The end of the year always sneaks up faster than we think. Between holiday chaos and setting New Year goals, it’s easy to miss out on some of the best financial opportunities of the year — especially the ones that could quietly save you thousands.
Here are three end-of-year moves I make (and recommend) to get my financial house in order before the clock strikes midnight on December 31st.
1. Roth Conversions: Playing the Long Game (Smartly)
If you’re in a relatively low tax bracket this year — either because of business dips, job changes, or just lower income — now’s the time to think about a Roth conversion.
A Roth conversion means moving money from a tax-deferred account (like a traditional IRA or 401(k)) into a Roth IRA — where future growth and withdrawals can be completely tax-free. Yes, you’ll pay taxes on the converted amount now, but if your tax rate is low, that hit could be minimal compared to what you’d pay later.
Why act now?
The current tax code (via the Tax Cuts and Jobs Act) is set to expire in 2026, meaning taxes could increase after 2025. That gives us a short window to make these moves while taxes are relatively low.
I did this personally a couple of years ago when my income dipped during a career pivot. I moved a chunk of money over to my Roth, paid the small tax bill, and now that money is growing tax-free — forever. It’s like future-you gets a bonus check for being strategic now.
2. Tax Loss Harvesting: Turning Losses into Wins
Let’s be real — we all have that one stock (or five) that didn’t exactly live up to the hype this year. But here’s the good news: the IRS actually lets you benefit from those losses.
Tax loss harvesting is the strategy of selling underperforming investments to realize capital losses. You can then use those losses to offset gains or deduct up to $3,000 from your ordinary income each year.
Even better? You can reinvest that money into similar (but not identical) assets to keep your portfolio aligned. It’s like cleaning your financial house without losing your long-term strategy.
I did this last December — sold a tech stock that tanked, and bought a similar ETF. Not only did I lock in the loss for tax purposes, but the new ETF actually rebounded faster than expected. Win-win.
3. Negotiate Bills + Cancel Subscriptions: The Easiest $300 You’ll Ever Save
Okay, this one isn’t sexy, but it works: call your service providers.
Cell phone, internet, pest control, and car insurance — all of them often offer lower prices to new customers. If you call and say, “Hey, this is too expensive — what can you do for me?” you’d be shocked how quickly they find magically lower rates.
A few years ago, I did this right before the holidays. Called my internet provider, asked for a better plan — and boom, $35/month saved. Rinse and repeat with car insurance? Another $40. Then I finally canceled those lingering subscriptions I’d totally forgotten about (looking at you, random fitness app). Altogether, I freed up nearly $250/month.
Most families can save $100–$300/month doing just this.
Bottom Line?
Before the ball drops, make these three moves:
💰 Consider a Roth conversion if your taxes are low
📉 Harvest losses and reallocate smartly
📞 Negotiate your bills and cancel the fluff
Future-you (and your bank account) will say thank you.
Want help figuring out if a Roth conversion or tax-loss harvesting makes sense for you? I’m not a CPA, but I do know some amazing ones. Drop us a message at info@hollifieldfinancial.com, or call our headquarters office at (843) 900-3099.
