You’ve already set your 2026 business targets. Here’s how we help you determine whether they actually serve your life.

Key Takeaways ·       What’s the difference between planning “for” vs. “from” my business? Planning for your business focuses on revenue and growth. Planning from your business asks how those results translate into your personal financial security and goals. ·       Why do business owners neglect their personal finances? The instinct to keep the business alive often takes priority over personal wealth-building, but this can become a trap if it’s the permanent standard rather than a temporary season. ·       How often should I revisit my business goals? At minimum, twice per year. Quarterly check-ins help you stay accountable and catch misalignments between business performance and personal financial needs before they become problems.

If you’re reading this in January, your 2026 business goals are likely already set. You’ve mapped out revenue targets, profitability benchmarks, and growth initiatives, and you know what you want your business to accomplish this year.

But here’s a question worth sitting with: Do you know what you need from your business this year?

Most business owners plan for their business with precision and plan from their business almost as an afterthought. They focus on what the entity needs to thrive without asking what the entity should be doing for them personally. Revenue goals get set. Personal wealth-building gets deferred.

At The Next Level Planning Group, we work alongside you in the space where your business and your life meet. Throughout the year, we work together to intentionally align the two, so your business decisions can support your personal financial security for the long term.

The Trap: When the Business Comes First (at Your Own Expense)

There’s a moment on every flight when the attendant reminds you to put on your own oxygen mask before helping others. The logic is simple: you can’t help anyone if you’re not breathing.

Business owners face a version of this choice constantly, and the instinct to usually to keep the business alive, protect employees, and avoid pain for others. But too often, that can lead to sacrificing their own financial wellbeing year after year.

We met with a business owner in his 70s who had run a successful real estate business for decades. On paper, he’d done well. But the reality was more complicated: He had never built wealth outside the business.

His lifestyle had grown to match (and sometimes exceed) what the business generated. Now, to maintain that lifestyle, he was pulling money from his investments and retirement accounts to prop things up. In essence, the business had to live in order for him to live. And that’s not living.

This pattern doesn’t happen overnight. It builds gradually, through seasons that feel temporary but become permanent. A tough year requires personal sacrifice…then another…then it’s just how things are. The business becomes the priority at all costs, even your own future.

As your advisor, it’s our job to help ensure all of your goals (business and otherwise) are supporting the life you’re working towards.

So, how is it all done?

Smarter Business Goals: Looking Back Before Looking Forward

Before we set sights on the year ahead, we take time to understand what actually happened last year. One of the ways we help you think through this is through what we call a professional and personal “Review and Preview.” These check-ins are designed to help us measure progress, align actions with your goals, and make any necessary adjustments.

For example, when we met with a client at this time last year, he had outlined both his business goals (client acquisition, revenue, assets under management) and then something more personal: he wanted to practice piano three times a week.

Related: Smart Diversification Strategies for Business Owners

Throughout the year, we checked in on all of it, not just the business metrics, but the piano practice. Are you making time for the things that matter outside of work? Are you building toward a life, or just building a business?

This kind of accountability matters. Business owners are often so focused on the entity that they can lose sight of why they built it in the first place. Having someone ask the important questions can be the difference between goals that exist on paper and in bank accounts versus goals that actually shape how you live.

Questions Designed to Connect Your Business Goals to Your Personal Reality

During a “Review and Preview,” we’ll typically ask a few core questions:

• What actually happened last year? Before we look ahead, we take time to look back together. Did you hit your targets? If not, why? If you did, what made the difference—market conditions, a key client, a strategic shift? Understanding what truly drove last year’s results helps us pressure-test this year’s goals and keep expectations grounded in reality, not wishful thinking.

 

• How much did you make, and how much do you actually keep? Your business income is often your personal income (whether you took it home or not). We look closely at what’s showing up on your tax return versus what’s actually landing in your bank account. That clarity is essential for making smart decisions about compensation, distributions, and lifestyle spending.

 

• How much cash truly needs to stay in the business? When we see excess cash sitting on the balance sheet (cash you’ve already paid tax on), we help you define what’s needed for operations and growth versus what can be put to better use in your personal plan. This is where intention replaces inertia.

 

• What do your margins really allow? Revenue alone doesn’t tell the full story. A capital-intensive manufacturing business with thin margins operates very differently than a high-margin services firm. We factor in your actual margin reality so we can set realistic expectations for what your business can sustainably provide.

Every question we ask is grounded in one guiding lens: what does this really mean for you, personally?

Why Your Spouse Needs the Full Picture

Many advisors don’t ask to include spouses in these conversations. We do. We want both partners involved, especially in the initial planning process, because there’s simply too much at stake for one person to hold all the information alone.

One dynamic we see repeatedly: a business owner who understands both the business and personal finances, paired with a spouse who only sees part of the picture. The business-owning spouse is immersed in the details, the other spouse trusts that things are handled, and everyone is happy.

We worked with a business owner who had built substantial wealth, somewhere in the range of $50 to $60 million across his business and investments. His wife’s financial comfort came down to one number: she wanted to know there was $200,000 in the bank. If that number was there, she felt fine.

Related: Defining “Enough” and Planning for Surplus Wealth

And she was fine. But if anything had happened to her husband, she would have been completely in the dark about the rest. The businesses, the investments, the tax implications, the estate structure—all of it would have been a mystery.

What we do in situations like this is open the aperture. We’re not trying to make the non-business spouse an expert. But they need to understand the contours: the general structure of the balance sheet, where the documents are, and who to call if something happens.

Making This the Year You Plan From Your Business

Your 2026 goals are in place. Our focus now is making sure those goals are working for you and supporting the life that business is meant to fund.

That’s why, together, we continue to ask a slightly different set of questions. Not just “How do we grow?” but “How does that growth show up in your personal financial life?”

As your business evolves, new questions naturally come up. If something has shifted, an opportunity has emerged, or a decision is on your mind, reach out. We’re always happy to look at how it fits into the bigger picture.

If you’re not yet working with us, we invite you to schedule a complimentary SWOT Session and learn more about how we partner with business owners to build smarter goals that serve both their businesses and their lives. Because when it comes to what matters most, good is just not good enough.

Key Takeaways: ·       Will Social Security run out of money? The trust fund may be depleted by 2034, but benefits aren’t likely to disappear entirely. ·       Should I claim early to “get mine” before cuts happen? Probably not. Even with a 25% benefit reduction, waiting until age 70 is still often the better financial choice. ·       What changed in January 2025? The Social Security Fairness Act eliminated penalties affecting 2.8 million public service workers, though it adds pressure to the trust fund timeline.

 

It’s hard to miss the Social Security headlines lately: Trust fund depletion. Benefit cuts. Questions about whether the system can sustain itself.

For professionals who’ve spent decades watching that Social Security deduction come out of every paycheck, these headlines land differently. And that reaction makes sense—when you sense scarcity coming, the instinct is to secure what’s yours while you still can.

But here’s what we want you to know:

1. Social Security does face real funding challenges.
2. Your claiming strategy probably doesn’t need a panic-driven overhaul.

Let’s walk through what’s actually happening with Social Security, what the next decade realistically looks like, and why the core math around when to claim remains surprisingly stable.

Related: Retirement Planning for High Achievers

Where We Are Today: Social Security in 2026

Right now, Social Security is functioning exactly as intended and benefits are being paid in full. From a beneficiary’s perspective, everything “works.”

But underneath that surface stability, demographic forces have been creating pressure for decades. In 1945, there were only about two Social Security beneficiaries for every 100 workers paying into the system. Today, there are roughly 37 beneficiaries per 100 workers.

This shift stems from two significant trends working in tandem:

1. First, people are living much longer than Social Security’s architects anticipated when they designed the system in the 1930s
2. Second, families are having fewer children than previous generations

Together, they create strain on a pay-as-you-go system where current workers fund current retirees.

Recent Legislative Change: The Social Security Fairness Act

Before we dig into claiming strategies, there’s one legislative change worth mentioning, particularly if you spent part of your career in public service.

Recently, Congress passed the Social Security Fairness Act, eliminating the Windfall Elimination Provision (WEP) that had reduced benefits for approximately 2.8 million Americans receiving pensions.

This primarily affected teachers, firefighters, police officers in many states, federal employees under the Civil Service Retirement System, and people whose work had been covered by foreign social security systems. These workers often found themselves penalized on their Social Security benefits despite having also worked jobs where they paid into the Social Security system. This year, after the elimination of the WEP, we had one client whose monthly benefit jumped from $950 to $3,600—genuinely life-changing money.

