Sometimes I've found that withholding a bit extra from my W-2 job is easier than dealing with quarterly payments for small self-employment income. You can file a new W-4 with your employer and just add an additional amount to be withheld from each paycheck. Way less paperwork than tracking and submitting quarterlies.

Just wanted to add another perspective for anyone in a similar situation - if your side gig income is truly inconsistent like yours, consider keeping a simple monthly tracking spreadsheet. I learned this the hard way when my freelance writing income jumped unexpectedly one quarter and I suddenly owed way more than expected. What I do now is track my monthly self-employment income and multiply by 15.3% (self-employment tax rate) plus my marginal tax rate to estimate what I should be setting aside. If I hit the point where I'm on track to owe more than $1,000 for the year, I either make a quarterly payment or increase my W-2 withholding like others mentioned. The inconsistency actually works in your favor right now since you're staying under the thresholds, but having a system in place will save you stress if your income grows. Better to be prepared than scrambling to catch up on payments later!

As someone who's been living abroad for over 5 years, I want to emphasize how important it is to start planning your tax situation BEFORE you move. The complexity increases significantly once you're already established overseas. A few additional points that might help: 1. **State tax obligations** - Don't forget about your home state! Some states like California are notoriously aggressive about claiming you're still a resident for tax purposes even after you move abroad. Make sure you properly establish non-residency before leaving. 2. **Social Security and Medicare** - If you're paying into foreign social systems, understand how this affects your US Social Security benefits. Some countries have totalization agreements that can help, but others don't. 3. **Keep meticulous records** - Save everything! Foreign tax documents, proof of residence, bank statements, employment contracts. The IRS can ask for documentation going back several years, and getting copies of foreign documents later can be expensive and time-consuming. 4. **Consider professional help for your first year** - Even if you use AI tools or try to DIY later, having a qualified international tax professional handle your first year abroad can help you establish the right foundation and avoid costly mistakes early on. The good news is that once you understand the system and establish your filing routine, it becomes much more manageable. But those first couple of years can be overwhelming if you're not prepared.

One crucial aspect that hasn't been covered yet is the timing of when you establish foreign residency for tax purposes. The IRS uses different tests than many foreign countries to determine residency, which can create gaps or overlaps in your tax obligations. For example, if you move to Canada mid-year, you might be considered a Canadian resident from the date you arrive, but still a US resident for the entire tax year under the substantial presence test. This means you could have dual residency status and owe full taxes to both countries for that transition year. To minimize this issue, plan your move for early in the tax year if possible, and research both countries' residency rules carefully. Some countries have tie-breaker rules in their tax treaties that can help resolve dual residency situations, but you need to understand how to properly apply them. Also, don't forget about estimated tax payments. If you're earning foreign income that isn't subject to US withholding, you may need to make quarterly estimated payments to avoid penalties, even if you'll ultimately owe nothing after applying the foreign earned income exclusion or foreign tax credits. The transition year is often the most complex from a tax perspective, so extra planning and possibly professional guidance for that year can save you significant headaches and money.

Columbus TAC has limited walk-ins. Tuesdays best. Arrive by 8AM. Bring two forms of ID. Have all documents organized. Expect 3+ hour wait even if accepted. No guarantee you'll be seen. Better to call for appointment. No cell phones allowed inside. No food or drinks. Parking is $10 nearby. Security is strict about what you can bring in.

I had a very similar dependent verification issue last month and ended up going to the Columbus TAC as a walk-in. Here's what worked for me: I arrived at 7:45 AM on a Wednesday (before they officially opened) and was about 8th in line. They have a paper sign-in system now that starts around 8:15 AM. The triage staff member was actually quite helpful - she reviewed my documentation and determined my case could be handled that day. Total time was about 4 hours from arrival to resolution, but they completely sorted out my dependent verification and even helped me understand why the online system had rejected my documentation. Pro tip: bring snacks and a phone charger if you go this route, and make sure you have certified copies of birth certificates, not just regular photocopies. The staff really know their stuff once you get past the access barriers.

Just went through a very similar NSO exercise situation with Carta last month, so I feel your pain on that 37% withholding rate! While it does feel steep upfront, I learned a few things that might help with your decision: First, that withholding rate is indeed standard for supplemental wages over certain thresholds - Carta has to follow IRS requirements and doesn't have much flexibility there. But the good news is that this is essentially an advance payment on taxes you'll owe anyway, so if you're over-withheld, you'll get it back as a refund. One thing that really helped me was calculating my total tax liability for the year including the NSO income, then comparing that to my total withholdings (regular payroll plus the NSO withholding). In my case, I was actually slightly over-withheld, which meant I didn't need to worry about underpayment penalties and would get a small refund. Also consider that the $15,300 in withholding covers not just federal income tax, but also FICA taxes that you'd owe regardless. The Social Security and Medicare portions ($6.2% + $1.45% = $7.65%) alone account for about $3,100 of your total withholding, which leaves roughly $12,200 for federal and state income taxes on $41,250 of income - that's actually closer to a 29% effective rate on just the income tax portion. If cash flow is your main concern, definitely ask your company about same-day sale options or whether you can exercise in smaller batches over time.

The withholding rates you're seeing are unfortunately standard for NSO exercises through automated platforms like Carta. As others have mentioned, the 37% total isn't negotiable since it follows IRS supplemental wage requirements. However, here's something that might help with your decision-making: since you're exercising a relatively large number of shares ($41,250 in taxable income), you should definitely consider the timing implications. If this significantly increases your tax bracket for the year, splitting the exercise could save you substantial money. Also, don't forget about the AMT implications - while NSOs don't trigger AMT at exercise like ISOs do, the large income addition could affect your overall AMT calculation if you have other preference items. One practical tip: before you commit to the full exercise, run a quick calculation of your total tax withholding for the year (regular payroll + NSO withholding) versus your estimated tax liability. Many people find they're actually over-withheld when they do this analysis, which can provide peace of mind about the upfront cost. If you're still concerned about cash flow, definitely explore the batched exercise option with your company. Even if the withholding rates stay the same, spreading it over 2-3 transactions can make the cash impact much more manageable.

One thing nobody's mentioned - you might be able to avoid this issue entirely in the future by using Venmo Business Profile instead of a personal account. It charges a small fee but it's specifically designed for business transactions and gives you better record-keeping options.

Just want to add my perspective as someone who went through this exact situation! I'm a freelance web designer and made the same mistake using personal Venmo for client payments in my first year. I was panicking about whether I could deduct my subcontractor expenses. The good news is that you're totally fine to claim these as business expenses. The IRS cares about the substance of the transaction, not the payment method. Keep your Venmo records showing the business purpose in the payment descriptions, and consider creating a simple spreadsheet that lists each payment with details about what work was performed. One tip that really helped me - I went back and asked each freelancer to send me a brief email confirming what services they provided and when. This created additional documentation beyond just the Venmo transactions. It was awkward to explain but everyone was understanding once I said it was for tax compliance. Also definitely switch to Venmo Business or a proper business bank account going forward. The fees are worth it for the cleaner record-keeping and professional appearance. You've got this - it's a common mistake and easily fixable!