Holding a significant portion of your wealth in one or a handful of individual stocks can be both exhilarating and nerve-wracking. While the rewards of watching a single company’s meteoric rise can be life-changing, the risks of a lack of diversification are just as great. The problem is that liquidating these positions often means getting hit with daunting tax bills. We walk through practical solutions and the new tools now available to investors seeking diversification without immediate tax consequences.
The Real Risk of Concentration
It’s tempting to simply hang onto a winning stock, postponing taxes until you're in a lower bracket or retired. But over 90% of stocks underperform the market long term. Individual company fortunes can change abruptly—think Enron, Lehman Brothers, or stock collapses from $50 to $0.50. Banking your whole plan on one company’s continued success is a risk that can jeopardize even the soundest of financial plans. Taking calculated steps to shift your assets, even if taxes are due eventually, is often essential for long-term stability.
Modern Options for Tackling Concentrated Stock
Technology and innovation in the investment industry are opening doors once reserved for the ultra-wealthy. Here are four tax-deferral solutions we discuss:
1. Exchange Funds
Exchange funds allow investors to pool their highly appreciated stocks with others, resulting in a diversified basket—often 20–30 stocks. You maintain your original cost basis, and after a 7-year lock-up period, you can access a more diversified portfolio.
There are usually high entry minimums ($250,000–$500,000) and the investor must be an accredited. It requires a long holding period and comes with added complexity, costs, and delayed K-1 tax forms. At the end, you still owe taxes if you sell, but you’ve reduced single-stock risk.
2. Section 351 Funds
If you hold several different stocks or even ETFs that no longer fit your strategy, Section 351 exchanges allow you to transfer them into a new, broadly diversified fund with tax deferral. This is similar in spirit to a 1031 real estate exchange but designed for securities. This option gives you flexibility, but it only works with publicly traded investments in taxable (not retirement) accounts
3. Separately Managed Accounts (SMAs)
SMAs have become popular for allowing greater customization. In an SMA, instead of owning an index fund, you hold the constituent stocks directly—allowing for tax loss harvesting and the exclusion of specific stocks. This offers personalized values-based investing but creates more complex tax reporting and can create complications for you and your CPA.
4. Tax Aware Long/Short Strategies
Recently popular but highly complex, these leverage SMAs and add a long/short overlay, aiming to maximize loss harvesting regardless of overall market conditions. This uses leverage and shorting, increasing risk and management costs. It gives greater potential for tax loss harvesting, but introduces tracking error and liquidity constraints. This is best for specific, high-need scenarios.
Keep Your Broader Plan in Mind
Always return to your broader financial plan. Look at that accumulated stock position in the context of your overall financial plan and everything else that's happening in your goals and life. These tactics are tools, not silver bullets. Sometimes, the simplest (if less glamorous) move—selling, paying taxes, and reinvesting—might be your best decision.
Concentrated stock positions can be both an opportunity and a source of anxiety. Before chasing the latest “shiny object,” evaluate your situation with the help of an advisor. Find the approach that aligns with your risk, liquidity needs, and long-term goals. Sometimes, boring really is better—for both your taxes and your sleep.
Outline of This Episode
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The first quarter of 2026 brought a whirlwind of market events—geopolitical shocks, surging energy prices, and a notable shift away from mega-cap US growth stocks. Despite the turbulence, the markets proved remarkably resilient, underscoring the importance of diversification and a long-term approach. We discuss lessons investors can use to navigate uncertainty and build lasting wealth.
The global markets were down about 2.7% in Q1 2026, a relatively modest decline given the scale of bad news, including significant geopolitical events like military conflicts in Iran and political surprises such as Trump acquiring Greenland. The markets absorbed a lot of negative data, yet diversification protected against steeper losses.
Volatility is expected in financial markets. Every year presents reasons to doubt or withdraw, but those who stay invested and look beyond the day-to-day noise are generally rewarded. History shows markets tend to recover and even thrive in the aftermath of geopolitical turmoil, with average positive returns 6 to 12 months after such events.
Despite periodic shocks, a disciplined investor reaps significant rewards. From 1970 onward, investing a dollar in global equities would now be worth $142, provided the investor simply did nothing and held on. This long-term mindset is crucial. Panicking in response to short-term news and market swings risks locking in losses and missing the eventual recovery and growth. Instead, reframing volatility as the price paid for higher returns can foster the discipline needed for long-term success.
