I've been helping people navigate cash income tax situations for years, and you're definitely on the right track by setting aside 30% and asking the right questions early. Here are a few additional tips that might help: First, consider getting an EIN (Employer Identification Number) for your landscaping work, even as a sole proprietor. It's free from the IRS website and makes you look more legitimate as a business entity. You can still file on Schedule C, but having an EIN gives you more credibility and separates your business identity from your personal SSN on some forms. Second, look into opening a Solo 401(k) or SEP-IRA once you're established. As self-employed, you can contribute a significant percentage of your earnings to retirement accounts, which reduces your current tax liability while building for the future. This is one of the few advantages of being self-employed vs. being a W-2 employee. Third, keep detailed records of any training, licensing, or certification costs related to landscaping. These are fully deductible business expenses that many people overlook. Same goes for work-related phone calls, internet usage for scheduling/communication, and even a portion of your home if you use it for business planning or storage. The most important thing is to stay consistent with your record-keeping from this point forward. The IRS respects taxpayers who make good faith efforts to comply, even if the situation isn't perfect. You're already ahead of most people just by thinking about this proactively.

Rachel, you're being incredibly responsible by setting aside 30% and thinking about this proactively! One thing I haven't seen mentioned yet that might be relevant to your specific situation as a landscaper - if you're providing your own equipment (mowers, trimmers, hand tools, etc.), those are legitimate business deductions that can significantly reduce your tax burden. Also, since landscaping is seasonal work in many areas, you might want to consider whether your income varies significantly throughout the year. If so, you could potentially benefit from income averaging strategies or at least plan your quarterly estimated payments around your peak earning periods. The advice about Schedule C and treating yourself as self-employed is spot on. Just make sure to keep receipts for everything work-related - fuel for equipment, replacement tools, work boots, even sunscreen if you're outside all day. The IRS allows deductions for ordinary and necessary business expenses, and landscaping has quite a few of those. One last tip: if your boss ever decides to start issuing 1099s in the future, make sure your reported income aligns with what you've been filing. Consistency in reporting is key to avoiding red flags.

Just wanted to add that you should also consider opening a dependent care FSA through your employer if they offer one! Since you mentioned daycare costs might come up, you can set aside up to $5,000 pre-tax to pay for childcare expenses. This would reduce your taxable income and save you money on both federal and state taxes. Also, if your girlfriend does go back to work at some point during the tax year, make sure you recalculate who's providing more than half the support. The IRS looks at the total support provided for the entire year, not just while she wasn't working. But based on your income level and the fact that you're covering all major expenses, you should still easily meet the support test even if she has some part-time income later. Keep all those receipts and records that others mentioned - they're super important if you ever get audited on the Head of Household status!

Having a new baby definitely counts as a qualifying life event! You should be able to enroll in a dependent care FSA within 30 days of the birth. Contact your HR department ASAP since there's usually a strict deadline for making changes after a qualifying event. One more tip - if you do end up adding your baby to your employer's health insurance plan, make sure to compare the total costs carefully. Sometimes the premium savings from having the baby on Medicaid vs. your employer plan can be significant, but you might also miss out on additional tax benefits like being able to use a health savings account (HSA) if your employer offers a high-deductible health plan with HSA eligibility. Also, don't forget that if you do pay for your baby's health insurance through your employer, those premiums are typically paid with pre-tax dollars, which reduces your taxable income even further. Just another factor to consider in your overall financial planning!

Has anyone tried a "summarized" approach with an explanatory statement? My CPA did this for me last year when I had a similarly complex situation. Instead of reporting 70+ individual lines, we: 1. Reported one summary line for covered securities on 8949 Box A 2. Reported one summary line for non-covered securities on 8949 Box B 3. Attached a detailed statement showing all calculations The key was making sure the totals matched what would have been reported if done line-by-line. The statement included all individual transactions and wash sale calculations. My CPA said this is an acceptable approach as long as the detailed backup is included.

