BRIAN FLYNN

Financial Advisor, Managing Partner & Co-Founder

High-touch, meticulous wealth management for on-the-move executives.

EAST COAST

October 27, 2025
Brian Flynn

The Forced Sale: Why Your Illiquid Estate Could Cost Your Family Everything

There’s a common misconception that being wealthy on paper means having cash on hand. This is why so many high-net-worth estates are “asset-rich, cash-poor,” with significant wealth tied up in illiquid assets.

Imagine you’ve passed away, and your estate holds millions in a family business, a cherished vacation home, or a concentrated stock position. Your executor, now responsible for settling your affairs, discovers a sizable estate tax bill due in a mere nine months. Alongside that are administrative costs, legal fees, and outstanding debts.

The problem? There isn’t enough cash in the estate to cover these immediate obligations.

This is where the nightmare begins. To pay the necessary bills, your executor may be compelled to sell off valuable assets, often under immense pressure and potentially below their true market value. More than just a financial hit, this represents a potential erosion of the legacy you intended, transforming hard-earned assets into a forced liquidation just to satisfy a tax obligation.

The Cornerstones of the Liquidity Gap

Understanding where the problem originates is the first step toward preventing it.

  • The Immovable Tax Burden: State and federal estate taxes can represent a substantial percentage of your total estate’s value. These are fixed liabilities with strict payment deadlines.
  • Mounting Estate Expenses: Beyond taxes, an estate incurs a range of costs, including legal fees for probate, accounting services, appraisal costs, and any remaining debts you may have. These require cash, not just paper wealth.
  • The Challenge of Illiquid Assets: Many high-net-worth individuals hold significant wealth in assets that are not easily or quickly converted into cash without substantial loss. These often include private business interests, commercial or unique real estate, art collections, or concentrated stock positions.

Closing Your Estate’s Liquidity Gap

With foresight and strategic planning, you can shield your family from the harsh realities of a forced sale. Consider: 

  • Life Insurance: One of the most effective tools for solving an estate liquidity problem is a properly structured life insurance policy. Upon your passing, the death benefit can provide immediate, tax-free cash. To keep these funds outside of your taxable estate, the policy is often held within an Irrevocable Life Insurance Trust (ILIT).
  • Liquidity Reserve: For those with larger or exceptionally complex estates, designating a specific portion of your portfolio as an “estate emergency fund” can be a smart strategic move. This means holding certain assets in easily accessible forms, such as cash, money market funds, and short-term, highly liquid investments. The dedicated reserve ensures that a ready source of funds exists, preventing the need to disturb growth-oriented assets or make distressed sales.
  • Debt and Tax Planning: Working closely with an estate planning attorney and a financial advisor allows for a precise estimation of your estate’s potential tax liability and outstanding debts. In specific scenarios involving illiquid estates, certain provisions within the tax code may offer deferral options. For instance, Internal Revenue Code Section 6166 allows for an extension of time to pay estate taxes attributable to interests in closely held businesses.

These complex deferral mechanisms don’t eliminate the tax, but they can create a vital time cushion allowing your executor to arrange for the sale of assets under more favorable conditions, rather than a rushed, pressured liquidation.

The Risk of Inaction & Ongoing Oversight

Effective estate planning goes beyond financial instruments and should include things like: 

  • Family Communication: Transparent family conversations create a shared understanding of financial situations, fostering proactive problem-solving and collaborative planning. When heirs understand the nuances of the estate plan, they are better equipped to support the executor and avoid disputes during an already stressful time.
  • Continuous Review: An estate plan crafted years ago might not align with your current financial reality, new tax laws, or family dynamics. Regular reviews with your financial advisor help identify outdated documents, prevent unintended tax consequences, and ensure proper ownership designations.

Don’t Leave Your Family to Manage a Forced Sale

Your legacy deserves to be protected, not compromised by a lack of liquidity. Ignoring the “cash-poor” reality of an “asset-rich” estate is a gamble with your family’s future and the very assets you worked so hard to accumulate.