After years of muted performance, bonds are providing meaningful yields again. Short and intermediate-term bonds were roughly flat in Q1, but today’s yields—often in the 3 to 5% range—set the stage for more attractive future returns. Focus on high-quality, short maturity bonds to reduce unnecessary risk and secure a reliable income.
Safe-haven assets like gold and silver attracted attention amid market turbulence, with gold jumping nearly 8% this quarter. However, over the long run, gold pales compared to the S&P 500: from 1970, $1 in the S&P 500 grew to $341, while gold reached only $132. Gold and silver can take years, even decades, to recover from drawdowns, making them risky for wealth building. Bitcoin's rollercoaster ride further illustrates this point. It’s experienced five separate drops of over 70%—far more volatility than traditional stock indices.
Discipline and diversification—investing across regions, sectors, and asset classes—remain the best defense against unpredictable events. US small cap value stocks, for example, have outperformed the S&P 500 since 2001. No one can reliably pick the “best” asset every year; a diversified allocation ensures you participate in long-term growth while minimizing drastic falls.
Valuations also matter, if not as timing tools then as guides for future returns. Currently, international stocks offer more attractive valuations than US stocks, hinting at potential for higher future gains.
Financial independence isn't just about hitting a certain net worth or reaching a magic retirement number, it's a personal journey shaped by your habits, values, and the emotional baggage that money can carry. In this episode of the Financial Symmetry Show, we dig into Morgan Housel's "The Art of Spending Money," exploring the spectrum from financial dependence to independence.
The path to financial independence isn’t a straight line, nor is it solely defined by the size of your bank account. You could have a net worth of $10 million, $20 million, or more and still be fully financially dependent—perhaps on an employer, a board, or circumstances outside your control.
Morgan Housel’s framework outlines 15 levels of financial dependence and independence. Where you fall on this spectrum is shaped as much by your comfort zone, habits, and attitudes toward spending and saving as by your net worth. Someone making several million a year could feel just as constrained as someone living paycheck to paycheck if their spending or obligations keep them tethered to external demands.
The art of managing your finances goes far beyond crunching numbers. It requires conscious reflection on your spending habits and your emotional relationship with money. This is where the idea of “money scripts” comes in—subconscious beliefs and habits inherited from our upbringing or past experiences. These scripts can keep us locked in certain behaviors, such as an aversion to debt or an urge to accumulate at all costs, even if we've “outgrown” the underlying need that sparked them. Moving up the independence scale may require challenging these scripts and redefining what financial comfort means to you.
A powerful theme from Housel’s book is the idea that money you haven't spent still offers great value—freedom, flexibility, and the ability to shape your life according to your own terms. Unspent money isn’t just idle; it buys intangible benefits like independence and control over your time.
This view reframes common advice about spending more freely earlier in life or racing to pay off debts—even if it means missing out on long-term growth or flexibility. For many, retaining a mortgage at a low rate or holding investments for future choices can be as empowering as reaching zero debt. The key is striking the right balance between emotional comfort and financial efficiency.
The episode spends significant time unpacking levels 8–15 of Housel’s spectrum—the stages where true autonomy takes shape. At these levels, you’re free from the need for outside validation, able to avoid most debt, and no longer dependent on a paycheck to maintain your lifestyle. For some, a “slim” lifestyle and modest spending can deliver just as much security as a vast portfolio, while for others, continued work remains meaningful and fulfilling.
At the highest levels, you possess "walk away money"—the resources to exit any situation, disagree respectfully, and pursue your own path without concern for financial repercussions. Define what you want your money to accomplish—not just for yourself, but for your family and community.
Where do you fall on the dependence-to-independence spectrum? What would greater independence mean for your life, your family, and your legacy? Start by identifying your current level, reflect on the beliefs holding you back, and explore new, fulfilled ways of using your resources.
[00:00] Shifting perspectives on retirement spending
[04:16] Understanding financial independence levels
[08:24] Examining higher levels of independence
[15:45] Facing financial fears in retirement
[19:34] Rethinking spending habits and goals
[20:26] Finding your current level and setting personal targets
Connect on Twitter @csmithraleigh @TeamFSINC
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As women are living longer than men—on average, 5 to 7 years more—the later decades of life promise opportunities to cherish freedom and fulfillment. Yet, as this International Women’s Day episode of the Financial Symmetry Show reveals, these extra years often come with both unique financial challenges and disproportionate caregiving responsibilities. Allison Berger bring together Haley Modlin, Niamh Douglas, and Darian Billingsley to spotlight how the “Give to Gain” theme resonates deeply with women navigating retirement and caring for loved ones.
