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Why one job no longer cuts it for millennials, Gen Z

Hani Richter at Reuters wrote about polyemployment, the growing number of millennials and Gen Z workers holding two or three jobs at once, not to build a career but to cover rent. Polyemployment hit a decade high in 2025, and Gen Z makes up 55% of the polyemployed workforce. One baker she profiled went from $6,000 a month in a single head baker role to just under $3,000 across several gigs.

My contribution was the tax trap. The biggest mistake polyworkers make is getting blindsided by a tax bill in April because their employers never coordinated withholding. Each employer withholds as if that job were the worker's only income, which means each one applies the full standard deduction and the lowest brackets. Stack three W-2s that way and the total withheld can fall thousands short of what the combined income actually owes. Add a 1099 gig with no withholding at all and the April surprise gets bigger.

The fix is simple once you know it is coming. Adjust withholding on the largest W-2 job to account for the others, using the multiple-jobs section of the W-4, or make quarterly estimated payments to cover the gap. A worker who does that in February is fine. A worker who finds out in April owes the tax, plus a penalty, at the exact moment they have no cushion.

The second piece of advice is the same for everyone with irregular income: the emergency fund has to be bigger, because the income is less predictable and there is no single employer safety net.

Read the full article at Reuters →

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Jeff Judge Managing Partner
Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.
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