Trump’s Retirement Order Targets 57 Million Left Behind: How Gig Workers and Small‑Business Employees Stand to Gain
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Fifty‑seven million Americans like Maria Alvarez have spent decades outside the retirement system—not by choice, but by design. The article reveals how a little‑noticed 2018 Trump executive order dismantled a single technical rule that kept gig workers and small‑business employees locked out, and why that change may prove more financially consequential than many of the era’s headline policies. If you think retirement access is settled law, this story shows how quietly it was rewritten—and who finally gets a seat at the table.
At 6:30 a.m. in Phoenix, Maria Alvarez checks her phone before she checks the road. Uber’s heat map glows red. Another surge. She’ll drive until noon, switch to DoorDash through lunch, and squeeze in bookkeeping for two local contractors after dinner. Maria is 42, self-employed in everything but name—and until recently, locked out of the retirement system most Americans take for granted.
She’s one of roughly 57 million U.S. workers without access to an employer-sponsored retirement plan, according to the U.S. Department of Labor. For decades, that exclusion defined the gig economy and small businesses with fewer than 100 employees. Then, quietly, the rules shifted. A Trump-era executive order and the legislation that followed didn’t grab headlines like tax cuts or tariffs. But for workers like Maria, the changes landed with life-altering force.
The policy that cracked open a closed system
On August 31, 2018, President Donald Trump signed Executive Order 13847, directing the Treasury and Labor Departments to expand access to workplace retirement plans—specifically by loosening rules around Multiple Employer Plans (MEPs). The idea sounded technical. The impact wasn’t.
Before the order, MEPs existed but came with a poison pill known as the “one bad apple” rule: if one participating employer failed compliance, the entire plan could be disqualified. Small businesses steered clear. Gig workers didn’t qualify at all.
The executive order pushed regulators to remove that risk and allow unrelated employers—and eventually self-employed workers—to band together. Congress followed through with the SECURE Act of 2019, signed in December, which created Pooled Employer Plans (PEPs) starting in 2021. These plans let a professional fiduciary run a single 401(k) for thousands of employers and independent workers, spreading costs and liability.
The result: access at scale.
According to Vanguard, administrative costs for small-plan 401(k)s dropped by as much as 30% under pooled arrangements. Fidelity reported that employers with fewer than 50 workers began adopting retirement plans at nearly double the pre-SECURE rate by 2023. The system finally bent toward the people it had ignored.
Who actually benefits—and how the money moves
The winners fall into three overlapping groups, each gaining in a different way.
Gig workers and independent contractors
Gig workers used to rely on IRAs—good tools, limited power. Contribution caps remain lower than 401(k)s, and few platforms offered payroll-style automation. PEPs changed the math.
A solo driver earning $65,000 can now contribute up to $23,000 in employee deferrals for 2024 (or $30,500 if 50 or older), plus employer-style contributions if structured as a sole proprietor. That dwarfs the $7,000 IRA cap. More importantly, contributions can come directly from platform income, automated and disciplined.
Platforms didn’t need to sponsor plans. Financial firms stepped in. Guideline, Betterment for Business, and Human Interest launched pooled plans explicitly marketed to freelancers. Fidelity Advantage 401(k) and Vanguard Pooled Employer Plan followed, bringing brand trust and institutional pricing.
Maria joined one last year through Guideline. Her contribution rate: 8%. Her balance today: $9,400. “I never kept an IRA funded,” she told me. “This feels like a bill I pay myself.”
Small-business employees at firms under 100 workers
Small firms employ nearly 46% of the U.S. private workforce, according to the Small Business Administration. Historically, fewer than half offered retirement benefits. Cost and compliance scared them off.
PEPs rewired the incentives:
- Startup tax credits now cover up to $5,000 per year for three years to offset plan costs.
- Employers avoid fiduciary headaches; pooled plan providers assume responsibility.
- Employees get access to automatic enrollment and diversified funds, features once reserved for Fortune 500 plans.
