UpTrajectory Review

TheStreet's piece flags three deadlines closing before year-end: adjusting 401(k) contributions, completing a Roth conversion by December 31, and reviewing Medicare coverage before the December 7 enrollment window. The framing is familiar seasonal personal-finance fare, but the mechanics underneath have shifted in ways most coverage glosses over. SECURE 2.0's Roth catch-up mandate for high earners took effect January 1, 2026, and it changes both the tax math and the administrative burden for anyone running payroll or advising employees through it.

For a small-business owner, this is not just an employee problem. If your 401(k) plan lacks a Roth option, SECURE 2.0 strips catch-up eligibility entirely for participants 50 and older—a detail that could trigger compliance headaches, employee complaints, and potential plan-design revisions. The piece notes the rule caught many workers off guard, but the same is true for employers who sponsor the plans. If your plan document hasn't been updated or your payroll provider hasn't flagged the Roth designation requirement, the remaining weeks of 2026 are your last window to avoid a messy January.

The 2026 deferral numbers are worth internalizing: $24,500 standard, $32,500 with the standard catch-up for workers 50 and older, and $35,750 for those aged 60 to 63 under the enhanced catch-up tier. The piece also flags that contributions flow only through payroll and that deferral changes take a full pay cycle to process—meaning every uncorrected paycheck forces the remaining ones to absorb a larger share of the gap. That's a practical operational constraint, not just a planning footnote, and it applies whether you're the owner trying to max out your own deferral or the person processing payroll for a team.

We're skeptical of the piece's flat assertion that all three deadlines lock in permanently once the year turns. Roth conversions and Medicare enrollment do have hard December cutoffs, but 401(k) contributions are tied to payroll cycles, and some plans allow catch-up true-ups in the following year. The permanent-lock framing oversimplifies. That said, the Roth conversion window is genuinely use-it-or-lose-it for 2026 tax-year planning, and the Medicare December 7 deadline is immovable. The piece's strongest point is the payroll-processing lag, which most year-end retirement coverage ignores entirely.

Second-order effects cut in both directions. High earners forced into Roth catch-ups will see higher taxable income now in exchange for tax-free withdrawals later—a trade-off that may be rational but requires cash-flow planning for the April tax bill. Employers who added Roth provisions to avoid the SECURE 2.0 penalty may find that younger workers also switch to Roth, reducing the plan's pre-tax deferral base and altering nondiscrimination testing outcomes. And owners aged 60 to 63 who qualify for the $35,750 ceiling need to confirm their plan even permits the enhanced catch-up tier; not all do.

Watch for IRS guidance clarifying whether plans without Roth options can adopt one retroactively for 2026, and check whether your payroll vendor has built the Roth catch-up logic for high earners into its system. If you're an owner-operator, run a payroll projection now to see how many pay cycles remain and what per-check deferral rate gets you to your target. If you're advising employees, flag the $150,000 FICA wage threshold and the Roth designation requirement before the last processing cycle of the year. The December 7 Medicare deadline is the only true coverage cliff here; the rest are tax-planning choices, but they narrow fast.

“People who fall in that category need to financially be prepared for a larger tax bill.” — TheStreet

Takeaway: Confirm your 401(k) plan has a Roth option and your payroll system handles SECURE 2.0 catch-up rules before the final pay cycles of 2026.