What if the career you built isn’t the only chapter you’re meant to have? In this episode of The Clear Cut, Claire Hollander shares Chapter 9 of her book, A Clear Path Forward, and the story of her mother, Sheila, who left a career in law to pursue a very different dream: opening a vegetarian café in Oakland.

Claire reflects on what her mother’s journey taught her about entrepreneurship, resilience, leadership, and giving yourself permission to change direction later in life. She also explores the financial side of pursuing a second career and why turning a dream into something real requires more than courage. It requires a plan.

In this episode of The Clear Cut, Claire Hollander unpacks Chapter 8 of her book, A Clear Path Forward, and explores why tax planning can become even more important in retirement. Claire explains the difference between tax preparation and proactive tax planning, including how IRA and 401(k) withdrawals, Social Security taxation, Roth conversions, and inherited retirement accounts can affect your financial picture. Through practical examples, she discusses why how you access the wealth you’ve built can matter just as much as how much you’ve accumulated.

This episode discusses retirement planning, tax planning, retirement accounts, Social Security, estate planning, and general financial concepts for educational purposes only. It is not intended as financial, tax, legal, or investment advice. Individual circumstances vary, and listeners should consult with qualified professionals regarding their specific situation.

In this episode of The Clear Cut, Claire Hollander unpacks Chapter 7 of her book, A Clear Path Forward, and explores why adaptability may be one of the most important traits for long-term financial success. Using the transition to electric vehicles as a broader example of change, Claire discusses how evolving technology, shifting consumer behavior, and emerging economic trends can influence financial decisions. She also shares personal stories, practical planning insights, and why staying curious, informed, and willing to adapt can help you make more confident financial decisions in a rapidly changing world. 

In this episode of The Clear Cut, Claire Hollander unpacks Chapter 6 of her book, A Clear Path Forward, and explores one of the most overlooked financial risks people face: the potential cost of long-term care. Through real-life planning scenarios, Claire explains how an unexpected care event can affect retirement income, investment portfolios, and the legacy you’ve worked so hard to build. She also discusses how long-term care planning and life insurance have evolved, why insurance can be more than just a death benefit, and how these strategies may provide greater flexibility, tax advantages, and financial protection as part of a comprehensive financial plan.

This episode discusses long-term care planning, life insurance, retirement planning, and general financial concepts for educational purposes only. It is not intended as financial, tax, legal, or investment advice. Individual circumstances vary, and listeners should consult with qualified professionals regarding their specific situation.

In this episode of The Clear Cut, Claire Hollander unpacks Chapter 5 of her book, A Clear Path Forward, and explores why Social Security may be one of the most misunderstood aspects of retirement planning. Moving beyond the common question of when to file, Claire explains how Social Security fits into a broader retirement income strategy and why the timing of your decision can have a lasting impact on your financial future. She discusses full retirement age, delayed claiming strategies, spousal and survivor benefits, and common mistakes that may reduce lifetime income.