As a Certified Financial Planner and the founder of Future-Focused Wealth, I help high earners create financial strategies that actually work in real life — not just on paper. And if you’re anything like my clients (or me), you’re staring down the end of the year wondering how the calendar flipped so fast.

This list isn’t meant to make you panic. Let’s be honest — some of these moves, like reviewing your estate plan or evaluating your insurance, probably should’ve happened earlier in the year. But if you’ve been working with me through the Wealth on Purpose™ framework, odds are we’ve already tackled these proactively as part of your bigger strategy.

Still, if you’re a DIY-er — or just need a gut check before 2026 hits — these are the smart, timely financial moves I want you to have on your radar.

Think of this as a final pass, not a scramble. You don’t have to do everything this week. But you do deserve to move into the new year with clarity, intention, and zero financial regret.

Holiday Season = A Prime Time for Money Conversations (Without Ruining Christmas)

Before we jump into the checklist of year-end to-dos, there’s one powerful (and often overlooked) opportunity I want you to consider:

Talk about money with your family.

No, not a full-blown financial intervention. Not a shame-fest. Not a two-hour lecture over turkey.

I’m talking about thoughtful, grounded, proactive conversations that strengthen your financial legacy, bring clarity to loved ones, and set the tone for better decision-making in 2026 and beyond.

Why Now?

The holidays are one of the few times a year when people are actually in the same room. If you’ve got family coming together — parents, adult kids, siblings, even close friends — this is your window.

It’s not about airing your entire net worth over pie. It’s about planting seeds and creating space for clarity, especially on the things that matter most.

Not Sure Where to Start? Try These Topics:

• “Hey, have you seen this binder I’ve been putting together?”
  
  (Pull out your Future-Focused Wealth financial binder and walk through what’s in it — not every detail, but enough that someone knows it exists and where to find it.)
• “We’ve been working on updating our estate plan. Just wanted you to know where things stand in case something unexpected ever happens.”
• “We’re thinking through long-term care or future healthcare decisions. Have you ever talked about that with your own planner?”

These aren’t lectures — they’re invitations. They open the door to future transparency and better family alignment.

Guidelines for a Holiday Financial Chat That Doesn’t Derail the Day

1. Read the room. If people are stressed, tired, or three cocktails deep — maybe wait.
2. Keep it short. This isn’t a deep-dive. Think headline, not annual report.
3. Lead with context, not control. “I want to make sure you’re not left guessing” goes a lot further than “I need to explain my finances to you.”
4. Use your binder as a conversation starter. It’s visual, it’s organized, and it helps steer the conversation away from overwhelm.
5. Don’t expect decisions. This is a door-opener — not a strategy session.

Why This Matters

Most family money drama doesn’t come from greed. It comes from confusion. Surprises. Lack of planning. And while we can’t control everything, we can communicate better — especially about things like:

• Where important documents live
• Who your financial planner is
• What your wishes are around healthcare, giving, or legacy
• What not to do in a crisis

A 10-minute conversation now can save your loved ones hours (or years) of stress down the road.

So yes, pull up the Netflix holiday movie and grab a hot cocoa. But before everyone heads home, consider opening up your binder and saying:

“Hey — just in case something ever happens… I want you to know we’ve got a plan.”

That one sentence? Might be the most valuable thing you say all season.

Backup Plan: How to Exit a Heated Money Conversation Without Ruining the Holiday (or Pulling a Kevin McCallister)

Let’s just call it like it is: talking about money with family during the holidays can be… dicey.

Even when you show up calm, grounded, and binder in hand, there’s always a chance someone’s going to get that look in their eye — you know, that look — and suddenly you’re wondering if you should’ve just stayed home like Kevin.

“Look what you did, you little jerk!”

— Uncle Frank, probably not a CFP®

(Exactly the kind of energy we’re trying to avoid.)

So, before you walk into that conversation, let’s arm you with a strategic bailout plan — just in case things get a little too real around the cranberry sauce.

Your “Holiday Financial Exit Plan” (Also Works for Burnt Pies and Political Rants)

1. Know the warning signs.

If voices start rising, chairs scoot back, or someone breaks out the phrase “well back in my day…” — consider that your official exit cue.

2. Deploy the safe phrase.

Try these crowd-pleasers:

• “Totally hear you. Let’s pick this back up after the holidays — I want to do it justice.”
• “I can tell this is important. Let’s schedule a time where we’re not juggling gravy and grandkids.”
• “Let’s hit pause before we have to put someone in a timeout. And I don’t mean the kids.”

3. Pivot like a pro.

Redirect without raising eyebrows:

• “So, has anyone actually finished shopping yet?”
• “We’re out of wine. This feels like a more immediate crisis.”
• “Anyone want to watch Elf and pretend adulthood doesn’t exist?”

4. Make a note to follow up — when emotions aren’t simmering on the stovetop.

A quick post-holiday text goes a long way:

“Hey — I’m really glad we started that convo. Let’s talk more in January when things calm down.”

5. And finally… give yourself some grace.

You’re not trying to solve generational wealth gaps over green bean casserole. You’re opening the door, planting seeds, and showing leadership — even if the conversation gets awkward.

Bonus Tip: Choose Your Players Wisely

You don’t have to loop in the whole family reunion. Start with the people who actually need to know:

• Your healthcare proxy
• Your executor
• The kid who knows how to open PDFs

Keep it simple. Keep it strategic. Keep it off the holiday highlight reel.

Because let’s be honest — if the family wants drama, they can queue up The Grinch. Your money convo? Doesn’t need to be the main event

The List: My Go-To Year-End Financial Moves

(Cue Dick Clark… or whoever’s counting us down these days)

Now that we’ve tackled the let’s-talk-money-with-family-without-burning-the-house-down conversation, let’s shift gears to your year-end financial strategy.

This isn’t some copy-paste list from a finance blog written by a guy who still thinks CDs are hot (not the musical kind — the bank kind). This is a CFP-crafted, client-tested game plan I use with high earners, business owners, and real families who want to end the year smarter than they started it.

Now, full disclosure:

This list is not one-size-fits-all. It’s a prioritized order I tend to follow with clients — based on decades of planning experience and more end-of-year strategy sessions than I can count. But your exact order may vary depending on your goals, your income, your tax bracket… or whether you opened your mail this month.

If you’ve been working with me through the Wealth on Purpose™ framework, chances are a lot of these are already in motion. If you’re DIY-ing? This is your “get ahead before the ball drops” checklist.

Because let’s be real: come midnight on December 31st, when the confetti’s flying and someone’s fake-counting backwards from ten on TV… I want you raising a glass knowing your money moves are already locked in.

Let’s get into it

1. Don’t Miss Those RMDs (Required Minimum Distributions)

If you’re 73 or older, or you’re managing money for someone who is, this is not optional — RMDs have to come out of tax-deferred retirement accounts by December 31st. Miss it, and the IRS may slap you with a penalty of 25% of what you should have withdrawn. Ouch.

That includes:

• Traditional IRAs
• 401(k)s (unless you’re still working for that employer)
• SEP and SIMPLE IRAs

But here’s the thing — even if you’re not 73 yet, you’re not off the hook.

This is a perfect time to check in with aging parents or elder family members who might not have this buttoned up. Many people miss RMDs simply because they don’t know they need to take them — especially if they’re retired, widowed, or no longer working with an advisor.

Pro Tip:

Helping a parent organize their RMD can also open the door for tax-smart gifting.

Let’s say they don’t need the full amount — this could be a chance to:

• Help fund a grandchild’s education (via a 529 plan)
• Contribute toward family holiday travel or experiences
• Or even support a cause with a Qualified Charitable Distribution (QCD) — which allows up to $100,000 to go straight to a charity, tax-free, and counts toward their RMD

RMDs aren’t just a line item. They’re a moment to be thoughtful — and strategic — about how wealth moves through generations.

