One option nobody mentioned - could you park further away for free/cheaper and take public transit the rest of the way? That's what I do. Park at the suburban train station for $4/day instead of $22/day downtown. Might not work for your location but worth looking into!

Just to add another perspective - if you're able to work from home even part of the time, that could significantly reduce your annual parking costs. Even if you could negotiate 1-2 days WFH per week, that would cut your $1,850 annual expense by 20-40%. Given that your employer isn't willing to help with parking, they might be more open to flexible work arrangements that would naturally reduce your commuting expenses. Worth bringing up in your conversation with HR about commuter benefits - frame it as a cost-saving solution for employees dealing with the parking situation.

7 Does anyone know if I can contribute to my HSA after I've already filed my taxes? I just realized I didn't max out my 2024 contribution and I know the deadline is April 15, 2025, but my taxes are already done...

HSA contributions can be tricky at first, but once you understand the basics it gets much easier! Just to add to the great advice already given - make sure you keep good records of all your HSA transactions throughout the year. Your HSA provider should send you Form 5498-SA showing total contributions and Form 1099-SA if you made any withdrawals. One thing that often trips people up is understanding that HSA contributions are "above-the-line" deductions, meaning they reduce your adjusted gross income even if you don't itemize deductions. This makes them incredibly valuable tax-wise! Also, if you're new to HSAs, remember the "triple tax advantage" - contributions are tax-deductible, growth is tax-free, and withdrawals for qualified medical expenses are tax-free too. It's one of the best tax-advantaged accounts available. Don't stress too much about the amendment - the IRS is actually pretty understanding about HSA reporting issues since these accounts have become more common but the rules can be confusing. You're definitely doing the right thing by getting it sorted out!

Has anyone else had issues with switching accounting methods on Schedule C after the first year? I started with accrual and realized cash would have been better, but the hassle of filing Form 3115 to change methods has been a nightmare!

For a new sole proprietor with that revenue level ($40-50k), cash method is definitely the right choice. You're correct that it's straightforward - income when received, expenses when paid. Regarding the donations for future classes, since people are giving money with the expectation of receiving services (even if not yet scheduled), this is advance payment for services, not a true donation. Under cash method, you'll recognize this income when received. This is actually quite common for service businesses - think gym memberships, annual software subscriptions, etc. One practical tip: keep good records showing what these advance payments are for and track when you deliver the corresponding services. This helps with business planning and ensures you're fulfilling your obligations to those who prepaid. Cash method will serve your client well, especially starting out. The simplicity alone is worth it, and most small service businesses never need to switch to accrual unless they hit the $25M gross receipts test or have significant inventory.

Former mortgage lender here. The "keep your mortgage for the tax deduction" advice is one of the most misunderstood financial tips out there. Quick example: If you pay $10k in mortgage interest and are in the 22% bracket, you're not "saving" $2,200. You're spending $10k to save $2,200 IF you itemize AND your total itemized deductions exceed the standard deduction. That's like spending a dollar to get 22 cents back. Congrats on being mortgage-free! That's a huge achievement and gives you incredible financial flexibility. The psychological benefit of no mortgage payment is massive and doesn't show up in tax calculations.

I kept my mortgage specifically for the tax deduction for years until I actually ran the numbers. Here's what I found: Mortgage: $280,000 at 4.5% Annual interest: ~$12,420 Tax bracket: 24% Potential "tax savings": $2,981 BUT... since the standard deduction was $27,700 for us, and our other itemized deductions were only about $8,000, we weren't getting ANY tax benefit from $10,700 of that mortgage interest ($27,700 - $8,000 = $19,700 needed to hit standard deduction). So we were only getting tax benefit on $1,720 of our interest, saving us just $413 in taxes while paying $12,420 in interest. Don't listen to people who don't understand how itemized deductions actually work!

Does anyone know if this base wages limit also applies to self-employment tax? I do freelance work and also have a regular job, so I'm wondering if I should be calculating this differently on my Schedule SE.

This is such valuable information! I had no idea about the Social Security wage base limit until recently either. One thing that might help others understand this better: the limit exists because Social Security benefits themselves are capped. Since there's a maximum monthly benefit you can receive in retirement (around $3,345/month in 2022 for someone retiring at full retirement age), it makes sense that contributions are also capped. What's interesting is that this creates a somewhat regressive tax structure where Social Security tax takes a smaller percentage of total income as you earn more. Someone making $50,000 pays 6.2% SS tax on their entire income, but someone making $300,000 effectively pays only about 3% of their total income in SS tax. For anyone tracking this year over year, these limits do tend to increase pretty substantially each year with inflation adjustments, so it's worth checking annually if you're in that income range!