The tradeoff is that eliminating these provisions increases total Social Security payouts, which puts additional pressure on the trust fund and slightly accelerates the depletion timeline. It’s a policy choice that prioritizes fairness for public service workers while making the broader funding challenge marginally more urgent.

2034: The Timeline on Everyone’s Mind

Under current projections, and assuming no policy changes whatsoever, the Social Security trust fund is on a path to be depleted in 2034.

That does not mean Social Security will cease to exist. What it does mean is that incoming tax revenue alone would only cover about 75-80% of scheduled benefits.

In practical terms, if Congress does nothing between now and then, benefits would need to be reduced by roughly 20-25% across the board once the trust fund runs dry. That’s the scenario everyone fears, and it’s the one driving the “claim early before it’s too late” instinct.

But here’s the critical question: Is the only option to solve the funding shortfall a reduction in benefits?

Congress has multiple tools at its disposal to address the Social Security funding shortfall. Understanding these options helps clarify why an across-the-board 25% benefit cut is just one possible outcome. Congress could:

• Reduce Benefits. This gets the most attention because it’s what people fear most. Benefits could be reduced across the board for higher earners and future beneficiaries while protecting current retirees, or adjusted through changes to the cost-of-living formula.
• Raise the Payroll Tax Rate. Currently, workers and employers each pay 6.2% of wages in Social Security taxes (12.4% total). If that rate increased by about 3.65% (bringing the employee share to roughly 9.85%) it would fully address the funding gap. Note that Congress raised payroll tax rates in the early 1980s when Social Security faced a similar solvency crisis. It’s not popular, but it’s a lever that’s been used historically.
• Increase or Eliminate the Wage Base. Here’s something many people don’t realize: You only pay Social Security taxes on income up to $184,500 (as of 2026). Every dollar you earn beyond that threshold is exempt from Social Security tax. Congress could raise this cap to $300,000, eliminate it entirely, or adjust it in various ways to capture more revenue from high earners.
• Adjust the Full Retirement Age (FRA). The government could gradually increase the age at which people can claim full retirement benefits. This reduces the number of years the system pays out while giving the trust fund more time to rebuild. The full retirement age has already been adjusted before, rising from 65 to 67 for those born in 1960 or later.

Now we get to the question that matters most for your planning: Given this uncertainty, when should you actually claim your Social Security benefits? Let’s run the numbers for different scenarios, because this is where the math becomes both fascinating and reassuring.

	If you’re 62 and deciding whether to claim now or wait until 70…	If you’re 67 (full retirement age) and deciding whether to claim now or wait until 70…
No Changes to the System	·       Claiming early means eight years of smaller monthly checks ·       Waiting means your benefit increases 8% for every year you delay ·       The break-even point is age 81 ·       After age 81, you’re better off for every remaining year of your life having waited	·       Claiming now means three years of smaller monthly checks ·       Waiting means continuing to increase your benefit by 8% annually ·       The break-even point is age 78 ·       After age 78, waiting wins for the rest of your life
A 20% Benefit Reduction in 2034	·       The break-even age shifts from 81 to 84—only three years later ·       After age 84, you’re still better off having waited, even with reduced benefits	·       The break-even age shifts from 78 to 80—only two years later ·       After age 80, you’re still better off having waited
A 25% Benefit Reduction in 2034	·       The break-even age shifts to 85 ·       After age 85, waiting still wins	·       The break-even age shifts to 81 ·       After age 81, waiting still wins

Even in genuinely bad outcomes for Social Security, the fundamental strategy doesn’t flip on its head. The break-even ages shift by two to four years—meaningful, yes, but not enough to overturn the core wisdom of delaying benefits when you have the financial means to do so.

If Congress implements a combination of solutions (raising the wage base, increasing the tax rate, and making modest benefit adjustments), the actual impact on your break-even age would likely be smaller than these scenarios suggest.

Beyond the Claiming Decision

Of course, Social Security is just one piece of your retirement income puzzle. We work with you to build a plan that accounts for any number of future scenarios (both good and bad). That typically looks like:

• Maintaining diverse income sources beyond Social Security (investment portfolios, rental income, pensions, part-time work)
• Stress-testing your retirement plan against various scenarios, including reduced Social Security benefits
• Building adequate liquidity so you can delay Social Security without compromising your lifestyle
• Understanding how Social Security fits into your broader tax strategy throughout retirement
• Revisiting your plan regularly as both your circumstances and the legislative landscape evolve

These conversations require the kind of nuance that goes beyond break-even calculators and generic advice. They’re about understanding your complete financial picture and making decisions aligned with your specific goals, resources, and risk tolerance.

Related: Smart Diversification Strategies for Business Owners

Looking Toward the Future

Watching news coverage about Social Security, trust fund depletion, and potential benefit cuts feels unsettling when you’ve paid into this system your entire working life. It feels like the rules are being changed in the middle of the game, and in some ways, they are.

But here’s what we want you to take away: Social Security will need adjustments over the next decade, but those adjustments likely won’t be dramatic enough to fundamentally alter the claiming strategies that have served retirees well for decades.

More importantly, the best defense against Social Security uncertainty isn’t trying to game the timing of your claim. It’s building a comprehensive retirement plan that remains resilient regardless of what policy changes emerge over the next decade.

If this raised any new questions about your Social Security benefits or future retirement income, we’d love to schedule a meeting and run through the numbers with you. We’re here to help you model different scenarios and visualize how potential changes could affect your overall retirement plan.

And if you’re not yet working with The Next Level Planning Group and you’re wondering how Social Security fits into your broader retirement strategy, let’s connect in a complimentary SWOT session. We help professionals like you build retirement plans designed to remain solid, regardless of what changes lie ahead.

 

Plot twist: They might actually be the same thing

Key Takeaways ·       When should I harvest gains instead of losses? During low-income years, you may qualify for the 0% capital gains rate, making it smart to intentionally realize gains. ·       What is “tax gain hoarding,” and why is it a problem? Over-harvesting losses can leave you with a very low cost basis, making it hard to diversify or rebalance without triggering big tax bills. ·       How does volatility affect tax harvesting? The 30-day wash-sale rule forces you to sit in cash or buy substitutes, both risky in volatile markets. Missing a quick rebound can cost more than the tax savings.

Tax loss harvesting can be one of the most powerful tools in tax-efficient investing. When markets drop, realizing losses can offset gains, reduce your tax bill, and potentially save thousands.

But like any powerful tool, it needs to be used strategically. In high-income years, aggressive loss harvesting can save thousands. In low-income windows, strategic gain harvesting can save even more. And sometimes, the best move is doing nothing at all.

The complexity isn’t in understanding these strategies individually. It’s in coordinating them with your income trajectory, liquidity needs, concentration risk, and estate goals, and being willing to adjust as circumstances change.

Related: Click here to read “Roth Conversion Strategies: Our Guide to Smarter Tax and Estate Planning”

When Tax Loss Harvesting Makes Perfect Sense

If you’re in your peak earning years, realizing losses is often the right move. A $10,000 short-term capital loss could save you $3,700 in federal taxes (at the 37% bracket) plus state taxes and Net Investment Income Tax. Over a career, these savings compound significantly.

Loss harvesting also works beautifully for long-term wealth you won’t touch for decades. You defer taxes now, let the money compound, and your heirs may receive a step-up in basis that eliminates the gains entirely.

The strategy becomes problematic only when it’s applied reflexively—regardless of your income level, timeline, or portfolio composition. That’s when ‘good tax planning’ can accidentally create bigger problems.

The Myth: “Capital Gains Are Always Bad”

We recently met with a couple in their mid-50s whose income dropped sharply when the husband left a corporate job to start a consulting business. When we asked what tax strategy they used during that first low-income year, he said, “Nothing. We just enjoyed not paying taxes.”

But once we reviewed their portfolio, we found over $1 million in embedded gains across a few concentrated stocks. During those low-income years, they could have realized $100,000–$150,000 in gains at a federal tax rate of 0%, an opportunity their previous advisor missed entirely.

Most people assume capital gains are always taxed at 15%, but today’s tax code includes a 0% bracket for many taxpayers in lower-income years. In other words, they had a free chance to reset their cost basis, and no one told them.

When we showed this couple what they’d missed, they were (rightfully) furious. Those tax-free gains are now gains they’ll have to realize later, likely owing tens of thousands in unnecessary taxes.

Related: Click here to read “Smart Diversification Strategies for Business Owners”

The 0% Strategy: In years when your income is unusually low, you can intentionally realize capital gains and pay zero federal tax. It’s a rare window to clean up your portfolio for free.

