Has anyone here actually done what the OP is asking about? I'm in almost the identical situation (retired from state job, now working part-time with 401k access). My HR department at the new job got confused when I told them about my 457b contributions earlier this year. They kept saying I was over the limit already, but I showed them the IRS guidelines about separate limits.

I'm in a similar situation but with a twist - I'm 58 and considering whether to use the special 3-year catchup provision for my 457b or wait until I'm eligible for the regular age 50+ catchup. My state plan allows the special catchup starting 3 years before normal retirement age (which is 60 for me). One thing I learned from my benefits coordinator is that you can't use both the special 3-year catchup AND the age 50+ catchup in the same year - you have to choose whichever gives you the higher contribution limit. In most cases, the special 3-year catchup allows much higher contributions because it lets you make up for years when you didn't max out your contributions. For anyone considering this, make sure you understand your plan's normal retirement age definition. Some state plans define it differently than others, which affects when you become eligible for the special catchup provision.

Can someone explain this to me like I'm 5? I get around $1400 back every year but I have no idea what all this 4(b) and 4(c) stuff means. Where on the actual form do I put stuff to get more money in my check? My HR department is useless and just gave me the form with no explanation.

I had the exact same problem and finally got it sorted out! Here's what worked for me after years of getting $800-1000 refunds: The key is understanding that you want to increase your "take-home" pay by reducing withholding, and the easiest way is through Step 4(b) "Deductions" on your W-4. Here's the simple math: Take your typical refund amount and multiply by 4. So if you usually get $1000 back, put $4000 in Step 4(b). This tells your payroll system to withhold less tax because it thinks you have more deductions. I put $3200 in Step 4(b) last year (I was getting about $800 refunds) and my bi-weekly paycheck went up by roughly $62. Got my refund down to just $150 this year, which is pretty much perfect. Just make sure you don't go overboard - you want to get close to zero refund without owing money. Start conservative and you can always adjust it again next year if needed!

This is a really important question to get right! I'm a tax professional and I can confirm what others have said - unmarried couples absolutely cannot file jointly, regardless of living situation or engagement status. This is one of the most fundamental IRS rules. What concerns me is that a tax professional advised you to do this. Either there was a miscommunication about which tax year you were discussing, or they're suggesting something that could get you in serious trouble with the IRS. Filing jointly while unmarried is considered filing a false return, which can result in penalties, interest, and potential fraud charges. Your best options as an unmarried couple are: 1. Both file as Single 2. One files as Head of Household if they have a qualifying dependent 3. One claims the other as a dependent if income/support tests are met I'd strongly recommend getting a second opinion from another tax professional before proceeding. The savings aren't worth the risk of IRS penalties down the road.

As someone who went through a similar situation last year, I can't stress enough how important it is to get this clarified immediately. My partner and I were also told by a tax preparer that we could "basically file together" and it turned out they meant we should coordinate our filings to maximize deductions (like one taking all charitable contributions, the other taking all business expenses), not actually file a joint return. The distinction is huge - coordinating your separate returns is smart tax planning, but filing a joint return while unmarried is illegal. I ended up calling the IRS taxpayer advocate service (877-777-4778) to get official clarification, and they were very clear about the rules. Given that you mentioned you're getting married in December, you might want to consider whether it makes sense to move up your wedding date if the tax savings are substantial. Being married by December 31st would allow you to file jointly for the entire 2024 tax year when you file next year. But for your current 2023 taxes, you definitely need to file as unmarried individuals. Please don't risk it - the penalties and interest on incorrect filings can be brutal, and it's not worth the stress of wondering if the IRS will catch it later.

Does anyone know if the "no donation necessary" option affects anything? Omaze always has that fine print saying no purchase/donation necessary to enter. I've been using the free entry option for like a year now (haven't won anything lol) but wondering if I did win, would the taxes be different than if I had donated?

Something that might help clarify the confusion is to check the specific language on each Omaze campaign page. Different campaigns can have different charitable percentages - I've seen some where only 10-15% goes to charity while others might be 50-60%. Also, keep in mind that Omaze should send you an email confirmation after each donation that breaks down the tax-deductible portion. If you're not getting these, definitely reach out to their customer service because you'll need that documentation for your records. One last tip - if you're planning to do regular Omaze donations throughout the year, consider keeping a simple spreadsheet tracking each donation amount and the deductible portion. It'll save you a headache come tax time when you're trying to figure out your total charitable contributions for the year.

This is such a thoughtful approach to generational wealth planning! I'm in a similar situation with three kids in their twenties, and your post really resonates with my concerns about balancing generosity with encouraging independence. One thing that's helped us is starting small to test their financial responsibility before committing to larger trust structures. We began by gifting smaller amounts ($5K-$8K annually) with loose conditions - like matching their emergency fund savings or education expenses - just to see how they handle it. This gave us confidence about their decision-making before we considered more formal arrangements. I'm particularly interested in the tax pass-through strategy you mentioned for trusts. From what I understand, the beneficiaries would need to receive enough distribution to cover their tax liability on the trust income, which could complicate your goal of controlling when they receive funds. Have you considered whether your kids would be comfortable with the additional tax complexity on their returns? The Roth IRA funding approach seems like a great starting point regardless of what else you decide. It teaches retirement planning habits and has those built-in restrictions you want, plus the tax-free growth is incredible over decades. Even if it doesn't use your full annual exclusion, the long-term impact could be substantial. Looking forward to hearing what your estate attorney recommends! These conversations are so valuable for those of us navigating similar decisions.

This is exactly the kind of thoughtful planning more families should be doing! I went through a similar decision process with my four adult children last year and ended up with a hybrid approach that's worked really well. We started with maxing out Roth IRA contributions as gifts (great suggestion in your post) and then added a simple family loan program for major purchases. When they want to buy a house or start a business, we offer loans at 1-2% interest that convert to gifts if they meet certain milestones - like maintaining the property well or keeping the business profitable for two years. One thing our CPA emphasized that I don't see mentioned much here is the importance of documenting everything properly, even for informal arrangements. We keep written records of all gifts and conditions to avoid any IRS scrutiny later. Also, if you do go the trust route, consider having annual family meetings to review distributions and goals - it keeps everyone on the same page and reduces the "controlling parent" perception. The generation-skipping considerations mentioned earlier are spot-on if you're thinking long-term. We structured our plan to benefit potential grandchildren too, which actually made our kids more supportive since they could see how it might help their future families. Your attorney meeting should be very productive with all this research! The key is finding the right balance between control and family harmony.