Reach out to our team today to stress-test your current estate liquidity plan and ensure your legacy is truly secure.

This material is distributed for informational purposes only. Investment Advisory services offered through Journey Strategic Wealth, a registered investment adviser registered with the U.S. Securities and Exchange Commission (“SEC”). The views expressed are for informational purposes only and do not take into account any individual’s personal, financial, or tax considerations. Opinions expressed are subject to change without notice and are not intended as investment advice. Past performance is no guarantee of future results. Please see Journey Strategic Wealth’s Form ADV Part 2A and Form CRS for additional information.

Securities offered through Purshe Kaplan Sterling Investments, Member FINRA/SIPC, Headquartered at 80 State Street, Albany NY 12207. Purshe Kaplan Sterling Investments and Journey Strategic Wealth are not affiliated companies. Not FDIC Insured. Not Bank Guaranteed. May lose value including loss of principal. Not insured by any state or federal agency.

ABOUT THE AUTHOR

BRIAN FLYNN

Financial Advisor, Managing Partner & Co-Founder

Prior to founding Journey Strategic Wealth, Brian was a Managing Director at Magnus Financial Group. Brian has previously held positions at Dynasty Financial Partners, Merrill Lynch and DHF Capital.

RESOURCES

The Forced Sale: Why Your Illiquid Estate Could Cost Your Family Everything

The Forced Sale: Why Your Illiquid Estate Could Cost Your Family Everything

by | Oct 27, 2025 | Brian Flynn | 0 Comments

There’s a common misconception that being wealthy on paper means having cash on hand. This is why so many high-net-worth estates are “asset-rich, cash-poor,” with...

Timing Is Everything: How the Calendar Impacts the Success of Your Business Sale

by | Sep 9, 2025 | Brian Flynn | 0 Comments

In life and in business, we instinctively understand the power of timing. We time a difficult conversation, a major career move, or a pivotal investment. For a business...

Turnkey Philanthropy: Aligning Purpose With Strategy

by | Jul 31, 2025 | Brian Flynn | 0 Comments

Many families I work with want to make charitable contributions, but don’t have a clear structure for maximizing their impact, leaving their philanthropic efforts...

The High Earner’s Guide to Tax Efficiency: Navigating the Tax Trap of Success

by | Jun 19, 2025 | Brian Flynn | 0 Comments

Reaching your career and business goals is a significant achievement. Whether you’ve successfully scaled your company, closed a major deal, or received a promotion,...

Is Your Wealth Truly Protected? Key Questions About Diversification

by | May 23, 2025 | Brian Flynn | 0 Comments

For those who’ve built significant wealth, the landscape of investment shifts beyond growth to prioritize wealth preservation, expansion, and the impact of their...

4 Impactful Ways to Spring Clean Your Finances

by | Mar 30, 2025 | Brian Flynn | 0 Comments

Spring cleaning isn’t just for your home. Don’t forget about the part of your life that often gets the most cluttered—your finances.  A financial spring cleaning gives...

What is a Financial Windfall? A Guide to Managing Sudden Wealth

by | Feb 26, 2025 | Brian Flynn | 0 Comments

You’ve probably heard the story of Jack Whittaker: after winning $315 million in Powerball in 2002, his life unraveled through divorce, lawsuits, and tragic family...

Investing in Hindsight: 7 Lessons From 2024 to Drive Success in 2025

by | Feb 6, 2025 | Brian Flynn | 0 Comments

As any avid golfer knows, even the most well-planned shot can be thrown off course by an unexpected gust of wind or a hidden bunker. And just like on the golf course,...

5 Tips for Last Minute Year-End IRA Contributions: Making the Most of Your Retirement Savings

by | Jan 6, 2025 | Brian Flynn | 0 Comments

As we approach the end of the year, many of my clients are thinking about how to maximize their retirement contributions. If you’re in the same boat and...