And career transitions aren’t the only time this strategy shows up. We regularly see 0% capital gains opportunities in situations like:

• Business owners with major write-offs: Large equipment purchases or other capital investments can create big deductions. In some years, clients’ taxable income drops so low that they can realize significant capital gains at a 0% federal rate.
• Early retirees before Social Security: Those “in-between” years after leaving a primary career but before turning on retirement income are often ideal for strategic gain harvesting.

Ultimately, the sophistication isn’t in avoiding gains; it’s in timing them. Our goal is for you to pay 0% when possible, 15% when necessary, and avoid the 20%+ bracket whenever we can.

What Happens When You’re Too Good at Harvesting Losses?

A few months ago, we reviewed a $1 million portfolio for a prospective client whose previous advisor had been overly aggressive with tax loss harvesting, selling every possible loser to offset gains.

The result was a cost basis under $400,000 and more than $600,000 in embedded gains.

They wanted to rebalance, diversify, fund 529s, and pay down their mortgage, but psychologically, they were stuck. It can feel impossible to realize a $600,000+ gain, even though the gain exists whether they sell or not.

This is tax gain hoarding: letting so much appreciation build up that your wealth becomes functionally “trapped.” Beyond the psychological hurdle, tax gain hoarding creates some very real (and very expensive) problems:

Concentration Risk

We see this all the time with employee stock purchase plans. You buy shares at a 15% discount, hold them for a year to avoid short-term gains… then the stock jumps 40%, and you don’t want to sell. More shares vest, those have gains too, and before you know it, a huge chunk of your wealth is tied to one company, all because you’re avoiding taxes.

That original discount was found money. Our motto: Don’t let the tax tail wag the investment dog. Tax decisions shouldn’t override the bigger-picture strategy we’ve built with you.

Portfolio Drift

If we’ve designed a 50/50 mix of stocks and bonds, and stocks experience a strong rally, the allocation can shift to 60/40 or even 70/30 over time.

When that happens, we evaluate whether rebalancing is appropriate, considering both the investment implications and the tax impact, so that your portfolio doesn’t quietly take on more risk than intended.

Tax Loss Harvesting: If it Feels as Simple as Mowing a Lawn, You’re Doing it Wrong

The complexity of tax loss harvesting becomes especially clear in volatile markets. When you harvest a tax loss, the wash sale rule requires you to avoid buying the same (or “substantially identical”) investment for 30 days, leaving you with two imperfect choices:

Imperfect Option 1: Sit in Cash

You sell the position and wait out the 30 days. But if the market rebounds—say 8% on $100,000—you’ve just missed an $8,000 gain. In many cases, that loss outweighs the tax benefit.

Imperfect Option 2: Buy a Substitute Investment

Instead of sitting in cash, you swap into something similar by selling the S&P 500 fund and buying a large-cap fund.

After 30 days, do you sell the substitute? If it’s up, you may trigger short-term gains, taxed at much higher ordinary income rates. If you hold it for a year to get long-term treatment, you might still end up with gains you never intended to create.

This is where a sophisticated approach matters most. In down markets, there are more loss-harvesting opportunities, but the stakes of getting the execution wrong are also higher.

The key isn’t just knowing that you can harvest losses. It’s knowing when it’s actually worth doing.

A Smarter Approach to Tax Harvesting

The smarter alternative to reflexive loss harvesting or gain hoarding starts with your specific goals and timeline.

If you’ll need money from an account soon, we avoid strategies that could trap you with unnecessary embedded gains. For long-term or legacy assets, we tailor the opposite approach (harvesting losses and holding gains) because your heirs may receive a step-up in basis that eliminates those taxes entirely.

We also proactively watch for low-income windows where you can potentially realize gains at 0% or reduced rates.

All of this works because we’re looking at the full picture of your tax bracket, cash flow, allocation, estate goals, concentration risk, and income sources.

If you have any new questions or are wondering what harvesting opportunities we’re looking at on your behalf right now, reach out—we’d love to offer clarity wherever we can.

And if you’re not yet working with us, this integrated approach is exactly what we built TNLPG to deliver. If you’d like to explore whether this partnership is a fit, you can learn more about our introductory SWOT Session here.

 

Tax-law is subject to frequent change; therefore it is important to coordinate with your tax advisor for the latest IRS rulings and specific tax advice, prior to undertaking an investment plan. Any tax or legal information provided here is merely a summary of our understanding and interpretation of some of the current income tax regulations and is not exhaustive. Investors must consult their tax advisor or legal counsel for advice and information concerning their particular situation.

A practical, high-impact guide to closing the year intentionally

Key Takeaways:·       When should I start year-end tax planning? Now. The strongest strategies need coordination between your wealth advisor and CPA well before December 31. ·       What’s the difference between reactive and proactive tax planning? Reactive planning reports what already happened. Proactive planning creates opportunities to reduce your tax burden throughout the year and into the future. ·       Can you really save taxes on charitable giving even with the high standard deduction? Absolutely. Through strategic approaches like bunching donations and donor-advised funds, you can potentially capture meaningful tax benefits.

April usually claims the tax planning “spotlight,” but we can’t change the script after the play is over.

Some of the most impactful work often happens right before the calendar flips. In the year’s final stretch, strategic decisions can help turn into real clarity and momentum for what’s next.

That’s why year-end is when we’re reviewing your numbers, coordinating with your tax professionals, and making any needed adjustments before January arrives. Think of this checklist as a peek into the key areas we’re already watching on your behalf and the smart, thoughtful levers we pull to help you close out the year with intention.

Our Year-End Tax Planning Checklist: Charitable Giving, Roth Conversions, and Beyond

CPA Coordination: Turning Reactive Tax Prep into Proactive Planning

One of the biggest advantages of year-end planning is making sure your financial life and your tax strategy are actually working together. Most CPAs excel at what they’re designed to do: ensuring compliance and reporting what already happened. That’s incredibly valuable and necessary. But what often gets missed is the proactive coordination before year-end, where strategic timing can turn good tax preparation into powerful tax planning.

That’s where our role shifts from “advisor” to “connector.” We bridge the gap between your financial plan and your tax return, making sure the smart ideas don’t show up as surprises in April. Part of this coordination is making sure strategies don’t accidentally work against each other. For example, timing a Roth conversion, charitable gift, and loss harvesting in the wrong order can reduce the potential impact.

When the right conversations happen now, not months after the year closes, you get a smoother filing season and a strategy that supports the bigger financial picture we’re building together.

What we make sure is happening for you:

• Sharing the right information with your CPA before year-end, not after
• Making sure tax-loss harvesting, Roth conversions, and charitable strategies are clearly reflected in your tax plan
• Flagging anything unusual (income dips, business changes, big transitions) that should factor into your tax approach

Tax-Loss Harvesting: Looking Beneath the Surface of Your Portfolio

One of our biggest annual to-dos is looking at your tax-loss harvesting opportunities. When we review your accounts for tax-loss harvesting, we’re not relying on the single gain/loss line you see on your statement. That number is just the headline.

Behind that headline are many separate “lots,” created each time dividends reinvest, and each with its own gain or loss. An investment can show an overall gain while still holding pockets of losses worth capturing. That invisible layer is where the real opportunity lives, and it’s why this process can make a meaningful difference—sometimes even saving clients tens of thousands of dollars.

Quick Recap: What’s a “Lot-Level Analysis?” A lot is a mini-purchase of the same investment. Every time you buy shares or your dividends reinvest, you’re creating a new lot, each with its own price and gain/loss. A lot analysis is like taking an X-ray of those hidden layers, letting us pinpoint the smartest shares to sell for tax savings without tripping wash-sale rules.

Most investors can’t see this hidden layer on their statements, and most can’t evaluate it on their own. Identifying the right lots to harvest (without derailing your long-term strategy) often requires professional-level tools and careful coordination.

What we’re assessing for you:

• Which hidden lots are worth harvesting (and which aren’t)
• How the timing aligns with your income and current tax bracket
• How to execute the move cleanly without affecting your long-term strategy

Retirement Contributions: The Low-Hanging Fruit

Before we move into the more advanced strategies, we always start with the simplest (and surprisingly powerful) question: Are your retirement contributions where they need to be before year-end?

This is the “low-hanging fruit” that can quietly add up over time. Making sure these dollars land in the right place (and on time) sets up everything else we do together—and helps ensure you’re getting every available benefit before the calendar resets.

