2025 Year-End Wealth Planning Checklist

• How have my goals and needs changed in 2025?
• What do I want to do differently in 2026?

The OBBBA effect: expectations vs. reality

Throughout 2025, many investors and wealth planning advisors alike were on the edge of their seats awaiting the rollout of the One Big Beautiful Bill Act (OBBBA). Plot twist, the bill didn’t bring the sweeping changes many anticipated, but it still carries important implications for tax and financial planning. Some of the most notable ripple effects include:

• Charitable giving rules: Modified deduction limits and reporting requirements have made timing and structure more important when planning donations.
• SALT (state and local tax) deductions: Adjustments to state and local tax deduction thresholds may shift where and how you realize deductions.
• Alternative Minimum Tax (AMT): Adjusted exemption levels and phase-out thresholds mean more high-net-worth individuals may now find themselves exposed to AMT. This can domino across strategies such as exercising stock options, timing large charitable contributions and planning the recognition of income versus deductions.
• Estate planning considerations: Minor shifts in exemption calculations may influence gifting strategies sooner rather than later.

The key takeaway? Even modest adjustments in tax law can have an impact on your broader financial strategy. Year-end is the perfect time to revisit these details to ensure you’re taking advantage of the opportunities—and sidestepping surprises.

With valuable insights and guidance from Michelle Slawny, Director of Wealth Planning at Associated Bank, we’ve outlined the areas to focus on as you prepare for year-end.

Tax planning

OBBBA has reshaped parts of the tax landscape for both individuals and businesses. Year-end is a great time to assess how these changes affect you. Slawny shares, “I always encourage people to get an idea of what their income looks like year to date and if they anticipate being in a lower tax bracket—before December 31.”

Encouraging people to find ways to accelerate their income in some way, Slawny suggests, “Look to see if there's a bonus that can be paid in 2025 instead of 2026. Or a Roth conversion is another way to fill up their tax bracket. Keep in mind there's timing there—you can't do a Roth conversion that's effective in 2025 after December 31, so be mindful of the deadline.”

For those trying to take full advantage of their 401(k) and/or HSA accounts, Slawny reiterates the importance of having them fully funded. “The 401(k) has to be through payroll deduction—and it’s important to max that out. But HSAs don't have to be through payroll. Sometimes people don't realize that they can write a check, even in January or February, to make up for any missed contributions. So, while it's not that December 31 deadline, I would still encourage people to make sure they’re fully funded.”

Slawny says one of the silver linings of OBBBA “is the increase in the SALT deduction from $10,000 to $40,000. For clients in high-tax states like Wisconsin, Minnesota and Illinois, this can make itemizing worthwhile again. But the catch is—under AMT, those SALT deductions are limited, so the benefit could be offset.”

When it comes to proactive planning, Slawny shares a valuable tip, ““For high-income individuals who may fall into AMT in 2026, there’s real value in accelerating deductions into 2025. That could mean paying property taxes or state income taxes early, effectively doubling up this year to maximize the benefit before AMT changes take hold.”

From a big picture perspective, she cautions, “The new AMT rules create a zig-zag effect—on one hand, you get more room to deduct under OBBBA, but on the other, AMT limits what you can actually use. The key for high-net-worth clients and wealthy families is to plan these moves now, while you still have flexibility, rather than waiting until 2026 when your options may be far more limited.”

Ask yourself: Have recent life changes—or OBBBA itself—shifted my tax situation?

• Review how OBBBA impacts charitable giving rules, SALT (state and local tax) deductions and business investments
• Consider your charitable contributions and whether it’s better to make any of them this year or wait till the start of next year
• Maximize contributions to tax-advantaged accounts (401(k), IRA, HSA)

Investing

Markets have been anything but predictable, driven by inflationary pressures, shifting interest rates and global uncertainty. Many investors have found themselves with concentrated positions or portfolios that no longer match their risk appetite.