Protecting Your Wealth: Insurance Strategies for UHNW Family Offices

by | Nov 19, 2024 | Brian Flynn | 0 Comments

When it comes to managing wealth, ultra-high-net-worth (UHNW) families face challenges and risks that demand a level of foresight and sophistication far beyond what...

Three Ways AI Is Transforming the Client Experience in Wealth Management

by | Oct 18, 2024 | Brian Flynn | 0 Comments

The rise of AI has impacted nearly every industry, application, and interaction we have, from Spotify’s smart playlists to Amazon’s product recommendations to custom...

5 Tips for Managing Wealth After Selling Your Business

by | Sep 17, 2024 | Brian Flynn | 0 Comments

Selling your business may be one of the biggest financial moves you’ll ever make. Often, the real challenge starts after the deal closes. With a significant...

Final IRS Regulations on Inherited IRAS: What Do They Mean for You?

by | Aug 12, 2024 | Brian Flynn | 0 Comments

Last month, the IRS released its new Final Regulations for Required Minimum Distributions (RMDs) for inherited IRAs, and it’s crucial to understand what they might mean...

Legacy Planning for Ultra-High-Net-Worth Families: Secure Your Wealth for Future Generations

by | Jul 22, 2024 | Brian Flynn | 0 Comments

Imagine the legacy you’ve created, the wealth built over decades, carefully nurtured businesses, and valuable assets, all seamlessly transitioning to the next...

Building a Philanthropic Legacy: Charitable Giving Strategies for New Jersey’s High Earners

by | Jun 5, 2024 | Brian Flynn | 0 Comments

There may come a time when you and your family achieve a certain sense of financial peace of mind. Your bills are paid, your emergency fund is full, and now you’re...

Finding the Right Financial Advisor in New Jersey: What to Look for as a High Net Worth Investor

by | May 13, 2024 | Blog, Brian Flynn | 0 Comments

Being a high-net-worth individual (HNWI) brings a sense of financial security and opens doors to unique opportunities. However, managing significant wealth also comes...

Estate Planning for High-Net-Worth Families in New Jersey: Key Considerations and Strategies

by | Apr 19, 2024 | Blog, Brian Flynn | 0 Comments

Estate planning is the ultimate strategic move for high-net-worth individuals (HNWIs). Think of it as the blueprint for safeguarding your wealth, ensuring it flows...

Presidential Election Forecast: How Will Markets and Your Finances Be Impacted?

by | Mar 25, 2024 | Brian Flynn | 0 Comments

Every four years, Americans across the country head to the polls and decide who will take on the position of President for the next four years. Between yard signs,...

How Diversification Reduces Risk in Your Portfolio

by | Feb 20, 2024 | Brian Flynn | 0 Comments

One of the most fundamental concepts of investing is diversification. It’s why people say, “Don’t put all your eggs in one basket” and often incorporate a wide array of...

Building Your Wealth with Private Credit: What Every Investor Should Know

by | Jan 19, 2024 | Brian Flynn | 0 Comments

The traditional 60/40 portfolio of stocks and bonds may feel like a well-worn path, but savvy investors are looking for diverse opportunities. In a world where...

Tax-Efficient Wealth Transfer: The Family Trust & FLP Playbook

by | Jan 4, 2024 | Brian Flynn | 0 Comments

Affluent families, especially those operating business ventures together, face unique financial challenges and complexities — particularly when it comes time to...

Estate Planning for Business Owners: Tax-Efficient Ways to Transfer Your Company to the Next Generation

by | Nov 27, 2023 | Brian Flynn | 0 Comments

It’s never too early for business owners to start thinking about their business’s future sale or transfer. In fact, the longer the lead time, the more opportunity...

The Hidden Tax Traps of Retirement Account Withdrawals and How to Avoid Them

by | Oct 6, 2023 | Brian Flynn | 0 Comments

Retirement marks a major step in one’s life. During rough days at the office or in the midst of difficult managerial decisions, retirement served as a motivational goal...