The $0 set‑aside: the side‑gig mistake that hurts most
Quick reality check: your side gigs don’t withhold taxes. At all. DoorDash, freelance design, tutoring on weekends, nobody’s skimming your paycheck for the IRS. Which feels great in the moment, until April rolls around and you’re staring at a tax bill that nukes your cash flow. I’ve watched high earners with multiple 1099s have a perfectly good Q4 get wrecked because they kept a $0 set‑aside. It’s the #1 error I’m seeing this year from multi‑gig folks, and 2025 has plenty of them.
Here’s the part that sneaks up on people. You owe two layers of tax on your net profit (revenue minus expenses), not on gross receipts:
- Income tax at your marginal bracket; and
- Self‑employment (SE) tax at 15.3% on most of your net earnings (that’s 12.4% Social Security up to the annual wage base and 2.9% Medicare). There’s also an extra 0.9% Medicare surtax on wages/SE income above $200,000 for singles ($250,000 for joint filers). The SE tax calculation applies to 92.35% of your net earnings, an odd IRS quirk, but it matters.
I’m over‑explaining one thing on purpose: it’s net profit that drives taxes. Your $10k month isn’t $10k for tax. If you spent $2k on software, mileage, and a new mic, your taxable base is lower. But, circling back, if you don’t track those costs as you go, you’ll overpay, because you’ll be guessing in April when your memory’s fuzzy and receipts are MIA.
Rule of thumb for right now: park 25%-35% of net profits in a separate savings account each week. Start at 30% if you’re unsure. Then refine once you’ve got three months of real numbers. With money market yields still around the mid‑5% range this fall (thanks to a Fed funds rate that hasn’t budged much in 2025), your tax stash actually earns something while it waits. Small win.
Timing matters. The IRS wants estimated taxes quarterly, typically mid‑April, mid‑June, mid‑September, and mid‑January. Miss them and you’ll see underpayment penalties plus interest show up, which adds up fast by Q4 when cash is already tight from holiday spend and year‑end gigs. Penalties are tied to IRS interest rates that have sat in the high single digits for much of 2024-2025, so the meter isn’t slow.
What you’ll get from this guide on how-to-pay-taxes-on-multiple-side-gigs is simple and practical: a weekly cash‑bucket system that scales across platforms, the exact math to estimate SE + income tax without over‑saving, and a clean way to true‑up quarterly so April doesn’t become a liquidity event. I’ll also show you how to tag expenses in real time so you’re reserving against net, not gross, because that’s the difference between setting aside 35% forever and dialing it down once the numbers are real.
Bottom line: waiting until April is what blows up cash flow. Treat taxes like rent, paid on schedule, not when the landlord’s on the doorstep.
Map your gigs, your forms, and your cash flow (without overcomplicating it)
Start with a one-page list of what you actually do and how the money shows up. Don’t overthink it. If you deliver for DoorDash on Saturdays, design logos at night, tutor two students, and sell candles on Etsy, write those four lines, then tag each with (a) how you’re paid, (b) which IRS form you might see, and (c) where it goes on your return. You’re building a simple routing map so April isn’t a forensic exercise while you’re also juggling Q4 holiday gigs and a boss who schedules 5pm meetings, which, yes, still happens in 2025.
- Deliveries/Rideshare: Paid via a platform payout (weekly/daily). Expect a 1099-K if the platform/processors hit the threshold. Mileage is your biggest expense, track it, even if it’s just your phone’s trip log.
- Freelance design/copy/consulting: Clients paying you directly will usually issue a 1099-NEC if you earn $600+ from them in a calendar year. If they don’t, income is still reportable.
- Tutoring/lessons/coaching: Same as freelance services, likely 1099-NEC from schools or programs; individual parents often don’t issue forms, but the income still counts.
- Craft sales (Etsy/Shopify/Whatnot): Platform processors may send a 1099-K. Track cost of materials and shipping; that’s your cost of goods and supplies, not tips in a jar.
On the forms: 1099-NEC is for services, the common trigger is $600 or more paid by a client in a year. For 1099-K, it depends on the payment network threshold. As announced in 2024, the IRS used a $5,000 1099-K threshold for tax year 2024 forms sent in early 2025. The agency has also said it’s moving toward a $600 standard, so keep an eye on 2025 guidance; we could see changes that affect what lands in your mailbox in early 2026. Either way, you’re required to report all income whether or not a form shows up. That’s not me being pedantic; that’s how the matching works.
