Richard: Our detailed retirement planning process includes:   

• A spending strategy tailored to your income goals
• Social Security timing recommendations
• Coordination of health care benefits
• Discussion around how your spending will change throughout retirement
• Stress-testing your retirement projection with many what-if scenarios
• Timing your exit to maximize any unvested incentive stock options (ISOs), non-qualified stock options (NSOs), or RSUs

Employees at large companies are often in a fortunate position — the benefits packages tend to be genuinely strong — but that also means there are a lot of moving parts to coordinate, and the stakes are high.

The first thing I do is make sure no one is leaving free money on the table. That means capturing the full 401(k) match before anything else. From there, we look at whether pre-tax or Roth contributions make more sense given where they are in their career and what their income looks like today versus in retirement.

For employees who receive equity compensation — RSUs, stock options, or an ESPP — that’s often where the bigger conversation happens. Equity can be a tremendous wealth-building tool, but it also creates real risks: concentration in a single stock and a tax bill that catches people off guard at vesting. I help clients build a thoughtful diversification strategy so they’re not overexposed to any one position, and we plan proactively for the tax implications so nothing comes as a surprise.

For employees on a high-deductible health plan, I also make sure they’re maximizing their HSA — not just as a healthcare fund, but as a long-term investment vehicle. Most people don’t realize it’s one of the most tax-efficient accounts available.

What I enjoy most about working with employees of large companies is that they’re often sharp, motivated, and have real wealth-building potential through their benefits alone. My job is to bring all the pieces together — the 401(k), the equity, the HSA, the taxable accounts — into one coordinated strategy so that every dollar is working as efficiently as possible.

The first conversation is really about listening more than talking. My goal is to understand not just where someone stands financially, but where they want to go — and what’s standing in the way.

I usually start with some foundational questions: Where are you in your career, and how are you thinking about the next five to ten years? Are you planning to stay with this employer long-term, or is there a possibility of a transition down the road? Those answers shape almost everything else.

From there I get into the specifics of their benefits. Are they capturing the full employer match on their 401(k)? How are they invested inside the plan, and does that still make sense given their timeline? If they receive equity compensation — RSUs, stock options, an ESPP — I want to understand how much of their net worth is tied to a single company’s stock, because concentration risk is one of the most common and underappreciated issues I see.

I also ask about taxes. Not in a technical way at first, but questions like: Did anything surprise you on your tax return last year? Are you feeling like you’re paying more than you should? That opens up a conversation about whether we can do better through smarter use of pre-tax accounts, HSAs, or deferred compensation if it’s available.

And then I ask the question that often matters most: What does financial security actually look like for you? The answer is different for everyone. For some people it’s retiring early. For others it’s funding their kids’ education without derailing their own retirement. For executives it might be building enough outside their employer that they have real optionality. Understanding that goal — that specific vision — is what drives everything else we do together.

Without question — the HSA, or Health Savings Account. It’s the most underutilized financial tool I see across the board, and it’s a shame because the tax advantages are extraordinary.

Most people treat the HSA like a flexible spending account — they contribute a little, pay their medical bills out of it, and move on. What they’re missing is that the HSA is actually a triple tax-advantaged account: contributions go in pre-tax, the money grows tax-free, and withdrawals for qualified medical expenses are tax-free. No other account does all three.

What I encourage clients to do, if their cash flow allows, is pay current medical expenses out of pocket and let the HSA grow invested for the long term. After age 65, you can withdraw the money for any reason — not just medical — and it essentially functions like a traditional IRA. But if you do use it for healthcare costs in retirement, which most people will have plenty of, it’s completely tax-free. That’s a powerful combination.

The other benefit I’d mention is deferred compensation, for those who have access to it. Non-qualified deferred compensation plans are available at many large employers for higher-earning employees, and they can be a meaningful way to reduce current taxable income and build wealth outside of the standard retirement account limits. But they come with real complexity and risk that needs to be understood before participating — which is exactly where having an advisor in your corner makes a difference.

Absolutely — and this is actually one of my favorite conversations to have, because most employees are sitting on benefits they’ve never fully explored.

