This has been such a valuable discussion! I'm actually dealing with a very similar situation - about $22k in annual dividends that I've been auto-reinvesting for years, and now I need around $15k for some unexpected medical expenses. Reading through all these responses, I'm realizing I've been approaching this way too simplistically. The idea of using specific identification to sell shares with the highest cost basis (like recent dividend reinvestments) is brilliant - I had no idea you could even choose which specific shares to sell! I'm definitely going to look into that partial dividend strategy too. Having 30-40% automatically go to cash would give me that liquidity buffer for situations exactly like this, while still getting the compound growth benefits on the majority of the dividends. One follow-up question though - for those of you doing the partial cash approach, do you find it creates any issues with your overall investment timeline? I'm wondering if having that cash sitting around earning minimal interest affects long-term returns significantly, or if the flexibility and reduced transaction costs make up for it. Also, huge thanks to everyone who shared those tool recommendations. I had no idea there were services specifically designed to optimize these kinds of investment tax decisions!

This thread has been incredibly helpful! As someone who's been making the same mistake of auto-reinvesting everything without thinking about the tax implications, I'm definitely going to implement some of these strategies. One thing I wanted to add that might help others - if you're using a robo-advisor like Betterment or Wealthfront, many of them actually handle the tax-loss harvesting and specific share selection automatically. I switched to Betterment last year specifically because they do tax-loss harvesting and will automatically sell shares with the highest cost basis to minimize capital gains when you need to withdraw money. For those who prefer managing their own investments, the partial dividend cash strategy sounds perfect. I'm going to set up a 40/60 split (40% cash, 60% reinvest) at Schwab - this should give me that liquidity buffer while still getting most of the compounding benefits. Also want to echo what others said about keeping detailed records. Even if your brokerage tracks cost basis, having your own spreadsheet with dividend reinvestment dates and amounts has saved me so much time during tax season. Takes maybe 10 minutes per quarter to update but makes everything so much cleaner when you need to make tax-efficient selling decisions. Thanks everyone for sharing your experiences - this is exactly the kind of practical advice that makes a real difference!

Does anyone know if TurboTax automatically applies your loss carryover from the previous year if you used TurboTax for both years? I swear it used to do this automatically but now I cant find where its pulling that data from.

I went through this exact same struggle last year! The Capital Loss Carryover Worksheet can be really confusing at first. Here's what helped me get through it: First, you definitely need your 2023 tax return - specifically Schedule D and Form 8949 if you filed one. Look for line 21 on your 2023 Schedule D, which shows your net capital loss for that year. For your situation with $4,300 in losses, you're right that there's a $3,000 annual limit for deducting capital losses against ordinary income. So if your net loss last year was more than $3,000 after accounting for any gains, the excess carries forward. The worksheet asks for your prior year AGI to determine if you need to use the Capital Loss Carryover Worksheet or if you can use a simpler method. Most people with straightforward situations can just enter the carryover amount directly on Schedule D. One thing that tripped me up initially - make sure you're looking at your NET capital loss from last year, not just the gross losses. TurboTax should have calculated this for you on last year's Schedule D. If you can't find your 2023 return, you can get a transcript from the IRS website or call them. Don't stress too much - once you have the right numbers, it's actually pretty straightforward!

Has anyone had experience with settlements that include back pay AND emotional distress? My understanding is they're taxed differently - wages are subject to both income tax and employment taxes, while emotional distress is only subject to income tax.

Based on everything discussed here, it sounds like you're in a pretty straightforward situation compared to some of the more complex settlements mentioned. Since your $27k settlement appears to be primarily for lost wages from your employment dispute, you'll likely need to report the full amount as taxable income and can deduct your attorney fees as an above-the-line deduction (which effectively means you're only taxed on the $18k you received). For setting aside money for taxes, I'd recommend being conservative and setting aside about 25-30% of the $18k you actually received (so roughly $4,500-$5,400). This should cover both federal and state taxes depending on your bracket. Given the timing and amount, you should also consider making estimated tax payments to avoid underpayment penalties. The tools and services others have mentioned (taxr.ai for calculations and Claimyr for IRS questions) seem like they could save you a lot of headache in figuring out the specifics for your situation. Don't let this stress you out too much - employment settlements are pretty common and the tax treatment is well-established once you know the rules!