Here’s the boring-but-important bit that saves headaches: 1099-K reports gross payment volume that processors handled (fees come out later), and 1099-NEC reflects what a client paid you for services. Don’t wait for forms to “tell” you your income, match platform payouts to your own ledger monthly. I carve out 10 minutes on Sunday, download the payouts from Uber, Etsy, Stripe, PayPal, whatever, and tick them off against my bank deposits. If something’s off by even $12.48, I flag it; small gaps snowball when you’re running five streams.
On Schedule C: Multiple gigs can mean multiple Schedule Cs, but you only need separate ones if they’re truly different trades. A delivery business and a design studio are different; design and tutoring might live together if they’re both personal services with overlapping expenses. One Schedule C keeps it clean; two or more makes sense when the economics, expense buckets, and platforms are distinct. Don’t create three just because you have three apps, create them because you have different businesses.
Keep the admin light: one “gigs” checking account, one cash reserve bucket for taxes, and a single spreadsheet with four columns: date, source (DoorDash/Etsy/Client A), gross payout, fees. Tag mileage and materials weekly. That’s it. You can fancy it up later if you really must.
Quick reality check for Q4 2025: consumer spending is choppy, but holiday promos are already pulling sales into November, which means more small payouts hitting your accounts at weird times. That’s fine, just stick to the same map: record gross, record fees, stash tax on the net. If you keep the flow simple and repeatable, you won’t drown in paperwork, and you won’t be guessing when those forms show up in January.
Turn chaos into math: tracking income, expenses, and self‑employment tax
Turn chaos into math: here’s how you translate the week’s swirls of pings and payouts into numbers you can actually plan around. If it feels messy, that’s normal. The trick is short, repeatable habits (not a fancy app ) that turn your gigs into a simple ledger you trust.
Track by gig, every week (10-15 minutes, max):
- Gross receipts (what the platform/client says they paid you before anything comes out)
- Platform fees (service fees, boosts, listing fees; tag them by app)
- Mileage (business miles only; start and end odometer or a reliable tracker)
- Supplies/materials (packaging, printer ink, ingredients, small tools)
- Phone (portion used for work), internet (portion), and software (subscriptions, cloud storage)
- Merchant/payment fees (Stripe, Square, PayPal, Etsy payment processing)
Why weekly? Because you will not remember Saturday night’s 47-mile run by Thursday; neither will your phone after an update. Small, boring, consistent beats heroic catch-up, every single time.
Mileage rules that actually matter: use the IRS standard mileage rate for the year you file. For 2024 the rate was 67.0¢/mile (IRS, 2024). If you’re filing a 2025 return next spring, you’ll use the 2025 rate the IRS announces, and yes, you can switch methods year to year if you qualify. Prefer actual costs (gas, insurance, depreciation)? Fine, but keep solid records for every vehicle expense. Most folks do better with standard mileage because it’s simpler and often richer if you rack up miles.
Home office and the “real” overhead: a legit, regular & exclusive workspace unlocks a home office deduction. You can use the simplified method ($5/sq ft up to 300 sq ft) or actual expenses (rent, mortgage interest, utilities) pro‑rated by business use. Add a reasonable slice of phone and internet. Equipment (camera, laptop, tools) goes on Form 4562 for depreciation; Section 179 may allow immediate expensing if your profit supports it. Document it or don’t bother, the numbers only help if they’re defensible.
Self‑employment tax, the part people forget until April: this is on net earnings (after expenses). For 2025, Social Security applies up to $174,900 of wages and self‑employment income (SSA, 2025). Medicare keeps going above that. The SE tax rate is 15.3% on most net earnings up to the Social Security cap (12.4% SS + 2.9% Medicare), then 2.9% Medicare after that; high earners also face the Additional 0.9% Medicare surtax at higher income levels. You only pay this on about 92.35% of your net (that’s the SE tax “base”), and half of the SE tax becomes an adjustment on your 1040. Confusing? Yep. But here’s the takeaway: expenses you track reduce SE tax, not just income tax.
What actually moves the needle?
- Mileage when you drive a lot (it can dwarf every other line
- Platform + merchant fees ) they’re constant, and they add up fast in Q4 promos
- Home office + phone/internet allocation (meaningful if you truly work from home
- Equipment with proper depreciation/179 ) one decent laptop or camera changes your tax picture
Cash control so taxes don’t ambush you: use a separate checking account for gigs and do a weekly sweep to your tax bucket. Simple rule of thumb: sweep 25%-30% of net (after expenses) for federal, then add your state rate. Are there edge cases? Sure, if you’ve got W‑2 wages with withholdings or you’re above the Social Security cap, your percentage can drop; we’ll hit quarterly estimates in a minute. Example: net $1,000 this week → move $250-$300 to taxes the same day the payout lands.