Equity compensation is usually the first place I look. Whether it’s RSUs, stock options, or an Employee Stock Purchase Plan, these can represent a significant portion of someone’s total compensation — and they come with real decisions attached. When do you sell? How much do you hold? What’s the tax impact? I see a lot of employees either ignore these questions entirely or make emotional decisions about their company stock rather than strategic ones. Getting this right can make a meaningful difference in long-term wealth building.

Education savings is another area worth a dedicated conversation, particularly for employees with young children. A 529 plan isn’t an employer benefit in the traditional sense, but many large employers offer payroll deduction into 529 accounts, which makes the habit easy to build. More importantly, it’s a conversation that often gets delayed until it’s too late to let compounding do its work.

Life insurance and disability coverage are benefits people tend to click through during open enrollment without really thinking about. Group coverage through an employer is a great starting point, but it’s rarely sufficient on its own — especially for higher earners — and it doesn’t travel with you if you leave the company. I like to make sure clients understand what they actually have and where the gaps are.

Finally, I always ask about any financial wellness programs or legal services the employer offers. These are frequently overlooked and can provide real value, particularly around estate planning basics like wills and healthcare directives — documents that everyone needs but most people put off indefinitely.

The common thread across all of these is that benefits only create value if you actually understand and use them. My job is to make sure nothing valuable falls through the cracks.

A job transition is one of those moments where the financial decisions you make in a short window can have a lasting impact — for better or worse. I always encourage clients to slow down and think through a few key areas before they hand in their notice.

The first thing I look at is vesting schedules. Whether it’s a 401(k) employer match, RSUs, or stock options, leaving before a vesting date can mean walking away from meaningful compensation. Sometimes it’s worth negotiating a start date with the new employer to capture a vesting event that’s just weeks away. That’s a conversation most people don’t think to have.

Equity is the other big pre-resignation consideration. If you hold vested stock options, there’s typically a limited window — often 90 days — to exercise them after you leave. Missing that deadline means forfeiting them entirely. RSUs that haven’t vested yet are generally gone when you walk out the door, so understanding exactly what you’re leaving on the table is critical before making any final decision.

On the benefits side, I encourage clients to take stock of their health insurance situation before their last day. COBRA is always an option but can be expensive, so knowing how quickly the new employer’s coverage kicks in helps avoid any gaps.

For the 401(k), there’s no need to rush a decision, but shortly after leaving I’d recommend rolling it over to an IRA or the new employer’s plan rather than leaving it scattered across former employers. It’s easier to manage, typically opens up more investment options, and keeps your financial picture clean and consolidated.

And finally — the offer letter itself. Before signing, I always encourage clients to look at the full compensation picture at the new employer, not just the base salary. How does the equity package compare? What’s the 401(k) match? Is there a vesting cliff? Understanding the complete package helps make sure the move actually makes financial sense from day one.

The transition from a steady paycheck to drawing down from multiple income sources is one of the most significant financial shifts a person will ever make — and in my experience, the people who navigate it most successfully are the ones who start planning it seriously three to five years out, not three to five months out.

The first thing I work through with clients approaching retirement is what I call the income gap analysis. We add up all the guaranteed income sources they’ll have — Social Security, any pension, annuity income if applicable — and compare that to what they actually need to live comfortably. Whatever’s left is what the portfolio needs to cover, and that shapes everything from asset allocation to withdrawal strategy.

Social Security timing is one of the highest-impact decisions in this phase and one of the most misunderstood. Claiming early can make sense in certain situations, but for many people delaying — even by a few years — results in a meaningfully higher monthly benefit for the rest of their life. We model this out carefully based on health, other income sources, and whether there’s a spouse involved.

Healthcare is another area that deserves serious attention, particularly for anyone looking to retire before Medicare eligibility at 65. Bridging that gap can be expensive, and it needs to be factored into the retirement budget explicitly rather than treated as an afterthought.

On the portfolio side, I work with clients to gradually shift their thinking from accumulation to distribution — which is a fundamentally different challenge. It’s not just about how much you’ve saved, it’s about sequencing withdrawals intelligently across taxable accounts, tax-deferred accounts like IRAs and 401(k)s, and tax-free accounts like Roth IRAs to minimize the tax drag over time. Getting that order of operations right can add real longevity to a portfolio.

