Don't panic! You absolutely can handle this on your own, especially for your first year. I was in the exact same situation when I started contracting - couldn't find an accountant anywhere and was totally overwhelmed. Here's what I wish someone had told me when I started: **Start simple:** You don't need to figure out S-corps or LLCs right away. Just focus on tracking your income and expenses properly this first year. You can always form an entity later once you understand your income patterns. **Essential first steps:** - Open a separate business checking account (makes everything cleaner) - Start tracking ALL business expenses immediately - home office, internet, phone, computer equipment, software subscriptions, etc. - Set aside 25-30% of every payment for taxes in a separate savings account - Make quarterly estimated tax payments (due dates are Jan 15, April 15, June 15, and Sept 15) **Marriage question:** Don't make major life decisions based on taxes alone! The marriage penalty/benefit depends on both your incomes, so run some scenarios with tax software first. For your first year, I'd recommend using TurboTax Self-Employed or FreeTaxUSA. They're designed for 1099 contractors and will walk you through everything. You can always upgrade to an accountant next year once you have a full year of data and know what questions to ask. You've got this! The first year feels overwhelming, but it gets much easier once you establish good systems.

I completely understand the panic - I went through the exact same thing when I transitioned to 1099 work two years ago! The good news is that while an accountant is definitely helpful, it's not absolutely essential, especially for your first year. Here's my practical advice for getting started: **Immediate priorities:** - Open a separate business bank account ASAP (makes tracking so much cleaner) - Start tracking every business expense from day one - dedicated workspace, internet, phone, equipment, software, professional development - Set aside 35-40% of each payment for taxes (federal + state + self-employment tax) - Sign up for quarterly estimated tax payments to avoid penalties **The S-corp question:** Don't stress about this yet. Generally only worth considering once you're consistently making $80K+ annually. The administrative costs and complexity usually outweigh benefits below that threshold. **Marriage decision:** Never make major life decisions purely for tax reasons! Run some scenarios with tax software to see the actual impact, but remember the "marriage penalty" varies greatly based on both partners' incomes. For your first year, I'd recommend starting with TurboTax Self-Employed or FreeTaxUSA - they're designed specifically for contractors and will guide you through everything. You can always hire an accountant next year once you have a full year of data and better understand your specific situation. The first year feels overwhelming, but you absolutely can handle this! Focus on good record-keeping habits now, and everything else will fall into place.

This is such a helpful thread! I'm dealing with a similar situation but with a twist - I have two roommates who each pay different amounts ($700 and $500) because one has the larger bedroom. Do I need to calculate separate percentages for each roommate's space, or can I just use the total amount they pay ($1,200) against the total percentage of the house they occupy together? Also, if I'm reporting this on Schedule E, do I need to treat this as two separate rental activities or can I combine it all as one rental income source? I'm using a 4-bedroom house where I occupy one bedroom and they occupy the other two, plus we all share common areas. Thanks for all the great advice in this thread - definitely going to look into some of the tools mentioned here!

Great question about handling multiple roommates with different payment amounts! You can definitely combine both roommates into one rental activity on Schedule E - there's no need to treat them as separate rentals since they're both part of the same property. For calculating the percentage, you'll want to base it on the total square footage that both roommates use combined. So if your two roommates together occupy 50% of the house (their bedrooms plus their proportional share of common areas), you'd use 50% as your deduction percentage against the total $1,200 monthly income they pay. The fact that they pay different amounts doesn't affect the calculation - what matters is the total space they occupy versus the total rental income you receive. You'll report the combined $14,400 annual income ($1,200 × 12) on Schedule E and deduct the same percentage of your eligible expenses against that total. This is actually a pretty common scenario, and the IRS is used to seeing single-property rentals with multiple tenants paying different amounts. Just make sure to keep good records of all payments received from both roommates and maintain documentation of your square footage calculations for your deduction percentage.

