulates in the margins. Berlin and Viswanathan point to Buy Now, Pay Later services that “split purchases into manageable looking chunks, often with zero interest and no visible consequence.” But because payments scatter across weeks and apps, users chronically underestimate what they owe.
In a city where image matters, it’s easy to finance a lifestyle that looks successful before the success actually arrives. You might be “over-relying on credit to fund your business ventures” and “buying-now-paying-later your lifestyle,” as the authors put it.
“The aesthetic of making it can bankrupt you before you actually do,” shares Viswanathan.
Image Credit: TruWorth
Six Figures and Still Spiraling
Here’s what nobody talks about at the rooftop networking events:
Even when you’ve made it, you may still just be getting by.
Some of the most financially stressed people in LA are pulling six figures.
Berlin and Viswanathan address this directly. “You made the right moves in your career, are making six figures… and you might still feel trapped,” they write. “More income doesn’t automatically equal more wealth. Higher earnings may mean you’re constantly upgrading your lifestyle, buying a bigger house in a cooler neighborhood, going for a better car… and you’ve got little room for savings or strategic investments.”
Each upgrade feels necessary in the moment, even justifiable. The problem is that very quickly, what used to be a stretch for you – the shoes you couldn’t have splurged on a year ago, the added features on your car – become your new baseline. Behavioral economists call this hedonic adaptation. Each little better thing adds up, and over time, it becomes what you expect, and we stop noticing it. We aren’t necessarily even enjoying these nice things the way we might have before, as we treat it like our new normal. So, we’ve got to earn more, to buy more, and through that all, our expenses keep ballooning to match our ever-inflating lifestyle.
It’s like you’re on a treadmill, running faster to stay in place.
Especially in LA, what you wear and drive and where you live and dine send powerful signals about your success, and it’s hard not to inflate our lifestyles. Social media turns every friend’s glamorous vacation into a benchmark. Every colleague’s apartment tour becomes a measuring stick. You’re comparing yourself to the highlight reel of everyone around you.
The thing is, that influencer with the brand deals might be drowning in credit card debt. That entrepreneur celebrating a funding round might not be paying themselves a salary. But all you see is the wins. And all you feel is behind.
As Berlin and Viswanathan observe, “We are continually exposed to publicly visible markers of success in others, but rarely with enough context to know how real or stable any of it is.”
When Hustle Stops Feeling Like Progress
So how do you build sustainable wealth without sacrificing the flexibility you moved to LA for in the first place?
It starts with understanding what you’re actually chasing. “There is something deeper we’re after, a core motivation that is what is driving our decisions around our finances, careers, and lifestyles,” Berlin shares.
If you’re charting your own path, whether through the content you’re creating or startup you created, you might be driven by freedom.
In Wealth and Why We Seek It, Berlin and Viswanathan identify freedom as one of four core motivations driving financial behavior, alongside security, status, and meaning. “The need to choose one’s own path, to act without constant constraint, is one of the most powerful motivators for human behavior,” they write. “What could be more empowering than taking full responsibility, calling your own shots, and not relying on anyone else to build or grow?
Doing things solo is very much what got you here. But eventually, you might find yourself resisting structure, collaboration, and planning because they feel like constraints. We all need other people – whether it’s expertise, or advice or guidance – but when we’re motivated by freedom, we can end up getting trapped by independence bias, “the tendency to default to solo problem-solving, even when shared effort would be more effective.”
The antidote isn’t abandoning your independence. It’s building systems that support it. That might mean finally setting up that SEP IRA. Hiring an accountant instead of guessing on quarterly taxes. Creating boundaries around work hours so hustle doesn’t consume everything else.
The authors describe another core driver for influencers and entrepreneurs – status. “Success used to be expressed through job titles or homeownership,” they write. “Now it shows up through lifestyle markers: the right apartment, the right aesthetic, the right rhythm of travel and self-care.”
“Whether you’re an influencer in entertainment or fashion, an artist or cultural creator, a tech entrepreneur, we often need to look like we belong in the room in order to get a foot in the door,” Viswanathan shares. “There’s nothing wrong with doing what it takes to be relevant and create opportunities. The challenge comes when we get so caught up in looking the part, we forget our bigger purpose or dream.”
Whether you’re caught up doing it alone, or are inflating your spending to keep pace with an impossible image you’re projecting of yourself, a real shift starts by getting honest with yourself.
“It’s a good time to pause and reflect on why you’re making the choices you do,” Berlin and Viswanathan write, “and explore what it might look like to do differently.”
Image Credit: TruWorth
Real Freedom Has a Foundation
Los Angeles will always reward the bold. But boldness without a foundation is just expensive impulsivity.
Wealth and Why We Seek It by Johann Berlin and Uma Viswanathan offers a framework for ambitious independents ready to build real wealth, not just the appearance of it. Learn more on the official website.
Because real freedom isn’t just the ability to do whatever you want. It’s having the resources to keep doing it.