Q4 2025 reality check: holiday promos are pulling receipts into November, but platform fees and ad spends are spikier than usual. Don’t chase the spikes; record the gross, the fees, and the miles, then sweep your tax share. If you do that, January’s 1099s are just confirmations, not surprises, and your SE tax math will be boring, which is exactly what you want.
Minimum viable system: one gigs account, one tax bucket, a weekly 15‑minute ledger by gig (gross, fees, miles, supplies, phone/software, merchant fees). Keep receipts in a single cloud folder. No screenshots graveyard, that’s not a system.
Quarterly taxes without the headache: safe harbors and due dates
Here’s the sleep-at-night version. The IRS gives you two safe harbors that avoid most underpayment penalties: pay at least 100% of last year’s total tax, or 110% if your AGI was over $150,000 (married filing separately: $75,000). Or, pay 90% of this year’s total tax as you go. Hit one of those, and you’re largely out of the penalty woods even if your income bounces around. That’s the whole point, predictability over perfection.
Due dates you can tattoo on a sticky note: estimates for this year (2025) were due Apr 15, Jun 17 (because the 15th was a weekend), and Sep 15. The final 2025 estimate is due Jan 15, 2026. In a normal year it’s April, June, September, and January. If you file your 2025 return and pay the balance by Jan 31, 2026, you can usually skip that Jan 15 voucher, but only if your withholding and payments cover the tax for the year.
The simple year‑to‑date method (good for seasonal gigs): each quarter, project your full‑year profit based on what’s actually happened. Say by the end of September you’ve netted $36,000 and you expect Q4 to add another $12,000 because holiday promos are hot right now (they are, Q4 ad conversions are spiky this year). That’s a $48,000 annual profit estimate. Recompute your income tax and self‑employment tax on that number, then compare to what you’ve already paid year‑to‑date. Pay the difference with your September or January estimate. Yes, it’s a bit of math, but it stops you from wildly overpaying in slow quarters or underpaying when Q4 pops.
W‑2 withholding can do the heavy lifting: if you’ve got a day job, bumping your W‑4 withholding in Q4 is the cleanest way to catch up. Withholding is treated as if it were paid evenly throughout the year, which means it can cure earlier underpayments. Change the W‑4, increase withholding for a few paychecks, and it counts toward the same safe harbor. I’ve done this more times than I care to admit, Payroll is faster than the IRS payment portal when you’re trying to fix a shortfall late in the year.
Annualize with Form 2210 if you were light earlier this year: if your income is lumpy, spring was dead, but November/December are strong, you can use the annualized income installment method on Form 2210 to match tax to when you actually earned it. That can reduce or eliminate penalties even if your Q1 or Q2 payments were small. One caution: it’s paperwork, not magic. You still need support for the timing of those earnings.
Quick checklist to stay penalty‑proof:
- Hit a safe harbor: 100% (or 110% if AGI > $150k) of 2024 total tax, or 90% of 2025 tax.
- Know the dates: Apr 15, Jun 17, Sep 15, and Jan 15 (of the following year).
- Seasonal? Use the year‑to‑date method and recalc each quarter.
- Short on cash? Increase W‑2 withholding now; it backfills earlier quarters.
- Had uneven income? Consider Form 2210 annualization to reduce penalties.
Small clarification before we move on, because this trips people up: safe harbor is based on total tax, that’s the line that includes income tax and self‑employment tax. It’s not just the income tax piece. I know that sounds obvious, but I’ve seen seasoned freelancers miss it and underpay by the SE chunk. Expensive mistake.
Also, yes, the IRS adjusts underpayment interest rates quarterly, and they’ve been elevated the last two years. I won’t spam you with the decimal points because they change, but the direction is clear: paying late costs real money right now. With Q4 in full swing and ad CPMs jumping around, the combo of a weekly tax sweep plus a W‑4 tweak is the most painless way to land the Jan 15 payment without drama.
Bottom line: pick a safe harbor target, calendar the dates, and use payroll withholding as your shock absorber. If it got messy earlier this year, Form 2210 can soften the edges. Not perfect, just consistent, that’s the win.
