Ask most business owners about their company retirement plan, and the conversation turns administrative within seconds. How many employees participate. What the match looks like. Whether the recordkeeper is doing its job.  

Fair questions. But not strategic ones. 

That narrow framing is the missing link. A retirement plan is not just an HR line item or a task handed to a recordkeeper and/ or third-party administrator. For a closely held business, it can be one of the more versatile levers on the shelf — a tax planning lever, a talent lever, a personal wealth lever, and a business value lever, all at the same time. 

When we sit down with a business owner for the first time, the retirement plan is usually the last thing they expect to discuss. More often than not, it is one of the first things worth examining. Almost every other decision — how the owner takes compensation, how the business plans for taxes, how the owner prepares to exit — ties back to it. 

Why the Disconnect Happens 

The disconnect tends to be structural, not intentional. Business owners operate in two worlds, and their advisors rarely cross between them. 

The Business Side 

The business has its own advisors: a CPA, a payroll provider, a recordkeeper and/or third-party administrator for the retirement plan, sometimes a group benefits broker. 

Each does a specific job well. None of them is responsible for how those business decisions flow back into the owner’s personal financial plan. 

The Personal Side 

The personal side has its own ecosystem: a financial advisor, an estate attorney, sometimes a separate CPA. 

They typically see the owner’s brokerage accounts, household cash flow, and retirement projections — without deep visibility into the business, its balance sheet, or the plan document itself. 

The retirement plan sits right in the middle. When no one owns the middle, the owner ends up making decisions in silos. 

A match structure gets chosen because it is easy to administer. A deferral limit gets hit because no one flagged a Safe Harbor option. A cash balance plan gets dismissed because no one modeled what it would do for the owner’s personal tax bracket. 

None of these calls are wrong in isolation. But none of them are strategic, either. 

What a Coordinated Retirement Plan Actually Does 

When a retirement plan is designed with the wider financial picture in mind, it starts to do work on multiple fronts. 

Business Tax Planning 

Retirement plan contributions are one of the few levers that can meaningfully shift a business’s tax position year to year. 

Depending on the structure — 401(k) with profit sharing, cash balance pension, combination plans — contribution limits can range from modest to substantial. For an owner with a strong income year, the right plan design can shift significant dollars from current taxation into tax-deferred retirement assets. 

This only works when the plan is designed alongside the tax return — not after it. That requires your advisor, your CPA, and your plan designer to be talking to each other. 

Owner Wealth Accumulation 

Most of a business owner’s net worth is tied up in the business itself. That concentration makes diversification difficult, especially before a sale. 

A well-structured retirement plan gives the owner a tax-advantaged vehicle to move wealth off the balance sheet of the business and into a diversified portfolio over time. 

That is not a small thing. It can shift the risk profile of the owner’s entire financial plan years before any transaction takes place. 

Employee Attraction and Retention 

In most industries, competitors have caught up on salary. Benefits — especially retirement benefits — are increasingly where the differentiation happens. 

A thoughtfully designed plan with automatic enrollment, a meaningful employer contribution, and financial wellness support tends to produce higher participation and better long-term outcomes for employees. That matters for retention. 

It also signals something about the kind of business an owner is running, which is part of what Firm-to-Family® means: caring for the people you care about, including the people on your payroll. 

Cash Flow Planning 

A retirement plan is a multi-year cash commitment. 

Plans with employer contributions need to be modeled into the cash flow forecast, not just the benefits budget. When that modeling happens inside the broader financial plan — debt service, owner compensation, capital reserves — the plan design gets right-sized for the business. 

When it does not, owners either overcommit or, more commonly, underuse the plan. 

Succession and Exit Readiness 

This is where the ripple effects are most visible. 

Buyers look at retirement plans during due diligence. An underfunded, poorly administered, or non-compliant plan can delay a transaction, reduce the purchase price, or create post-close liability. 

A thoughtfully managed plan does the opposite. It cleans up the picture and makes the business easier to value and easier to transition. For the owner, the dollars accumulated inside the plan over the years of ownership are often the bridge between the sale proceeds and personal retirement income. 

The Questions Worth Asking 

If you are a business owner, the diagnostic questions are simpler than they sound: 

• Is your retirement plan designed with your personal tax situation in mind, or is it a template pulled off a recordkeeper’s shelf? 

• Is anyone modeling how your plan contributions affect your personal financial plan five, ten, and twenty years out? 

• Are the people responsible for your plan talking to the people responsible for your personal wealth, your estate, and your eventual exit from the business? 

If the answer to any of those is no, the plan is likely doing a fraction of the work it could be doing. 

How Gatewood Brings the Full Picture Together 

The point of looking at the full picture is not to add complexity — it is to stop making decisions in isolation. 

That is what Firm-to-Family® is built to address. Gatewood brings a team of specialists around the same table, working from the same information. For a business owner, that means the person designing your retirement plan is talking to the person modeling your personal cash flow, who is talking to the person thinking about your eventual exit. 

A retirement plan that sits inside that kind of framework tends to do more with less friction — not because the plan itself is different, but because it is finally being asked to do the work it was capable of all along. 

If you would like to talk through how your current retirement plan fits into your wider business and personal financial plan, we would welcome the conversation.

Important Disclosures: 

Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. Gatewood Wealth Solutions and LPL Financial do not provide legal or tax advice or services. 

All investing involves risk including loss of principal. No strategy assures success or protects against loss.   

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. 

This information is not intended to be a substitute for specific individualized tax or legal advice. We suggest that you discuss your specific situation with a qualified tax or legal advisor. 

Why the Best Retirement Plans Are Built Around People, Not Just Compliance 

What if the retirement plan you offer your employees is actually pushing your best people out the door?

It is a question that stops most business owners in their tracks. And the honest answer, more often than they expect, is yes. 

In my experience working with business owners over the past decade, across plan auditing, consulting, corporate benefits administration, and fiduciary advisory, the pattern is remarkably consistent. 

A retirement plan gets established because the CPA recommended it or because a competitor was offering one. The paperwork gets filed, the box gets checked, and then something happens. Nothing. The plan sits there. Participation stays low. Employees either do not enroll, do not understand their options, or do not contribute enough to make a meaningful difference in their financial future. 

And here is the part that rarely gets measured: the employees who leave for a better benefits package somewhere else. 

A retirement plan is not a box to check. It is a statement about how you value the people who build your business.  

Employee expectations have shifted. People still care about compensation, but as concerns about retirement among younger workers continue to rise, benefits play a larger role in how employees evaluate where they work.  

A recent Employee Benefit Research Institute (EBRI) survey found that 78% of workers say retirement benefits are a major factor in deciding whether to stay with an employer or explore other opportunities. The plan itself is no longer just a benefit. It is a recruiting and retention tool.  

So what separates a retirement plan that employees actually use and value from one they ignore? 

That is a great question, and it is the one we help business owners answer every day. But before we get into the strategies, consider the data. These numbers tell the story of why a well-designed retirement plan matters and what happens when plan design is left on autopilot. 

Sources: Employee Benefit Research Institute, Selerix, Gallup, JP Morgan, PLANSPONSOR, Vanguard How America Saves 2025, Bank of America Participant Pulse 2025.   

The data is clear. Plan design matters. Communication matters. Follow-through matters. And the business owners who treat their retirement plan as a living, breathing part of their benefits strategy are the ones retaining their best people. Below are seven ideas that can turn a retirement plan from a dusty compliance obligation into one of the most powerful tools in your business.

1. If They Cannot Find the Door, They Will Never Walk Through It

Think about the last time you tried to sign up for something online and the process was so frustrating you just closed the browser. That is exactly what happens with retirement plan enrollment when the process is too complicated, too manual, or too full of jargon employees do not understand. 

The biggest barrier to retirement plan participation is not employee apathy. It is enrollment friction. 

Amazon changed the way all of us think about transactions. One click and it is done. That expectation for a frictionless experience did not stay in online shopping. It followed consumers into every part of their lives, including the workplace. 

Employers want frictionless administration. Employees want frictionless enrollment. And when there is friction, things simply do not get done. 

When employees have to track down forms, decipher unfamiliar terminology, or figure things out on their own, many simply do not enroll at all. They intend to get around to it, but life gets in the way and the months turn into years. 

Over time, that delay can create a significant retirement readiness gap between employees who got started early and those who kept meaning to. 

The fix is often simpler than business owners expect. Clear enrollment steps during onboarding, written guides in plain language, a portal that is intuitive to access, and default contribution rates employees can adjust to their comfort level. 

Think of it like a GPS. If you hand someone a destination and a simple route, they will drive. If you hand them a paper map with no markings, most of them will stay parked. 

Has anyone on your team audited your enrollment process from the employee’s perspective in the last 12 months? 

That is a great question, and one we walk through with every business owner we work with. You would be surprised how often the answer reveals gaps nobody knew existed. 

And with SECURE 2.0 now requiring automatic enrollment for plans established after December 29, 2022, the landscape has changed. New 401(k) plans must enroll eligible employees at a default contribution rate between 3% and 10% of compensation, with annual automatic escalation of at least 1% per year until the rate reaches between 10% and 15%. 

Employees can always opt out or adjust, but the default puts them on the right path from day one. 

2. Your Match Is Only as Good as Your Message

Employer contributions are one of the most direct ways to tell employees their participation matters. A well-designed match does not just help employees save. It sends a message: we are investing in your future alongside you. 

But plans can fall short when matches are poorly explained, structured in ways employees do not fully understand, or set so low that employees do not recognize the value. When employees cannot clearly see what they are getting, they contribute less than they otherwise would. That reduces engagement and diminishes the perceived value of the plan as a whole. 

An employer match that nobody understands is an employer match that nobody uses. 

There are several approaches that tend to move the needle. A traditional match up to a set percentage is the most common. Non-elective contributions provided regardless of employee deferral remove the participation barrier entirely. Tiered match designs that reward higher savings rates or employee longevity can encourage people to increase their contributions over time. 

Think of a match like a fitness center membership subsidy. If the company pays 50% of the monthly fee and employees know about it, most of them will sign up. 

But if the subsidy is buried in an email nobody reads, the gym stays empty. The match itself is only as effective as the communication around it. 

When was the last time you surveyed your employees to find out if they understand how the match works and what they need to contribute to get the full benefit?

3. The Roth Question Your High Earners Cannot Afford to Ignore

A Roth feature can be a powerful addition for employees who expect their tax situation to change over time or who value having options when it comes to how their retirement income will be taxed. 

Still, many employers either do not offer a Roth option at all or fail to explain when it might be useful. In some cases, employees default into pre-tax contributions simply because that is the only option presented clearly. 

Do your employees know they may have the option to contribute on a Roth basis, and do they understand when that choice could benefit them?  

That is a great question, and one that matters more in 2026 than ever before. Under SECURE 2.0, starting this year, employees who earned more than $150,000 in FICA wages in 2025 are now required to make their catch-up contributions on a Roth basis. This is not optional. 

If your plan does not currently offer a Roth option and you have employees in that income range who are 50 or older, they cannot make catch-up contributions at all until Roth is added to the plan. 

If your plan does not offer Roth and you have high-earning employees over 50, SECURE 2.0 just took their catch-up contributions off the table.  

Beyond compliance, the Roth option tends to resonate with younger employees early in their careers, employees who want flexibility in future withdrawal taxation, and those balancing current budgeting with long-term planning. Without understanding their options, employees may miss opportunities to build tax diversification that could save them significantly in retirement.

4. Stop Handing Out Textbooks and Start Having Conversations 

Most employees do not skip retirement plan participation because they are uninterested. They skip it because they are unsure. They do not know what options apply to them or how they will benefit. The information they receive feels either too technical or too generic to be useful. 

Think of it this way. If you walked into a restaurant and the menu was written entirely in a language you did not speak, you would probably walk out, even if the food was excellent. 

Retirement plan education works the same way. The content might be valuable, but if it is not delivered in a way employees can absorb, it does not matter. 

The goal of plan education is not to make employees smarter about retirement. It is to make them confident enough to take the next step. 

Short sessions, plain language, and recurring touchpoints tend to resonate more than a single annual meeting. Education is most effective when it is practical and action-oriented, giving employees space to ask the questions that actually matter to them. 

Questions like: How much should I contribute to receive the full match? What is the difference between Roth and pre-tax? How do I choose investments if I am not an expert? What should I contribute to hit my target retirement date? 

Some employers rely on dense materials, one-time presentations, or overly technical explanations. Others assume employees will figure it out on their own. 

And many point to the online education tools provided by their plan custodian as evidence that resources are available. Those tools exist, and some are quite good. But the reality is that very few employees actually use them. 

Employers who rely too heavily on promoting these digital libraries are satisfying a compliance requirement, not meeting their employees where they are. There is a meaningful difference between making information available and helping someone make a decision and act on it. That difference usually comes down to in-person guidance or one-on-one conversations, the kind of support that turns confusion into confidence. 

If you sat down next to one of your newest employees and asked them to explain how your plan works, could they do it?

5. One Size Fits Nobody

One of the most common missed opportunities in retirement plan design is treating every employee the same. Plans are sometimes designed with a single average employee in mind, without considering how financial needs and priorities evolve over the course of a career.  

