Daniel and Rachel Harper, a couple in their late 40s, have spent years building a successful law practice in Chicago. Their income has always been strong, ranging from $500,000 to $1.5 million annually depending on firm performance. But everything changed when they won a landmark case, resulting in a $5 million windfall.
That case dramatically shifted their financial picture. Their invested assets grew to $8 million almost overnight. With the new wealth came new questions: Should one of them retire? Both? Is now the time to invest aggressively or cautiously? Could they finally buy the home they’ve always wanted?
They chose to continue working for another year but started reshaping their lives. They purchased a historic $1 million home in the town where they first met, putting another $1 million into renovations to make it a gathering place for family and friends. Their Chicago home will eventually be sold, and their total assets have since grown to $10 million.
Their two children are in college, and Daniel and Rachel are now focusing on what comes next. They envision long stays abroad—immersing themselves in local culture for weeks or months at a time. They aren’t especially focused on generational wealth planning. Their primary goal is to enjoy the wealth they’ve worked so hard for, while also giving back to causes they care about.
The Harpers want to use their money intentionally, especially as they think about a retirement that could last more than 40 years. We’re helping them build a retirement plan that includes a large travel budget and lump-sum real estate expenses while still maintaining long-term security. Understanding what they can safely spend today without jeopardizing their future lifestyle is key.
One of their top priorities is reducing taxes through charitable giving. We’re exploring donor-advised funds (DAFs), qualified appreciated stock donations, and timing strategies to maximize deductions in high-income years. These approaches support their philanthropic goals while creating room for tax savings.
With a large sum entering the market, dollar-cost averaging or strategic phased investing helps manage risk and ease their transition from cash-heavy to long-term growth portfolios. We’re also ensuring their investment strategy supports income needs in early retirement, with enough liquidity for large purchases and travel.
After years of actively managing income and expenses, Daniel and Rachel are looking for simplicity. We’re consolidating accounts, automating savings and distributions, and designing a plan that doesn’t require daily oversight. The goal is to reduce decision fatigue and free up mental space for what matters to them—time with each other, family, and their favorite places around the world.
This sudden wealth created opportunities but also pressure. We’re helping them adjust to this new reality without overextending or second-guessing every decision. That means setting boundaries on spending, building a flexible financial model, and aligning their plan with the values that led them here in the first place.
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