What we’re checking on your behalf:

• Whether you’re on pace to max out your 401(k) or still have room to contribute
• If you’re eligible for a deductible IRA contribution and whether it makes sense
• For solo-preneurs, whether your Solo 401(k) or SEP IRA needs a final boost
• Whether any changes in income or employment this year affect your contribution strategy

Roth Conversions: Taking Advantage of Low-Income Windows

Some tax strategies require critical timing, and Roth conversions are one of them. The opportunity usually appears when life shifts, like between retiring and collecting Social Security, when a job change creates a dip in income, or when your business has a slower year.

These “low-income windows” can quietly open the door to moving money from an IRA to a Roth IRA at a far lower tax cost than otherwise.

What we’re evaluating together:

• Whether you’re in a temporarily lower tax bracket this year
• How much room is left in your current bracket before triggering a higher one
• Whether converting now reduces what you’d pay later in retirement
• How the move aligns with your long-term plan and cash flow

We’ve seen the impact of this firsthand. One client hit a multi-year stretch of unusually low income, and we were able to convert almost $800,000 to Roth with virtually no tax.

That’s an unusually big example, but the takeaway is universal: When your tax bracket dips, even briefly, a well-timed conversion can create lasting, tax-free growth.

Related: Click here to read “Roth Conversion Strategies: Our Guide to Smarter Tax and Estate Planning”

Charitable Giving: Making Sure Your Generosity Counts

Charitable giving is deeply meaningful for many clients, but the tax benefits may not be as significant as expected. With today’s higher standard deduction, many retirees (especially those without a mortgage) end up giving year after year without receiving any tax benefit, simply because their contributions don’t exceed the $33,100 standard-deduction hurdle for married couples under 65 (couples over 65 receive a higher standard deduction based on their income).

That’s where strategies like bunching and donor-advised funds (DAFs) can help. Instead of smaller annual gifts that get swallowed by the standard deduction, you can combine several years of giving into one larger contribution, often using low-basis stock, to unlock a deduction now and then distribute donations to charities over time. The IRS allows deductions up to 60% of your income for cash and 30% for stock, with unused amounts carrying forward.

These strategies and others make sure your generosity counts on both the heart and the balance sheet.

What we help you consider:

• Whether your current giving is producing any tax benefit
• If “bunching” several years of donations into a single year would get you over the standard-deduction hurdle
• Whether a donor-advised fund would let you make a larger, strategic gift now and give to charities gradually over time
• Whether cash or low-basis stock is the smarter funding choice

Related: How Donor-Advised Funds Can Help High Achievers Build Lasting Charitable Impact

529 Contributions: Capturing State Tax Benefits Before the Deadline

For clients who contribute to 529 college savings plans, the year-end deadline matters more than most people realize. Many states offer a state income tax deduction for contributions, but only if the money hits the account before December 31. It’s an easy win, and one we make sure not to leave on the table.

Even if you contribute regularly throughout the year, we still double-check whether a final top-up makes sense. A small year-end contribution can sometimes create a meaningful state tax benefit, and it’s one of those simple moves that’s easy to miss in the holiday rush.

What we review:

• Whether your state offers a tax deduction for 529 contributions
• How much additional contribution (if any) maximizes the benefit
• Whether it makes sense to fund multiple 529s for kids, grandkids, or other beneficiaries
• How this fits alongside your broader savings and cash-flow picture

It’s a straightforward strategy, but timing is everything. A well-placed contribution before year-end can help support education goals and reduce your state tax bill, all with one clean move.

Ending the Year with a Clear, Cohesive Plan

Everyone’s tax picture is different, which is why we tailor our approach to your income, goals, and life stage. We start with the fundamentals, making sure opportunities like retirement contributions don’t slip through, then move into more sophisticated strategies when they make sense.

The strategies in this checklist work best when we can act quickly. If anything here raised new questions about your specific strategy, or if your circumstances have shifted since we last connected, please reach out to your advisor. These final weeks of the year can create opportunities that simply won’t exist in January.

And if you’re reading this and realizing you don’t currently have advisors looking at these strategies on your behalf, let’s talk about what that partnership could look like in a complimentary Financial SWOT session. Because when it comes to what matters most financially, good isn’t good enough.

From donor-advised funds to matching gifts, discover how intentional giving helps families pass down more than wealth.

 

 

Key Takeaways: ·       When should we start teaching kids about giving? As early as they understand money. Even young children can learn to allocate cash into give, save, and spend categories. ·       What’s an easy way to involve older children in charitable giving? Set aside a portion of your family’s annual giving and let them research organizations that matter to them. ·       How can we make holiday gifts more meaningful as a family? Consider matching your children’s contributions, turning giving into a shared family value while amplifying impact.

 

The holidays have a way of slowing life down just enough to make space for the conversations that matter most. Around the table, gratitude turns into purpose, and generosity becomes a shared vision for the future.

A challenge that many families face, however, is turning those moments of inspiration into meaningful action.

That’s where thoughtful planning makes all the difference. When you design giving strategies that reflect your family’s values (whether through donor-advised funds, matching gifts, or coordinated charitable plans), you create opportunities for every generation to participate. Over time, giving becomes not just something your family does, but a reflection of who you are together.

The Power of Multi-Generational Giving

The question we hear most often isn’t “How do I give more?” It’s “How do I help my kids understand why giving matters?”

You’ve worked hard to build significant wealth, but what often matters more is building a legacy. For many of our clients, legacy is more than their children inheriting financial assets; it’s shared values and traditions through the generations.

From our experience, the families who successfully pass down the “generosity gene” don’t leave it to chance. They create intentional moments to involve the next generation, inviting them to take part in both the heart and the strategy of giving:

• They talk about causes that matter, not just where to give, but why those causes align with their family’s story and values.
• They invite children to participate, encouraging ideas, research, and even decision-making around family gifts.
• They lead by example, making generosity visible, expressing gratitude often, and showing that wealth is a tool for good, not just accumulation.

When families give together, they don’t just share financial resources; they share perspective. Younger generations begin to see that generosity is part of who the family is, not just something they do. And that understanding becomes one of the most meaningful parts of any family legacy.

Related: The Hidden Cost of Financial Silence in Wealthy Families

Six Family Giving Strategies

Once gratitude opens the door, you need practical ways to turn intention into action. Here are six strategies you can implement to ensure generosity takes root for the entire family.

1. Start with an Intentional Family Conversation

Between work demands, activities, and daily logistics, sometimes giving conversations get pushed aside until they never happen at all.

The holidays offer a natural opening. Everyone’s already together and reflecting on gratitude, so it’s often the right moment to talk about what comes next. Start with the “why”: What matters to us as a family? What kind of difference do we want to make?

Your children will begin to see giving as part of who your family is, not just something you occasionally do. And when the time comes for them to make their own financial decisions, generosity is already wired into how they think.

2. Use Donor-Advised Funds (DAFs) as Teaching Tools

With a donor-advised fund (DAF), the money’s already set aside for charity and tax-deducted. Now the only question is where it goes and when—and that’s a question your children can help answer.

We’ve seen this play out in a few ways with clients. Some families allocate a percentage of their annual giving, then let their adult children research organizations and make the final call. Others give each child a specific dollar amount to direct. Either way, you’re giving them real responsibility with real impact.

With this approach, your kids aren’t being handed a hypothetical exercise. They’re managing actual resources, researching real organizations, and seeing the results of their decisions. It builds confidence and engagement without putting their own money at risk while they’re learning.

3. Create Matching Opportunities

Matching programs can make giving feel more powerful. When your child or grandchild donates $10 and you match it, they’re not just giving $10 anymore—they’re mobilizing $20 or $30. That shift can change how they think about their own impact.

The mechanics of matching are fairly straightforward. Your child contributes from their own money, and you match it dollar-for-dollar (or even 2-to-1). The ratio matters less than the principle: their generosity gets amplified, and they see it happen in real time.

Matching doesn’t just increase the dollars donated this year; it builds the habit of giving into their financial decision-making for decades to come while providing opportunities for you to collaborate on this “project” as a family.

We work with several clients who’ve built matching programs into their family giving strategy, sometimes extending it to grandchildren as well. If you’re thinking about how to structure something like this or how it fits with your other charitable plans, we’re happy to talk through it with you.

4. Introduce Structured Giving at a Young Age: The Three Bucket Framework

Whether your family is just beginning to teach young children about money or you’re helping adult children build financial independence, you want them to know that every dollar they receive has a purpose.

