As we observe the five-year anniversary of the COVID-19 pandemic, the workforce has undergone a profound transformation. In the early days of the pandemic, millions of Americans were fired from jobs in retail, hospitality, and other industries. In order to make ends meet, they joined the growing ranks of “nonstandard” workers, taking on gig work, starting businesses, and exploring other forms of independent employment. Many never went back.
Now, nearly one-third of U.S. workers are independent contractors, gig workers, or solopreneurs, drawn by the promise of greater flexibility and higher earnings. They found that rather than orienting their lives around work, they can orient their work around their lifestyle. This isn’t just a pandemic-era blip; it’s a structural reordering of the economy that’s reshaping how Americans earn a living and navigate their careers. It’s had a profound impact on migration patterns as well, shaping not just how we work but where.
These changes are unfolding alongside rapid technological advancements that are redefining what it means to build a successful business. Want to create payment processing or HR software? A decade ago, that meant selling to big corporations, pitching tech that made large organizations more efficient. That’s no longer the case. Platforms like Uber and Instacart have proven that historically fragmented markets can now be interconnected at scale, transforming entire industries.
Social media, meanwhile, has eroded the cost of marketing for solopreneurs while fueling a culture that’s reframing self-employment as far more than a side hustle. Scroll through Instagram or TikTok, and you’ll find endless videos about flipping houses to rent on Airbnb, running online reselling stores, and other ways of turning everyday assets into revenue streams.
As the population of such workers explodes, so does the opportunity to invest in software and other technology to support this fast-growing but fragmented segment of the economy—along with the infrastructure that makes independent work more sustainable. Today, the New American Enterprise is being built around the needs of workers themselves.
Ensuring financial stability of the self-employed
Independence, it turns out, comes with some trade-offs. Unlike traditional employees, independent workers are on their own when it comes to essentials like taxes, healthcare, and long-term financial planning. Financial stability, in particular, can be a challenge. Without employer-backed payroll systems, tax withholding, and benefits management, solopreneurs must navigate a complex web of financial responsibilities—often without the tools or knowledge to do so effectively.
As a result, many face steep tax burdens, unpredictable cash flow, and lost opportunities to maximize their earnings. Fortunately, a growing number of financial infrastructure platforms are stepping in to bridge the gap. Payment processors like Square and Venmo are leveling the playing field by granting small vendors and business owners access to the same powerful financial tools that were once reserved for large enterprises. Meanwhile, platforms like BeSolo streamline tax filings, accounting, and benefits administration, helping independent workers manage their finances with the same efficiency as full-time employees.
The false choice between flexibility and financial stability is disappearing.
Upskilling the independent workforce
To succeed in the long run, independent workers—like their corporate counterparts—must continuously adapt by learning new skills, keeping up with evolving labor market demands, and mastering new technologies. Unlike corporate employees, however, solopreneurs can’t rely on HR departments or employer-sponsored training programs to keep them competitive. The traditional workforce development system, largely designed to funnel workers into corporate roles, has yet to catch up to this reality.
That’s beginning to change. Emerging platforms like Manifest are rethinking professional development for the self-employed, leveraging AI-driven insights and a peer-to-peer learning model to deliver real-time business guidance for independent business owners. These tools fill a critical gap, offering small business owners and gig workers the kind of strategic support and training that was once limited to well-connected corporate professionals.
Making independence sustainable
As more workers choose self-employment, the need for systems that reduce administrative burdens is growing. Managing bookkeeping, compliance, and benefits is time-consuming, and without the right infrastructure, independent workers risk spending as much time on paperwork as they do on their actual businesses. The explosion of independent work has given rise to a new category of digital tools designed to act as a solopreneur’s back office, allowing workers to operate with the same efficiency as larger companies.
It’s not merely about efficiency, however. It’s about expanding access and opportunity as more workers—especially Gen Z and other younger employees—reject traditional employment and traditional employers in favor of self-directed work. Streamlining these complexities doesn’t just make independent work easier; it makes it a truly sustainable career path.
The number of Americans working for themselves will only grow in the years ahead. The market for solutions that support them remains vast and largely untapped, offering a significant opportunity for those who recognize it. Independent workers aren’t waiting for permission—they’re already building the future of work. More investors and entrepreneurs would be wise to start building alongside them.
Yigal Kerszenbaum is the founding managing partner of JFFVentures.