Congratulations on your marriage and new job opportunities! I completely understand the W-4 confusion with multiple jobs - it's one of those things that seems way more complicated than it should be. Here's the simplest approach that has worked well for me and many others in similar situations: **For your highest-paying job ($54,200):** - Complete all sections normally (Steps 1-4) - Check "Married filing jointly" in Step 1 - Use Step 2(b) Multiple Jobs Worksheet OR (better yet) use the IRS Tax Withholding Estimator online - Claim any dependents/credits in Step 3 - Put any additional withholding amount in Step 4(c) based on the calculation **For the other two jobs ($23,900 and $16,500):** - Only complete Step 1 (check "Married filing jointly") - Leave Steps 2 and 3 completely blank - You can add extra withholding in Step 4(c) if needed, but often it's not necessary The key principle is that your tax credits and filing status should only be claimed ONCE (on the highest-paying job), and the additional withholding calculation accounts for having multiple income sources. I'd strongly recommend using the IRS online estimator rather than the paper worksheet since it handles 3+ jobs much better. You can find it by searching "IRS Tax Withholding Estimator" - it's free and walks you through everything step by step. This approach should help you avoid both underwithholding (owing money) and overwithholding (giving the government an interest-free loan). Good luck!

Congratulations on your marriage and new job opportunities! This is actually a pretty common situation, and while it can feel overwhelming at first, it's definitely manageable once you break it down. Here's what I'd recommend based on your three jobs totaling $94,600: **Quick approach:** 1. **Designate your highest-paying job ($54,200) as your "main" W-4** - this is where you'll claim your married filing jointly status and handle all the complexity 2. **Use the IRS Tax Withholding Estimator online** - it's free and much easier than the paper worksheet for 3+ jobs 3. **Keep the other two W-4s simple** - just mark "married filing jointly" and leave Steps 2-3 blank The estimator will tell you exactly how much extra to withhold in Step 4(c) on your main job to account for all three incomes. This way, you're not trying to split calculations across three forms. **Why this works:** Your tax situation is based on your combined income, not individual jobs. So having one job handle the "heavy lifting" of withholding while the others just do basic withholding is totally fine - it all evens out at tax time. I'd aim for owing/getting back less than $500. The estimator will show you a projection so you can see if you're on track. You can always adjust mid-year if your actual income ends up different than expected. Don't stress too much about getting it perfect - the fact that you're being proactive about this puts you way ahead! Good luck with everything! 🎉

As someone who went through this exact same confusion last year, I wanted to add that another factor that can affect your blended rate calculation is state taxes if you live in a state with income tax. While your federal blended rate might be 19.2%, don't forget that many states have their own progressive tax systems too. Some tax software will show you a combined effective rate that includes both federal and state taxes, which can be helpful for understanding your total tax burden. Also, @a6594b194df9 (Lola), since you mentioned owing money to the IRS - make sure you're looking at your withholding and estimated payments. Sometimes people get confused thinking their blended rate determines what they owe, but what you actually owe depends on how much tax was already withheld from your paychecks throughout the year. Your blended rate just tells you what percentage of your income went to taxes overall. If TurboTax is showing you owe money, it's likely because not enough was withheld during the year, not because your blended rate calculation is wrong.

Great question! I was confused about this same thing when I first started doing my own taxes. The key thing to remember is that the U.S. has a progressive tax system, which means different portions of your income are taxed at different rates. Think of it like climbing a staircase - you don't jump straight to the 32% rate. You start at 10% for the first chunk of income, then 12% for the next chunk, then 22%, and so on until you reach the 32% bracket. Your blended (effective) rate is the average of all these rates weighted by how much income falls in each bracket. To double-check your calculation in TurboTax, you can look at Form 1040 line 16 (total tax) and divide it by line 15 (taxable income). That should give you your blended rate of around 19.2%. The fact that you're seeing this rate means you're likely in a good income range where the progressive system is working in your favor - much of your income is being taxed at those lower rates rather than the full 32%. If you're still concerned about accuracy, you can always run through the tax brackets manually or use the IRS tax tables to verify, but TurboTax is generally very reliable for these basic calculations.