When it comes to investments and individual portfolios, Slawny says to celebrate the wins, but to be smart with your next move. “We've had a very strong year. It was a little bumpy at first because of the tariff conversation. But so far, all the major indexes are positive.” She also reminds investors that balance is key. “If people have not been rebalancing, that might mean the stock portion of their account is a little overweighted. They may find themselves at 55/45 versus a 50/50 portfolio.”

Even though the market has done well, Slawny advises rebalancing back to 50/50 in this scenario because we do have a lot of volatility and uncertainty looming. While some clients may be all about the gamble, she recommends taking some chips off the table. “We're selling high, we're selling the equities that have done really well, which means we're capturing some of those profits within our accounts and reinvesting in the fixed income side of things.”

Ask yourself: Is my portfolio still aligned with my goals and risk comfort?

• Review the level of diversification in your portfolio and rebalance where necessary
• Evaluate your risk capacity—not just willingness, but financial ability to weather losses
• Explore tax-loss harvesting opportunities before year-end

Cash & liquidity

Short-term interest rates may trend lower into 2026, while the long-term outlook remains clouded by inflation and rising federal debt. If you’re nearing retirement or simply value flexibility, it may make sense to increase your cash cushion. This can give you the confidence to spend a little while staying prepared for life’s surprises.

And per Slawny, “I would say now is the time to sell some investments, raise that cash while the market is high, even if that means capital gains may be due.”

“More recently, I've heard something from newer retirees,” Slawny continues. “And that is they wish they would have had more cash in their early retirement years.”

“I think if someone is within five years of retirement, it probably makes sense to reevaluate their portfolio and see how much they have in checking, savings, money market, deposit accounts—and bump that up.” Then the spending peace of mind is there for when those moments of spontaneity arise.

On the other hand, holding too much cash can cause you to miss out on those higher returns, especially if interest rates are favorable. It's always good to evaluate your position and ensure it lines up with your needs.

Ask yourself: Is my cash strategy still a good fit?

• Identify any large upcoming expenses or liquidity needs
• Review emergency reserves (12–18 months of expenses is a strong guide)
• Assess reinvestment risk from falling short-term rates and explore opportunities to increase returns on cash

Wealth planning

Beyond taxes and investments, year-end is also the time for a holistic financial check-up. Think of it as a pulse check to confirm that your plan continues to protect you and your loved ones.

Estate planning and insurance are important components of a complete financial plan that sometimes don't get the amount of attention they deserve.

Taking time to review your will, trust documents and other key records helps ensure your assets are passed on exactly as you intend—minimizing confusion, disputes and unnecessary legal costs. Life changes are a natural trigger for an update, but year-end is also a timely trigger to make sure everything is current.

The same goes for insurance. Your needs shift as life evolves—family dynamics, career moves and new opportunities all play a role. That’s why revisiting your coverage each year is so valuable. And a conversation with a wealth professional can help you see what’s available, what’s changed and what’s right for you.

Ask yourself: Am I confident my plan still supports my top priorities?

• Review and update estate documents (wills, trusts, powers of attorney, healthcare directives)
• Confirm beneficiary designations across accounts
• Review insurance coverage (life, disability, liability, long-term care)
• Ensure your financial plan reflects your current goals and values

Looking ahead

With potential shifts in tax policy and estate exemption levels on the horizon, now is the time to prepare—not react. The more proactive you are in 2025, the more freedom you’ll have to navigate uncertainty with confidence in 2026.

Prefer to plan together?

Year-end planning doesn’t have to feel overwhelming. Our role is to help you evaluate, prioritize and act with clarity. Together, we can ensure your 2025 ends on a strong note and your 2026 begins with confidence, direction and opportunity.

Slawny reassures that reaching out is “an opportunity to sit down with someone, to talk about all the numbers, charts and graphs, to ask questions. I spend a good part of my time talking with folks, helping them understand the why. How does this work? Why does it affect me? Why is it important?”

“Ultimately, it's a combination of having that plan and having the road map to get you there.” Because if you understand the why, then the plan means something.

Learn more about how to approach your year-end planning or get in touch with our team at PrivateWealthPlanning@associatedbank.com to schedule a conversation today.