I dealt with a very similar RSU/ESPP wash sale situation two years ago and ended up going the summary route after consulting with a tax attorney. Here's what I learned from that experience: The IRS actually has guidance in Publication 550 that allows for "adequate identification" of securities transactions, which can include summary reporting when individual line reporting becomes impractical. The key requirements are: 1. Total accuracy - your summary must produce identical results to line-by-line reporting 2. Complete documentation - maintain detailed records showing all calculations 3. Clear explanatory statement attached to your return What made my situation work was creating a comprehensive worksheet that tracked every single transaction chronologically, identified all wash sale periods, and showed how losses were disallowed and basis was adjusted through each chain. Then I reported two summary lines (one for covered, one for non-covered) with the final adjusted numbers. The explanatory statement was about 3 pages and included a transaction summary table, wash sale calculation methodology, and the specific rule citations I was following. My tax attorney emphasized that showing your work is more important than the format you use to report it. Been audited once since then (unrelated issue) and the IRS examiner actually complimented the clarity of the wash sale documentation. Sometimes being thorough and organized trumps following the "standard" approach when that approach becomes unmanageable. Just make sure you're confident in your calculations before summarizing - any errors get magnified when you're not reporting line-by-line.

Accountant here. Many employers mess up state withholding after employee relocations. The W2C may take months - I've seen them take until August or September in some cases! If you're getting a refund, file now and amend later. If you'd owe money, definitely file an extension and wait for the W2C. The April deadline is about PAYING not filing - as long as you pay what you owe, the extension to file is automatic and penalty-free.

I'm dealing with almost the exact same situation right now! Moved from Massachusetts to Florida in late 2023, and my employer kept withholding MA state taxes for months after I relocated. The frustrating part is that Massachusetts has a 5% flat rate while Florida has no state income tax, so I've been massively overpaying. Based on what everyone's shared here, I think I'm going to go ahead and file my return as-is this week. The math works out that I'll get a substantial refund just from the federal side, and then when I finally get my W2C (whenever that happens), the Massachusetts refund will just be a nice bonus later in the year. Has anyone had experience with Massachusetts specifically for this type of amendment? I know some states are more complicated than others when it comes to part-year resident returns and corrected withholding.

I can really relate to your situation! I was in almost the exact same boat when I started my tax internship last year - I had basically no practical tax knowledge despite taking accounting classes. Here's what really helped me get through those first few weeks: First, don't underestimate the value of your tutoring and communication experience. Those skills transfer really well to tax prep because you'll be explaining concepts to clients and asking clarifying questions. The ability to break things down simply is huge in this field. For immediate preparation, I'd recommend starting with the IRS's basic taxpayer education materials rather than jumping into complex professional resources. The "Understanding Taxes" section on irs.gov has interactive lessons that explain concepts without being overwhelming. Also, YouTube channels like "Professor Farhat Accounting Lectures" have great beginner-friendly tax videos. Here's something nobody told me: bring a small notepad and pen everywhere during your first week. Write down every acronym, form number, or process someone mentions. Tax work has SO much jargon, and having your own reference will help you follow conversations better. Most importantly, remember that your firm chose you for a reason, even if your transcript wasn't perfect. They saw potential in you. Focus on being reliable, asking thoughtful questions, and showing genuine interest in learning. Those qualities matter way more than coming in with existing knowledge. You're going to do better than you think - the fact that you're already seeking advice shows you have the right mindset for success!

Hey Dylan! I totally get the panic you're feeling - I was literally in your exact shoes two years ago. Zero practical tax knowledge, accounting classes I barely remembered, and somehow landed an internship I felt completely unqualified for. Here's the truth: you're going to be fine. Tax firms hire interns precisely because they expect to train you from scratch. They want teachability over existing knowledge every single time. My crash course strategy was simple: I spent one weekend learning Form 1040 line by line (just understanding what goes where, not memorizing), then focused on the most common supporting documents - W-2, 1099-NEC, 1099-INT, Schedule A basics. The IRS website has great plain-English explanations for all of these. But honestly? Your tutoring background is going to be your secret weapon. Tax prep is mostly about asking the right questions, listening carefully, and explaining things clearly - skills you already have. When a client hands you a stack of documents, you'll know how to organize information and ask clarifying questions. Start with IRS Publication 17 (free download) - it explains everything in taxpayer-friendly language rather than technical jargon. Practice filling out a basic 1040 with a W-2 scenario you find online. That's literally 80% of what you'll see as an intern. Most importantly: ask questions constantly, take detailed notes, and never pretend to know something you don't. The supervisors who trained me said the worst interns were the ones who nodded along pretending they understood everything. You've got this! The fact that you're preparing ahead already puts you miles ahead of most interns.