A 28-year-old early in their career is focused on learning the basics and managing cash flow. A 45-year-old mid-career is thinking about increasing contributions and planning around family needs. A 58-year-old approaching retirement is evaluating timing, catch-up contributions, and what their income will look like on the other side. 

Think of it like a shoe store that only carries one size. The product is fine. It just does not fit most of the people walking through the door. 

A plan that speaks to one life stage and ignores the others will lose the employees it cannot reach. 

And in 2026, the numbers work in favor of employees who are paying attention. The standard 401(k) deferral limit is now $24,500. Employees age 50 and older can contribute an additional $8,000 in catch-up contributions, for a total of $32,500. 

Under SECURE 2.0, employees between the ages of 60 and 63 can take advantage of the super catch-up, contributing an additional $11,250 instead of the standard $8,000, for a total of $35,750. That is a meaningful increase for employees in their peak earning years who want to accelerate their savings. But only if they know the option exists. 

SECURE 2.0 also reduced the service requirement for long-term part-time employees. Starting in 2025, employees who work at least 500 hours per year for two consecutive years must be eligible to make elective deferrals, even if they do not meet the plan’s normal eligibility requirements. 

This means more of your workforce may now have access to your plan than you realize. 

6. You Cannot Save for Tomorrow When Today Is on Fire

Retirement planning does not exist in a vacuum. Many employees are simultaneously managing emergency savings gaps, high-interest debt, student loans, rising household expenses, and anxiety around market volatility. 

Asking them to think about retirement when they are stressed about next month’s rent is like asking someone to plan a vacation while their house is on fire. 

Employees who are financially stressed today are not thinking about retirement tomorrow. And no amount of plan design will change that. 

Some employers focus exclusively on retirement savings without acknowledging the financial pressures employees face day to day. The result is predictable: employees feel forced to choose between short-term stability and long-term planning, and in many cases, they opt out of retirement contributions entirely because other financial needs feel more urgent. 

Does your benefits strategy address the financial pressures your employees face today, or only the retirement they may not be thinking about yet? 

That is a great question, and one that often shifts how business owners think about their entire benefits package. 

Retirement benefits become more impactful when paired with education or tools that help employees stabilize short-term decisions while still planning for the long term. Emergency savings programs, student loan assistance, financial literacy workshops, and access to guidance during major life transitions all contribute to a workforce that feels supported enough to participate in a retirement plan with confidence.  

7. A Plan Without Follow-Through Is Just a Filing Cabinet 

Some employers treat the retirement plan as a one-time project. The plan gets established, the enrollment meeting happens, and then it runs on autopilot. But employees benefit most when there is visible follow-through: regular check-ins, reminders, and access to support as questions arise or life circumstances change. 

Think of it like planting a garden. You do not just put seeds in the ground and walk away. You water, you weed, you check on things. 

A retirement plan needs the same kind of attention. Periodic reminders tied to raises, bonuses, or annual reviews. Clear points of contact when employees need guidance. Updates when plan features change or new options become available. 

The difference between a plan that exists and a plan employees actually use is almost always the follow-through. 

Without ongoing support, employees may stick with outdated contribution levels, miss opportunities to adjust their strategy as their lives change, or feel uncertain about whether they are making informed decisions. The plan itself may be well designed. But if nobody is tending the garden, the results will disappoint everyone. 

Who on your team is responsible for checking in on the plan after the initial setup is done? 

If the answer is nobody, you are not alone. And that is one of the most common reasons plans underperform. The good news is that it is one of the easiest things to fix. 

The Rules Changed. Did Your Plan? 

The regulatory landscape around retirement plans has changed significantly. SECURE 2.0, signed into law in December 2022, introduced over 90 provisions that are rolling out over several years. 

Several key provisions are now in effect or taking effect in 2026, and business owners who are not aware of them could face compliance issues. Here are the changes that matter most right now: 

Mandatory automatic enrollment: Plans established after December 29, 2022 must include automatic enrollment at a default rate between 3% and 10%, with annual escalation to at least 10% (up to 15%). Exemptions apply for businesses with 10 or fewer employees, businesses less than three years old, and church and governmental plans. 

Roth catch-up mandate for high earners: Starting in 2026, employees with FICA wages above $150,000 in the prior year must make catch-up contributions on a Roth basis. Plans without a Roth option will need to add one or those employees lose access to catch-up contributions entirely. 

Enhanced catch-up for ages 60 to 63: The super catch-up allows contributions of $11,250 instead of the standard $8,000 for employees in this age range. This provision is optional for plans, but offering it can be a meaningful benefit for experienced employees in their peak earning years. 

Long-term part-time employee eligibility: Employees working at least 500 hours per year for two consecutive years must now be eligible for elective deferrals. Business owners with part-time staff should verify they are tracking hours and enrolling eligible employees. 

Plan amendment deadline: Most plans have until December 31, 2026 to formally adopt plan amendments reflecting SECURE 2.0 changes, though plans must already be operating in compliance. 

The plan amendment deadline is December 31, 2026. Compliance is not optional, and the clock is running. 

One Team, One Plan, Your People: The Firm-to-Family® Approach 

Many of the ideas in this article are easy to understand on paper. Applying them is where the work happens. 

Every business is different. Every workforce has its own mix of ages, income levels, financial pressures, and goals. A plan design that works for a 50-person manufacturing company looks very different from one that works for a 200-person technology firm. 

I started my career as an auditor at a St. Louis-based accounting firm, where I saw retirement plans from the compliance and financial reporting side. I moved into retirement plan consulting, eventually advising on the management of over $1 billion in retirement assets. 

But the experience that shaped my perspective most was spending several years inside a large corporate employer, where I was responsible for benefits strategy, plan design, and administration for both active employees and retirees. That combination of managing plans from the inside and advising on them from the outside is something I carry into every client conversation at Gatewood. 

My role at Gatewood is to bring that dual perspective to every engagement. That means evaluating plan features, identifying participation gaps, benchmarking against industry standards, and providing ongoing support as employee needs change. It is not a one-time conversation. It is a relationship. 

Is your retirement plan keeping pace with your business, or is it still built for the company you were five years ago?  

Through our Firm to Family® approach, we do not treat your retirement plan as a standalone product. We bring together the right expertise to help you make coordinated decisions that consider your employees, your business goals, your tax situation, and the long-term impact on the people who depend on your leadership. To learn more about why this matters, read Firm to Family: Why Financial Planning Must Change When Others Depend on Your Decisions. 

That means your retirement plan consultant is working alongside Gatewood’s wealth planners, tax coordinators, and Investment Committee. If a plan design decision has tax implications for the business, we coordinate that. If an employee benefit strategy intersects with the owner’s personal wealth plan, we connect those conversations. 