And if it’s your first year navigating one? Double-check the start date and calculation rules — they’re not always simple. (And if you need help, you know where to find me.)

2. Use It or Lose It: Flex Spending Accounts (FSAs)

If you’ve got money sitting in a Flex Spending Account, this is your friendly CFP® reminder: check your balance now. Most FSAs are “use it or lose it,” meaning if you don’t spend it by year-end (or sometimes March, depending on your plan’s grace period), poof — it’s gone.

Most people know about the usual eligible expenses:

• Eye exams and prescription glasses
• Dental work
• Copays and deductibles
• Over-the-counter meds and feminine hygiene products (yes, finally)

But here’s what surprises a lot of folks — some FSAs now cover gym memberships and fitness programs, if they’re medically necessary and prescribed by a doctor. That’s right, your FSA might pay for you to sweat it out — with the right paperwork.

Here’s how it works:

1. Get a Letter of Medical Necessity from your doctor.
   
   It should state that physical activity is required to treat or prevent a specific condition (think: obesity, high blood pressure, diabetes, etc.).
2. Submit it to your FSA provider, along with proof of payment for your membership or program.
3. Reimbursement is not guaranteed, so check with your FSA administrator ahead of time to make sure your gym or program qualifies.

If you’re tired of only using your FSA for allergy meds and Band-Aids, this could be a solid way to invest in your health — before the money disappears.

And even if the gym isn’t your thing, make sure to stock up on eligible items, schedule any last-minute appointments, and clear that balance before December 31st (unless your plan offers a grace period or carryover)

3. Max Out Your Tax-Advantaged Accounts

(If It Makes Sense for Your Plan — and Your Sanity)

You’ve heard it before: Max out your retirement accounts before year-end! But the truth? Not everyone should — and not everyone can. So let’s be strategic, not frantic.

If you’ve got solid cash flow or a year-end bonus, topping off your tax-advantaged accounts can give you a solid tax benefit and set you up for long-term wins. Here’s how to think about it.

Retirement Accounts

• 401(k) / 403(b) contributions
  
  2025 limit: $23,000, with a $7,500 catch-up for those 50+.
  
  If your employer plan allows last-minute changes, this is your chance to give yourself a pre-tax raise before the year ends.
• Traditional IRAs
  
  Contribute up to $7,000 (or $8,000 if you’re 50+), but keep in mind income limits apply for tax deductibility if you also have a workplace retirement plan. Not deductible? Read on for a smarter pivot.

Enter: The Backdoor Roth IRA

If your income is too high to contribute directly to a Roth IRA — hello, phase-outs — you may be able to pull off a Backdoor Roth IRA move

Here’s the high-level overview:

1. Contribute to a Traditional IRA (non-deductible).
2. Wait a hot minute (or coordinate it immediately — ask a pro).
3. Convert that contribution to a Roth IRA.
4. Pay taxes only on any gains, not the contribution itself.

But here’s the fine print:

• If you have other pre-tax IRA balances, the IRS will treat the conversion as a proportion of pre-tax and after-tax dollars. That means you could owe more than expected if you don’t plan carefully — thanks to the pro-rata rule.
• This strategy should never be DIY’d off a blog post. Have a professional check your current IRA balances before pulling the trigger.

Done right, this is one of the few legal workarounds for high earners who want to grow tax-free wealth. Done wrong? It’s a paperwork and tax nightmare.

Health Savings Accounts (HSAs)

Still the crown jewel of tax-advantaged accounts:

• 2025 limits: $4,300 for individuals / $8,650 for families
• $1,000 catch-up at age 55+

Use it now, or grow it as a long-term health nest egg. Triple tax benefit? Yes, please.

Pro Tip: It’s Not “Max Out at All Costs”

Tax-deferred accounts are great — until they leave you cash-poor or bloated with tax liability later. Before you go all in, ask yourself:

• Do I have the liquidity to support this?
• Will this reduce my current tax burden — or delay it?
• Is this aligned with my broader strategy (and not just what social media says “smart people” do)?

Because real planning isn’t about stuffing accounts to the brim.

It’s about knowing which ones to fill, how much, and why.

And if you’re not sure? That’s exactly what we help with. Future-Focused Wealth means making decisions that work for you, not just your tax preparer.

4. Consider a Roth Conversion (Before the Clock Strikes Midnight)

Let’s talk about one of the smartest year-end moves you can make if you’re thinking long-term: Roth conversions.

This isn’t a trendy TikTok finance tip. This is real strategy for high-income professionals, early retirees, business owners, and anyone who wants more tax control in retirement. And the window to act? It closes on December 31st.

What Is a Roth Conversion?

A Roth conversion means moving money from a Traditional IRA (or a pre-tax retirement account like an old 401(k)) into a Roth IRA. You’ll pay income taxes now on the amount converted, but the payoff is massive:

• Tax-free growth for life
• Tax-free withdrawals in retirement
• No Required Minimum Distributions (RMDs)
• Flexibility and control in how you access your money

Sound dreamy? It is — if it’s done right.

Why It’s a Powerful Year-End Move

Here’s why now — not later — is your moment:

• Your 2025 income is mostly baked in, so you know your tax bracket. That makes this the best time to see how much you can convert without jumping tax brackets.
• We’re in a tax sweet spot. Many tax brackets are set to rise in 2026 when parts of the 2017 Tax Cuts and Jobs Act expire.
• Markets are still volatile — which can be your friend. If your portfolio dipped this year, converting those assets now locks in a lower value and gives you more tax-free upside.
• You can’t undo this later. Roth conversions have to be completed by December 31, and there’s no recharacterization anymore. Miss the deadline, and the window closes.

Who Should Be Thinking About This?

You’re a prime candidate if:

• You expect to be in a higher tax bracket in retirement
• You’re in a lower income year (like after retiring early, selling a business, or before Social Security kicks in)
• You want to reduce future RMDs
• You want to leave tax-free money to heirs
• You’re looking to diversify your tax exposure (which is just fancy talk for not putting all your eggs in the taxable basket)

Even if a full conversion doesn’t make sense, a partial Roth conversion could be a game-changer. This is where strategy — not guesswork — matters.

What You Need to Know

• You’ll owe taxes now on the amount you convert. Ideally, those taxes should come from a separate account — not the converted funds — to get the full benefit.
• Converting too much could push you into a higher tax bracket, mess with Medicare premiums, or phase you out of other tax credits. This is where your financial planner and CPA become your best friends.
• There’s no going back. Once the clock strikes midnight on December 31st, it’s locked in.

Real-World Example

Let’s say you’re in the 24% tax bracket and have $20,000 of headroom before hitting the next bracket. Converting $20K from your Traditional IRA into a Roth now means you’ll pay $4,800 in tax — and never owe another dime on that money (or its growth) again.

That’s not budgeting. That’s wealth engineering.

Want a Step-by-Step Breakdown?

Roth conversions are powerful — but only when they’re personalized. That’s why I created a free, easy-to-follow guide:

Download the Roth Conversion Guide→

Hover text: “Learn if a Roth conversion fits your income, goals, and tax strategy.”

Inside you’ll get:

• Clear breakdowns of who should consider a conversion
• Tax bracket planning worksheets
• Common mistakes to avoid (and how to avoid them)
• And how this strategy fits into a comprehensive financial plan — not just a one-off decision

Whether you’re a DIYer or working with a professional, this guide will give you the insight you need to make the best move before 2026.

5. Realize Investment Losses (Tax-Loss Harvesting)

Nobody likes seeing red in their investment account, but if you’re playing the long game — and you should be — a temporary loss can become a strategic move, especially at year-end.

Tax-loss harvesting lets you take advantage of market dips by selling investments that are worth less than what you paid for them. You use that loss to offset capital gains or reduce up to $3,000 of regular income. It’s not just cutting your losses — it’s leveraging them for long-term benefit.