This has been such an informative thread! I'm in a similar situation with my freelance graphic design LLC and was making the same mistake of thinking I could somehow bypass taxation by contributing directly from my business account. Just to summarize what I've learned here for anyone else reading: You MUST pay yourself from the LLC first, pay taxes on that income, and then use the after-tax dollars for Roth contributions. There's no way around this - the IRS requires Roth contributions to come from properly reported earned income. The Solo 401(k) with Roth option sounds like the best path forward for those of us with LLCs making decent income. Being able to contribute up to $23,500 in Roth money (plus potentially more in traditional contributions) versus just $7,000 with a regular Roth IRA is a huge difference for retirement planning. One question I still have - if I set up a Solo 401(k), can I still contribute to my existing Roth IRA in the same year, or do I have to choose one or the other? I've had my Roth IRA for about 8 years and would hate to lose that 5-year clock if possible.

This thread has been incredibly helpful! I'm a tax attorney who works with a lot of small business owners, and I wanted to add a couple of important points that might save people some headaches: First, regarding the S-Corp election discussion - there's a "reasonable salary" requirement that the IRS takes seriously. If you elect S-Corp status, you MUST pay yourself a reasonable W-2 salary for the work you perform, even if it means higher payroll taxes. You can't just pay yourself $20k salary and take $70k in distributions to avoid payroll taxes. The IRS has been cracking down on this, and penalties can be severe. Second, for those considering Solo 401(k)s, remember that if you ever hire employees (even part-time), you'll generally need to include them in the plan, which can get expensive and complicated. A SEP-IRA might be a better choice if you think you'll expand your team. Finally, I'd strongly recommend working with a qualified tax professional before making major changes to your business structure or retirement strategy. The tax code is complex, and what works for one person's situation might create problems for another. The services mentioned in this thread (like taxr.ai) might be helpful for analysis, but they shouldn't replace professional advice for significant decisions. Great discussion overall - it's refreshing to see people taking retirement planning seriously!

3 has anyone dealt with the 1098-T form in this situation? my daughter's school sent her the form with HER ssn on it since she's the student, but if i'm claiming her and the education credit, do i need to somehow get that form reissued to me? how does this work with electronic filing?

This is such a helpful thread! I'm in a similar situation with my college sophomore who paid about $12,000 in tuition from her summer job earnings. One thing I learned from my tax preparer last year is to keep really detailed records of what you're paying for your kids' support - not just the big things like housing and health insurance, but also groceries, phone bills, car insurance, etc. The IRS "more than half support" test includes ALL living expenses for the year. I created a simple spreadsheet tracking what I pay vs what she pays, and it was eye-opening. Even though she paid her own tuition, I was still covering about 65% of her total support costs. This documentation gave me confidence to claim her as a dependent and take the American Opportunity Credit on my return. The key is looking at TOTAL support for the year, not just who paid the biggest single expense. Tuition might be the largest line item, but when you add up housing, food, insurance, transportation, etc., parents often still provide the majority of support even for working college students.

Just to share my experience - I had a similar situation last year with small amounts from different gig apps. I reported everything and it was totally fine. Used the Schedule C and listed each company separately. It's not worth risking an audit or penalties just to save a little bit on taxes!

Just wanted to add my perspective as someone who went through this exact situation last year! I had small amounts from multiple gig apps too - around $800 total spread across three different platforms. I initially thought I could skip reporting the really small amounts (like a $60 payment from one app), but after doing some research and talking to a tax preparer, I learned that ALL income needs to be reported regardless of amount. The $400 threshold people mention only applies to whether you owe self-employment tax, not whether you need to report the income at all. The good news is that reporting multiple small gig incomes isn't as complicated as it sounds. You can combine similar gig work (like all your delivery driving) on one line of Schedule C, or list them separately if you prefer to keep better records. Just make sure to keep track of your business expenses - even small things like phone chargers, car air fresheners, or parking fees can add up to meaningful deductions! One tip: start keeping better records now for next year. I use a simple spreadsheet to track income from each app and take photos of any business-related receipts. Makes tax time so much easier!