Good point. I once had an employer who withheld federal but completely missed setting up state withholding. Ended up owing $2,300 to my state at tax time. It was a nightmare.

That's a really smart approach! Do you know if there are any drawbacks to front-loading 401k contributions early in the year? My company matches 4% of each paycheck - would I lose out on matching if I max out too early?

That's an excellent question about front-loading! Many employer matching programs are designed to match per paycheck, not as a lump sum. So if you max out your 401k early in the year and stop contributing, you might miss out on matching contributions for the remaining paychecks. Some companies have what's called a "true-up" provision that will give you the full match you're entitled to at the end of the year regardless of when you made your contributions. You should definitely check with your HR department about this before front-loading. Without a true-up provision, it's usually better to spread your 401k contributions throughout the year to maximize the employer match.

HSAs don't count toward your IRA or 401k limits - they're completely separate! For 2024, HSA limits are $4,150 for individuals and $8,300 for families (plus $1,000 catch-up if you're 55+). It's actually one of the best tax-advantaged accounts because it's triple tax-advantaged.

Just adding to what the other person said - HSAs are actually BETTER than 401ks and IRAs from a tax perspective. You get tax-free contributions, tax-free growth, AND tax-free withdrawals for medical expenses. If you can afford to max it out, definitely do it before worrying about maxing your IRA!

1 That's interesting! I've never heard of Opportunity Zones before. Do these need to be in specific locations? And does the investment have to be through some special fund or can I just buy property directly in these areas?

3 Yes, Opportunity Zones are specific census tracts designated by the government as economically distressed communities. You can find maps online showing exactly where they're located in each state. You generally need to invest through a Qualified Opportunity Fund rather than buying property directly. The fund then invests in property or businesses within the Opportunity Zones. The main tax benefits are deferring your current capital gains tax until 2026, getting a reduction on those taxes if you hold the investment long enough, and potentially paying zero tax on the new gains from your Opportunity Zone investment if you hold it for at least 10 years.

15 This is actually a really smart question. Often people focus so much on avoiding taxes that they don't consider the overall financial picture. For capital gains tax deferral, you have to weigh several factors: the time value of money (what could you earn with those tax dollars if you defer paying them?), potential future tax rate changes (will rates be higher or lower when you eventually pay?), and the transaction costs of whatever strategy you're using to defer taxes (like setting up special entities or funds). For many investors with moderate gains, simply paying the tax and maintaining flexibility in your investments often works out better than complex deferral strategies. Complex tax strategies usually make the most sense for very high-value transactions where the savings outweigh the costs and complications.

Do you have a template for this spreadsheet you could share? I'm just starting to get PR packages and want to be prepared.

I don't have a shareable template, but it's pretty simple to create. Just make columns for all the info I mentioned. I also add columns for: - Percentage of business use vs. personal use - Photos of the item (I link to a Google Photos folder) - Email documentation from the company - Shipping/customs documentation The most important thing is consistency. Update it immediately whenever you receive something new. I learned this the hard way after trying to reconstruct a year's worth of product receipts from memory and email searches. Now I have a dedicated "unboxing station" where I photograph everything, record the details, and don't touch the product until it's properly documented.

Yes! I had this issue with a camera company. They 1099'd me for a $1900 camera that was actually selling for $1100 everywhere. I gathered screenshots of the actual market price from multiple retailers on the date I received it, then contacted their accounting department directly (not PR team). They issued a corrected 1099-NEC with the accurate value.

I tried disputing values and the company refused to change anything. They said they use MSRP regardless of sales or market value. I ended up just having to pay taxes on the inflated amount.

Yikes, that's exactly what I'm worried about. What specific documentation should I make sure my employer has? And what does "exclusively for work" actually mean in practice? Can I occasionally use my work computer to check personal email or is that a no-no?

For documentation, your employer needs to have a written policy that states employees must submit expenses within a reasonable time (usually 60 days), provide receipts or similar documentation, and return any excess reimbursement within a reasonable time. They should have you fill out a form showing the business purpose of each expense. On the "exclusive use" question - that's actually a bit of a gray area. The strict interpretation is that the space should only be used for business, but in reality, the IRS recognizes that's nearly impossible with a desk in a living room. What matters most is that you're using it primarily for work during working hours. Occasional personal use (checking email, etc.) won't invalidate the arrangement. Just don't try to claim a space that's clearly used for multiple purposes (like your dining table).

That's what my company does too! They give us $150/month for "home office expenses" but it's fully taxed. I asked about submitting actual expenses instead and they said it was too much administrative work for them to track. Super frustrating.