Hey Lucas! I totally get the stress of trying to catch up on back taxes - been there myself. One thing that really helped me was creating a simple spreadsheet to track all my missing documents and the different methods I was trying. That way I didn't duplicate efforts or forget which employers I'd already contacted. For those old employers, even if the restaurant closed down, try searching online for the company that owned it or check with your state's business registration database. Sometimes they'll have forwarding contact info for payroll companies that handled their records. Also, don't forget to check if you have any old pay stubs lying around - those can help you calculate the info you need even without the actual W-2. The IRS transcript route that Harper mentioned is definitely your most reliable backup plan. Just a heads up though - when you do start filing those back returns, consider doing them in chronological order (oldest first) since some years might affect others. Good luck getting everything sorted out! Your partner sounds like a keeper for pushing you to get this handled.

Lucas, I feel you on this situation! I went through something similar when I moved states and lost track of several years of tax documents. Here's what worked for me: First, definitely start with the IRS Wage and Income Transcript like Harper mentioned - it's free and gives you all the key numbers you need. But here's a pro tip: if you're planning to file multiple years at once, consider getting a tax professional involved. They can help you navigate any penalties and potentially get some of them waived, especially if this is your first time being delinquent. For the employers that might be out of business, try checking with the state's Department of Labor or equivalent agency. They sometimes maintain records of businesses that have closed and can point you to who might have the payroll records now. One more thing - if you end up owing money from those back years, don't panic about paying it all at once. The IRS has payment plan options that are way more reasonable than people think. Getting into compliance is the most important step, and it sounds like you're already on the right track by taking action now instead of continuing to put it off. Your partner definitely has the right idea encouraging you to get this sorted - it'll be such a relief once it's behind you!

One option I haven't seen mentioned yet - your brother could file Form 2848 (Power of Attorney) to authorize a tax professional to act on his behalf. This might be worth the cost because tax pros often have access to dedicated practitioner priority service lines at the IRS that have much shorter wait times. A good enrolled agent or CPA who deals with payroll tax issues could likely get this resolved much faster than trying to navigate it alone. They can request the PIN reissuance, update the address, and even negotiate a payment plan with more favorable terms than what's typically offered through automated systems.

Your brother should also consider calling the IRS Federal Tax Deposit Processing Center directly at 1-800-555-4477. This is a specialized line specifically for EFTPS and federal tax deposit issues, separate from the general business tax line. They may be able to expedite his PIN replacement or provide alternative solutions. In the meantime, he should document everything - keep records of all calls, dates, reference numbers, and any correspondence. This documentation will be crucial if he needs to request penalty abatement later or if he ends up working with the Taxpayer Advocate Service. Also, make sure he's still filing his quarterly employment tax returns (Form 941) even if he can't make the payments yet. Filing on time, even without payment, can help reduce some penalties and shows good faith compliance efforts to the IRS. The key is to act quickly on multiple fronts - try the specialized phone line, consider the Form 8109 option mentioned earlier, and start documenting his efforts to resolve this. The IRS is generally more willing to work with taxpayers who are proactive about resolving issues rather than those who just ignore them.

As someone who's been in tax for over 20 years, I'd strongly recommend starting with the CPA route. Here's why: the barrier to entry is lower, you'll start earning income sooner, and you'll get real-world experience that will make you a better professional regardless of whether you later add a JD. I've seen too many people go straight to law school without understanding what tax work actually entails day-to-day. The CPA path gives you that foundation. Plus, many employers will help fund law school if you decide to pursue it later - but they rarely help fund CPA programs for attorneys. One thing I'll add that others haven't mentioned - consider your personality type. CPAs tend to work more collaboratively with clients on planning and compliance. Tax attorneys often deal with more adversarial situations - audits, disputes, litigation. Both are valuable, but think about what energizes you more. The money will come with either path if you're good at what you do. Focus on which type of work excites you more, and don't underestimate the value of getting into the workforce sooner rather than later. You can always add credentials, but you can't add back years of experience.

This is such a great discussion! As someone currently working as a CPA in tax, I wanted to add another angle - consider the type of clients you want to work with long-term. If you're drawn to working with individuals and small businesses on planning and compliance, the CPA route is probably your best bet. But if you're more interested in complex corporate transactions, high-net-worth estate planning, or tax controversy work, you might find the JD opens more doors. One thing I've noticed is that having both credentials can really set you apart, especially in boutique tax practices or if you want to start your own firm someday. Clients love knowing their advisor can handle both the technical tax work AND represent them if issues arise with the IRS. My advice? Start with the CPA since you're already so close to having the credits. Get 2-3 years of solid experience, then reassess. You'll have a much clearer picture of what specialized areas interest you most, and you'll be in a better position to make law school financially viable. Plus, you might find that the CPA path gives you everything you're looking for career-wise. Good luck with whatever you decide - both paths can lead to rewarding careers in tax!

Anyone know which specific TurboTax version I need to handle business equipment like this? I'm using the Deluxe version now but wondering if I need to upgrade to handle depreciation properly.

Great question! I went through something similar last year with my consulting business. One thing I learned the hard way is to keep detailed records of the business use percentage for each item, especially for mixed-use items like your phone and laptop. For TurboTax, you'll want to create a simple spreadsheet tracking: - Purchase date and amount for each item - Business use percentage (be realistic - the IRS can audit this) - Which depreciation method you chose and why The furniture situation is interesting because at $8,200, you're getting into territory where the depreciation vs. Section 179 choice really matters. Since you mentioned this is a side gig, consider whether you expect your income to grow next year. If so, spreading the furniture depreciation over time might give you deductions when you're in a higher tax bracket. Also, don't forget about the home office deduction if you're using a dedicated space! The furniture could support that claim. TurboTax Self-Employed (which you'll need for proper business asset handling) has a good workflow for calculating this. One last tip - take photos of your setup and keep all receipts. The IRS loves documentation for business asset claims, especially for home-based businesses.

Has anyone tried adjusting their W-4 to increase withholding on just one person's paycheck instead of both? My wife and I found it easier to have extra withholding from just the higher income so we could better track it, rather than messing with both paychecks.

One strategy that's worked really well for us is maxing out HSA contributions if you have access to a high-deductible health plan. It's triple tax-advantaged (deductible going in, grows tax-free, tax-free withdrawals for medical expenses) and can really help reduce your taxable income. With two kids, you probably have plenty of medical expenses to justify it. Also, don't overlook the Child and Dependent Care Tax Credit - it phases out at higher incomes but you might still qualify for some benefit. And if your employer offers dependent care FSA, you can set aside up to $5,000 pre-tax for childcare expenses. For the side income withholding issue, consider setting up a separate business checking account and automatically transferring 25-30% of each payment into a "tax savings" account. Then make quarterly estimated payments from there. It helps psychologically because you never see that money as "yours" to spend.