What happens when your net worth is concentrated in a single asset—like a family business—and you want to diversify without triggering a big tax bill? In this episode, we talk through real scenarios from clients navigating legacy planning, lifestyle transitions, and wealth transfer decisions. We cover strategies for reducing concentration risk using gradual sales, ESOPs, and hedging tools like options, along with ways to balance liquidity and long-term planning.
We also explore how to prepare emotionally and practically for retirement when the structure of work disappears but the desire for purpose remains. From part-time transitions to extended travel and volunteering, we discuss how to “test drive” your next chapter. Then we turn to a common concern: how to gift generously to your kids each year without creating entitlement. We talk strategies like matching gifts, incentive trust planning, and building strong financial literacy to support lifelong responsibility and independence.
And this week’s special segment is a bonus question from a long-term client: what happens if you accidentally over-contribute to your retirement accounts after receiving a large bonus?
Have a burning finance question we should discuss in the next episode? Email us at podcast@scholarfinancialadvising.com
Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice, the opinions. expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principle, past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance.