Anybody have recommendations for how to handle expenses when you're doing both freelance and a part-time W-2 job? I'm still at my design agency 20 hrs/week but building up freelance clients too.

Hey Giovanni! Welcome to the freelance tax world - it's definitely overwhelming at first but you'll get the hang of it. A few quick points to add to the great advice already given: Since you're 8 months in and haven't made quarterly payments yet, you'll likely owe a penalty when you file. For 2025, you can avoid penalties by paying 100% of last year's tax liability (110% if your AGI was over $150k) or 90% of this year's liability through quarterly payments. Since you missed the first few quarters, calculate what you should have paid and make a catch-up payment ASAP. One thing I learned the hard way - keep separate business and personal bank accounts even if you're not formally incorporated. It makes tracking income and expenses SO much easier come tax time. Also, consider getting a business credit card for all your freelance expenses - the statements become your expense records. For your monthly income range ($4,800-5,500), you're definitely going to want to bump that savings rate up to at least 30%. Don't forget about state taxes too if you're in a state that has them. And seriously, start tracking EVERYTHING now - mileage, client meals, software subscriptions, even that new ergonomic chair for your home office. The IRS loves documentation, so keep those receipts!

Your turbo tax may have actually known what it was doing when it prompted you to use those SLCSP amounts. Did they ask you specifically about your employment situation and whether you were offered coverage? I use HR Block and it asked me detailed questions about my job status changes and when I had access to employer coverage throughout the year. It then automatically adjusted my premium tax credit eligibility month by month.

I went through something very similar when I changed from full-time to part-time status mid-year. The IRS does treat declining employer coverage during open enrollment as making you ineligible for premium tax credits, even if you can't enroll later when you need it. However, your part-time switch in May is the key here. When you became part-time and lost eligibility for employer coverage, that's a legitimate qualifying event that restores your eligibility for premium tax credits going forward. I'd recommend amending to claim credits only for May through December. Make sure to document the exact date your employer coverage eligibility ended due to the part-time change - this will be important if the IRS has any questions about your amendment. Also, double-check that your employer truly doesn't offer any coverage to part-time employees, as some companies have different rules or waiting periods. You'll want to be certain about this before filing the amendment.

To all those having trouble reaching a human at IRS. I just ran across this video that gave me a shortcut to reach a human. Hope it helps! https://youtu.be/_kiP6q8DX5c

Tax topic 152 is completely normal and just indicates your return is being processed. I had the same code for about 3 weeks before my refund was approved. The key thing is to be patient - the IRS is still working through a backlog from previous years. If it's been more than 21 days since you filed, definitely check your account transcripts online to see if there are any specific codes that might indicate what's holding things up. Most of the time it's just a matter of waiting your turn in the queue. Keep checking WMR and your transcripts for updates!

Has anyone successfully had penalties waived without hiring a tax pro? I'm in a similar situation with my photography LLC and got hit with $2,600 in penalties even though I filed closure paperwork in 2019. I've been unemployed for 7 months and really can't afford this or a tax professional.

This is exactly the kind of bureaucratic nightmare that makes dealing with the IRS so frustrating. You clearly did everything right - submitted proper closure documentation, followed up multiple times, and kept detailed records. The fact that they're now penalizing you for their own processing delays is completely unfair. I want to echo what others have said about filing Form 843 for penalty abatement. Your situation screams "reasonable cause" - you have documented proof of timely submission, multiple attempts to follow up, and the IRS's own letters acknowledging processing delays. Make sure to emphasize in your abatement request that the penalties resulted from IRS administrative delays, not any failure on your part to comply. Also, don't forget to mention your current unemployment situation when requesting abatement. The IRS has provisions for economic hardship considerations, and being unable to pay without severe financial distress is a valid factor they must consider. Your case has all the elements for a successful abatement - you just need to present them clearly and persistently. Keep fighting this. You shouldn't have to pay penalties for the IRS's own administrative failures.

One thing to consider is whether your company allows a "cashless exercise" option. With the spread between $8 and $200 being so large, you'd need $8,000 cash to exercise all options, plus potentially a large AMT bill. A cashless exercise would let you exercise and immediately sell enough shares to cover your costs, then keep the remaining shares. This is essentially a partial disqualifying disposition but can be a good middle ground if you don't have the cash on hand for a full exercise.

This is a complex situation that really highlights why ISO planning should ideally start early! Given your $90k capital loss carryover, you're right that it won't help with AMT on the ISO exercise, but there are still some strategic considerations. One approach worth exploring: if you're comfortable with some market risk, consider exercising just a portion of your options now (maybe 200-300 shares) and spreading the rest over the next year or two. This could help minimize the AMT hit while still capturing some gains. Also, timing matters for your capital loss usage. If you do a disqualifying disposition, you'll have $192k in ordinary income but can only use $3k of your losses against it this year. However, any capital gains you generate from other investments or future stock sales can be fully offset by your loss carryover. Given the volatility risk Isaac mentioned with newly public companies, I'd lean toward taking at least 50-70% of your gains off the table immediately after lockup expires. You've already won the lottery here - don't risk losing it all for tax optimization. Have you checked if your company offers any tax gross-up benefits or financial planning resources for employees dealing with stock options? Many tech companies provide these services specifically because ISO taxation is so complex.