The same way we serve our wealth management families, we serve our business clients: as one integrated team, not a collection of disconnected advisors. For a closer look at what that team approach looks like in practice, see From Firm to Family: Why Your Financial Plan Deserves a Team. 

The best retirement plans are not built by checking boxes. They are built by someone who understands your business, your people, and where you are headed. 

If you are thinking about how your retirement plan fits into the bigger picture of supporting your employees and growing your business, we are here to help you work through it.

Important Disclosures

Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. Gatewood Wealth Solutions and LPL Financial do not provide legal or tax advice or services. 

All investing involves risk including loss of principal. No strategy assures success or protects against loss.   

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. 

This information is not intended to be a substitute for specific individualized tax or legal advice. We suggest that you discuss your specific situation with a qualified tax or legal advisor. 

A Roth IRA offers tax deferral on any earnings in the account. Qualified withdrawals of earnings from the account are tax-free. Withdrawals of earnings prior to age 59 ½ or prior to the account being opened for 5 years, whichever is later, may result in a 10% IRS penalty tax. Limitations and restrictions may apply. 

You’ve spent decades building something remarkable. Early mornings, late nights, difficult decisions, and countless sacrifices have transformed your vision into a thriving business. Now, as you contemplate your exit, one question looms larger than all others: How do you know if the wealth you’ve created actually makes it into your retirement?

What are the most important pre-retirement tax considerations when selling a business?

The most important pre-retirement tax considerations when selling a business often include entity structure, timing of the sale, deal structure, and how retirement planning integrates with sale proceeds. Addressing these areas early—ideally years before you’re ready to sell—can help you align tax decisions with your long-term personal goals and preserve significantly more wealth.

The difference between a well-planned exit and a rushed one can easily mean hundreds of thousands—or even millions—of dollars in unnecessary taxes. More importantly, it can determine whether your hard-earned wealth truly serves the life you’ve envisioned for yourself and the legacy you want to leave behind.

The Three Tax Pillars Every Business Owner Must Address

Preparing the business for sale involves far more than polishing the balance sheet. Here are three critical tax pillars that owners navigate to safeguard the future of those they care about:

1. Entity Structure: The Foundation That Determines Everything

Your business’s legal structure is the foundation that determines how your sale will be taxed, how much flexibility you’ll have in negotiations, and ultimately, how much wealth you’ll preserve.

C-Corporations: Navigating the Double Taxation Trap

If you operate as a C-Corporation, you’re facing one of the most significant tax challenges in business transitions. The structure of your deal—stock sale versus asset sale—can dramatically alter your after-tax proceeds.

Here’s the tension that exists in nearly every C-Corporation transaction: buyers typically prefer asset sales because they can step up the basis of acquired assets and claim valuable future depreciation. From their perspective, this makes perfect economic sense. For you as the seller? An asset sale followed by liquidation creates a double taxation nightmare—first, your corporation pays tax on the gain, then you pay tax again when those proceeds flow through to you as a shareholder.

A stock sale, by contrast, is typically taxed once at long-term capital gains rates. The difference isn’t trivial—it’s often the equivalent of an additional year or two of retirement income simply evaporating in taxes.

This is why the structure conversation needs to happen years before you’re ready to sell, not months. When you’ve planned ahead, you enter negotiations with leverage. You can structure the deal on terms that work for your tax situation, not just accommodate the buyer’s preferences.

The QSBS Opportunity You Can’t Create Retroactively

If you’ve owned qualifying C-Corporation stock for more than five years, you might be sitting on one of the most powerful tax benefits in the code: Qualified Small Business Stock (QSBS) treatment. This provision can exclude up to $15 million of capital gains per issuer from federal taxation—or potentially even more under the 10× basis rule.

But did you know that QSBS eligibility must be established at the time of stock issuance and maintained throughout the holding period? You cannot create it retroactively. If you haven’t already evaluated your QSBS eligibility, this conversation needs to happen now, before you’re deep in deal negotiations.

S-Corporations: Simpler, But Still Strategic

S-Corporations offer cleaner tax treatment as pass-through entities, meaning sale proceeds are generally taxed once at the shareholder level. However, complexity emerges in how the purchase price is allocated among different asset categories.

In an asset sale, certain portions of the proceeds—such as depreciation recapture or inventory—may be taxed at ordinary income rates, while the remainder qualifies for capital gains treatment. The allocation of value among these categories isn’t arbitrary; it’s negotiated between buyer and seller, each with different tax motivations.

And here’s where advance planning becomes invaluable: the difference between an optimal allocation and a suboptimal one can represent hundreds of thousands of dollars in additional taxes. When you understand these dynamics years in advance, you can structure your operations to maximize the portions that will receive favorable tax treatment.

Partnerships and LLCs: Complexity Hiding in Plain Sight

If your business operates as a partnership or multi-member LLC taxed as a partnership, you’re dealing with pass-through taxation, but don’t mistake simplicity for ease. The allocation of sale proceeds among goodwill, equipment, real estate, and other assets creates dramatically different tax outcomes for each partner.

Adding another layer of complexity, each partner’s individual tax basis and capital account must be considered. Without advance coordination, you risk not just higher taxes, but uneven outcomes among partners—a recipe for conflict at precisely the wrong time.

Sole Proprietorships: Maximum Flexibility, Maximum Planning Needed

As a sole proprietor, you’re typically selling business assets rather than equity interests. This means your transaction will generate a mix of capital gains and ordinary income depending on how proceeds are allocated among equipment, inventory, goodwill, and other assets.

Without entity-level shielding, thoughtful allocation and timing become even more critical. The good news? You have complete control. The challenge? You need to exercise that control strategically, and preferably years before you’re ready to sell.

2. Timing and Deal Structure: When Flexibility Creates Wealth

The structure of your transaction matters as much as the price. How you receive proceeds, when you close, and how you coordinate the sale with other planning strategies can materially influence what you ultimately keep.

Installment Sales: Smoothing Tax Impact Across Multiple Years

Rather than receiving all proceeds at closing and facing a massive one-year tax bill, consider structuring part of the sale as an installment sale. This approach allows you to recognize gain as payments are received over time, potentially keeping you out of the highest tax brackets and preserving more wealth overall.

However, installment sales aren’t a magic solution. Interest income is taxed at ordinary income rates, and certain components—particularly depreciation recapture—may be taxed immediately regardless of payment timing. The analysis requires sophisticated modeling to determine whether this strategy truly benefits your specific situation, but when it works, the tax savings can be substantial.