And then there’s the psychological side, which doesn’t get talked about enough. After decades of saving and accumulating, actually spending that money can feel deeply uncomfortable for a lot of people. Part of my job in this phase is helping clients feel confident and grounded in their plan — so they can enjoy retirement rather than worry their way through it.

I have a lot of respect for people who have taken ownership of their finances and done the work on their own. That discipline and engagement is actually a great foundation for a productive relationship with an advisor. The question I’d encourage them to ask isn’t “have I done okay so far?” — because the answer is probably yes — but rather “is doing this alone still the right approach given where I am and where I’m headed?”

The complexity argument is the most straightforward one. Early in a career, personal finance is relatively simple — contribute to the 401(k), build an emergency fund, avoid bad debt. But as income grows, equity compensation enters the picture, taxable accounts accumulate, families expand, and retirement starts moving from a distant concept to an actual horizon, the number of interconnected decisions multiplies quickly. At that point, the cost of a suboptimal decision — whether it’s a tax mistake, a poorly timed equity sale, or a Social Security claiming error — can far exceed the cost of professional guidance.

I’d also ask: how much time are you actually spending on this, and is that the best use of your time? Many of the people I work with are high achievers who are extremely capable of managing their own finances. But capability and bandwidth are two different things. If financial decisions are getting made reactively — or worse, getting deferred — because life is busy, that’s worth examining honestly.

Another honest question is around blind spots. We all have them. A good advisor isn’t just a technician — they’re a thinking partner who can challenge assumptions, stress test a plan, and flag things you might not know to look for. Most people don’t know what they don’t know until something goes wrong, and by then the cost of finding out can be significant.

And finally, I’d suggest looking at a few key moments as natural triggers for seeking a second opinion: a job change, an inheritance, a major equity vesting event, a divorce, or the death of a spouse. Any one of those situations involves enough complexity and enough at stake that having an experienced guide in your corner is genuinely valuable — not just reassuring.

The goal of a first conversation with an advisor shouldn’t be to hand everything over. It should be to get an honest assessment of where you stand, what you might be missing, and whether there’s enough value on the table to make the relationship worthwhile. A good advisor will tell you the truth either way.

Working with employees of large companies over the years, a few patterns come up consistently — and they’re worth naming because recognizing them is half the battle.

The first is what I’d call benefits paralysis. Large employers offer generous and often complex benefits packages, and the sheer number of decisions — 401(k) elections, health plan choices, equity grants, deferred compensation options, life insurance levels — can be genuinely overwhelming. The path of least resistance is to set something up during onboarding and never revisit it. I see people years into their careers still invested in the default target-date fund they selected on day one, with life insurance coverage that made sense when they were single but is now completely inadequate for a family. My job is to bring structure and intentionality to decisions that otherwise get made by default.

Concentration risk is another challenge I encounter constantly. When someone has worked at the same company for a long time and received equity compensation along the way, it’s very common for a disproportionate share of their net worth to be tied up in a single stock — their employer’s. There’s often an emotional attachment to that stock, a sense that loyalty or conviction should translate into holding. But from a pure risk management standpoint, having your income and your investment portfolio both dependent on the same company’s fortunes is a vulnerability. I help clients think through diversification in a way that feels rational rather than disloyal.

Lifestyle creep is a quieter challenge but a very real one, particularly among high earners at large companies. As compensation grows — base salary increases, bonuses, equity — spending tends to grow with it, sometimes faster. I work with clients to make sure that as their income rises, their savings rate and investment contributions are rising proportionally, not just their expenses. Building real wealth is about the gap between what you earn and what you spend, not the absolute level of either.

Tax complexity is something a lot of employees underestimate until it bites them. Between equity vesting events, bonus income, potential deferred compensation, and investment accounts, the tax picture for a high-earning employee at a large company can get complicated quickly. I work closely with clients — and coordinate with their CPAs where appropriate — to make sure we’re being proactive rather than reactive when it comes to tax planning.

And finally, there’s the challenge of integration — or the lack of it. Most people manage different pieces of their financial life in isolation. The 401(k) is one conversation, the equity compensation is another, the mortgage is another, the insurance is another. Nobody is looking at the whole picture at once. That’s precisely what I do. Bringing everything together into a single, coherent strategy is where the real value of financial planning lives.