Why This Matters (Especially Right Now)

2025 has been a weird year for investors. A lot of high earners are sitting on positions that haven’t quite bounced back, especially in tech, commercial real estate, or sector-specific ETFs. If you’ve realized gains this year — from a home sale, business deal, or portfolio rebalance — offsetting those gains with losses can significantly reduce your tax bill.

This isn’t about bailing on an investment. It’s about playing smarter with what the market gives you.

How It Works

1. Identify losing positions in your taxable brokerage accounts.
2. Sell the asset to realize the loss.
3. Use the loss to offset capital gains — and up to $3,000 of ordinary income if needed.
4. Reinvest in a similar but not identical asset to stay invested and avoid the wash sale rule.

A quick example: If you sell an S&P 500 ETF at a loss, you might buy another index fund with similar exposure but a different structure — like switching from SPY to VOO — so you stay in the market without violating IRS rules.

Wash Sale Rule: Don’t Miss This

If you sell a security for a loss and buy the same or “substantially identical” one within 30 days before or after the sale, the IRS disallows the loss. That’s called a wash sale — and it defeats the whole purpose. Stick with replacements that give you similar market exposure without triggering the rule. Your advisor or tax pro can help with this if you’re unsure.

Real-World Example

Let’s say you sold company stock this year for a $40,000 gain. Meanwhile, your tech ETF is still down $10,000. If you harvest that loss before December 31, you can reduce your taxable gain to $30,000. If you’ve got more losses, you can carry those forward and use them in future years.

This is one of the easiest ways to actively reduce your tax bill without reducing your long-term strategy.

This Is a Strategy — Not Market Timing

This isn’t about abandoning your investments. It’s about making a tactical move within a broader financial plan. Losses are going to happen — this is how you make them useful.

And yes, we build this into the Wealth on Purpose™ system, because portfolio strategy and tax planning go hand-in-hand. It’s not about beating the market. It’s about using every tool available to build a stronger plan.

Want to See Where You Can Harvest?

We include tax-loss harvesting reviews for our clients each year — especially those with sizable gains, complex portfolios, or planned liquidity events. If you’re not already reviewing your investment tax exposure annually, it’s time.

Ready to get strategic with your losses? Let’s look at it together.

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6. Evaluate Your Tax Withholding or Make an Estimated Payment

W-2 employee or business owner — either way, it’s time to make sure Uncle Sam isn’t planning a surprise party for you next April.

Checking your tax withholding now helps avoid two things: a massive bill in April or an interest-free loan you just gave the IRS all year. Neither option is a win.

Why This Matters for High Earners

If your income changed this year — bonuses, job change, side income, RSUs vesting — your withholdings might not reflect the reality of what you owe. And let’s be honest: most people set their withholding when they started their job… and haven’t touched it since.

Small miscalculations become big tax-time problems when your income creeps higher or you start layering in different income streams.

If you’re self-employed or a business owner? Quarterly estimates are even more important — and by Q4, it’s your last chance to make corrections.

What to Do Right Now

1. Pull out your last pay stub and compare it to last year’s total taxes paid. Are you on track to pay more, less, or about the same?
2. Use the IRS withholding estimator — or better yet, your CPA — to plug in your expected income and deductions.
3. If you’re behind:
   • Adjust your W-4 now to increase withholding for the final paychecks of the year.
   • Make a one-time estimated tax payment before December 31 to avoid penalties.
4. If you’re over-withholding:
   • Consider scaling it back slightly to avoid giving the IRS an interest-free loan.

Either way, the goal is to land the plane smoothly — not with a $9,000 refund or a $9,000 surprise bill.

High-Income Catch: The Medicare Surcharge and Net Investment Income Tax

If you’re crossing certain thresholds ($200K for individuals, $250K for couples), don’t forget that additional taxes might apply — including the 0.9% Medicare surtax and the 3.8% net investment income tax.