Pre-Sale Gifting: Aligning Tax Efficiency with Legacy

If you have family or charitable goals, transferring ownership interests before a binding sale agreement is in place can accomplish multiple objectives simultaneously. Pre-sale gifting allows future appreciation to pass to heirs or charitable organizations outside your taxable estate, reducing both income and estate taxes while advancing your legacy goals.

But timing is everything. Once you’ve entered into a binding sale agreement, these opportunities largely disappear. The IRS views such transfers as attempts to assign income, and they’re generally ineffective for tax purposes.

This is why conversations about gifting strategies need to happen years before you’re ready to sell, not months. When structured properly, pre-sale gifting can reduce your tax burden significantly while ensuring the people and causes you care about benefit from your success. When attempted too late, it’s simply ineffective.

The Danger of “Just in Time” Planning

Here’s what we see repeatedly: by the time you’re actively negotiating with a buyer, many of your most powerful tax planning tools are already off the table. QSBS eligibility can’t be created retroactively. Gifting strategies lose effectiveness once a sale is imminent. Entity restructuring may be impossible or prohibitively expensive.

The most successful exits share a common characteristic—they’re planned years in advance, giving owners maximum flexibility to structure transactions on favorable terms while coordinating with broader wealth transfer and retirement strategies.

3. Retirement and Beneficiary Planning: From Illiquid Business Owner to Financially Independent

The income generated by the sale may fundamentally change the owner’s retirement picture, requiring a new approach to tax-advantaged accounts.

A liquidity event fundamentally reshapes your financial life. You’re transitioning from business owner—where most of your wealth was tied up in illiquid equity—to retiree, where liquid assets must generate the income and security you need for potentially 30 or 40 years.

This transition demands a comprehensive reassessment of how you’re saving for retirement, how those assets will be invested, and ultimately, how wealth will transfer to the people and causes that matter most to you.

401(k) and Profit-Sharing Plans: The Foundation of Tax-Efficient Retirement Savings

In the years leading up to your sale, maximizing contributions to a 401(k)—including employer profit-sharing contributions—can shelter significant income from taxation. For 2026, these plans offer substantial contribution limits, provide administrative simplicity, and allow you to combine pre-tax and Roth contributions for valuable tax diversification in retirement.

Just as importantly, don’t overlook beneficiary designations. These accounts pass directly to named beneficiaries outside of your will or trust, making proper designation essential. After decades of accumulation, the last thing you want is for retirement assets to transfer inefficiently or to unintended beneficiaries simply because paperwork wasn’t updated.

Cash Balance Plans: Accelerating Tax-Deferred Savings Before Your Exit

For business owners seeking to dramatically accelerate retirement savings, a Cash Balance Plan offers a powerful complement to a traditional 401(k). When implemented several years before an exit, these plans allow substantially higher deductible contributions—particularly valuable for older owners with consistent, significant income.

We’re not talking about modest increases. Depending on your age and income level, Cash Balance Plans can enable annual contributions exceeding $200,000, all tax-deductible, all growing tax-deferred. Over a three to five-year period before a sale, this strategy can shelter meaningful income while building a substantial retirement asset.

Because Cash Balance Plan balances can represent a significant portion of your net worth after sale, coordination with beneficiary designations, trust structures, and estate documents becomes critical. These accounts need to be integrated into your comprehensive wealth plan, not treated as standalone vehicles.

Employee Stock Ownership Plans (ESOPs): An Alternative Path with Tax Benefits

If you’re committed to preserving your company culture and rewarding long-term employees, an ESOP might offer a compelling alternative to a traditional sale. ESOPs allow you to sell all or part of your business to employees while potentially unlocking significant tax benefits.

In qualifying C-Corporation transactions, you may be eligible to defer capital gains taxes indefinitely under a Section 1042 election by reinvesting proceeds into Qualified Replacement Property—typically diversified securities. Beyond tax considerations, ESOPs can support legacy objectives by keeping the company independent, maintaining existing relationships, and ensuring employees benefit from the value they’ve helped create.

That said, ESOPs involve complexity, ongoing administrative requirements, and reduced flexibility compared to traditional sales. They’re not right for every situation, but for owners whose priorities include employee welfare and business continuity, they deserve serious consideration.

Beneficiary and Legacy Considerations: Giving Your Wealth Purpose

After your sale closes, you’ll likely experience a fundamental shift in your balance sheet—from illiquid business interests concentrated in a single asset to liquid investments spread across retirement accounts, taxable accounts, and potentially real estate or alternative investments.

This transition creates an ideal opportunity—perhaps the best opportunity you’ll ever have—to comprehensively review and align your beneficiary designations, trust structures, and charitable strategies. Are your retirement accounts designated to the right beneficiaries? Do those designations coordinate with your trust documents? Have you considered charitable strategies that might reduce taxes while supporting causes you care about?

Alignment matters. When retirement accounts, investment accounts, and estate documents work together cohesively, wealth transfers efficiently, taxes are minimized, and your intentions are honored. When they don’t, the results can be costly, time-consuming, and emotionally difficult for your heirs.

Evaluating Your Pre-Sale Tax Strategy

How can you know whether your current pre-sale tax plan is effective? Start by asking these questions:

• Have you reviewed your entity structure to determine whether it’s optimized for your exit timeline?
• Do you understand the tax implications of various deal structures—stock sale versus asset sale, installment sale versus lump sum?
• Are your retirement savings strategies maximized in the years leading up to your sale?
• Have you explored whether QSBS treatment or other specialized tax provisions apply to your situation?
• Are your advisors coordinating with each other, or working independently without a unified strategy?

If you can’t answer these questions confidently, gaps likely exist in your planning—gaps that could cost you significantly when it’s time to exit.

The Value of Firm-to-Family® on Your Behalf

Selling a business is rarely just a financial transaction. It’s a transition that affects family members, employees, and long-term plans that extend well beyond the closing date. Navigating that transition requires coordination across multiple areas — tax planning, retirement strategy, investment decisions, and legacy considerations — all working together over time.

At Gatewood, the Firm-to-Family® approach is designed for moments when coordination matters most. Business owners are clients of the firm, not of a single advisor. That means planning decisions are guided by consistent standards of advice and a shared understanding of long-term goals, rather than changing based on who happens to be involved at a given stage of the process.

Because specialists across planning, investments, retirement strategies, and tax awareness collaborate around the same objectives, exit planning remains aligned from early preparation through life after the sale. Entity structure, deal design, retirement funding, and beneficiary considerations are evaluated in context — with continuity that holds even as roles change or new advisors become involved.

This firm-wide approach helps business owners move through a major transition with clarity and perspective, knowing decisions are informed by collective experience and structured to support what comes next — for themselves and for the people who depend on them.

