Every year around this time, I swear the calendar hits fast-forward.
We go from the first-day-of-school pictures…
to pumpkins and costume chaos…
to Thanksgiving pies…
And suddenly we’re staring down the holidays, wondering how the year disappeared faster than the candy your kids “didn’t notice” you ate.
And along with that rapid-fire season comes the advisor’s annual duty: The official year-end planning blog.
So, let’s walk through the REAL year-end moves that matter, simply, calmly, and without drowning in jargon.
Underneath this post, you’ll find the a link to the full, interactive year-end checklist if you would like to go deeper!
Why Year-End Planning Matters More Than People Think
The final weeks of the year are when you can still influence your tax bill, fine-tune your cash flow, and set up 2026 to start smoothly. After December 31, many doors swing shut until next year, so now is the time to look at a few key areas.
Nothing here requires spreadsheets the size of Rhode Island. It’s just knowing which levers exist and deciding whether they’re worth pulling this year.
1. Cleaning Up Your Investments Before the Ball Drops
Tax-Loss Harvesting
If some investments in your taxable accounts are down, you may be able to realize losses to offset gains or even reduce up to $3,000 of ordinary income. It’s one of the few times losing money can actually help you.
Capital Gain Distributions
Mutual funds often distribute gains this time of year. Sometimes the smartest move is not buying more right before the distribution hits.
Staying in Your Preferred Tax Bracket
Income thresholds matter. A little planning can help prevent income from spilling into higher brackets or bumping capital gains from 15% up to 20%.
The 0% Capital Gains Bracket
One of my favorite under-the-radar opportunities. If your income is low this year, maybe due to retirement or a job change, you may be able to realize long-term capital gains tax-free. Yes, zero tax.
2. Roth Conversions and Other Tax Moves
This is one of the most strategic times of year to evaluate a Roth conversion. If you are in a lower-than-usual tax bracket, filling up that lower bracket with a conversion can be incredibly valuable over time.
This is also when we look at:
- Maximizing 401(k) or HSA contributions
- Timing deductions
- Reviewing business income if you are self-employed
- Coordinating charitable giving (especially appreciated securities or QCDs)
These are simple, intentional adjustments that can add up over the years.
3. IRMAA, Medicare, and the “Sneaky Surcharges.”
If you are on Medicare or approaching it, your income today can change what you pay two years from now. This is the moment to check whether you are nearing an IRMAA threshold so a late-year decision does not accidentally trigger higher premiums.
4. Required Minimum Distributions (RMDs)
If you’re required to take RMDs, they need attention before year-end. Inherited IRAs have different rules, and employer plans can’t all be aggregated. Missed RMDs are not the kind of surprise anyone wants heading into January.
5. Cash Flow & Flexible Spending Accounts
A quick review can prevent money from disappearing into the “use it or lose it” void. Some FSAs allow rollovers, others offer grace periods, and some work like Cinderella’s carriage and expire at midnight on New Year’s Eve, any remaining dollars just vanish.
If you’ve met your deductible, it might also make sense to knock out any final medical appointments now.
6. Education Funding & Gifting
Year-end is gift-planning season:
- Annual gifts up to $19,000 per person are tax-free
- 529 contributions can be “superfunded” over 5 years
- Newer rules make 529-to-Roth transfers possible in certain cases
If college planning is on the horizon, these moves can help shift strategy in a meaningful way.
7. Estate Planning Touchpoints
If your family changed this year, births, deaths, marriages, divorces, or relocations, it’s worth reviewing your estate documents before the year turns over.
A quick review now avoids much bigger headaches later.
Why I Use Holistaplan (And Why It Helps You)
Holistaplan is a tax analysis tool I use to uncover planning opportunities and give you a clear, visual summary of where we can potentially save you money on taxes.
A big part of year-end planning is this kind of analysis; your tax return is not just paperwork, it is a roadmap.
Holistaplan helps me quickly see things like:
- Which tax bracket you are in and how close you are to the next one, so we can decide how much income to recognize this year without unnecessarily pushing you into a higher tax rate.
- How your income level might affect things like Medicare premiums (IRMAA), so we can be intentional about your income and avoid surprise jumps into more expensive premium tiers when it makes sense to do so.
- Where charitable giving or timing of income could be especially beneficial, helping your donations and deductions work harder for you in higher-income years and potentially keeping you out of higher tax or Medicare premium brackets.
- How much capital gains you have realized and how that fits into the bigger picture, so we can decide whether to realize more gains, look for losses to offset them, or hold off to avoid tipping you into higher tax or Medicare tiers.
In plain terms: Holistaplan helps me find the “hidden” planning opportunities inside your tax return so we can make smarter, more informed decisions together.
I know year-end can feel like a sprint. Between school concerts, travel, holiday prep, and trying to remember where you hid the gifts…financial planning might not be at the top of your festive list.
But a few thoughtful steps now can make April a lot kinder and set up 2026 on solid footing.
If you’d like me to review your 2024 tax return through Holistaplan and highlight your specific year-end opportunities, as a family financial planner, I’m happy to help.
Enjoy the season, enjoy the ride, and be kind to Future You at tax time.