A 2022 analysis by the Employee Benefit Research Institute found that automatic enrollment alone boosts participation rates from 62% to over 85%. That gap compounds into six figures over a career.
Owners and founders themselves
Here’s the underreported angle: business owners benefit more than anyone. PEPs allow founders to shelter income aggressively while offering a benefit that attracts talent.
A 38-year-old agency owner earning $150,000 can defer the max, add profit-sharing contributions, and reduce taxable income—without managing a plan solo. Providers like Gusto, Paychex, and ADP bundle payroll with pooled plans, collapsing admin time.
One Chicago marketing firm I interviewed saved $18,000 annually after switching from a standalone 401(k) to a pooled option. The owner reinvested the difference into raises. Retention jumped. The plan paid for itself.
Real lives, real consequences
Policy lives or dies by outcomes. Three years into full PEP availability, the outcomes tell a clear story.
Case 1: The landscaper Darnell Brooks runs a six-person landscaping business in Columbus, Ohio. He skipped benefits for years. “Margins were thin. One mistake could sink us,” he said.
In 2022, his accountant flagged the SECURE Act credits. Darnell adopted a pooled 401(k) through Fidelity PEP. Cost after credits: zero in year one, $1,200 in year two.
Every employee enrolled. One, a 24-year-old crew lead, bumped contributions to 10% after watching his balance cross $5,000. Darnell plans to match 3% next year. “I didn’t know how badly they wanted this,” he said.
Case 2: The part-time retailer Linda Chen works 25 hours a week at a family-owned hardware store in San Jose. No benefits. No leverage.
When California’s state auto-IRA mandate loomed, the owner chose a private pooled plan instead. Linda now contributes $150 a month into a low-cost target-date fund. Her balance won’t make her rich. It will make her independent.
Case 3: The multi-hyphenate creative Jason Reed designs logos, edits podcasts, and teaches a night class. Three income streams. Zero benefits—until he joined Vanguard’s pooled plan for self-employed workers.
He consolidated contributions, set quarterly estimates, and finally saw a trajectory. “For the first time, retirement feels proportional to how hard I work,” he said.
What critics miss—and where the gaps remain
The policy isn’t flawless. Fees still matter. Some pooled plans charge asset-based fees north of 0.60%, eroding long-term returns. Not all gig platforms integrate smoothly with contribution systems. And access doesn’t guarantee participation—especially for workers living month to month.
But critics who dismiss the reforms as cosmetic ignore a structural truth: retirement access precedes retirement adequacy. You can’t save in a plan you’re barred from.
Data backs this up. The Federal Reserve’s 2023 Survey of Consumer Finances shows that households with workplace plans hold nearly 3x the retirement assets of those without, controlling for income. Access changes behavior.
The Trump order didn’t solve inequality. It dismantled a bottleneck.
Practical steps readers can take this month
If you’re a worker, founder, or freelancer, the window is open. Here’s how to move through it deliberately.
For gig workers and independents
- Compare Guideline Solo 401(k), Betterment for Business, and Vanguard Pooled Employer Plan for fees and automation.
- Prioritize plans with automatic quarterly contributions tied to income.
- Use a target-date fund unless you actively rebalance.
- Ask your CPA about SECURE Act startup credits—they expire after three years.
- Look for payroll-integrated providers like Gusto with Guideline, Paychex PEP, or ADP Retirement Services.
- Start with automatic enrollment at 3%. Let inertia work for you.
- If your employer lacks a plan, bring data. Show them pooled options and tax credits.
- Push for automatic enrollment. Opting out is easier than opting in later.
The quiet reordering of retirement
No rallies celebrated pooled employer plans. No cable news countdowns tracked their rollout. Yet millions of workers now hold accounts they couldn’t open five years ago.
Maria finishes her last ride at dusk. She checks her balance again—not the heat map, the retirement one. It’s modest. It’s real. And for the first time, it belongs to a system built with her in mind.
The retirement crisis won’t end with a single order or act. But access is destiny. And access, finally, arrived for the people left behind.