Important Disclosures:
The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

This information is not intended to be a substitute for specific individualized tax or legal advice. We suggest that you discuss your specific situation with a qualified tax or legal advisor.

In my experience working with retirement plan sponsors and professionals across all stages of wealth building, I’ve seen how even small updates to IRS contribution limits can create meaningful opportunities—if they’re understood and applied strategically.

Each fall, the IRS releases updated retirement contribution limits—and while the numbers may appear dry, these annual adjustments hold real power for long-term wealth building.

The 2026 limits are now official, and for high earners and retirement savers alike, they present fresh opportunities for tax-efficient planning.

Here’s What’s Changing for 2026

Below is a comprehensive chart showing the updated retirement plan contribution limits for 2026, alongside 2025 levels:

*Includes allowable employer contributions (match, profit sharing)

**No super catch-up applies to IRAs—only the standard amount

Why These Increases Matter to Your Financial Future

For individuals in their peak earning years or business owners maximizing retirement savings, these higher limits create significant opportunities:

Tax reduction today. Increased pre-tax deferrals allow you to reduce your current taxable income while building retirement assets.

Tax-free growth potential tomorrow. Greater Roth contribution capacity enables long-term tax-free accumulation and qualified distributions.

Business owner advantages. Higher total limits provide expanded flexibility for employer match and profit-sharing contributions within business retirement plans.

Accelerated savings for near-retirees. Super catch-up contributions offer those aged 60–63 the ability to meaningfully close savings gaps in critical years.

Key Planning Reminders for 2026

Mandatory Roth catch-ups for high earners. If you’re over 50 and earned more than $150,000 in FICA wages in 2025, your 401(k) catch-up contributions must be made on a Roth basis per SECURE Act 2.0 provisions.

Super catch-up limitations. The enhanced catch-up provision applies only to employer-sponsored plans like 401(k)s and SIMPLE IRAs—not to Traditional or Roth IRAs.

Annual indexing matters. These limits adjust yearly for inflation. Staying current ensures you capture your full available contribution space and compound the benefits over time.

How Gatewood Helps You Plan Proactively

At Gatewood Wealth Solutions and Gatewood Tax & Accounting, we take a multi-disciplinary approach to retirement savings that goes far beyond tracking IRS limits. Our comprehensive planning coordinates:

• Strategic tax positioning using Holistiplan’s advanced tax forecasting to optimize your tax brackets and Roth conversion opportunities
• Cash flow modeling through eMoney’s 5-year projections and comprehensive Retirement Income Planning
• Business owner strategies including 401(k), SIMPLE, and SEP contribution design for entrepreneurs and corporate executives
• High-income planning featuring backdoor Roth IRA strategies that respect IRS aggregation rules and pro-rata calculations

We don’t just react to IRS changes—we proactively integrate them into your holistic financial plan, aligning your savings strategy with your long-term goals and values.

Make the Most of Your 2026 Planning Window

Contribution limits are merely numbers on a page unless you have a strategic plan to leverage them effectively. Whether you’re approaching retirement or navigating your peak earning years, now is the time to ensure these increases work for you.

Let’s discuss how the 2026 contribution limit increases fit into your comprehensive financial strategy.

Schedule your planning meeting with Gatewood Wealth Solutions or contact Gatewood Tax & Accounting to develop a tax-optimized contribution strategy tailored to your unique situation.

At Gatewood, we believe that retirement savings is not just about maximizing contributions—it’s about aligning every dollar with your life’s purpose. Our team of credentialed professionals is here to guide you through each planning opportunity with expertise and care, helping you build enduring wealth with confidence for life’s key moments. Because at Gatewood, we don’t just plan for retirement—we plan for what truly matters to you.

Important Disclosures

The information provided is for educational purposes and should not be considered specific tax or investment advice. Please consult with qualified professionals regarding your individual circumstances.

A Roth IRA conversion—sometimes called a backdoor Roth strategy—is a way to contribute to a Roth IRA when income exceeds standard limits. The converted amount is treated as taxable income and may affect your tax bracket. Federal, state, and local taxes may apply. If you’re required to take a minimum distribution in the year of conversion, it must be completed before converting.

To qualify for tax-free withdrawals, you must generally be age 59½ and hold the converted funds in the Roth IRA for at least five years. Each conversion has its own five-year period, and early withdrawals may be subject to a 10% penalty unless an exception applies. Income limits still apply for future direct Roth IRA contributions.

Securities and advisory services offered through LPL Financial, a Registered Investment Advisor. Member FINRA/SIPC. Tax and Accounting services offered through Gatewood Tax and Accounting, a separate legal entity and not affiliated with LPL Financial. LPL Financial does not offer tax advice or tax and accounting related services

What if the 401(k) plan you thought was protecting your employees—and your business—is actually a ticking time bomb of liability, compliance issues, and hidden costs?

When Everything Fell Apart

Meet Sarah, CEO of a growing manufacturing company with 150 employees. For years, she’d relied on her payroll company to handle the 401(k) plan. “One-stop shopping,” they called it. Simple. Convenient. Until the Department of Labor audit letter arrived.

The problem started small. A few late deposits here, some missing participant notices there. But as investigators dug deeper, they uncovered a web of compliance failures: investment fees that hadn’t been properly disclosed, a plan document that hadn’t been updated in five years, and fiduciary responsibilities that no one was actually fulfilling.

The final tally? $425,000 in penalties and legal fees. Three months of management time consumed by the audit process. And worst of all—the realization that her “simple” solution had been putting her business and her employees at risk for years.

Sarah’s story isn’t unique. It’s happening to business owners across America who believe their 401(k) is being properly managed, only to discover too late that convenience doesn’t equal competence.

What This Means: The Hidden Reality of 401(k) Management

As an executive or business owner, your time is valuable, and managing retirement benefits shouldn’t be a hassle. But here’s what most business owners don’t realize: a 401(k) plan is one of the most complex financial products your business will ever purchase.

Under ERISA guidelines, plan fiduciaries—which often includes CEOs, CFOs, HR directors, and other executives—carry personal liability for plan decisions. This isn’t just corporate liability that insurance can cover. This is personal liability that can follow you home.

The complexity is staggering. Investment selection and monitoring. Fee benchmarking and disclosure. Participant communications and education. Compliance testing and documentation. Vendor oversight and management. Each area has its own regulatory requirements, potential penalties, and litigation risks.

Yet most business owners handle their 401(k) plan with the same level of attention they give their office supplies.

Why This Matters: The Cost of Getting It Wrong

The statistics are sobering. According to the Department of Labor, there are over 2,000 ERISA-related lawsuits filed annually, with the average settlement exceeding $2 million. These aren’t just cases against massive corporations—small and mid-sized businesses are increasingly in the crosshairs.