We discuss:
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Receiving an unexpected inheritance while already in retirement can spark a mixture of emotions—gratitude, uncertainty, and even a bit of overwhelm.
In this episode, we dig into the practical and emotional aspects of managing an inheritance, answer common questions, and guide listeners toward making wise and meaningful decisions.
With over $105 trillion expected to change hands in the coming decades, the need to understand how best to handle inherited wealth has never been more important.
We discuss:
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Many people begin their financial lives confidently handling everything on their own. They set up retirement accounts, save diligently, and make decisions that feel reasonable at the time. But as life evolves, that confidence can quietly erode. In this episode, we speak directly to the do-it-yourself investor who has started to wonder whether going it alone still makes sense.
We unpack the most common reasons people resist working with an advisor, from concerns about fees and loss of control to confusion about what financial advisors actually do. We also share what typically triggers the shift from DIY to professional help, often a late-night moment of uncertainty sparked by taxes, retirement timing, or growing complexity.
This conversation offers a candid look behind the curtain of comprehensive financial planning. It explores what advisory fees really buy, how proactive planning reduces costly mistakes, and why time, interest, and expertise eventually fall out of balance for many successful professionals. The goal is not to push a decision, but to help listeners decide when and if partnering with an advisor could add meaningful value to their financial lives.
[00:00] Who this episode is for and why DIY investors start asking bigger questions
[02:00] Why many people prefer to manage their finances alone
[05:00] The common misconceptions about financial advisors and fees
[07:00] The questions that prompt people to seek professional advice
[12:00] What a financial advisor fee actually pays for
[18:00] How complexity, risk, and missed opportunities compound over time
For many people, managing finances alone feels simpler. Setting contributions on autopilot and avoiding difficult decisions can be comforting, especially early on when life and finances are relatively straightforward. Cost concerns also play a major role, as do-it-yourself investors often question whether advisory fees are worth paying.
Control is another powerful factor. Turning over financial decisions to someone else can feel uncomfortable, even when things are no longer as simple as they once were. Add in confusion about the financial services industry and fear of being judged for past decisions, and it becomes clear why many people delay seeking help, even when doubts begin to surface.
Most people don’t wake up one day and decide to hire a financial advisor without a reason. It usually starts with a specific question they no longer feel confident answering. Am I truly able to retire when I think I can? Am I saving enough for college without sacrificing my own future? Why do my taxes feel higher every year?
Other common triggers include managing company stock compensation, holding too much cash without a clear plan, or simply feeling overwhelmed by the growing complexity of life. As careers advance, families grow, and assets accumulate, the margin for error narrows and the cost of mistakes increases.
A key theme in this episode is that financial planning goes far beyond investment management. Comprehensive planning helps turn vague goals into concrete decisions, supported by realistic projections and scenario analysis. It brings clarity to tax planning throughout the year, not just at filing time, and helps diversify not only investments but tax exposure as well.
The hosts also discuss personalized investment strategies, behavioral coaching during market volatility, and identifying opportunities that can be missed without an objective third party. Risk management, from insurance coverage to concentrated stock positions, and estate planning round out the picture, ensuring that plans hold up not just today, but across decades and generations.
Ultimately, the decision to work with an advisor is deeply personal. The team emphasizes that it’s not about finding the lowest fee, but about understanding the value provided. For many, advisory fees represent an investment in better decisions, reduced risk, and greater confidence over time.
As financial lives grow more complex, the question often becomes less about whether someone can manage everything themselves and more about whether they still want to. This episode offers a framework for evaluating that decision thoughtfully, with clarity and intention
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The holiday season inspires generosity, but smart gifting can go far beyond festive moments and gifts under the tree. On the show this week, we’re digging into the world of gifting strategies, just in time for the end of 2025. Whether you’re navigating last-minute holiday shopping, planning gifts for loved ones, or looking to maximize your charitable donations, this episode is packed with practical advice and fresh ideas.
We break down everything from tax implications of gifting cash, stocks, and even real estate, to making the most of donor-advised funds and qualified charitable distributions to help you balance generosity with smart financial planning, so you can give with both a warm heart and a wise mind.
