The Clear Cut

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. 

This episode discusses financial planning, investing, consumer trends, 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 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. 

This episode discusses Social Security claiming strategies, retirement income 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 continues her exploration of attention, productivity, and cognitive performance, building on insights from an executive leadership program at UC Berkeley Haas and a lecture from neuroscientist Dr. Sahar Yousef. Claire examines why procrastination, multitasking, and constant interruptions may be undermining focus and draining valuable mental energy. She introduces practical concepts such as Most Important Tasks (MITs), focus sprints, energy management, and batching communication to help listeners become more intentional with their time and attention. Through actionable strategies and thought-provoking reflections, Claire shares how protecting cognitive capacity can lead to greater productivity, presence, and control over how each day is spent. 

This episode discusses productivity, attention, and technology habits inspired by executive education coursework and publicly discussed behavioral research. The content reflects general educational concepts and personal experiences and is not intended as medical, psychological, or professional advice. 

In this episode of The Clear Cut, Claire Hollander explores the hidden ways modern technology may be draining focus, energy, and cognitive capacity throughout the day. Inspired by an executive leadership program at UC Berkeley Haas and a lecture from neuroscientist Dr. Sahar Yousef, Claire breaks down concepts like “brain leaks,” Zoom fatigue, smartphone addiction, and constant overstimulation—and how they may be affecting productivity, emotional regulation, and overall well-being. Through practical examples and actionable strategies, she shares simple ways to create healthier boundaries with technology, reclaim attention, and become more intentional with how mental energy is spent. 

This episode discusses productivity, attention, and technology habits inspired by executive education coursework and publicly discussed behavioral research. The content reflects general educational concepts and personal experiences and is not intended as medical, psychological, or professional advice. 

In this episode of The Clear Cut, Claire Hollander unpacks Chapter 4 of her book A Clear Path Forward, tackling the rising trend of Gray Divorce and its financial impact. From dividing assets with after-tax value in mind to navigating Social Security, pensions, and the family home, Claire shares strategies for protecting your future. Through reflective Q&A, she offers guidance on building the right advisory team, avoiding common pitfalls, and taking steps to move forward with clarity and confidence. 

In this episode of The Clear Cut, Claire Hollander dives into Chapter 3 of her book A Clear Path Forward, exploring the powerful link between physical health and financial health. From the emotional challenges of starting hard family conversations to the practical need for organizing vital documents, Claire unpacks why waiting until a crisis strikes can create unnecessary chaos. Through real client stories and reflective Q&A, she shares strategies for preparing loved ones for the realities of aging, long-term care, and estate planning. Tune in to learn how proactive planning can ease burdens, protect relationships, and truly become the ultimate gift to your family. 

What does it take to transition from a career in civil litigation to building a thriving luxury event planning business? In this episode of The Clear Cut, Claire Hollander sits down with Tiffany Klein, owner of Rosecrest Special Events, to explore her remarkable journey. Tiffany shares how her background as a litigator shaped her approach to timelines, contracts, and problem-solving—and how those skills now fuel her creativity in crafting extraordinary events. From intimate milestone celebrations to show-stopping productions featuring world-class talent like Chris Stapleton, Tiffany reveals what goes into designing experiences that guests will never forget. Tune in for insights on entrepreneurship, creativity, and the art of gathering with intention.