This is a question I genuinely love, because I think everyone should approach hiring a financial advisor the way they’d approach any other important professional relationship — with real curiosity and a willingness to ask direct questions. The right advisor will welcome the scrutiny. Here’s what I’d encourage people to ask:

How are you compensated? This is the most important question on the list and the one people are most reluctant to ask. Understanding whether an advisor is fee-only, fee-based, or commission-based tells you a great deal about where their incentives lie. There’s no single right answer, but you deserve a clear and honest explanation — not a vague or defensive one.

Are you a fiduciary, and in what capacity? A fiduciary is legally required to act in your best interest. Some advisors are fiduciaries all the time, some only in certain contexts, and some not at all. Knowing where your advisor stands on this — and when — matters enormously.

What is your experience working with clients in situations like mine? If you receive equity compensation, have significant assets in a company retirement plan, or are navigating a specific life transition, you want an advisor who has real familiarity with those circumstances — not someone who will be learning on your time.

What does your typical client look like? This helps you understand whether you’ll be a priority or an afterthought. An advisor whose practice is built around clients at a very different income or asset level may not be the best fit, regardless of how capable they are.

How often will we meet, and what does ongoing service look like? A financial plan isn’t a document — it’s a living relationship. You want to understand upfront how proactive the advisor will be, how accessible they are between scheduled meetings, and what you can expect when your circumstances change.

Who else is on your team, and who will I actually be working with day to day? At larger firms especially, the person you meet with initially isn’t always the person managing your relationship. It’s worth understanding the structure before you commit.

And finally — can you explain a time you told a client something they didn’t want to hear? A good advisor isn’t just a validator. They push back when it matters, flag risks you might be overlooking, and prioritize your long-term interests over your short-term comfort. How an advisor answers this question tells you a lot about their character and their willingness to have honest conversations.

The goal of these questions isn’t to trip anyone up — it’s to find someone you can trust completely with one of the most important areas of your life. The right advisor will answer every one of them directly and without hesitation.

Honestly, yes — and the same few things come up more often than you’d expect, even among people who are financially engaged and working at sophisticated organizations.

The one that surprises me most consistently is how many people don’t know what they actually own inside their 401(k). They know they’re contributing, they have a general sense of the balance, but when I ask what they’re invested in and why, there’s often a long pause. A lot of people are in whatever default option they selected years ago and have never revisited it. For something that may ultimately be one of their largest assets, that level of inattention is striking — though I understand how it happens. Life gets busy, the account is out of sight, and as long as the balance is going up it’s easy to assume everything is fine.

Another thing that comes up frequently is a genuine surprise at how much equity compensation they’ve accumulated — and how concentrated that makes them. People receive grants periodically, the stock does well, and before long a significant portion of their net worth is tied to a single company. When I show someone that number visually, as a percentage of their total picture, it often lands differently than they expected.

I’m also consistently surprised by how many people have never looked carefully at their insurance coverage — life, disability, long-term care. They enrolled in whatever the employer offered during onboarding, accepted the default amounts, and haven’t thought about it since. For someone whose income and family situation have changed substantially over the years, that coverage is often badly misaligned with their actual needs.

And then there’s estate planning. I would say the majority of people I meet for the first time — across all income levels — either have no will at all or have one that’s badly out of date. People know they need it, they intend to get to it, and somehow it never rises to the top of the list. It’s one of the first things I encourage clients to address, because it’s not just a financial document — it’s how you take care of the people you love when you’re no longer able to do it yourself.

What ties all of these together is that they’re not failures of intelligence or effort — they’re failures of attention and integration. People are busy, the financial system is complex, and without someone periodically looking at the whole picture, important things quietly fall through the cracks. That’s exactly the gap a good advisor fills.

Absolutely — and this is an area where the complexity increases significantly and the cost of not having a coordinated plan can be substantial. Highly compensated employees and executives often have access to a layer of benefits that goes well beyond what’s available to the broader workforce, and each one comes with its own set of decisions, tax implications, and risks.

Nonqualified deferred compensation plans are one of the most powerful tools available to executives, and also one of the most misunderstood. The ability to defer a significant portion of income — sometimes hundreds of thousands of dollars — into a future tax year can be enormously valuable for someone in a high bracket today who expects to be in a lower bracket in retirement. But these plans are fundamentally different from a 401(k). The deferred amounts are technically still a liability of the employer, meaning they’re at risk if the company runs into financial trouble. The distribution elections are also largely irrevocable once made. Getting the strategy right from the beginning matters enormously.