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We talk with hundreds of individuals and families every year, and many of the questions they ask come back to one core concern. Can my retirement plan really survive the messy, unpredictable situations that happen in real life. Instead of only looking at straight line projections or average returns, Chad and Allison walk through how to “stress test” your plan with real world what if scenarios so you can build confidence before a crisis hits.
In this episode, you will hear three of the biggest what if questions clients have been asking over the past year.
Rather than focusing on doom and gloom, the goal is to rehearse these situations on paper so that when life happens, you already have a plan for how to respond.
We also share a simple three-step framework you can use to run your own retirement stress test at home. You will learn how to identify the what-ifs that matter most to you, estimate their impact on your spending and timeline, and choose proactive moves that make your plan more resilient. Along the way, they discuss sequence of returns risk, health insurance bridges before Medicare, using taxable brokerage accounts strategically, and how to think about funding future healthcare needs without overpaying for insurance you may not need.
Outline of This Episode
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When people think of what could haunt their retirement, they often imagine running out of money, facing unexpected expenses, or living too long. But as we discuss in this episode, there’s a more insidious villain: sequence of return risk.
Sequence of return risk refers to the threat of poor investment returns occurring early in your retirement years, just when you start withdrawing funds. Even if the average returns over your retirement are sufficient, early losses can irreparably damage your nest egg and dramatically increase the odds of running out of money.
To bring these concepts to life (with a Halloween twist), we walk through a scenario featuring Jamie Lee Curtis’s iconic character, Laurie Strode, imagining her retirement through 25 years of market ups and downs. The outcome all depends on her initial withdrawal strategy and, crucially, how her portfolio is allocated.
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Tax planning often slips to the bottom of our financial to-do lists—until a surprise bill or missed opportunity crops up. But behind the scenes, the right process for an ongoing tax strategy can put you leagues ahead, reducing uncertainty and helping you capitalize on changes. On the show this week, we’ll walk through the seven stages of tax planning, highlighting key insights and practical actions you can take.
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Planning for retirement isn't just about hitting your savings targets and hoping for the best. It's about getting creative, asking new questions, and challenging your own assumptions.
We follow the retirement planning journey of a fictional couple, Dwight and Angela, who are three to five years from retirement, using the SIFT framework shared by Rohit Bhargava and Ben duPont in their book “Non-Obvious Thinking”, to shed light on hidden financial opportunities.
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Planning for your child’s college education can feel overwhelming, especially when faced with skyrocketing tuition costs and countless savings options. This week on the show, we’re discussing the question of exactly how much you should save in a 529 college savings plan.
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Recently, an executive order has set the stage for 401 (k) providers to potentially start offering investments like private equity, private real estate, digital assets (think bitcoin), commodities, and more—options typically reserved for pension funds and institutional investors. But what does this really mean for everyday savers?
We break down the differences between traditional 401k offerings and these new alternatives, discuss the risks and potential rewards, and share questions you should ask yourself before making any changes to your investment lineup.
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Are you taking advantage of all your Roth opportunities? We break down the differences between the Roth IRA, Roth 401(k), or the Mego Backdoor Roth 401(k). by comparing your choices with another favorite summer treat - ice cream.
We break down the basics, benefits, and ideal life stages for each account type—whether you’re just scooping your first vanilla cone with a Roth IRA, adding some flavor with a Roth 401(k), or going all-out Neapolitan with the Mega Backdoor Roth.
We also share smart tips on tax brackets, income planning, and how to maximize your options for a sweeter financial future. If you’re looking to optimize your retirement savings and want more flexibility, this episode is the perfect treat.
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The second quarter of 2025 was anything but dull in the financial world. But despite the turbulence, both US and international stocks finished the first half of the year up over 10%. Over the last 12 months, markets have performed robustly, returning 14-19%.
Bonds have also held their own, with 6% returns over the last year. Investors have endured a roller coaster ride, especially after the dramatic market drop following tariff announcements and the subsequent quick recovery.
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Tax season may feel far off, but with sweeping legislative changes just passed, proactive financial planning starts now. In this episode, we’re sharing our accessible, in-depth breakdown of the new Big Beautiful Bill, highlighting ten key tax provisions that every taxpayer should understand.
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When is enough, enough? Many investors have recently found solace in growing their cash reserves, whether in their checking accounts, savings accounts, or certificates of deposit (CDs). With attractive yields and recent market turbulence still fresh in mind, it’s easy to assume that loading up on cash is a safe strategy.