The “Three-Bucket Framework” helps bring that purpose to life by dividing money into giving, saving, and spending:

• Each child divides their money (whether from gifts, allowance, or earnings) into those three buckets.
  • For example, say your child receives $10 for allowance. Give it to them in $1 bills to easily split into percentages, such as 10% for giving ($1), 20% for saving ($2), and 70% for spending ($7).
• Giving comes first, reinforcing that generosity is a core part of money management and a priority to the family.
• This early structure builds lifelong habits and normalizes charitable thinking from the start.

For young children, keep it tangible. Consider using labeled jars or envelopes so they can see their money accumulate in each category. Talk about where the “give” portion might go and let them help choose.

5. Broaden the Definition of Giving

Not every meaningful gift shows up on a tax return. Some of the most impactful family giving happens when you volunteer together, donate time instead of dollars, or simply show up for people who need help.

We’ve had clients talk about volunteering at food banks with their kids, assembling care packages for people experiencing homelessness, or coordinating donation drives within their communities.

Writing a check is abstract, especially for younger kids. Handing someone a meal, packing a bag with essentials, or sorting donations at a shelter makes generosity tangible. Your children see the people their actions help, and that sticks with them in ways a balance sheet never will.

It also reinforces that wealth isn’t just financial. Your time, energy, and presence have value, too.

Related: Defining “Enough” and Planning for Surplus Wealth

6. Leverage Tax-Smart Tools for Older Generations

As you or your parents move into or through retirement, the way you give can be just as important as how much you give. We know that the right strategies let you maximize impact while minimizing tax liability, while demonstrating to younger generations that thoughtful planning enhances generosity rather than diminishing it.

Some tools we use frequently with clients include:

• Gifting appreciated stock through a DAF: Donating investments that have grown in value is one of the most tax-efficient ways to give. Instead of selling the stock and paying capital gains tax, you can transfer shares directly to a charity or contribute them to a donor-advised fund (DAF). This way, you avoid capital gains, receive a deduction for the full market value, and can give more to the causes that matter most.
• Bunching charitable contributions: If you typically give each year but don’t itemize deductions, consider “bunching” several years of donations into one tax year to exceed the standard deduction threshold. Pairing this approach with a DAF lets you claim the deduction upfront while distributing grants to charities over time, preserving flexibility in your giving plan.
• Qualified Charitable Distributions (QCDs): If you’re 70½ or older, you can donate directly from your IRA to a qualified charity. This satisfies your required minimum distribution without adding to your taxable income, which is particularly valuable if you don’t need the full RMD for living expenses.

Related: How Donor-Advised Funds Can Help High Achievers Build Lasting Charitable Impact

These aren’t exotic strategies; they’re standard tools we build into comprehensive plans when they make sense.

Building Your Legacy, Together

Comprehensive financial planning isn’t just about growing wealth. It’s about aligning your resources with what matters most to you and your family.

We’re always available to discuss how your charitable giving fits into your broader financial strategy. Whether you want to explore donor-advised funds, set up a family matching program, or think through tax-smart giving strategies, reach out anytime. These conversations are exactly what we’re here for.

If you’re not yet working with The Next Level Planning Group, we partner with successful professionals and families who understand that comprehensive financial planning goes beyond investment returns. If you’re looking for an advisor who brings both technical expertise and genuine care to the table, we’d welcome the conversation.

Key Takeaways: ·       What are common benefits of executive compensation packages? They offer more than salary, from tax perks and discounts to flexibility and ownership in company growth. ·       How can you help avoid concentration risk in executive compensation? By diversifying over time so your wealth isn’t tied too heavily to one company. ·       What is a 10b5-1 plan? A preset trading plan that lets executives sell shares on a schedule, even with insider restrictions.

 

Executive compensation packages can be some of the most powerful (and most complex) tools in an executive’s financial life. Salary and bonuses may be familiar territory, but once you add RSUs, PSUs, stock options, performance units, deferred comp, and severance agreements, the picture quickly becomes more layered and complex.

One of the most intricate situations we’ve navigated involved an executive approaching retirement with eight distinct forms of compensation spanning two companies, including a 401(k) with after-tax contributions and two different types of deferred compensation plans. Each type had its own vesting schedule, tax implications, and payout dates, and not all of them vested upon retirement. The question wasn’t just “when can I retire?” It was, “how can all these different pieces fit together to create a sustainable monthly income?”

At first, he wasn’t certain that these pieces would be able to come together to create the necessary income stream to retire when and how he wanted. When we mapped the different pieces out, met with plan sponsors to understand the nuances of the different plans, and implemented regular check-ins, the full picture came into focus. Within three months, he gave his notice, confident that the retirement he wanted was both possible and sustainable long-term.

Related: Retirement Planning for High Achievers

Stories like this remind us that an executive compensation package is never just about the dollar figure on a statement. Each piece, from grant dates and strike prices to vesting schedules and even severance terms, can carry opportunities, risks, and ripple effects across the rest of your financial life.

The Value Beyond the Dollar Amount

When most people think about their executive compensation package, they focus on the number of shares or the headline value. That’s a reasonable starting point, but it captures only part of the picture. Hidden value often exists in several forms:

• Tax treatment advantages. Certain types of stock options, like incentive stock options (ISOs), can qualify for capital gains treatment instead of ordinary income. Even though these funds are typically subject to a holding period, that difference may amount to tens of thousands of dollars when you’re in a higher earning year. We work with you and your tax professional to help you determine when to exercise and how to follow any necessary timelines or rules needed to qualify for those tax advantages.
• Discount opportunities. Stock purchase programs may allow you to purchase shares at a discount, sometimes up to 15% below market price. Even after factoring in taxes related to the discounts, you can generally expect a bigger bang for your buck.
• Flexibility and control. Having the choice to hold or sell shares gives you the ability to align decisions with your goals. RSUs, for instance, are taxed as income when they vest, but if sold immediately, you may avoid or minimize capital gains exposure.
• Participation in growth. As an executive, ownership isn’t always just financial. It can feel deeply personal, especially when your wealth grows alongside the company’s success.

Compensation is also surprisingly versatile in that your equity can often be redirected toward other goals. Many people are surprised to find they can use their stock to fund charitable goals, provide liquidity for a major purchase, or create an income stream to be used in retirement.

Different Mindsets Around RSUs

Restricted stock units (RSUs) are the most common type of equity compensation we see, and clients usually fall along a spectrum of strategies:

• Treating RSUs like a bonus. Some sell immediately when shares vest. Taxes are withheld upfront, concentration risk is avoided, and the proceeds can fund expenses or be reinvested in a diversified portfolio.
• Holding everything. Others are confident in their company’s future and keep every share, sometimes paying taxes out of pocket to avoid selling at vesting. This works best for those already diversified elsewhere. The key is timing: selling within a year means short-term capital gains; waiting a year qualifies for more favorable long-term rates.
• The hybrid approach. Many choose a middle ground, like selling 80% of vested shares while keeping 20%. This covers taxes, builds diversification, and still allows participation in company growth. Identifying a target ratio can help create a repeatable, disciplined plan that’s flexible enough to adjust as circumstances change.

There’s no single “right” choice. The key is having a strategy that fits your goals, risk tolerance, and tax situation.

We’ve also seen how emotions can play into these decisions. One client who had spent decades at a Fortune 100 company had built up a large position through the company’s stock purchase program. From the start, he told us he never wanted to sell unless there was a very good reason. Rather than push against that, we worked together to define what “a good reason” looked like.

Over time, he became comfortable selling shares to fund meaningful goals, like his retirement and his children’s futures. And in retirement, the stock became a steady income source with minimal tax impact. By reframing the conversation around how the stock could serve his life, instead of just treating it as numbers on a statement, he was able to honor his loyalty while still moving forward with confidence.

Risks That Deserve More Attention

Equity compensation can be exciting, especially when your company is thriving, and the stock price keeps climbing. But one of the most valuable exercises we walk through with clients is asking: What happens if this stock goes to zero?

That question isn’t about creating fear; it’s about clarity. Seeing how your plan looks without the company stock makes it easier to decide whether holding on is worth the risk, or whether selling some now could potentially help provide lasting security.

A few common risks associated with executive compensation packages include:

• Concentration risk. When your salary, bonus, and portfolio are all tied to the same company, your financial future depends heavily on a single source of success. Diversification helps reduce that vulnerability, and we often work with clients to determine what portion of their net worth can reasonably stay concentrated in one company.
• Complex tax implications. Each type of equity has its own rules: RSUs are taxed at vesting whether you sell or not, which can create “phantom taxes.” ISOs may trigger the Alternative Minimum Tax (AMT) if not carefully managed. Timing decisions on exercising or selling can make a major difference in outcomes.
• Liquidity challenges. Equity value doesn’t always translate into cash. Privately held stock can remain uncertain until an IPO or sale, and even public company shares may be subject to blackout periods or insider restrictions. Knowing when you can actually access funds is crucial to realistic planning.