Even if your regular income is dialed in, investment gains or capital distributions could push you over those lines. That’s another reason why reviewing withholding and realizing losses (see Section 5) go hand-in-hand.

Strategic Tie-In: Roth Conversions and Tax Planning

If you’re doing a Roth conversion this year — especially a large one — that added income could easily bump you into a higher tax bracket. Evaluating withholding after a conversion ensures you’re not caught off guard.

This is why financial planning isn’t a once-a-year conversation. It’s a living, breathing strategy that adjusts with every smart move you make.

Need help analyzing your numbers or planning your next best move before December 31? That’s exactly what we do in our year-end reviews — especially with our Wealth on Purpose™ clients who want to avoid drama in April.

7. Make Strategic Charitable Donations

Generosity is a core value for many of my clients — but if you’re going to give, give smart. A well-timed charitable contribution can lower your tax bill, help you feel more aligned with your values, and support causes you care about without hurting your long-term strategy.

And no, this isn’t just about dropping a few bucks in a year-end fundraiser. If you itemize deductions, the right charitable approach can create meaningful tax savings.

Here’s how to do it strategically:

• Donate appreciated assets like stocks or mutual funds. You’ll avoid capital gains tax on the growth, and you’ll still get the full deduction based on the fair market value. It’s a double win — reduce your taxes, and do good at the same time.
• Use a Donor-Advised Fund (DAF) to frontload your giving. You can donate a larger lump sum now (and claim the deduction this year), then distribute it to charities over time. This is especially useful if you had a high-income year or expect to take the standard deduction in future years.
• Consider Qualified Charitable Distributions (QCDs) if you’re over 70½ and taking Required Minimum Distributions (RMDs). You can send up to $100,000 from your IRA directly to a qualified charity — and it doesn’t count as taxable income.

Key Deadline:

All charitable donations must be completed by December 31st to count for the 2025 tax year. That includes wire transfers, DAF contributions, and stock gifts — not just the check you write at 11:59 PM on New Year’s Eve.

Bonus Tip:

If you’re planning to gift to family and donate to charity this year, consider how both strategies play into your broader tax picture. We often build a dual strategy for clients who want to maximize impact without overstretching.

Giving is powerful. But giving with a plan? That’s legacy-building.

8. Use Your Annual Gifting Exclusion to Gift to Family and Friends

Want to spread some wealth before the year wraps? The IRS lets you gift up to $18,000 per person in 2025 without triggering gift taxes or using any of your lifetime exemption. If you’re married, that’s $36,000 per recipient when you and your spouse split the gift.

This isn’t just about writing a check to your kids or grandkids. It’s about intentional wealth transfer — getting money out of your estate and into the hands of those who matter most, while avoiding unnecessary taxes and red tape.

Strategic Gifting Ideas:

• Fund a 529 plan for education — contributions grow tax-free, and some states even offer tax deductions or credits.
• Gift cash or investments to adult children to help with home down payments, student loan payments, or financial independence goals.
• Help aging parents with healthcare costs or home support — especially if they’re not yet tapping into their own retirement plans.
• Start the conversation about financial stewardship. A well-timed gift can be a powerful opportunity to share values, vision, and purpose — not just dollars.

Important Mechanics:

• Gifts must be completed before December 31st to count toward the 2025 annual exclusion.
• If you’re gifting appreciated assets, watch the cost basis — the recipient inherits it, which matters if they plan to sell.
• Don’t assume all gifts are “free money.” Depending on what and how you give, there may be paperwork (and strategy) involved. That’s where professional planning comes in.

And a note on boundaries…

Gifting should feel good — not obligatory, stressful, or like you’re bailing someone out for the tenth time. If the idea of family gifting brings up drama or pressure? Revisit the Wealth on Purpose™ framework to make sure you’re not compromising your own peace of mind or long-term plan.

Gifting isn’t just about generosity. It’s about impact. And when done intentionally, it can be one of the most rewarding parts of your financial life.

