I just looked it up and unfortunately my state isn't included in the Direct File pilot program yet. Seems like it could be a good option in the future though! I'll probably go with one of the free alternatives mentioned here instead of paying for TurboTax.

Is FreeTaxUSA actually reliable? I'm always worried about using less well-known tax software. Do they have good support if you have questions?

Does the standard mileage rate usually work out better than tracking actual expenses? My car is pretty old and fuel efficient but I'm driving a TON for deliveries.

In my experience, standard mileage usually works out better for newer cars or fuel-efficient vehicles. I drive about 25,000 miles a year for deliveries in a 2018 Corolla, and the standard deduction gives me around $16,000+ in deductions which is way more than I'd get itemizing. For older vehicles that might need more repairs or gas guzzlers, tracking actual expenses could potentially be better. The key is to try calculating both ways for a month and see which gives you the bigger deduction. Just remember if you choose actual expenses in the first year, you're generally stuck with that method for the life of that vehicle.

This is actually a really good point. I worked in insurance for years and this arrangement could potentially void the insurance coverage entirely. Most policies require that the regular drivers be listed, and if there's a claim and they discover misrepresentation, they can deny everything.

Thank you! I've already updated both my W4 forms for this year, but I'll definitely use that calculator to double-check everything. Is it normal to owe this much though? I'm still shocked at how big the difference was.

Yes, unfortunately the amount you owe is pretty typical for this situation. When you add a second job with similar income, you're essentially doubling your income but your withholding isn't doubling the tax paid because each employer is calculating withholding based on their portion only. For example, if you make $80K at one job, you might be withheld at an effective rate of about 12-15%. But when your total income is $160K, portions of that income are taxed at 22% or 24% brackets. That difference between what was withheld (at lower rates) and what you actually owe (at higher rates) is where that $5K+ bill comes from.

This is good advice. Also, make sure you're taking the standard deduction at a minimum ($12,950 for single filers for 2022). And if you made any charitable contributions or had work-related expenses that weren't reimbursed, those might help too.

Thanks for bringing this up! I do have some student loan interest from when payments were still required, and I contributed to my 401k at both jobs. I'll definitely look into those deductions. Do you think it could significantly reduce what I owe?

Thanks for mentioning the other requirements! I've been so focused on the income limits I forgot about vehicle price caps. Do you know if the $25,000 limit is before or after any dealer add-ons and fees?

The $25,000 limit is based on the sales price of the vehicle itself, before taxes and fees. However, dealer add-ons that are included in the purchase price (like extended warranties sold by the dealer) would count toward that limit. Be careful about dealers who might try to structure the deal in ways that artificially lower the vehicle price while adding "mandatory" add-ons to get around the price cap. The IRS looks at the actual purchase price of the vehicle as reported on your sales documentation.

this isnt correct, i got the ev credit last year and still claim mileage. my tax guy said its fine cause the credit is for buying the car, deductions are for using it. totally different things.

Careful with the cashless exercise suggestion - that only works if the company is publicly traded or has some kind of secondary market for the shares. Sounds like OP's company is still private with no immediate IPO plans.

Good point about the cashless exercise - I was assuming there might be a secondary market since it's a Series D company, but you're right that it's not guaranteed. Another option to consider is a net exercise if the company allows it. With a net exercise, you surrender some of your options to cover the exercise cost, so you get fewer shares but don't have to put up any cash. Won't help with the tax withholding for NSOs though.

I've had good luck with The Startup CPA (thinkthis.com). Not cheap but they actually understand equity compensation and saved me a ton on AMT planning. Worth the fee considering how much is at stake with these decisions.