Audit‑proof your deductions: receipts, mileage, and mixed‑use stuff
Keep what you can defend and ditch what you can’t. The IRS doesn’t hate deductions; it hates sloppy ones. My rule with clients: if you can show it, you can keep it. If you can’t show it, it’s a maybe at best, and maybe doesn’t survive an audit. And yes, there’s gray area; we just fence the gray with documentation.
- Receipts, but digital. Snap every business receipt and stash it in a folder or an app. Back it up to cloud + email. The IRS generally recommends keeping records at least 3 years (and up to 6 years if there’s a big income omission risk). I keep 7 for major stuff, overkill? maybe, but it’s easier than scrambling later.
- Mileage log that’s contemporaneous. Keep a log with date, business purpose, start and end odometer, and total miles. No retroactive guesswork in April. IRS Pub. 463 (2024) is clear: you need a contemporaneous log; re‑created logs are weak. If you use the standard mileage method, you can’t also deduct gas and depreciation on top, pick a method and stick it. With gas prices wobbling this fall and traffic up in Q4, miles are still gold if you track them right.
- Mixed‑use items: document the percentage. Phone, internet, car, only deduct the business percent you can defend. If your cell bill is $150 and you can document ~70% business use, deduct $105. If it’s really 50/50, then it’s 50/50. Be honest; rounding up isn’t a strategy, it’s a flag. For vehicles, if you choose actual expenses, apply your business‑use % to all costs (gas, insurance, repairs). If you choose standard mileage, that rate already bakes in most of that.
- Home office: exclusive and regular use. That corner of the dining table doesn’t qualify if your kids’ homework lives there at night. If it’s truly exclusive and regular, you’ve got two choices: the simplified method, $5 per square foot up to 300 sq. ft. (max $1,500), or actual expenses via Form 8829 (allocate mortgage interest/rent, utilities, etc.). My take: if you hate spreadsheets, the simplified method is plenty fine.
- Contractors: do the paperwork early. Pay a contractor $600 or more in a year? You generally need to issue a 1099‑NEC. Collect W‑9s before you pay them (you have use then). The 1099‑NEC is due to the IRS and the contractor by January 31. No EIN/SSN, no pay, sounds harsh, but it saves you from penalties.
- Report gross income; deduct fees separately. When platforms send 1099s, they’re usually reporting gross. Book your revenue gross and record platform fees, refunds, and chargebacks as expenses so your books tie to the 1099s cleanly. It’s the difference between a one‑email recon and a three‑week headache. Same idea, said differently: match their top‑line, take your fees below the line.
One more nuance I see with multi‑gig folks: each side gig can have different fee structures and 1099 timing. That’s fine. Just keep the source docs and reconcile gross for each stream. And yeah, it ain’t glamorous, but five minutes a week beats five days in February.
Quick guardrails: if you can’t explain it in two sentences and show a receipt or a log, don’t take it. If you can, take it confidently.
Lower the bill, legally: retirement, health, and QBI in 2025
This is the part of year-end that actually moves the needle for multi-gig folks: reduce taxable income without starving your cash. You’ve got three big levers right now, retirement, health, and the QBI deduction, plus some timing tricks that are old school but still work.
Retirement: Solo 401(k) or SEP-IRA
- Solo 401(k): If you want the most flexibility, this is usually my pick. You can put in an employee deferral (pre-tax) and an employer profit share. The catch: to make employee deferrals for 2025 income, you generally need the plan set up by 12/31 and elections in place before compensation is paid. Employer profit-share can typically be funded by your tax filing deadline (often to the extension date). I know, the setup timing trips people up every year.
- SEP-IRA: Dead simple, and you can both set it up and fund it by your filing deadline, including extension. It’s employer-only contributions, so usually a bit less juice than a Solo 401(k) if your net profit isn’t huge, but the procrastinator in me still loves the SEP for its late-game utility.
- Check the actual IRS limits for the year you’ll file. Dollar caps shift. Don’t guess. And if cash is tight right now, remember: you can prioritize your quarterly estimates and fund the retirement piece closer to filing. Cash first; deductions second.
Health: self-employed health insurance + HSA
- Self-employed health insurance deduction: If you’re not eligible for an employer plan, your premiums (medical, dental, some LTC) can reduce your AGI directly. That matters because it also feeds the ACA premium credit math. Folks miss this and overpay.
- HSA (with an HDHP): 2025 limits are $4,300 self-only and $8,550 family, with a $1,000 catch-up at 55+ (IRS, May 2024). HSAs are triple tax-advantaged and keep your cash flexible, use them now or let them grow. My take: if you already run an HDHP, the HSA is a no-brainer. If not, run the numbers; switching plans just for the HSA is case-by-case.