But there’s a hidden cost to keeping more money than you need. Not only does excessive cash limit your growth potential, but it can erode your long-term wealth, all because of a mix of emotional biases, historical events, and overlooked risks.
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At Financial Symmetry, our internship program has become a core pillar of our growth, innovation, and client experience.
Over time, our program grew from simply filling resource gaps to a foundational development engine, helping to shape the services Financial Symmetry offers and the team culture itself.
What has emerged from these iterations is the recognition that our best chance of success comes from integrating interns directly into the firm’s core wealth management processes. This hands-on approach creates a feedback loop where interns don’t just complete busywork; they contribute valuable perspectives and even shape workflows that staff rely upon to this day.
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Claiming Social Security as soon as you become eligible at age 62 is a common choice for Americans. While understandable, this decision can have significant, and often underappreciated, long-term consequences. For many, the urge to claim early may stem from financial necessity, lack of other income sources, or simply a desire to “get what you’ve paid for.” However, claiming early can reduce your benefit by as much as 30% compared to waiting until your full retirement age (typically around 67).
If you are in the fortunate position of having other income sources, such as a pension, 401(k), brokerage accounts, or IRAs, delaying Social Security becomes a viable strategy. This moves the decision away from immediate need and toward maximizing lifetime income, building multigenerational wealth, and supporting charitable or legacy goals.
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Chad and Mike break down the major moves in US and international markets from the past quarter, revealing why diversification works unexpectedly. They chat through the impact of recent tariff news, what those headlines might mean for the economy and your portfolio, and share evidence-based strategies for taking action (or not!) when markets get rocky.
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Market volatility is never comfortable, but with the right mindset and a thoughtful plan, you can face downturns not as a victim, but as an opportunist. On this episode of the Financial Symmetry Show, we’re sharing our advice on managing your finances amid turbulent markets and giving you a helpful checklist to guide your decision-making when headlines make your stomach flip.
[0:00] We discuss the importance of planning, reviewing its steps, and controlling expectations during unforeseen events.
[4:29] Evaluate income, expenses, job security, income sources, and potential risks in financial planning.
[7:14] Consider delaying major purchases or expenses if income is uncertain. Assess whether postponing could increase costs or cause issues.
[12:53] Prepare for significant financial events that may impact your portfolio, like downsizing a home or receiving a large sum.
[14:17] Evaluate your portfolio by considering your stock choices.
[17:32] Avoid panic selling stocks, which often leads to long-term financial regret.
[22:50] Take informed action for peace of mind; mindset and planning are key.
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Tax planning might not top everyone's list of leisure activities, but in the middle of tax season there’s a hidden opportunity. What if, instead of seeing it as a mere logistic hurdle, we embraced it as a moment to refine our financial strategy?
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What if your retirement lasts much longer than you anticipated? Increasing life expectancies have reshaped our understanding of retirement and financial planning in recent years, and we’ll likely become more concerned about effectively managing financial resources throughout a potentially very long life in the future.
In this episode, we’re sharing some insights gleaned from a recent industry conference focused on the impacts of longevity on retirement planning. There's a growing need to rethink how long you'll need your savings to last and how you approach your investment strategies to accommodate potentially decades more of life.
We’re discussing the intriguing idea of a 150-year lifespan and the emergence of cutting-edge longevity research and how this thought-provoking information challenges our traditional views on aging and needs us to rethink traditional financial planning strategies.
Whether it's reimagining retirement careers or evaluating the future of medical advancements, we have to align our wealth span with a potentially extended health span. Join us as we unravel the financial implications of living longer and healthier lives.
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We're spotlighting women's wealth in honor of International Women's Day and Women's History Month. Join us as we dig into some of the stats surrounding women's financial empowerment. From the rising number of women controlling wealth as they outlive their spouses to tackling stereotypes that hinder women's earning potential, this episode addresses the systemic barriers that impact women's financial journeys.
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Four categories are recognized under current regulations to qualify as an Eligible Designated Beneficiary (EDB). These include the surviving spouse, minor children of the decedent, a disabled or chronically ill individual as assessed at the time of the decedent's passing, and other individuals who are no more than ten years younger than the deceased account owner. If you fall into one of these categories, you'll be afforded more time and flexibility than Non-Eligible Designated Beneficiaries. This is due to recent regulatory changes, underscored by The Secure Act, altering the landscape of inherited IRAs.
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