I'm really sorry this happened to you - missing the 83(b) election is such a common mistake that catches so many startup employees off guard. The 30-day deadline is unfortunately non-negotiable, and there's no way to file it retroactively after this much time has passed. Since your equity had $0.00 FMV when granted, you would have owed virtually no tax with a timely 83(b) election. Now you'll face ordinary income tax on the fair market value at each vesting date instead of locking in the $0 value upfront. The key now is proactive tax planning. I'd strongly recommend: - Getting your company's current 409A valuation immediately to estimate what you'll owe when your first 25% vests - Starting to set aside 35-45% of the estimated vested value for taxes (covering federal, state, and payroll taxes) - Asking about your company's policy on share sales since many private startups don't allow employees to sell shares to cover tax obligations If your company's valuation has grown significantly since January 2024, you could face substantial tax bills that you'll need to pay out of pocket. Consider whether you'll need to make quarterly estimated tax payments to avoid underpayment penalties. The silver lining is there are no penalties for not filing the election, and your cost basis will be stepped up to the FMV at vesting, preventing double taxation on future sales. It's not ideal, but definitely manageable with proper planning. Don't be too hard on yourself - focus on getting prepared for the upcoming vesting events!

I feel for you on this - missing the 83(b) election is such a gut punch, but you're definitely not alone. I made the same mistake with my first startup equity grant and spent weeks beating myself up about it. The harsh reality is that the 30-day deadline is absolutely ironclad - I even tried reaching out to a tax attorney to see if there were any exceptions, but there simply aren't any. The IRS doesn't grant extensions or allow late filings for 83(b) elections, even in extraordinary circumstances. Here's what I learned from my experience: while you can't fix the missed election, the situation isn't catastrophic if you plan properly. Since your shares had $0.00 FMV at grant, you're essentially moving from paying no tax upfront to paying ordinary income tax as shares vest. The real question is how much your company's valuation has grown since January 2024. My advice would be to immediately request the current 409A valuation from your company - they should share this since it directly impacts your tax planning. If the valuation is still relatively low, your tax hit might be manageable. But if your startup has raised funding or grown significantly, start preparing for potentially substantial tax bills. I ended up setting aside about 40% of each vesting tranche's estimated value to cover all taxes, and that worked well. Also consider whether you'll need quarterly estimated payments - if you expect to owe over $1,000 beyond normal withholdings, the IRS expects quarterly payments to avoid penalties. The silver lining is that your cost basis gets stepped up at each vesting date, so you won't face double taxation when you eventually sell. It's not ideal, but definitely manageable with proper planning ahead of your vesting dates.

Pro tip: I scan all my tax documents (all copies) when I get them and save them in a folder with the tax year (like "2024 Tax Documents"). Then I keep the physical copies in a folder too. Makes it super easy if you need to reference them later. I've been doing my own taxes for 20+ years and have been audited twice. Having everything organized saved me massive headaches when the IRS came knocking!

Just remember that even if you're using tax software and don't need to mail in the physical W-2 copies, you should keep them for your records. The IRS can audit returns up to 3 years back (or even 6 years in some cases).

To clarify an important point: your federal AGI (Adjusted Gross Income) affects your state taxes, but your state tax liability has zero impact on your federal obligation. If your tax software shows you owe federal taxes, that means your withholding and/or estimated tax payments were insufficient to cover your tax liability for the year. The calculation is: Total Tax Liability minus Total Payments (withholding + estimated payments) = Amount Due or Refund.

This is a common situation for military families! The key thing to remember is that federal and state taxes operate independently - you can absolutely owe federal while getting a state refund. Since you mentioned you're a military family, I'd suggest double-checking a few military-specific items: Are you claiming the correct state of legal residence (which might be different from where you're currently stationed)? Did you account for any combat pay exclusions if applicable? Also, for next year, consider using the IRS withholding calculator after any PCS moves or changes in duty status, as these can significantly impact your tax situation. The Military Spouses Residency Relief Act can be tricky to apply correctly, so it might be worth having a tax professional who specializes in military taxes review your return to ensure you're getting all the benefits you're entitled to.

Quick tip from someone who messed this up their first year: don't forget about tax credits too, which are different from the standard deduction! Education credits like the American Opportunity Credit or Lifetime Learning Credit can save you thousands if you're still paying for school. Also, if your employer offers a 401k, contributing to it will lower your taxable income even further. At $58k, if you put 5% into your 401k, that's about $2,900 less income that gets taxed.

Just wanted to add something that helped me when I was in a similar situation - don't stress too much about getting everything perfect your first year! The IRS withholding calculator on their website (irs.gov/w4app) is actually really helpful for figuring out how to fill out your W-4 form correctly. Since you're starting mid-year, you might want to be extra careful with your withholding. Sometimes when you start a job partway through the year, the payroll system assumes you'll be making that salary for the full year and doesn't withhold enough for your actual situation. The IRS calculator takes into account when you started working and helps you adjust accordingly. Also, keep all your tax documents organized from day one - your W-2, any 1098-T forms if you're claiming education credits, receipts for any work-related expenses, etc. Makes filing so much easier! And congratulations on the new job!

This is a classic case of employee misclassification that's unfortunately very common with new graduates. Your employer is essentially having their cake and eating it too - they get all the control and benefits of having an employee (set schedule, specific work methods, integrated into their operations) while avoiding the costs and responsibilities that come with properly classifying you. The smoking gun here is the W-4 and I-9 forms. There's literally no legitimate reason for a true independent contractor to complete these documents. The W-4 is specifically for tax withholding from employee paychecks, and the I-9 is for employment eligibility verification. Independent contractors use W-9 forms instead. Beyond the tax implications (you're paying an extra ~7.65% in self-employment taxes), you're also being denied other important protections: workers' compensation coverage, potential unemployment benefits, overtime pay requirements, and any employer-sponsored benefits they might offer to other employees. The late paychecks add another layer of potential violations. Most states have strict laws about when employees must be paid, and even independent contractors have contractual rights to timely payment. My recommendation: Start documenting everything now, but also consider filing a complaint with your state's Department of Labor about the late payments and potential misclassification. State agencies often move faster than the IRS and can investigate multiple violations simultaneously. You can also file Form SS-8 with the IRS for an official worker classification determination. Don't let them exploit your newcomer status - you have real legal rights here, and this is costing you significant money.

What you're experiencing is textbook employee misclassification, and it's costing you real money every month. The fact that you completed W-4 and I-9 forms is the biggest red flag - these are exclusively for employees, never independent contractors. Here's what's happening: you're currently paying both the employee AND employer portions of Social Security/Medicare taxes (15.3% total) when you should only be paying the employee portion (7.65%). Your employer is essentially transferring their tax burden to you while maintaining full control over your work. The IRS looks at three main factors for classification: behavioral control (they set your schedule and methods), financial control (they provide equipment and workspace), and the relationship type (you were hired for a "full-time position" with promised benefits). You clearly meet all the criteria for employee status. Beyond taxes, you're missing out on overtime pay (which is required for employees), workers' compensation coverage, and unemployment benefit eligibility. The late paychecks add another layer of potential state labor law violations. Document everything immediately - save job postings, interview communications, emails about your status, screenshots of that payroll system, and detailed records of hours worked. Then consider filing with both your state's Department of Labor (for the late payments and misclassification) and Form SS-8 with the IRS for an official status determination. Don't let them exploit your new graduate status - this practice is illegal and you have strong grounds to challenge it.