Would we calculate those quarterly payments just based on our investment income or would we need to factor in possible underwithholding from our regular jobs too? And is there some calculator to figure out how much to send each quarter?

You'd want to account for both the investment income and any potential underwithholding from your jobs. The simplest approach is to take what you owed this year (your $4,300) and divide by 4 - that would be roughly $1,075 per quarter. That's assuming your income situation stays similar. There's actually a worksheet in the Form 1040-ES instructions that helps you calculate exactly what you should pay. Alternatively, if you pay at least 100% of last year's tax liability (or 110% if your AGI is over $150,000), you're generally safe from underpayment penalties even if you end up owing more when you file.

This is such a good point! My company withholds exactly 22% from bonuses regardless of my W-4 settings, and it's never enough. I always have to request additional withholding when I get my annual bonus.

4 Do you think coaching books or online courses would count as deductions? I've spent around $200 on coaching materials this year that help me plan practices.

9 Absolutely! Coaching books, online courses, and training materials that help you in your coaching role are typically deductible as ordinary and necessary business expenses. They're considered professional development expenses that directly relate to your work. Just keep receipts and documentation that shows what the materials were and how they relate to your coaching business. Digital receipts work fine too, just make sure you have a system to keep track of them.

12 Where on the forms do you deduct the 50% of self-employment tax? I've been filing 1099 income for 3 years and never knew about this!

Is there a specific app you recommend for keeping track of all this? I've been just taking random photos of receipts and it's a mess.

I use a combination of Google Drive for storing digital copies of forms and contracts, and then QuickBooks Self-Employed for tracking expenses, mileage, and income. The QB app lets you snap photos of receipts on the go and automatically categorizes them. For W-9s specifically, I just scan them with my phone and upload to the client's folder in Drive. I tried several expense tracking apps before settling on QuickBooks, and it's worth the monthly fee for the time it saves. Some people also like FreshBooks or Wave which are a bit simpler if you don't need all the features.

Wait so I'm confused. I did some graphic design for a company last year and filled out a W-9, but never got any tax forms from them. Should I be worried?

Does that QCD strategy help if you're not taking RMDs yet? I'm only 42 but I do donate about $3,000 a year to my church.

Unfortunately, the QCD strategy only works if you're at least 70.5 years old and are withdrawing from IRAs. At 42, your charitable donations would be itemized deductions rather than AGI reducers, and they go on Schedule A rather than directly reducing line 11. However, there is a strategy that might work for you - if you have a small business or freelance income, you might be able to structure some of your charitable giving as business sponsorships, which could be business expenses that reduce your AGI. This only works if there's a legitimate business purpose though, like advertising or promotion for your business.

Yes! I did this last year. If you're self-employed and not eligible for coverage through an employer (yours or spouse's), you can deduct 100% of your premiums. For me that was about $14,000 for my family plan! It's an adjustment to income on Schedule 1, so it directly reduces AGI.

I've always been told box 5 > box 1 = taxable income. Are you saying that's not necessarily true? I'm now wondering if I've been overpaying my taxes all these years by reporting scholarship income that maybe wasn't actually taxable.

Does the IRS actually audit people over unreported scholarship income? I'm not trying to avoid paying what I owe, but I'm in a similar situation to OP and now worried about the past 4 years.

I've had good experiences with FreeTaxUSA for scholarship situations. It asks specific questions about how the scholarship money was used rather than just comparing box numbers. Much better than TurboTax for this specific situation, and it's way cheaper too.

Thanks for the recommendation! I'll definitely give FreeTaxUSA a try next year. It's frustrating that TurboTax couldn't handle this properly - especially since we paid for their "premium" version specifically because my son had education tax forms. Appreciate you sharing your experience!