Executive equity compensation tends to be more complex than standard RSU grants. Stock options — particularly incentive stock options, or ISOs — come with specific tax treatment that requires careful planning around exercise timing, alternative minimum tax exposure, and holding periods. The difference between a well-timed and a poorly timed exercise can be measured in tens of thousands of dollars or more.

Supplemental executive retirement plans, sometimes called SERPs, are another benefit worth understanding thoroughly. These are employer-funded retirement arrangements designed to provide additional income beyond what qualified plans like the 401(k) allow, and the terms vary widely from company to company.

Executive life insurance arrangements — things like split-dollar policies or executive bonus plans — also come up frequently at this level and require a careful look to make sure they’re structured in a way that actually serves the executive’s interests and integrates properly with their overall estate plan.

And speaking of estate planning — at the executive level this conversation becomes significantly more involved. We’re often talking about wealth transfer strategies, trust structures, charitable giving vehicles, and in some cases business succession considerations. The financial plan and the estate plan need to be built together, not treated as separate exercises.

What I find most important with highly compensated clients is that all of these pieces — the deferred comp, the equity, the insurance, the estate plan, the investment portfolio — are looked at holistically and updated regularly as circumstances change. The opportunities at this level are genuinely significant, but so are the consequences of getting it wrong.

There’s one that comes to mind that I think illustrates the point really well — and it’s a situation I’ve seen play out in different variations more times than I can count.

I met with a client who had been with a large employer for about twelve years. She was sharp, successful, and by any measure financially responsible. She had been contributing to her 401(k) consistently, had no significant debt, and felt like she had a reasonable handle on her finances. She came to me not because something was wrong, but because her compensation had grown considerably and she wanted a second set of eyes.

When we sat down and actually mapped out her complete financial picture, a few things became immediately clear. First, she had accumulated a substantial amount of vested company stock through RSU grants over the years — far more than she had mentally accounted for — and it represented nearly half of her investable net worth. She had always thought of her portfolio and her equity compensation as two separate things. They weren’t. They were deeply connected, and the concentration risk was significant.

Second, she had been eligible for her company’s nonqualified deferred compensation plan for three years and had never enrolled. Nobody had ever walked her through how it worked or why it might be worth considering. Given her tax bracket, that was a meaningful missed opportunity — not catastrophic, but real.

And third, her estate plan consisted of a will she had drafted before she was married, before she had children, and before her net worth had grown to its current level. It was essentially obsolete.

None of these were failures on her part. She had done a lot of things right. But they were a perfect illustration of what happens when the pieces of a financial life are managed in isolation rather than as a whole. The moment I laid it all out on one page — the portfolio, the equity, the deferred comp eligibility, the estate plan gap — I could see the shift in her expression. It wasn’t alarm, it was clarity. She finally saw her complete financial picture for the first time.

That’s the moment I find most meaningful in this work. Not when something has gone wrong, but when someone who has been doing well realizes they could be doing significantly better — and that the path to get there is clearer than they thought.

I’ve worked closely with employees from Southern California Edison, and one of the biggest opportunities I see is helping them fully capitalize on a benefits package that’s stronger than most—especially when it’s coordinated properly. That includes maximizing the 401(k) match and catch-up contributions, but more importantly, aligning those savings with your pension and overall retirement income plan. The goal isn’t just to participate in the benefits—it’s to make sure each piece is working together in the most efficient way possible.

Where I spend a significant amount of time with clients is around the pension decision. This is one of the most important financial choices you’ll make, and it’s also one of the few that is truly irrevocable—you typically only get one opportunity to elect your option, and once it’s set, there’s no going back. We walk through all of the available payout options, survivor elections, and trade-offs in detail, and then model how each choice impacts your long-term income, taxes, and your spouse or family. It’s not just about picking the highest payment—it’s about choosing the option that best supports your overall financial plan.

Beyond that, I help clients build a clear withdrawal and tax strategy across their 401(k), pension income, Social Security, and brokerage accounts so that everything works together efficiently over time. If you’re looking for guidance on how to make the most of your benefits and want to be confident you’re making the right decisions—especially around your pension—I’d be glad to help you think through your options.