The Hidden Costs Include:

• Personal fiduciary liability that can pierce corporate protection
• DOL penalties ranging from thousands to millions of dollars
• Class-action lawsuits from participants seeking damages
• Lost productivity from management teams dealing with compliance issues
• Employee retention problems when plan quality suffers
• Missed opportunities to use retirement benefits as competitive advantages

But the real cost isn’t just financial—it’s the distraction from running your business. Every hour spent dealing with 401(k) problems is an hour not spent growing your company.

The Critical Pain Points Business Owners Face

1. Fiduciary Liability Confusion

Most business owners don’t even know they’re fiduciaries, let alone understand what that means. They assume their payroll company or “retirement plan advisor” is handling everything, only to discover they’re still personally liable for decisions they didn’t know they were making.

2. Investment Oversight Chaos

Your employees are depending on the investment options you’ve selected, but when was the last time someone with real expertise reviewed performance, fees, and appropriateness? Most business owners are making million-dollar investment decisions based on marketing materials and vendor presentations.

3. Compliance Nightmares
   

ERISA compliance isn’t optional. Late deposits, missing notices, inadequate disclosures, and outdated plan documents aren’t just administrative oversights—they’re violations that can trigger audits and penalties.

4. Fee Transparency Issues

Do you know what your employees are actually paying in fees? Can you document that those fees are reasonable? Most business owners can’t answer these questions, leaving them vulnerable to fee litigation.

5. Employee Engagement Problems

Your 401(k) plan is supposed to help attract and retain talent, but if employees don’t understand it or feel it’s not competitive, it becomes a liability instead of an asset.

An Analogy That Puts It in Perspective

Think of your 401(k) plan like the electrical system in your building. You can see the outlets and switches, and everything seems to work fine day-to-day. But behind the walls is a complex network of wiring, circuits, and connections that require expert knowledge to install and maintain safely.

You wouldn’t let your office manager rewire the building just because they’re good with spreadsheets. Yet that’s essentially what happens when business owners rely on payroll companies, PEOs, or generalist brokers to manage their 401(k) plans.

The consequences of electrical problems are obvious—fires, outages, safety hazards. The consequences of 401(k) problems are often hidden until it’s too late—then they can be devastating.

How Gatewood Solves These Critical Concerns

At Gatewood Wealth Solutions, we keep your priorities the priority. We understand that you didn’t start your business to become a retirement plan expert—you started it to pursue your vision and serve your customers.

Our Evidence-Based Approach:

Unlike providers who offer one-size-fits-all solutions, we design each plan based on empirical research and your specific business needs. We combine passive index funds for core exposure with targeted active management in market segments where skilled managers historically add value—international equity, fixed income, small-cap value, and large-cap growth.

True 3(38) Fiduciary Protection:

We don’t just advise on investments—we assume legal responsibility for them. As your ERISA 3(38) Investment Manager, we reduce your fiduciary burden while ensuring your plan operates in compliance with all regulatory requirements.

Comprehensive Oversight:

Our team of specialists provides strategic guidance tailored to your goals, helping you implement efficient, compliant, and structured retirement plans. We handle investment monitoring, fee benchmarking, compliance calendars, and participant education—everything you need for a successful plan.

How Gatewood Compares to Other Providers

• Large Payroll Companies (Paychex, ADP):

Payroll companies excel at payroll processing but treat 401(k) plans as add-on products. They typically offer limited investment lineups, minimal fiduciary support, and focus on administrative convenience rather than participant outcomes. When problems arise, you’re often shuttled between departments with no one taking ownership.

• PEOs like TriNet:

PEOs provide small and medium-size businesses with HR admin support and services, including access to benefits that small businesses may not typically provide. However, they focus on standardized solutions across their entire client base. Your plan becomes part of their master plan, limiting customization and often resulting in higher costs and fewer options for your specific workforce.

• Traditional Brokers:

Most retirement plan brokers are compensated through revenue sharing from investment companies, creating inherent conflicts of interest. They may not have the specialized credentials or processes necessary for proper fiduciary management, leaving you with the appearance of professional help without the substance.

Gatewood’s Key Differentiators 

CFA®-Led Investment Oversight:

Your plan is monitored by our CFA®-credentialed investment committee—not outsourced to third-party managers with limited customization like typical providers.

Dynamic Planning vs. Static Setup:

We use real-time dynamic planning to continually review fund menus, participant outcomes, and investment lineups to keep your plan optimized. Others often set the plan once and revisit infrequently, leading to outdated fund options.

Holistic Business Owner and Executive Coordination:

We go beyond plan administration by integrating your personal financial planning with your business retirement plan. For business owners, we coordinate the plan’s design with your personal retirement and tax strategy, optimizing contributions (401(k), profit-sharing, cash balance plans) to align with your long-term goals. For executives, we provide personal financial planning sessions to integrate company benefits—equity awards, deferred compensation, and stock options—into their broader wealth strategy.

Personalized Fund Selection:

We offer institutionally vetted funds with no proprietary product pressure or revenue-sharing arrangements that create conflicts of interest.

Individualized Employee Education:

We conduct personalized education sessions—from entry-level employees to senior management—using advanced planning tools like eMoney to help participants understand how their workplace savings integrates with their overall wealth strategy. This goes far beyond the generic group meetings most providers offer.

Firm-to-Family® Continuity Model:

Business owners and executives gain a dedicated Client Care Team—wealth advisor, planner, and coordinator—ensuring seamless service and alignment of corporate and personal planning. Unlike advisor-dependent providers, our team-based approach provides consistent, long-term continuity.

Specialized Expertise:

Our team includes Certified Plan Fiduciary Advisors (CPFA®) who focus exclusively on employer-sponsored retirement plans. This isn’t a side business—it’s our specialty.

Process-Driven, Not Product-Driven:

We start with your goals and design strategies accordingly, rather than trying to fit your needs into our products.

Relationship-Driven Approach:

With Gatewood, you gain a dedicated partner committed to the financial well-being of your loved ones now and for generations to come. We build long-term relationships focused on your success.

Integrated Wealth Management:

Unlike standalone retirement plan providers, we can coordinate your business retirement plan with your personal wealth management, creating synergies and efficiencies other providers can’t match.

Employee Education Excellence:

We help you empower employees through financial wellness education and one-on-one meetings, ensuring they understand how to make the most of their retirement benefits.

The Benefits of the Gatewood Approach

Reduced Fiduciary Risk: Our 3(38) fiduciary services significantly reduce your personal liability while ensuring professional investment management.

Enhanced Employee Outcomes: Evidence-based investment selections and comprehensive education programs aim to help your employees build more successful retirement savings. 