QBI: the 20% deduction is still here in 2025
The qualified business income deduction remains under current law for 2025: up to 20% of qualified pass-through income, subject to phase-ins, specified service trade/business (SSTB) limits, and W-2/wage/UBIA rules at higher incomes. Translation: dropping your taxable income with retirement or health moves can actually create or increase your QBI deduction. Watch interactions though, pre-tax retirement lowers QBI because it lowers business income. It’s a balancing act, not a dunk contest.
Year-end timing that still works (be consistent with your accounting method)
- Cash-basis? Delay invoicing a few big jobs by a week into January. Pull forward expenses you’d spend anyway: software annual plans, domain renewals, supplies. “Reasonably” is the operative word, no prepaying three years of stuff.
- Accrual-basis? Focus on recording liabilities and expenses you’ve incurred. Equipment you’ll actually use? Place it in service by year-end to tap depreciation. Section 179 and bonus rules still apply, check the current-year caps.
- Equipment: Buy what you’ll truly use. A camera body you’ll bill with? Sure. The third drone because it’s on sale? Probably not. Be able to explain it in two sentences.
Cash stress triage
- Pay your Q4 estimate first. Penalties are an easy own-goal.
- Calendar the retirement funding window: Solo 401(k) employer and SEP can be funded by filing deadline (SEP by extension). You can backfill when cash lands in late Q1.
Quick math guardrail
- Remember self-employment tax: 12.4% Social Security up to the 2025 wage base ($174,000 per SSA) + 2.9% Medicare, with the extra 0.9% at higher incomes. You deduct about half of SE tax above the line, which lowers AGI. Net effect on cash is around 7% less painful than the headline rate, give or take.
My two cents: Stack the easy levers, HSA + self-employed premiums, then use retirement to hit your target bracket. QBI is the cherry you improve after you see where the dust settles. And yep, screenshots and receipts now save you from “why did I do that?” in March.
Your year‑end game plan for multiple gigs (and a quick pep talk)
Alright, time to pull the threads together so April is just.. April. No midnight shoebox archaeology. In Q4 2025, start by reconciling your 2025 income against every platform dashboard you use, DoorDash, Etsy, Upwork, Stripe, PayPal, whatever’s in your mix. Export year-to-date earnings and payouts, then match them to your bank deposits. If a payout’s missing, open the ticket now while support still has holiday staffing. And while you’re in there, tag your expenses before 1099s show up in January: supplies, software, mileage, phone, internet, merchant fees. The IRS home office simplified method is still $5/sq. ft. up to 300 sq. ft. (max $1,500), easy and defensible when you’re short on time.
Set your final estimated payment for January 15 (the Q4 estimate). Quick guardrail math: combine your federal bracket with self-employment tax. For 2025, SE tax is still 12.4% Social Security up to the $174,000 wage base (SSA 2025) plus 2.9% Medicare, with an extra 0.9% Medicare surtax at higher incomes. You do deduct about half of SE tax above the line, so the net cash sting is a bit lower than the headline, call it roughly 7% less painful, like we said earlier. If you’ve been underpaying, bump the Q4 check to hit a safe harbor (generally 100% of last year’s total tax, or 110% if your 2024 AGI was over $150k). Not perfect for everyone, but it keeps penalties out of your hair.
Next, project your 2025 return with what you’ve got. A spreadsheet works, tax software works, a napkin with numbers and a coffee stain works in a pinch. Identify any last‑minute deductions you can genuinely justify: a needed laptop before year‑end, prepaid business insurance, professional dues, or catching up on HSA contributions if you were eligible. Don’t force it just to “use a deduction”, I’ve seen people buy gear they don’t need, then complain about cash in February. That’s not a strategy, that’s retail therapy with a 1099.
Autopilot for 2026: set a tax sweep that transfers a fixed percentage of net income every week into a separate high‑yield savings account. For most multi‑gig folks, 25-30% is a sane starting range; adjust if you’re in a higher bracket or have big QBI/retirement offsets. Given rates are still attractive at many online banks, think roughly 4-5% APY as we head through Q4, your tax cash can at least earn something while it waits. Add quarterly calendar reminders one week before each estimate due date so you’re not rushing a same‑day ACH that posts late (yes, I’ve done that, yes, it was annoying).