Equity can be a powerful wealth-building tool, but understanding these risks is what allows you to use it with confidence and build a plan that holds up in any market environment.

Vesting Schedules and Timing Nuances

For some, there’s an added layer of complexity: access to material nonpublic information. If you’re “in the know,” whether at a publicly traded company or one preparing for an IPO, trading your own stock isn’t always an option. In those cases, a structured plan called a 10b5-1 plan can help.

A 10b5-1 plan allows you to set up, in advance, how many shares you’ll sell and on what schedule. Once it’s in place, sales happen automatically, reducing compliance concerns while still giving you a way to turn equity into usable cash. For many executives, it’s a valuable tool for creating certainty in situations where flexibility is limited.

When Careers Shift: Severance and Transitions

Moments of career change often bring executive compensation into sharp focus. One of the first questions we ask when a client is leaving a company is simple:

What happens to your equity compensation?

The answer depends on the details. Some equity may be forfeited, especially if it’s unvested, but vested shares are often retained. That’s where tracking vesting schedules ahead of time becomes so important, so you know what you’ll keep, what you’ll lose, and when it all becomes available.

Severance packages can also add another layer of complexity. We work with you to review any documents, clarify what happens with existing equity, and understand how these pieces interact with the rest of your financial picture.

Once the dust settles, the core questions look familiar: What role will this stock play in your future? Should it be held, sold, or redirected toward other goals? Even after a transition, it’s important to align each piece of compensation with the life you want moving forward.

Putting the Pieces in Place

For many of you, we’ve already mapped out how your compensation fits into your larger financial life by identifying the risks, exploring strategies, and creating plans that bring clarity and confidence.

We proactively revisit your executive compensation and long-term incentive plans with you as opportunities and questions arise, identifying new risks, refining strategies, and helping ensure your plan evolves alongside your career and goals. If anything here resonated with you or raised new questions, we’re always happy to continue the conversation.

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And if you’re not yet working with us, we invite you to learn more about our Financial SWOT Session. This strategic analysis offers a chance to see your executive compensation package, and your broader financial life, through a sharper, more strategic lens.

Connect with our team.

Key Takeaways What’s the SECURE Act? It requires most heirs to withdraw inherited IRAs within 10 years, which can increase their tax bill. When is typically the best time for a Roth conversion? During lower-income years (often between retirement and RMDs), or while married and filing jointly. Do Roth conversions have annual limits? No. Unlike contributions, conversions don’t have a cap.

 

No one jumps at the chance to send the IRS money before it’s due. For decades, the common wisdom has been simple: defer, defer, defer. Put as much as possible into 401(k)s, IRAs, and business deductions with the promise that retirement will bring lower tax bills.

But “later” doesn’t always mean “less.” Required minimum distributions, Social Security income, and heirs inheriting large IRAs in their own high brackets can all transform deferred taxes into a bigger burden.

That’s where Roth conversions come in. In our conversations with clients, we’ve found that paying some taxes earlier often gives them greater flexibility later, both in retirement and in legacy planning. In certain situations, strategic conversions can help create flexibility in retirement, smooth tax brackets, and preserve more wealth for your family and causes.

Quick Recap: What’s a Roth Conversion? A Roth conversion is the process of moving funds from a traditional IRA or 401(k) into a Roth IRA. You’ll pay income taxes on the amount you convert today, but from then on, the growth and withdrawals are tax-free. Unlike RMDs, you also decide when and how much to convert, making timing an essential part of the strategy.

When Does a Roth Conversion Make Sense?

Roth conversions aren’t a blanket recommendation. They tend to be most effective in specific windows of time, often created by changes in your income, filing status, or tax law.

Between peak career income and required distributions (RMDs)

For many families, this “gap period” can be an ideal time to convert. You may no longer be earning at your highest levels, but you haven’t yet started Social Security or RMDs, which can push you into higher brackets. Converting during these years can often mean locking in lower rates and smoothing out your future income stream.

While married and filing jointly

Joint filers benefit from wider tax brackets than single filers, and that difference matters.

One family we worked with illustrates this well: The wife is 70, her husband 85, and together they’ve built more than $1.5 million in retirement assets. With his health declining, she knows that once she’s a widow, higher tax brackets will apply.

To help them prepare for the future, we began a series of conversions: $100,000 last year, $150,000 this year, and similar amounts planned in future years. By shifting assets now, more of her retirement income will be sheltered in a Roth by the time she’s a single tax-filer.

Related: Retirement Planning for High Achievers

Considering State Tax Rules

Federal brackets usually take center stage in conversion decisions, but state taxes can also tip the scales. Some states, like Illinois, don’t tax retirement account distributions at all, including Roth conversions.

One strategy of contributing to a Roth account is to fund a 401(k) and to then convert an equal amount to a Roth IRA.  This approach is a means of funding a Roth IRA with money that has only been taxed at the federal level and not the state level. It’s effectively using a conversion strategy to make a large contribution to a Roth IRA.

When Roth Conversions Don’t Make Sense

Just because you can convert doesn’t always mean you should. The right timing usually depends on both your tax situation today and what you expect in the years ahead.

During high-income years

We recently worked with a couple earning well over $1 million annually who were interested in converting $100,000 right away.

After running the numbers, we suggested waiting. With federal, state, and Medicare taxes combined, they were already facing an effective rate close to 45%. Converting in that environment would have meant paying about $45,000 in taxes. By waiting until retirement or during a year with less taxable income and lower tax rates, the opportunity to convert becomes much more compelling.

If you need to use IRA funds to pay conversion taxes

Roth conversions are most powerful when they fit naturally within your financial picture and the full amount can be converted.

That’s why we typically caution clients against using IRA funds to cover the tax bill, since doing so reduces the amount converted and the long-term benefit. We encourage clients to use cash savings or brokerage assets instead, so the full conversion amount can grow tax-free.

Estate Planning: Multi-Generational Roth Conversion Strategies

Roth conversions aren’t only about smoothing your own retirement income; they can also play a meaningful role in your family’s legacy planning.

The SECURE Act and the 10-year rule

Before 2020, children who inherited an IRA could “stretch” withdrawals across their lifetimes. The SECURE Act changed that. Now, most non-spouse heirs must fully deplete the account within 10 years. For children in their prime earning years who inherit IRAs, this often means taking large distributions on top of already high salaries, pushing them into even higher tax brackets.

Here’s how this might play out: Imagine you’re comfortably retired in the 22% bracket, with a goal of leaving your children a $1 million IRA. At your tax rate, that looks like a $780,000 gift after taxes.

But if your children inherit that account and withdraw it in the 32% bracket, the after-tax value is closer to $680,000. That’s $100,000 less than what you were envisioning for them, simply because of the comparative tax rates.

Many people in their 70s and 80s make Roth conversions less for their own benefit and more as a thoughtful gift to the next generation. By pre-paying taxes at their own lower rates, they reduce the tax bill on their IRA and help ensure more of their hard-earned wealth passes as intended.

When viewed this way, Roth conversions can become not just a tax strategy, but a legacy strategy to care for the people and causes that matter most.

How Much Should You Convert?

When we sit down with clients to explore Roth conversions, the first question is often “How much should we convert?”

In our experience, there’s no one-size-fits-all answer. The right amount usually depends on a mix of factors: your current tax bracket, future income expectations, cash available to cover the tax bill, and your long-term goals. We’ve found it most helpful to look at these pieces together and revisit the decision regularly, since life, tax laws, and income rarely stay the same for long.

Here’s how we can help you approach this decision:

• Filling the bracket: Often, we recommend converting just enough to “fill up” your existing tax bracket. The idea is that this allows you to take advantage of today’s rate without pushing additional dollars into a higher bracket. In years when income is unusually low, it might make sense to be more aggressive.
• Covering taxes wisely: Conversions are most effective when you can pay the taxes from non-IRA funds, such as a savings account or taxable investments. This ensures the full converted amount goes into the Roth, maximizing the long-term benefit of tax-free growth.
• Timing the tax bill: If you decide to convert later in the year, say in October, we would want to plan for estimated tax payments earlier (typically starting in March). Spreading out payments can help avoid unwelcome surprises the following April.