Beyond the core retirement benefits, there are a couple of areas at Southern California Edison that I find especially valuable to spend time on with clients—primarily the 401(k) and retiree medical benefits, because both can have a meaningful impact on long-term outcomes if handled correctly.

With the 401(k), it’s not just about contributing and getting the match—it’s about optimizing it. I help clients evaluate whether pre-tax or Roth contributions make more sense based on their current income and future tax expectations, ensure they’re taking full advantage of catch-up contributions, and align their investment allocation with how their pension already provides a fixed-income base. When coordinated properly, the 401(k) becomes a powerful complement to the pension rather than just a standalone account.

For more tenured employees, retiree medical benefits are another major planning opportunity that’s often overlooked. Understanding what coverage continues into retirement, how it bridges to Medicare, and what costs to expect can significantly impact when someone retires and how much income they need. I work with clients to factor these benefits into their broader plan so there are no surprises especially around healthcare, which is one of the largest and most uncertain expenses in retirement.

For employees at Southern California Edison who are considering leaving for another opportunity, the most important step before making any decision is to fully understand the impact on their pension. In many cases, the pension is one of the most valuable benefits they have, and leaving even a few years early can significantly reduce the lifetime income it provides. I strongly encourage employees to request a current pension estimate and, ideally, compare it to projections if they were to stay an additional 1–3 years. It’s not uncommon to see a meaningful increase in monthly income just by extending employment slightly, especially as you approach key milestones in the benefit formula.

Beyond the pension, it’s also important to review your 401(k), any deferred compensation, and healthcare benefits before resigning. Understanding what you’re giving up and how it fits into your overall plan helps ensure you’re making a fully informed decision, not just a career-driven one. I often walk clients through a side-by-side comparison so they can clearly see the trade-offs, including how replacing that pension income would impact their long-term financial picture.

For employees at Southern California Edison approaching retirement, the transition from a steady paycheck to drawing from multiple income sources is one of the most important financial shifts you’ll make. The best way to prepare is to work with a financial planner who can walk you through each step helping you clearly understand your options and how all the pieces fit together. This includes evaluating your pension election, coordinating withdrawals from your 401(k), deciding when to take Social Security, and building a plan that replaces your paycheck in a reliable and tax-efficient way.

A good plan doesn’t just focus on income it prepares you for the decisions behind that income. That means understanding how different choices impact your spouse, your taxes over time, healthcare costs, and how your investments are structured once you’re no longer contributing. Having a clear, well-thought-out strategy in place before you retire allows you to move forward with confidence, knowing you’ve explored your options and are making informed decisions every step of the way.

For employees at Southern California Edison who have managed things on their own, I’d say the most important thing to consider is the growing complexity of the decisions in front of you especially around your pension, 401(k), taxes, and retirement income. Many of these decisions are interconnected, and some—like your pension election are permanent. Even if you’ve done a great job saving and investing, having a second set of experienced eyes can help you avoid costly mistakes and identify opportunities you may not have considered.

In my view, there’s no “perfect” time to start today is always the right time. The right advice can have a lasting impact, whether you’re years away from retirement or right on the doorstep. It’s not about giving up control it’s about gaining clarity, confidence, and a well-thought-out strategy so you can make informed decisions and fully understand your options moving forward.

When evaluating a financial advisor, especially as an employee of Southern California Edison, it’s important to ask questions that help you understand whether they are truly acting in your best interest and have the experience to guide you through complex decisions like your pension. Here are some key questions I recommend:

• Are you a fiduciary at all times, and will you put that in writing?
• How are you compensated—fee-only, commission-based, or a combination?
• What are all the fees I will pay, both directly and indirectly?
• Do you have any conflicts of interest I should be aware of?
• What services are included in our relationship (investment management, tax planning, retirement planning, etc.)?
• How do you help clients make pension decisions, and have you worked with others in situations similar to mine?
• Can you walk me through your process for building a retirement income plan?
• How do you coordinate tax strategies with investment and withdrawal decisions?
• What does ongoing communication look like how often will we meet and review my plan?
• What credentials, experience, or background do you have that are relevant to my situation?
• How do you tailor advice for someone with my level of assets and stage of life?
• Can you provide an example of how you’ve helped a client avoid a costly mistake or improve their outcome?