Improved Retention and Recruitment: A well-designed, properly managed 401(k) plan becomes a competitive advantage in attracting and retaining talent.

Operational Efficiency: We handle the complex compliance requirements, freeing your team to focus on business operations.

Cost Transparency: We provide clear, comprehensive fee reporting so you always know what you’re paying and can document fee reasonableness.

Ongoing Partnership: Unlike transactional providers, we work with expertise and care to support your evolving business needs over time.

Building Enduring Wealth with Purpose

At Gatewood, we understand that wealth is personal—and that includes the wealth your employees are building through their retirement plans. The true value of planning is the confidence it creates—confidence for your employees in their financial future, and confidence for you that your business is protected from unnecessary risks.

We are process-driven, not product-driven. Our systematic approach to plan design, investment management, and ongoing oversight ensures that your 401(k) plan supports your business objectives while meeting your fiduciary obligations.

Your Next Step: From Risk to Confidence

Don’t let your 401(k) plan become a liability that threatens your business and your employees’ financial security. The question isn’t whether you can afford professional 401(k) management—it’s whether you can afford not to have it. 

Ready to transform your 401(k) from a compliance burden into a competitive advantage?

Contact Gatewood Wealth Solutions today for a complimentary plan review. We’ll analyze your current plan structure, identify potential risks and opportunities, and show you how our comprehensive approach can provide the peace of mind you need and the results your employees deserve. Schedule your consultation and discover why business owners across the region trust Gatewood to guide them through the complexities of retirement plan management. Because when it comes to your employees’ futures and your business’s protection, solutions, not answers make all the difference.

Important Disclosures:

This material was created for educational and informational purposes only and is not intended as ERISA, tax, legal or investment advice. If you are seeking investment advice specific to your needs, such advice services must be obtained on your own separate from this educational material.

According to a 2025 study[1]  highlighted by Inc., nearly 85% of employees believe their employer should help them navigate financial challenges. Let that sink in.

That’s not a “nice to have”—that’s a near-universal expectation.

And yet, in many workplaces, financial wellness is either ignored, underfunded, or mistaken for a once-a-year 401(k) meeting.

As someone who advises companies on retirement plans, I’ve seen this firsthand. And here’s the truth: the companies who acknowledge and respond to this growing expectation aren’t just helping their people—they’re strengthening their own business.

A Simple Metaphor: Financial Stress Is a Dashboard Warning Light

Imagine you’re driving a car and the oil light comes on. You ignore it—after all, the engine still runs. A few weeks later, you’re stalled on the highway with a major repair bill.

Employee financial stress works the same way.

It’s often invisible. But it’s real, it’s chronic, and it’s impacting performance, health, and retention. Financial pressure weighs heavily on decision-making, focus, and emotional health—especially when there’s no guidance or support.

The Science of Financial Stress at Work

Psychologists refer to this as cognitive load—when the brain is overloaded with mental “tabs,” it can’t focus. According to WebMD Health Services[3], financial stress is the #1 stressor across income levels, and 1 in 4 employees say it directly impacts their productivity.

Additional research from Morgan Stanley’s 2025 Workplace Financial Benefits Study[2] found:

• 84% of employees want help with personal financial planning
• 66% say financial stress affects their work or personal life
• 68% of employees would stay longer if their employer offered meaningful financial wellness support.

This is no longer just a benefits issue—it’s a talent strategy issue.

Why Most Employers Miss the Mark

Despite overwhelming data, many employers still believe financial guidance is too personal, too complicated, or already “covered” by the 401(k) plan.

But here’s the disconnect: most 401(k) plans offer basic education, not personalized guidance. And they often ignore broader financial issues—like budgeting, debt, or emergency savings—that dominate employee stress.

This is like handing someone a map but not teaching them how to read it.

Simple Ways Employers Can Step Into the Gap

You don’t have to overhaul your benefits package to make a difference. Here are practical, low-cost ways to respond to this need:

1. Offer “Financial Office Hours” – Offer easy to access one-on-one meetings with a financial advisor (ideally one with no product agenda) where employees can ask basic questions—judgment-free.
2. Survey Your Team – Ask: “What’s your biggest financial concern?” and “Would you like more support from the company?” It opens the door and shows empathy. You can modify future education initiatives around their answers.
3. Add Financial Touchpoints to Existing Benefits – During open enrollment or onboarding, include simple guides on budgeting, emergency funds, and debt management. You could even provide a scheduling link to the financial advisor’s office hours calendar.
4. Curate Trusted Tools – Recommend vetted budgeting apps, podcasts, or free online courses—employees often just need help knowing where to start.
5. Normalize the Conversation – Create a culture where financial wellness isn’t taboo. When leadership talks about it, others feel safer engaging.
6. Continue Onsite 401(k) Education Meetings – Keep offering in-person 401(k) sessions, but raise your expectations. Collaborate with providers to ensure the agenda and talking points address the real financial concerns of your team—not just investment basics. These sessions should help bridge the gap between retirement planning and everyday financial wellness. It should address common employee questions and give you time back in your day.

Final Thought: From Retirement Advisors to Financial Allies

As a retirement plan advisor, my role used to revolve around plan design, investment lineups, and compliance. But today, the companies we serve expect more—and rightly so.

By stepping into the financial wellness gap, we’re not just helping employees retire well. We’re helping them live better now.

And if 85% of your workforce wants this? The only real question is—what are we waiting for?

Sources:

[1] Inc. Magazine citing John Hancock’s 2025 Financial Stress Survey – 85% of employees believe their employer should support their financial well-being.

Source: Inc. (2025). The Next Frontier of Employer Support? Financial Wellness.
https://www.inc.com/2025/03/financial-wellness-workplace-employee-benefits.html

[2] Morgan Stanley Workplace Financial Benefits Study, 2025

84% want help with financial planning, 66% say stress affects work/life, 68% say they’d stay longer if supported.
Source: Morgan Stanley at Work. (2025). The State of the Modern Workplace.
https://www.morganstanley.com/articles/workplace-financial-benefits-2025

[3] WebMD Health Services (2024–2025 Report)

Financial stress is the top stressor and directly impacts productivity.
Source: WebMD Health Services. (2024). Employee Well-Being Trends Report.
https://www.webmdhealthservices.com/resources/2024-well-being-trends-report/

Important Disclosures:

This information was developed as a general guide to educate plan sponsors, but is not intended as authoritative guidance or tax or legal advice.  Each plan has unique requirements, and you should consult your attorney or tax advisor for guidance on your specific situation.  In no way does advisor assure that, by using the information provided, plan sponsor will be in compliance with ERISA regulations