Above all, Roth conversions often work best as part of your larger, flexible strategy. Rather than locking into a rigid multi-year plan, we evaluate opportunities annually to make sure the decision reflects your current circumstances and the broader tax environment.

Bringing Strategy into Focus

When we sit down with accomplished professionals and business owners, these conversations often center around something really important: having choices and control over your financial future.

This goes well beyond just tax planning. It’s about maintaining flexibility while potentially preserving significantly more wealth for the people and causes closest to your heart.

If this raised new questions about your own plan, let’s keep the conversation going. We can revisit your conversion strategy during our next review or set aside time to look specifically at how today’s tax environment may create opportunities for you.

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If you’re not currently working with us but this way of thinking about wealth feels aligned with your own values, we’d love to connect. A Financial SWOT Session will give us the chance to sit down together, talk through your current tax picture, and uncover opportunities that may help your investments and legacy work more in sync with what matters most to you.

Learn more about how Roth conversions might complement your financial planning.

Strategic philanthropy that aligns your giving with your wealth goals and family values

 

You already know the joy of giving: the spark that comes from supporting a cause you love and the satisfaction of knowing you’ve made a difference. Whether it’s education, healthcare, community development, or other priorities close to your heart, you want your charitable giving to create meaningful, lasting impact.

But too often, charitable giving happens in bits and pieces—checks written on the fly, donations squeezed in at year-end, receipts shuffled at tax time. Meaningful, yes, but not always as focused or powerful as it could be.

You’ve worked hard to build your wealth, and now it carries both opportunity and responsibility. The challenge isn’t whether to give, it’s how to do it in a way that truly reflects your vision and values.

This is where donor-advised funds become powerful, not just as tax tools, but as vehicles for intentional impact.

Donor-Advised Funds: Your Strategic Giving Platform

Think of a donor-advised fund as your personal charitable foundation. Here’s how it works:

• You add cash or appreciated assets (like stocks) to your donor-advised fund and get an immediate charitable tax deduction for the year you contribute.
• You can invest those assets with the potential for tax-free growth, giving your future grants opportunities for even more impact.
• You decide when and where to recommend grants to qualified charities, whether that’s right away or years down the road.

Beyond the administrative convenience, a donor-advised fund is a platform for coordinating your philanthropic goals with your broader financial strategy. You can contribute during high-income years and distribute thoughtfully over time. You can donate appreciated assets instead of cash. You can even bring your family into the process, using grantmaking as a way to share values and decisions across generations.

By separating when you make contributions from when you direct them to causes, a donor-advised fund gives you the freedom to be both strategic and deeply intentional with your generosity.

Giving in Action: How to Build Generational Impact

We recently worked with a couple on the cusp of retirement who captured this transition beautifully. After years of building successful careers, they wanted their generosity to carry the same level of intention that had guided their business and family decisions: strategic rather than scattered and reactive.

They were deeply generous people who saw their wealth not just as financial security, but as a tool to strengthen their family, community, and the causes closest to their hearts. As they entered their final high-earning year, they also had substantial appreciated stock that represented years of smart investing.

Instead of continuing their pattern of writing individual checks throughout the year, we helped them take a more strategic approach. By contributing that low-basis stock to a donor-advised fund, they effectively set aside ten years’ worth of charitable giving in one move.

The financial benefits were clear: they offset income in their highest-earning year, avoided capital gains taxes, and preserved their cash as they transitioned into retirement.

But the deeper impact went beyond numbers.

They now had a dedicated charitable fund that reflected their values, didn’t compete with their retirement needs, and could grow over time to support even more giving.

The shift didn’t just improve their tax efficiency. It aligned their philanthropy with their deeper values and created a sustainable way to support causes they cared about for decades to come.

The Ripple Effects of Strategic Timing

When your income fluctuates significantly (like from business sales, stock compensation, or other windfalls), strategic timing using a strategy called “bunching” can significantly increase your charitable impact.

A client normally at the high end of the 24% tax bracket has an event that bumps them into the 35% tax bracket. They normally give $10,000 per year. If they “bunch” five years’ worth of contributions into the year with the higher income, they save an extra $4,400 in taxes.*

$50,000 x 35% = $17,500 vs. $10,000 x 35% + $40,000 x 24% = $13,100

Bunching becomes particularly valuable if you normally claim the standard deduction. Many generous people don’t receive tax benefits from their charitable giving because their annual contributions don’t exceed the standard deduction threshold. Bunching lets you claim the large charitable deduction in your high-income year, then take the standard deduction in the following years when your income returns to normal levels.

If this client was taking the standard deduction each year, all of the donations in the high-income year would be extra tax savings, not just the tax rate difference.

The strategy works especially well when you’re in your highest tax bracket. A $100,000 contribution in a year when you’re earning $750,000 might save you $35,000 in taxes, compared to only $24,000 in tax savings if you made the same gift when earning $300,000.*

*Please note: Examples are for illustration only and based on current federal tax brackets and charitable deduction rules. Your actual results will depend on your income, filing status, and other factors. Always consult your tax professional for guidance on your personal situation.

Investing in Long-Term Impact

Here’s another advantage: the money in your donor-advised fund can be invested while it’s waiting to be distributed. Like an endowment, well-managed funds often grow over time, creating additional resources for charitable giving beyond your original contribution. It becomes a sustainable source of philanthropy that can fund causes you care about for decades.

The strategy improves efficiency without changing your values or priorities. You’re still supporting the same causes with the same annual amounts; you’re just structuring it to increase the resources available for impact.

Overcoming the Wealth Steward’s Dilemma

One of the biggest hurdles we help clients navigate is psychological rather than technical.

One client increased his annual giving from $10,000 to $20,000 after establishing a donor-advised fund. The psychological shift from “spending” money on charity to “deploying” resources already set aside for philanthropic purposes made increased generosity feel natural rather than sacrificial.

Similarly, successful people often take pride in their investment gains. When we suggest donating appreciated stock that’s grown significantly, they resist: “But look how well this Apple stock has performed.” We understand that attachment, but you can still maintain your investment position while dramatically increasing your charitable impact using a two-step process:

Donate the appreciated stock to avoid capital gains taxes, then immediately repurchase the same amount with cash. Same investment strategy, reset cost basis for future growth, and significantly more efficient charitable giving.

Integration That Actually Works

These strategies become most powerful when they’re woven into your comprehensive financial plan rather than treated as separate decisions.

We work closely with clients’ CPAs and estate attorneys because charitable giving intersects with tax strategy, business planning, and wealth transfer goals. Recently, a client who sold his business wanted to make a substantial charitable contribution as part of managing his tax liability. Our coordination with his accountant before the gift helped optimize the timing and structure.

Before his tax return was filed, we reviewed it to make sure the work we did was captured. We caught an error where $50,000 in charitable deductions had been overlooked, recovering over $10,000 in tax savings that could fund additional giving.

But integration goes deeper than tax coordination. Many of our clients use ongoing charitable contributions to offset Roth conversions, reducing future required distributions while supporting causes they care about. This giving strategy and retirement strategy work together to create the legacy they want.

Transferring Values, Not Just Wealth

Perhaps the most meaningful aspect of donor-advised funds is how they create natural opportunities to involve your family in philanthropic decisions.

We’ve helped clients establish annual family meetings where adult children research and present different charitable opportunities. Some families use holiday gatherings to review their charitable fund and decide together how to allocate grants for the year.

One family we worked with allows their adult children to each recommend specific charities from the family’s donor-advised fund. It’s become an annual tradition that helps the next generation grow their own generosity while staying connected to the family’s values.

This approach helps ensure you’re transferring more than just financial assets. You’re passing on the mindset that wealth comes with stewardship responsibility and the joy of using resources to support what matters most.

When Strategy Serves Your Deeper Purpose

We’ve worked with clients across the giving spectrum. Some wanted to keep every dollar after business sales, even if it meant paying significant taxes because giving wasn’t part of their vision. Everyone’s path is different.

But for clients who see themselves as stewards of what’s been entrusted to them, strategic philanthropy creates extraordinary opportunities. You can capture available tax benefits, potentially increase your total giving capacity, and most importantly, align your charitable impact with your values and family legacy goals.

This is where having advisors who genuinely understand your philanthropic objectives makes all the difference. Most financial planning treats charitable giving as a tax afterthought or refers you elsewhere for “the giving conversation.”

You’ve worked hard to build something meaningful. Your charitable strategy should reflect that same level of intention, sophistication, and long-term thinking that created your success in the first place.