These questions help you understand not just what an advisor does, but how they think, how they’re incentivized, and whether their experience aligns with the decisions you’re facing.

For highly compensated employees and executives at Southern California Edison, deferred compensation plans are one of the most important and often misunderstood benefits to get right. These plans can be a powerful tax planning tool, allowing you to defer income during your highest earning years and potentially recognize it later when you’re in a lower tax bracket. However, the elections you make when to defer, how much, and how distributions are structured are critical, as the wrong setup can lead to large, concentrated taxable income in future years.

At the same time, deferred comp comes with a unique risk that many overlook: those assets are not held in your name and are subject to the financial strength of the company. In other words, it’s not the same as a 401(k) there is employer risk involved. Because of this, the planning becomes a balance between tax efficiency and risk management. I work with clients to structure their elections thoughtfully, diversify their overall exposure, and ensure deferred comp is integrated properly alongside their pension, 401(k), and broader financial plan so it enhances not complicates their long-term strategy.

One moment that really stands out to me was working with an employee from Southern California Edison who came in assuming they needed to work several more years or weren’t sure they could retire at all. After walking through their full picture the pension, 401(k), and overall benefits it became clear they were already in a position to retire comfortably. You could see the shift immediately, from uncertainty to relief, as they realized how strong their benefits really were and how well they had been taken care of.

Those are some of the most rewarding conversations, helping someone see that they can confidently step into the next chapter of life. I often tell clients retirement is the longest vacation they’ll ever take and being able to help them get there sooner than expected, with clarity and confidence, is a pretty special part of what I get to do.

Dimensional provides a nice amount of free cash into your 401k as a match, so it’s important you’re contributing at least 6% of your salary to this retirement account. There’s a lot of confusion around whether to make pre-tax contributions or Roth contributions to your 401k, and this is highly dependent on other factors like your cash flow needs and your household marginal tax bracket. The truth is, there isn’t one static choice to make here – it could shift each year! I talk through these tradeoffs with each of my Dimensional employee clients on an annual basis to make sure they’re selecting the option that makes the most sense for short and long-term wants and needs.

Dimensional also offers two different medical plans, one being their HSA Health Plan, and I find that you might struggle to understand whether or not this high-deductible plan with a Health Savings Account is a sensible choice for your family. As of 2026, Dimensional gives a sizable amount of free cash into your Health Savings Account: $1500 for individuals and $3000 for families. I’ll help you understand the power of treating your HSA as a tax-free retirement account, and we create a system for investing the cash systematically and “paying yourself back” in the future for current medical expenses.

Dimensional employees have the unique advantage of working inside a company with strong ties to the independent financial advisor community, and the firm fosters a deep respect for the value of financial advice. Despite these ties, employees often feel like they’re supposed to know exactly how to DIY the management of their own personal finances because they work for a financial firm.

As Dimensional employees reach upper-level roles (Managers, Regional Directors, Vice Presidents), this is a good time to consider working with a professional. Maybe you lack the accountability and guidance to focus on your financial health amidst the demands of a successful career and busy home life. Or perhaps you’ve built a great foundation for wealth and you’re making a competitive salary, but what are you missing and how do you prioritize your financial to-do list?

There is also a big consideration for hiring an independent, unbiased professional to guide you and your spouse through all the household financial decisions, big and small. Perhaps you want to feel connected with your partner when it comes to money, especially around aligning how you use your financial resources to live your ideal lives.

For senior level Dimensional employees making $250K+ in total compensation, a percentage of your bonus is deferred into the Long-term Incentive Plan (LTIP) to purchase Phantom Units. Generally, the more you earn while working at Dimensional, the more your compensation is tied to the growth of the firm. It’s important from a financial planning perspective to manage this potential concentration risk where your human capital and a growing portion of your financial capital are both tied to the performance of the firm.

I also don’t see many highly compensated Dimensional employees taking advantage of their recent Mega-Backdoor Roth option inside the 401k plan. There are also many tradeoffs to consider with financial planning strategy to decide whether or not it makes sense to add more to the Roth/retirement bucket or to use extra cash flow in other ways.