9. Review Your Budget with Intention

Let’s be honest — most high earners don’t follow a traditional budget. You’re not clipping coupons or tracking every dollar spent at Starbucks. But if you’re making good money and still feeling like you’re financially winging it? It’s time to recalibrate.

This isn’t about restriction. It’s about alignment.

What to Look At

• Your top 5 fixed expenses — Are they still aligned with your goals, lifestyle, and season of life?
• Emotional spending patterns — Has the “I deserve this” button been getting a little too much use?
• Subscription bloat — How many auto-renewals are happening without your knowledge or consent?
• Income changes — Has your cash flow shifted and your spending not caught up?

Why Now?

The last quarter is your chance to end the year with clarity. You’re likely about to get hit with holiday spending, travel, end-of-year bonuses, or business expenses. The worst thing you can do is go into December without a handle on where your money’s really going.

Pro Tip: Don’t Budget for the Sake of Budgeting

Instead of obsessing over spreadsheets, focus on what I call your Purpose-Driven Cash Flow:

1. What are your financial non-negotiables?
2. What spending actually enhances your life?
3. What’s quietly draining your margin without delivering value?

This is where most financial advice misses the mark. It assumes you’re bad with money. You’re not. You’re just operating without a filter that connects your spending to your values.

At Future-Focused Wealth, our year-end reviews aren’t about shaming you for overspending on Uber Eats. They’re about designing a spending system that feels like you — and still gets you closer to your goals.

Don’t Let the Budget Be the Enemy

Your budget should be a reflection of your vision — not a punishment for having a busy, high-performing life. When you take the time now to check in, course-correct, and get real about what matters?

You don’t just spend better. You live better.

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10. Review Your Health Insurance and Open Enrollment Options

If you’ve ever glazed over during open enrollment, you’re not alone. But year-end is one of the few times you can make critical changes to your health coverage — and for high earners, a rushed or uninformed decision here can lead to thousands in wasted premiums, missed benefits, or out-of-pocket surprises.

What to Look For Before You Click “Submit”:

• Evaluate your current plan usage. Did you meet your deductible this year? Have more medical needs coming in 2026? You might want to upgrade — or downgrade — your plan accordingly.
• Compare HSA-eligible plans. If you’re healthy and have savings capacity, a high-deductible plan with a Health Savings Account (HSA) can be a powerful tax tool. You can contribute pre-tax, grow it tax-free, and use it tax-free on qualified medical expenses. Bonus: HSAs roll over forever and can double as a retirement healthcare fund.
• Look at coverage changes. Insurers update networks, drug formularies, and covered services every year. Make sure your doctor, medications, and preferred services are still in-network and covered.
• Check spousal and dependent options. If your spouse has their own plan, compare costs and coverage. Sometimes it makes more sense to stay on separate plans — especially if one partner has significant healthcare needs.

Open Enrollment Deadlines:

• Marketplace plans: Typically November 1 – January 15, but check your state’s exchange for exact dates.
• Employer-sponsored plans: These vary, but most employers set deadlines between mid-November and early December. Don’t assume it’ll roll over automatically — confirm and review.

Pro Tip:

This is also a great time to review your beneficiaries on your health insurance, life insurance, and workplace benefits. If your family or financial situation has changed, your paperwork should reflect that. (Yes, even if it’s boring.)

Your health plan isn’t just about coverage — it’s part of your overall financial architecture. Don’t treat it like a throwaway decision.

11. Check In On Your Estate Planning Documents

(And Loop It Back to the Family Money Conversation)

Yes, estate planning is about documents — wills, powers of attorney, healthcare directives, trusts, and all the other grown-up paperwork. But it’s also about people. The ones you love, the ones you’ve built a life with, and the ones who might one day have to make decisions without you.

That’s why this circles right back to those holiday family conversations we mentioned earlier. If you’ve got aging parents, grown kids, or even just a partner who’s not the financially savvy one — this is your moment. You don’t need to hand them a spreadsheet over stuffing. But you can say:

“Hey — I’ve put together some key documents in case anything ever happens. They’re in the binder in the hall closet. Let’s find time in January to go over it together.”

