Ah, the holidays… that magical time of year when you’re somehow expected to buy gifts, attend events, donate to fundraisers, bring side dishes, and still pretend you’re not googling “cheap holiday cocktails that still look impressive.”
It’s also the time when a lot of people look at their budget and think:
“You know what? I could use a little extra cash.”
If that’s you, hi, welcome — you’re in good company. Seasonal income can be a lifesaver this time of year.
But before you sign up to hang lights for your neighbors, pick up a second W-2 job at the mall, or DoorDash your way through every peppermint latte order in town, let’s talk about what that extra income really means. Financially, logistically, and emotionally.
Because if you’re going to hustle, let’s at least make sure the hustle is worth it.
W2 Work: The Classic “I Picked Up a Holiday Job” Move
Holiday retail jobs, warehouse shifts, stocking roles, gift-wrapping stations, you name it, companies are hiring. And truly, seasonal W-2 work can be a great way to earn structured, predictable income. But here’s what you need to know:
- Overtime & Extra Hours Are NOT Taxed More (Even Though It Feels Like They Are)
No, the IRS does not have a “holiday spirit surcharge.”
Overtime and extra hours are taxed the exact same way
as regular income.
What does happen is your paycheck withholding goes up temporarily because you earned more in that period. That’s why it can feel like someone’s punishing you for working harder, payroll math is rarely comforting.
- Adding a Second W2 Job Affects Your Withholding
If you have two employers at once, both assume they’re your only employer unless you update your W-4.
Without adjusting it, you may end up:
- Under-withheld (surprise tax bill in April)
- Over-withheld (great refund, but tighter weekly cash flow)
Use the “multiple jobs” checkbox on the W-4 or the IRS estimator to get this right.
- Know Your Company’s Rules on Second Jobs
Some employers have:
- Moonlighting policies
- Conflict-of-interest rules
- Noncompete clauses (rare, but real)
- Requirements to disclose a second job
You do not want a conversation with HR during the holidays. They’re tired too.
- Mind the Burnout
Working holiday shifts + your regular job + your actual life is a lot.
If you’re already tired, adding a second schedule might help your wallet but hurt your health, relationships, or performance at your main job.
This isn’t to scare you. I’m just saying, make sure the income is worth the energy cost.
Gig Work: The Flexible Friend With a Few Plot Twists
Driving, delivering, dog-walking, babysitting, hanging Christmas lights, shoveling walkways (probably not in Phoenix but I’ve heard this is a thing in other places), freelance projects. Gig work is everywhere during the holidays and it’s appealing for plenty of reasons:
- You control your hours
- You take only the jobs you want
- You get paid quickly
- You don’t need permission from HR
- Some gigs pay really well in December
But here’s the truth people don’t always talk about…
- No One Withholds Taxes for You
Every dollar from gig work is paid to you as-is.
There is no withholding, no payroll deductions, no friendly buffer.
A simple rule of thumb:
Set aside 20–30% of every payment for taxes
so you’re not shocked in April.
- Self-Employment Tax Exists (And It’s… Something)
Gig workers pay both halves of Social Security and Medicare — a combined 15.3% on net earnings.
If you’ve never paid it before, it’s a rude awakening.
It’s also why saving some of that income upfront is essential.
- Quarterly Taxes Might Apply
If your gig earnings are meaningful — even just through November and December — you might need to make an estimated tax payment in January.
(Or you can increase withholding at your main job instead. There’s flexibility.)
- You Can Deduct Work Expenses
Gig work lets you claim business deductions for ordinary and necessary expenses, like:
- Mileage
- Phone usage
- Supplies
- Home office costs
- Platform fees
These deductions reduce both income tax and self-employment tax. Talk to a professional about what counts as a write off because sometimes you can only take a percentage of a thing and other times you can’t take it at all. I’m not a tax expert.
- Earnings ≠ Profit
If you make $600 from light hanging but spend $150 on supplies and gas, your taxable income is $450.
A lot of people forget this and panic over paying tax on the full amount, you won’t.
Seasonal Side Hustles: Creative Ways to Boost Cash Fast
Let’s brainstorm some realistic, in-demand seasonal income ideas:
- Hanging Christmas lights
- Grocery or gift delivery
- Driving for holiday events
- Pet sitting during holiday travel
- Babysitting (the holiday party market is HOT)
- Seasonal retail shifts
- Gift wrapping services
- Freelance design, writing, or photography
- Selling baked goods (gluten-free girlies unite)
- Yard cleanups before winter storms
- Holiday decor setup or takedown
- Helping people move or store decorations
This time of year, people pay for convenience so your skills might be worth more than you think.
But Most of All: Protect Your Time, Energy, and Mental Health
More income is great.
But more obligations?
That can be stressful, especially during a season already shaped by expectations, emotions, and a whole lot of to-do lists.
So as you weigh your options, ask yourself:
- Does this income actually move the needle for me?
- Do I have the bandwidth right now?
- Will this create more stress than it solves?
- Is there a smarter or simpler alternative?
There’s no wrong answer, just the one that supports your wellbeing and your wallet.
The Bottom Line
There is absolutely nothing wrong with needing (or wanting!) extra income during the holidays.
It doesn’t mean you failed at budgeting.
It doesn’t mean you mismanaged your money.
It means you’re a human living in 2025 where December is basically a boss level in a video game.
Extra income can be empowering. Just make sure you understand the tax responsibilities, energy demands, and potential HR considerations before jumping in.
And remember: hustle if you need to, rest when you can, and give yourself grace along the way.
Happy Holiday Hustling!
Chandler