About 1099‑K in 2025: keep an eye on IRS updates for the 2025 tax year. The law still states a $600 threshold for third‑party network transactions, but the IRS has used transitional relief in recent years and signaled phased implementation (they floated $5,000 for 2024). Translation: the rulebook for who sends you a 1099‑K could tighten for 2025, or we get another phase‑in. If the $600 trigger fully applies, expect more forms in your mailbox from platforms that process payments, even if it’s mostly personal transactions or mixed activity, so reconcile now and don’t freak out if the forms look “high.” You report income correctly either way; the forms just drive matching.
One more practical thing I should’ve said earlier: back up your documentation. Screenshots of dashboards, CSV exports, bank statements, and a simple expense log. Tax prep gets messy when a platform changes its UI in February and the old reports vanish, happens more than you’d think.
And honestly, it’s okay that some of this has gray areas, allocating mixed‑use phone expense, deciding between actual vehicle costs vs mileage, choosing whether to accelerate income because your 2026 bracket might be higher if that new contract lands. That’s normal. Make a reasonable call, write down your method, and stick with it.
Pep talk: You’ve got this. Multiple gigs aren’t chaos; they’re a portfolio. When you bake taxes into the plan from day one, weekly sweeps, quarterly check‑ins, clean categories, you turn April into a formality and let the gigs fund real goals: debt payoff, a Solo 401(k), or that 3‑month cash buffer that lets you say “no” to the low‑margin work. And if something’s weird, okay, we adjust. That’s the job.
Frequently Asked Questions
Q: How do I figure out how much to set aside each week from multiple gigs?
A: Quick math: set aside 25%-35% of net profit (after expenses), start at 30% until you have three months of data, then fine‑tune. Park it in a money‑market, yields are still mid‑5% this fall 2025, so your tax stash earns while it waits.
Q: What’s the difference between income tax and self‑employment tax on my side gigs?
A: Two separate bites. Income tax is your normal federal (and state) bracket on your net profit. Self‑employment (SE) tax is 15.3% on most of your net earnings, 12.4% Social Security up to the annual wage base and 2.9% Medicare, with an extra 0.9% Medicare surtax if your combined wages/SE income tops $200k single ($250k joint). The SE tax calculation applies to 92.35% of your net earnings, not the full 100%, weird IRS quirk, but real. Translation: even if your income tax bracket is modest, SE tax still lands hard. That’s why a $1,000 net month isn’t really “free and clear.” Track expenses (mileage, software, gear, phone portion) to cut both taxes. Miss the deductions and you pay income tax + SE tax on dollars you didn’t actually keep. I’ve watched that mistake torch perfectly good Q4s.
Q: Is it better to make quarterly estimated payments or rely on the safe harbor and settle up in April?
A: Quarterlies are cleaner for cash flow and usually cheaper. The IRS safe harbor keeps you out of penalties if you pay in the smaller of: 90% of this year’s total tax, or 100% of last year’s tax (110% if your AGI was over $150k). That avoids penalties, but not the giant April bill. With multiple gigs, I’d do both: auto‑transfer 25%-35% of net to a high‑yield savings and send estimated payments each quarter. If you had a big income jump in 2025, relying on last year’s tax can still leave you underpaid and stressed in April. Quarterlies smooth it out and earn interest while you wait. I tell clients: penalty avoidance is step one; avoiding the April cash crunch is step two.
Q: Should I worry about underpayment penalties if most of my side‑gig income hits in Q4 this year?
A: Yes, but you can manage it. The IRS expects you to pay as you go. If your income is lumpy (hello, holiday surge), use the “annualized income” method on Form 2210 to match payments to when you actually earned the money. Example: Say Jan-Aug net profit was $6k, Sep-Oct jumps $12k, and Nov-Dec adds $18k. Instead of pretending it was even all year (which triggers penalties for Q1-Q3), you annualize: smaller or zero payments earlier, then larger ones in September and January when the income arrives. Practical playbook:
- Keep a weekly set‑aside of 30% of net in a separate account.
- After each spike month, make a mid‑quarter payment online at IRS Direct Pay, don’t wait for the formal due date if cash is in hand.
- If you also have W‑2 wages, ask payroll to jack up withholding for Nov-Dec; withholding is treated as paid evenly all year, which can erase penalties.
- File Form 2210 with the annualized schedule to document it. I’ve used this exact combo for late‑year earners in 2025, and it works.
@article{how-to-pay-taxes-on-multiple-side-gigs-without-shock,
title = {How to Pay Taxes on Multiple Side Gigs (Without Shock)},
author = {Beeri Sparks},
year = {2025},
journal = {Bankpointe},
url = {https://bankpointe.com/articles/pay-taxes-multiple-side-gigs/}
}