That alone creates clarity and calm when it matters most.

And a Word of Caution…

Now, sometimes those family conversations don’t go as planned. Tensions run high, old baggage surfaces, or someone says something that makes you want to grab your pie and peace out.

If that happens, pause.

Don’t make permanent legal decisions in the heat of a holiday meltdown.

Cutting someone out of your estate plan because of one rough dinner isn’t strategy — it’s reaction. And reaction is the enemy of good planning.

Instead, give it space. Come back to it with your advisor when the emotions cool and the big picture is back in focus.

Because a strong estate plan isn’t just about what happens when you’re gone — it’s about reinforcing your values, preserving your peace, and protecting the people (yes, even the complicated ones) who matter most.

Final Word: You Don’t Have to Do Everything — But You Do Need a Strategy

Let’s be real: trying to cram every possible financial move into the final days of the year is a recipe for burnout, not brilliance. This isn’t about scrambling — it’s about being strategic.

The truth is, not everything on this list applies to everyone. And if you’ve been working with me through the Wealth on Purpose™ framework, most of these have likely been baked into your plan already — on purpose, with purpose.

But if you’ve been flying solo, second-guessing your moves, or feeling like your money’s running you instead of the other way around? Now’s the time to pause, prioritize, and get intentional before 2026 kicks off.

You don’t need to overhaul your life in the next two weeks. You just need a clear path forward — and that’s what comprehensive planning is for.

Let’s take the guesswork off your plate. Schedule your year-end strategy session today

Let’s Get You Ready for 2026

Schedule a Year-End Strategy Session

• 📄 Download the Year-End Checklist
  
  

Frequently Asked Questions: Year-End Financial Moves

Q1: What happens if I miss the December 31 deadline for Roth conversions or RMDs?

A: You’re not out of luck — but it’ll sting.

• Roth conversions must be completed by December 31. If you miss it, there’s no do-over or extension. You’ll have to wait until next year and re-evaluate your strategy (hopefully with help).
• RMDs, on the other hand, come with real teeth: a penalty of up to 25% of the amount you should have taken. There’s an appeals process, but the IRS isn’t exactly handing out mulligans.
  
  Moral of the story: Don’t wait. These are some of the highest-impact moves you can make this year.

Q2: Can I still contribute to my IRA or HSA after December 31?

A: Yes — some deadlines extend into next year.

• IRA & Roth IRA contributions for 2025 can be made up until April 15, 2026 (or the tax filing deadline).
• HSA contributions follow the same rule — you can contribute up until tax day.
  
  But don’t confuse that with Roth conversions or 401(k) contributions, which do need to happen by December 31.

Q3: How much can I gift in 2025 without triggering taxes?

A: You can give up to $18,000 per person (or $36,000 if you’re married and splitting the gift) without touching your lifetime estate tax exemption.

These are called annual exclusion gifts — and they’re powerful. Gifting can be part of a long-term wealth transfer strategy, not just a holiday surprise.

Q4: I’m a high earner — is a Roth conversion really worth it?

A: Often, yes — especially if:

• You expect higher taxes in retirement
• You want more flexibility with future income
• You’re looking to reduce Required Minimum Distributions
• You plan to leave tax-free money to heirs
  
  A Roth conversion lets you trade a tax bill today for tax freedom tomorrow. But doing it wrong (or in the wrong year) can backfire — which is why we build it into your broader financial plan, not just your tax plan.

Q5: What if I don’t have time to tackle all 12 moves before year-end?

A: First — breathe.

Second — focus on the big levers:

1. RMDs (if they apply)
2. Roth conversions
3. FSA deadlines
4. Any gifting or charitable contributions
   
   Those are hard cutoffs. The rest? Still important, but we can layer them in with intention in January if you’re already working with us through Wealth on Purpose™.

Want more personal guidance?

Book your Year-End Strategy Session

Let’s walk through your next best moves together — no pressure, just clarity.