Does anyone know if you can deduct your actual DFS contest entry fees as a business expense? Like if I spent $5000 on contests but won $6000, can I just report the $1000 profit, or do I need to report $6000 income and then deduct the $5000 in fees separately?

This is such a timely question with the NFL season starting! I've been dealing with this exact confusion for the past two years. The key thing to understand is that the IRS doesn't actually view DFS and sports betting as the same activity, even though they both involve sports. DFS platforms successfully argued that their contests are skill-based competitions between players (similar to poker tournaments), while traditional sports betting is classified as gambling against the house. For tax purposes, this means: - DFS winnings go on Schedule C as business income, and you can deduct research subscriptions, data services, and contest entry fees as business expenses - Sports betting winnings go on Form W-2G and losses can only offset wins if you itemize on Schedule A The practical advice: keep separate records for each activity. I use different spreadsheets to track my DraftKings contests versus my occasional bets at the sportsbook. It makes tax season much less stressful when everything is already categorized correctly. Also worth noting that some states treat these differently too, so make sure you understand your state's specific rules in addition to federal requirements.

A little-known trick: if you make a large estimated payment in January of the following year (before filing), you might be able to apply it to the previous year's Q4 estimated payment. I've done this before when I realized I might face an underpayment penalty. The key is to specify on the payment voucher that you want it applied to the previous tax year's Q4 payment. This won't help with penalties from Q1-Q3 underpayments, but it can reduce the Q4 portion of any penalty.

This is such a common area of confusion! I went through the same thing last year with my mixed W-2 and consulting income. One thing that really helped me understand the penalty calculation was realizing that the IRS essentially wants you to "pay as you go" rather than catch up at year-end. So even if your total payments exceed your tax liability, you can still owe a penalty if those payments weren't distributed properly throughout the year. For your 2025 planning, increasing withholding is definitely the right move since it's treated as paid evenly throughout the year. But don't completely eliminate estimated payments if your self-employment income is substantial - you might just need to adjust the timing and amounts. Also worth noting: if your prior year tax liability was under $1,000, or if this is your first time owing an underpayment penalty, you might qualify for first-time penalty abatement even after filing. The IRS is surprisingly reasonable about waiving penalties for taxpayers with good compliance history.

Has anyone used TurboTax for reporting ESPP and RSU sales? I'm wondering if they have any built-in tools for calculating the correct cost basis. I transferred my shares to Fidelity last year and now I'm worried I might mess up my taxes.

One thing I'd add to all the great advice here - make sure you understand the "look-back" provision that many ESPPs have. This can significantly affect your cost basis calculation and whether you have a qualifying disposition. Many ESPPs allow you to purchase shares at a discount based on the LOWER of either the stock price at the beginning of the offering period OR the stock price at the end of the offering period. If your plan had this feature, your actual purchase price might be different than what you think, and this affects both your cost basis and the amount of discount that gets taxed as ordinary income. I learned this the hard way when I sold some old ESPP shares and discovered my cost basis was actually lower than I calculated because of the look-back provision. Check your original ESPP plan documents or contact your former employer's benefits team to confirm if your plan had this feature. Also, don't forget that some brokerages will automatically apply incorrect cost basis adjustments when you transfer ESPP shares. Make sure to review and correct these before you sell, or you might end up paying taxes on money you've already been taxed on.

Given your situation with multiple jobs totaling around $40k, I'd recommend taking a conservative approach to avoid owing taxes next April. Since your new full-time position will be your primary income source, that's where you should make your withholding adjustments. Here's what I'd do: On your new job's W-4, check the multiple jobs box AND add $35-45 extra withholding per paycheck on line 4c. This should cover the tax liability from all three jobs without drastically overwithholding. Keep your Target and bartending W-4s simple - just mark single with no other jobs. Since the bartending income is unpredictable and relatively small, don't stress too much about it. The extra withholding from your main job should provide a good buffer. The key advantage of this approach is flexibility. If you do end up quitting the bartending job, you won't need to scramble to update multiple forms. And if your Target hours fluctuate, the buffer from your main job withholding should still cover you. You can always use the IRS withholding estimator mid-year to fine-tune things once you have a better sense of your actual income patterns. Better to get a modest refund than face penalties for underwithholding!

I've been in a similar situation with multiple jobs and want to emphasize something important that hasn't been mentioned yet - make sure you're tracking your income throughout the year, especially with those variable bartending shifts. Since you mentioned you might only work the restaurant 1-2 times per month for around $150 per shift, that could still add up to $1,800-3,600 annually depending on tips. The unpredictable nature of service industry income makes it tricky for any withholding calculator. My recommendation would be to take a middle-ground approach: Use your full-time job's W-4 to handle the heavy lifting by checking the multiple jobs box and adding about $35 per paycheck on line 4c. This should cover your base tax liability from all sources. Then, set aside about 20-25% of your bartending earnings in a separate savings account as you go. If you end up owing a little at tax time, you'll have that cushion. If you don't need it, great - you've got some extra savings! This strategy has saved me from both overwithholding stress and tax-time surprises. Also consider doing a mid-year check-in around July to see how your actual income is tracking against your estimates. You can always submit a new W-4 to adjust if needed.

I went through this exact same situation about 8 months ago and it was so stressful! That "TAX REFUND PROC for RFND DISB" description is completely unhelpful - it's just the standard Treasury wording that shows up on everyone's tax refund, whether you get the full amount or not. The missing $1,100 definitely sounds like an offset, and I hate how the IRS Where's My Refund tool gives you zero warning about this. Mine showed the full expected amount right up until the day the money hit my account, then boom - I was short $1,400 with no explanation. What saved me tons of time and stress was calling the Treasury Offset Program at 800-304-3107. It's an automated system where you just enter your SSN and it immediately tells you which agency took money from your refund and how much. No waiting on hold, no confusing paperwork - just straight answers. In my case, it turned out to be an old state tax debt from when I moved across the country. I had completely forgotten about it because they'd been sending notices to my old address. Once I knew what agency to contact, I was able to call them directly and work out a payment plan that actually qualified me for a partial refund of the offset amount. Don't give up on that missing money! A lot of people in similar situations have been able to get at least some of it back when there were errors in the collection process or when they qualified for hardship programs. The key is finding out who took it first, then you can decide your next steps.

Hey Kyle, I totally feel your frustration! I went through the exact same thing a few months back - got hit with that confusing "TAX REFUND PROC for RFND DISB" description and was missing about $900 from my expected refund. It's such a punch to the gut when you're counting on that money! Everyone here has given you solid advice about calling 800-304-3107 - that Treasury Offset Program hotline is definitely your fastest bet to find out what's going on. I used it and found out within 2 minutes that I had an old overpayment from unemployment benefits during COVID that I'd completely forgotten about. One thing I'd add is to not panic if it turns out to be a legitimate debt. Even if the offset is valid, many agencies have programs that can help. In my case, I was able to get about half of my offset refunded because I qualified for a financial hardship waiver. It took some paperwork and a few phone calls, but I got $450 back about 6 weeks later. The "TAX REFUND PROC for RFND DISB" part is totally normal - that's just Treasury's standard description for ALL tax refunds. The real issue is that missing $1,100, but at least you'll have answers soon once you make that call. Keep us posted on what you find out!