For our existing clients reading this, if anything here had fresh resonance for you or brings new questions to mind, we’d be glad to continue that conversation together, whether that means exploring donor-advised funds or looking at other ways to further support your philanthropic goals.

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If you’re not currently working with us but this approach resonates with how you think about wealth and impact, we’d be happy to discuss this during a Financial SWOT Session. It’s a strategic analysis that applies the same rigorous thinking you use in business to your personal financial decisions.

Together, we can identify opportunities to coordinate your tax strategy, investment approach, and charitable goals into a comprehensive plan that serves your deepest values and creates the legacy you want.

Schedule your Financial SWOT Session  or learn more about it here.

Breaking Down Financial Silos to Align Money Decisions with Family Values

Successful professionals understand there are consequences to every financial decision they make. You know that decision-making has compound returns. But when it comes to family conversations about wealth, most hit an unexpected roadblock. 

Money is very personal and can be a tough subject, which is what creates silos in the first place. The problem of silos is compounded by fast-growing wealth, unique family dynamics, and unspoken expectations. The conversations about wealth either don’t happen at all, or they create conflict when they do. 

This pattern is common, but the good news is that there’s a better way forward. When families get this right, they create ongoing dialogue instead of crisis-driven discussions. They make major decisions together and view wealth as a tool that serves their family values rather than a source of stress. Most importantly, they respond to unexpected events from a place of preparedness rather than panic.

 

The Two Most Common Ways Families Handle Money (And Why Both Fail)

We see money addressed in two ways. Silence or conflict.

1. Silence

The silence sounds like this: “My parents never talked about money with us.” “My spouse is the spender, and I make the money.” “This isn’t my area of expertise; my partner’s better at this than me.”

What we find is that many families prefer to avoid conflict around the wealth situation, so they avoid the conversations entirely. 

When spouses say, “This isn’t my area of expertise” or keep separate accounts, they risk communication breakdowns or, worse, hiding from one another. When only one spouse meets with advisors, they risk being out-of-the-loop on significant family decisions.

2. Conflict

Conflicts happen when financial stress finally erupts and different approaches clash. One spouse makes a major financial decision without consulting the other. Disagreements about spending priorities turn into arguments about values and control. Children witness these tensions and develop their own anxieties about money.

We see couples argue about investment risk tolerance when they’ve never actually discussed their long-term goals. Parents clash over how much financial information to share with children. Families find themselves in heated discussions during estate planning because no one understands what others expect.

These conflicts often reveal deeper misalignments that have been building for years. Trust breaks down precisely when families need it most.

When families don’t communicate about wealth decisions, we see them face missed opportunities and real risks. These gaps show up during major financial transitions or unexpected life events.

If you recognize your family in either pattern, you’re facing more than just uncomfortable conversations. You’re looking at missed opportunities for financial empowerment, preparation gaps that leave family members vulnerable, and potential conflicts that could damage relationships for generations. 

It doesn’t have to be that way. In fact, we’ve worked with hundreds of families that faced similar issues and yet were able to “right the ship.” Below is what we’ve seen to be highly successful. 

 

How to Engage a Financially Disengaged Spouse

We consistently find there’s a component of empowerment that’s missed when spouses aren’t talking to each other. Not being on the same page about goals and objectives means only one voice gets heard. Different visions go unaddressed. 

When we see a partner say, “This isn’t my area of expertise” or “my partner’s better at this than me,” we know this is the time to address the communication gaps we’ve been discussing.

Here’s how we help couples move from financial silos to collaboration. It gets people on the same page, so their goals and objectives are tied together. 

When both spouses understand the financial picture, you can make decisions together instead of one person carrying the full burden. But more importantly, it creates shared confidence. When your spouse feels informed and involved, they’re prepared to step in during emergencies or major decisions. Without that preparation, you’re both vulnerable.

Many who started working with us have felt overwhelmed and hesitant to engage. What we find works is helping you realize you’re not alone in facing these challenges. One simple way we do this is by giving examples of clients who navigated similar situations and are now succeeding in planning together. 

Another way we make planning approachable is to invite both spouses to our planning meetings. One of our clients shared how she had never been included in meetings with their former financial advisor, not because he didn’t want her there, but because she had never been asked to be included. By this small, but significant gesture, our clients learn that financial planning is a partnership and healthy for a relationship.

To aid in involving both spouses meaningfully, we guide our clients through two exercises in our first few meetings: Financial Values Discovery and Exploratory Questions. They help get you and your spouse on the same page first. Once we understand what matters most to you, we can talk about how money enables those goals.

This approach helps the disengaged spouse participate without feeling intimidated by financial complexity. Rather than jumping into investment details or tax strategies that might feel overwhelming, we start with what they already care about deeply.

When you start with what matters to them personally, money becomes a tool to achieve their dreams rather than a complicated subject they need to master. The financially involved spouse sees their partner engage meaningfully, which strengthens the collaboration and reduces the burden of making all decisions alone.

 

The Values-First Framework for Family Wealth Education

Money is very personal. But we find the wealthiest families think of it like stewardship as a family. 

What we’ve found is that when families communicate effectively about wealth, they create spaces where people can have conversations without conflict. A values-first process allows you not to talk about money first.

It starts with values around your life and how money plays a role in that. We use exercises like a financial decision-making wheel where clients fill out explanatory worksheets separately, then discuss them together. This approach moves from what matters most to how money serves those priorities. We find it removes the emotional charge from financial discussions by grounding them in shared values.

This framework works across generations, too. We work with families where children range from very young to adults. The focus stays on stewardship, estate plans, and roles within the family. The conversation becomes specific and transparent about what inheritance could look like, but it always starts with family values and education about responsibility.

One family set up a giving fund for their son to give to charities he cared about. It taught him how to spend money thoughtfully and showed him how satisfying giving can be compared to just buying material things. Both tactically and practically, it prepared him for wealth responsibilities.

 

Estate Planning as a Family Communication Strategy

Estate planning gets put off when people don’t want to have difficult conversations. When disaster strikes, families face these decisions completely unprepared with nothing in order. They end up going through courts in a drawn-out nightmare. The very conversations they avoided become unavoidable under the worst possible circumstances. 

Estate planning conversations reveal how well families communicate about wealth. Couples who struggle with money discussions often avoid these crucial conversations entirely.

Good estate planning becomes a powerful communication tool, not just legal protection. It forces conversations about values, priorities, and hopes for future generations. When done well, it ensures everyone understands their roles and responsibilities before emotions run high.

We see the most successful families use estate planning as an opportunity to clarify expectations. Who takes responsibility for what? How should family businesses continue? What charitable causes matter to the family? These conversations, while sometimes difficult, create clarity that serves families for decades.

The families who avoid these discussions often discover their assumptions were wrong. One spouse thought the other wanted to keep the family business. Parents assumed their children understood the responsibilities that come with inherited wealth. These misalignments create confusion exactly when families need clarity most.

 

The Family Wealth Transformation That Lasts Generations

Families who successfully break down financial silos describe the change with key words: less anxiety, less stress, peace of mind. People feel more confident. They feel prepared.

But the changes go deeper than just feelings. Both spouses actively engage in financial decisions with a clear understanding of their roles. The financially involved spouse no longer carries the full burden alone. The previously disengaged spouse gains confidence to participate in important conversations and decisions.

Children develop healthy relationships with money that extend beyond just spending. They understand family values around wealth and grasp the responsibilities that come with inheritance. They learn stewardship concepts early, which prepares them to handle wealth thoughtfully rather than carelessly.

These families create ongoing dialogue instead of crisis-driven discussions. They establish regular family meetings about financial goals. They make major decisions collaboratively. Most importantly, they view wealth as a tool that serves their deeper family values rather than a source of stress or conflict.

The shift from avoiding difficult conversations to engaging with them thoughtfully creates a foundation that serves families through multiple generations. When unexpected events happen, these families respond from a place of preparedness rather than panic.

 

Your Next Step

If these patterns sound familiar and apply to your family’s situation, these discussions about wealth communication are exactly the kind of strategic planning that can make all the difference. We would love to hear any thoughts this article sparked about your own family’s financial conversations as we continue to partner with you on your journey. To learn more about our approach, visit our homepage. 

Andrew Lisi, CFP® CPWA®, and Ben Gardner, CFP®, are financial advisors with The Next Level Planning Group, where they specialize in helping high-achieving professionals and business owners navigate complex financial transitions and family wealth communication strategies. If you’re beginning to think about improving your family’s financial conversations, we’d welcome the opportunity to explore your options together.