Recent data from Newsweek paints a troubling picture of retirement in America: Two in five retired Americans (41%) say they can’t support their ideal retirement, and while 92% of them don’t currently have a side gig, 60% wish they did. Meanwhile, 63% of Americans aged 50 and up who haven’t yet retired say they’re considering picking up a side gig after they do.
These numbers don’t just highlight individual hardship—they signal a systemic failure in how we prepare for retirement in this country.
Retirement expectations vs. reality
The hard truth is that the vast majority of Americans are not even close to being financially prepared for retirement. And that’s not entirely their fault. The current economic climate is riddled with challenges that have been decades in the making. Inflation has eaten away at purchasing power, and proposals like the recent Trump tariffs will likely drive prices even higher in the near term.
At the same time, we’ve developed an unhealthy dependency on financial markets, assuming decades of bull markets would continue indefinitely. But now, those same markets are showing the underpinnings of instability—and given the current economic headwinds, that trend is likely to continue. Add in the mounting pressure of supporting adult children and grandchildren, many of whom cannot land jobs that pay a livable wage, and retirees are facing far more financial obligations than previous generations ever did.
For those still earning an active income, there’s at least some room to maneuver. But those on fixed incomes are especially vulnerable. With Social Security facing potential cuts of up to 25% by 2032 and increasing talk of more aggressive means testing, retirees relying on government programs could soon find themselves in severe financial distress. And it won’t stop there. Tax advantages tied to retirement accounts like IRAs and 401(k)s will likely come under attack as the government seeks new revenue—starting with the wealthy, but eventually affecting everyone.
A lifetime of overspending meets its consequences
If the numbers are bleak, they’re also unsurprising. We’re witnessing the natural consequences of decades of overspending—by governments and individuals alike.
At the federal level, both parties have kicked the can down the road, piling up debt and printing money, which dilutes the dollar and feeds inflation. Many Americans have lived individually as if economic prosperity were guaranteed, spending heavily and investing too little. This financial model was built on hope rather than strategy.
But the economic rules haven’t changed. Markets rise and fall. Inflation erodes value. And if you’re not preparing for downturns, you’re already behind. Too many people assumed the good times would last forever. They didn’t.
The rise of the retirement side hustle
There’s no question we’ll see more retirees—and those nearing retirement—pursuing side gigs. Why? Because they have to.
Costs aren’t decreasing, and meaningful improvement in the financial markets isn’t on the horizon. The same forces that got us into this situation have been at work for decades, so any meaningful recovery will likely take just as long—or longer.
This is a wake-up call. Both policymakers and the public need to ask a hard question: Do we have the courage to make the needed changes and endure the discomfort that comes with them? Because if we don’t, there may not be a way out.
Until those changes are made, retirees must plan for prolonged economic hardship and supplement their income creatively. But even that path is filled with hurdles.
Why side gigs aren’t a silver bullet
While side gigs offer a potential lifeline, they’re not a guaranteed solution—and they’re not equally available to everyone.
The job market is arguably the most difficult it’s been in decades. Younger workers struggle with a lack of experience, while older workers often lack the technological skills employers demand. Those who possess both are better positioned, but the pool of opportunities is limited—and competition is fierce.
Technology provides tools, but it also introduces new obstacles. Take dropshipping, for instance—a common side hustle model that involves selling inexpensive products (often from China) online. It operates on thin profit margins and relies on low import costs. Trump’s tariffs could crush this business model overnight.
Other popular options like coaching and consulting are also harder to succeed in now due to the rise of AI tools like ChatGPT and Grok. Many people see these services as a faster, cheaper alternative to hiring human experts, even though the accuracy of AI-generated content is often questionable. That makes it more challenging for real professionals to stand out—unless they can clearly demonstrate their value.
In other words, side gigs aren’t a cure-all. They’re a stopgap—one that still requires skills, tech literacy, and market adaptability to work.
What needs to change
This growing dependence on side gigs in retirement is a symptom of deeper economic dysfunction. We need both individual resilience and systemic reform. That means:
- Personal preparedness: Retirees and those nearing retirement must prioritize financial education, diversify income sources, and adapt to new technologies.
- Policy reform: Lawmakers must address inflation, protect Social Security, and reassess the sustainability of retirement tax incentives.
- Cultural change: Americans need to shift from a mindset of perpetual growth and consumption to one of long-term planning and resilience.
We’re entering an era when traditional retirement is no longer the norm—it’s a luxury. If we want to restore it as a viable future for most Americans, we’ll need to change how we prepare for it and shape the economic policies around it. Until then, the retirement hustle will continue to rise.
