Divorce doesn’t just split a household, it often splits the story you thought your money was telling. After a settlement, many people feel frozen, especially if a former spouse handled the finances. On Modern Family Matters, CPA and CFA Jesse Hurst explains that post-divorce retirement planning starts with calming the noise and taking small, confident steps. Instead of drowning you in jargon, the goal is clarity: where you are today, where you want to go, and whether your resources can realistically get you there. That means building a practical financial plan around cash flow, taxes, and real life priorities, not around fear or shame.
A core theme is financial education that actually sticks. Jesse uses pop culture, classic rock, movies, and familiar stories to translate concepts like asset allocation, risk tolerance, and diversification into language people remember. When you’re rebuilding after divorce, you may be managing a 401(k), IRAs, brokerage accounts, CDs, and a house for the first time on your own. The “puzzle” feels overwhelming because it’s rarely a coordinated portfolio. A relatable frame lowers the temperature, makes the process less intimidating, and helps you participate as a true partner in decisions rather than feeling talked over.
The episode also reframes what money is for. Retirement after divorce can trigger anxiety that you can never travel, help your kids, or enjoy life again. Jesse argues that money is a means, not an end, and that “compound return” is not the goal. The goal is outcomes like being debt-free, creating experiences with family, and funding the life that matters to you. Practically, that means evaluating levers such as how long you work, expected income, when to claim Social Security, and how to set a sustainable spending level. Once you reach “enough,” you stop over-saving and start planning intentionally for spending and giving.
Finally, the conversation gets specific about taxes and transitions that trip people up. After divorce, you typically keep the original cost basis in investments you receive, which can create capital gains tax surprises later. After a spouse’s death, assets may receive a step-up in basis, changing the tax planning picture. Widow(er)s can also face a painful shift when filing status changes to single, shrinking tax brackets and deductions. Jesse’s practical starting point is an inventory and a vision: look at the “box top” first, then sort the pieces. That includes reviewing real estate holdings, rental property cash flow, and concentration risk, and deciding when it makes sense to sell non-performing properties to improve liquidity and diversify. With the right legal, tax, and financial guidance, the new normal becomes manageable.
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Lewis Irwin Landerholm
Founding Partner
Lewis Landerholm realized the importance of family and justice from a very young age. With grandparents in the legal field, a mother in education and a father who was a domestic violence counselor, Lewis was raised by a family dedicated to helping people. His role models taught Lewis that the world is a complicated place where education and a helping hand could make all the difference.
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