Has anyone used TurboTax to report a business sale? I'm trying to figure out if the self-employed version can handle this or if I need to upgrade to their business version?

I just went through this exact same situation when I sold my consulting firm last year. The key thing that helped me was understanding that you need to treat this as an asset sale, not a stock sale, which means each component of your business gets reported differently. For your client list and goodwill (the intangible value you built up over 8 years), these qualify as Section 197 intangibles and should be reported on Form 4797 Part I since you held them for more than a year. This gives you long-term capital gains treatment, which is much better than ordinary income rates. The installment sale aspect is important too - you'll definitely need Form 6252 to report the payments you'll receive over the next two years. This lets you spread out the tax liability rather than paying it all upfront on the 70% you received. One thing that caught me off guard was Form 8594 (Asset Acquisition Statement) - both you and the buyer need to file this with consistent asset allocations. Make sure your purchase agreement specifies how the sale price is allocated across different asset categories, or you might run into issues later. I'd strongly recommend getting professional help for this if you can. The classification of assets can make a huge difference in your tax bill, and there are specific rules about what qualifies for capital gains vs ordinary income treatment that aren't always intuitive.

This is such helpful information for anyone navigating early Social Security benefits! I'm 64 and went through this same confusion last year. One thing I'd add is to keep really good records of all your income sources. When I had my annual review with SSA, they wanted documentation showing the difference between my earned income (from a small consulting gig) versus my unearned income (dividends, capital gains, etc.). Also, if you're planning to do any freelance or consulting work, make sure you understand the self-employment rules. Even small amounts of self-employment income count toward that earnings limit, and you might owe self-employment taxes on top of regular income taxes. @1acc35497938 For your specific situation with stock dividends and capital gains - you're in the clear! Those won't affect your SSA payments at all. Just watch out if you decide to do any paid work or consulting on the side.

This thread has been incredibly helpful! I'm 63 and in a similar situation with dividend income and was worried I'd have to sell fewer stocks to avoid reducing my benefits. It's such a relief to know that investment income doesn't count toward the earnings limit. One thing I want to emphasize for anyone reading this - make sure you understand your full retirement age (FRA). For most of us born in the late 1950s and early 1960s, it's somewhere between 66 and 67. The earnings limits and penalties only apply BEFORE you reach your FRA. Once you hit that magic birthday, you can earn unlimited amounts without any reduction to your Social Security benefits. I'd also recommend checking your Social Security statement annually at ssa.gov to make sure they're calculating your benefits correctly and have accurate records of your earnings history. Catching errors early can save a lot of headaches later. Thanks to everyone who shared their experiences - it's made this whole process much less stressful!

Has your year-to-date income reached a new tax bracket threshold? The withholding calculation can suddenly jump when you cross into a new bracket since the system thinks your annual income will be higher.

I went through something very similar last year and it turned out to be a combination of factors. First, definitely check with HR about your W-4 - but also ask them specifically about any recent payroll system updates or migrations. Many companies switched payroll providers in 2024-2025 and during these transitions, employee withholding settings often get reset to default values (usually zero allowances, which maximizes withholding). Also, make sure to get a copy of your current W-4 on file and compare it to what you remember submitting. Sometimes during system migrations, the data doesn't transfer correctly and you end up with completely different withholding settings. One more thing - if you're paid bi-weekly, some payroll systems will annualize your income based on recent pay periods that included bonuses or overtime, which can temporarily bump you into higher withholding calculations even after the bonus period ends. This usually corrects itself after a few pay cycles, but it's worth asking HR about. The good news is that if this is an employer error, they should be able to fix it quickly for future paychecks. And like others mentioned, any excess withholding will come back to you as a larger refund next year, though I know that doesn't help with your immediate cash flow situation.

Has anyone used TurboTax to handle their Solo 401k deductions? I'm trying to figure out if their self-employed version walks you through this correctly or if I need to manually enter things somewhere.

I just went through this exact process when I set up my Solo 401k last year! The confusion about where to report it is totally understandable - I made the same mistake initially. Just to reinforce what Katherine mentioned, both the employer and employee portions of your Solo 401k contributions go on Schedule 1, Line 16 as adjustments to income. DO NOT put them on Schedule C as business expenses - that's a common error that can get you in trouble. Here's what helped me understand it: Think of yourself as wearing two hats. As the "employee," you're deferring salary (even though you don't technically get a salary as self-employed). As the "employer," you're making a retirement contribution for your employee (yourself). Both of these reduce your taxable income but they're not business operating expenses. One thing to watch out for - make sure your Solo 401k provider gives you clear documentation showing the breakdown between employer and employee contributions. You'll need this for your records and it makes tax time much smoother. The setup is definitely worth it though! I was able to contribute way more than I could with a traditional IRA, and the tax savings were significant.

Just wanted to add one more perspective as someone who works in financial planning. The decision you're facing is actually a really common one, and you're asking all the right questions. From a pure tax standpoint, you're in great shape. That $1,400 loss will directly reduce your taxable income, potentially saving you $300-500+ depending on your tax bracket. Robinhood will handle all the reporting with their 1099-B form, and you'll just transfer those numbers to Schedule D on your tax return. But here's something I tell all my clients in similar situations: think of paying off high-interest debt as a guaranteed investment return. If your credit cards are charging 20% APR, paying them off is like earning a guaranteed 20% return on your money - and that's after-tax money! Even the best investors struggle to consistently beat 20% returns. The emotional/psychological component is huge too. I've seen clients hold onto losing investments out of pride or hope, all while paying crushing interest on credit cards. Meanwhile, the stress of debt often leads to poor financial decisions down the road. My recommendation would be to liquidate, eliminate the debt, build a small emergency fund with any remaining money, and then start investing again from a position of strength. You'll sleep better, have more disposable income each month, and can make investment decisions based on opportunity rather than desperation.

I went through a very similar situation about a year ago - had about $6,000 invested that dropped to around $4,200, while carrying credit card debt at 23% APR. The hardest part was accepting that sometimes the best investment move is to step back and get your foundation solid first. What really helped me make the decision was calculating the actual numbers. My credit cards were costing me about $180/month in interest alone. Even if my investments had recovered 20% that year (which would have been amazing), I still would have lost money overall due to the interest payments. Meanwhile, eliminating that debt gave me an immediate 23% "return" and freed up $180/month to rebuild my finances properly. The tax loss deduction was honestly just icing on the cake - I was able to deduct about $1,800 in losses, which reduced my tax bill by roughly $400. So between the tax savings and eliminating the interest payments, I came out way ahead despite "losing" money on the investments. One year later, I'm debt-free, have a solid emergency fund, and I'm back to investing - but this time with money I can actually afford to lose. The peace of mind is worth more than any potential market gains. Sometimes the best financial decision feels like giving up, but it's actually setting yourself up for long-term success.