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Ep 338: The Midlife Plot Twist: Rewriting Your Money, Relationships, and Life Story with Lindsay Goldwert
Episode 338
Tuesday, 25 August, 2026
Midlife comes with plenty of taboo topics that rarely get discussed together: money, sex, and the fantasy of burning it all down. Melissa Joy, CFP® sits down with Lindsay Goldwert, a writer whose work has appeared in The New York Times, New York Magazine, Slate, and MarketWatch, and the author of Bow Down: Lessons from Dominatrixes on How to Be a Boss in Life, Love, and Work, a Glamour Magazine Best Book of 2020. Lindsay is now the co-author of The Midlife Plot Twist: How to Reboot Your Life Without Burning It Down (Even If You Really, Really Want To), out this September. She and Melissa talk about why it is so hard for women to ask for what they want, and why that difficulty tends to build up quietly until it boils over.The conversation covers why financial planning benefits from a therapist's sense of empathy, how couples can use a financial planner as a neutral party for hard conversations, and why proactively involving a financial planner before a relationship ends, not after, tends to lead to better outcomes for everyone.Lindsay and Melissa also get into how small, incremental investments in friendships, hobbies, and curiosity pay off over a lifetime, why knowing what you do not want is just as valuable as knowing what you do want, and why midlife deserves to be treated as a plot twist worth celebrating rather than a crisis to survive.What You'll LearnWhy asking for what you want is especially hard for women, and how that difficulty compounds over time if left unaddressedWhy a good financial planner should function like a financial therapist, holding space for feelings as well as numbersHow bringing a financial planner into a relationship can give every partner's voice a seat at the table, and why that matters most in unequal power dynamicsWhy getting financial planning support before a relationship ends, rather than after, tends to lead to fairer and faster outcomesHow to have tough money conversations with aging parents about wills, executors, and financial oversight before a crisis forces the issueWhy small, incremental investments in friendships, hobbies, and curiosity are a legitimate use of money for long term health and longevityWhy knowing what you do not want anymore is just as valuable as knowing what you do wantWhy midlife deserves reframing as a plot twist to celebrate rather than a crisis to surviveGuest Bio:Lindsay Goldwert is an editorial director and writer whose work has appeared in The New York Times, New York Magazine, Slate, MarketWatch, and many others. She is the author of Bow Down: Lessons from Dominatrixes on How to Be a Boss in Life, Love, and Work (Simon & Schuster, 2020), a Glamour Magazine Best Book of 2020, and the co-author, with Gabrielle Moss, of The Midlife Plot Twist: How to Reboot Your Life Without Burning It Down (Even If You Really, Really Want To) (Running Press, September 2026).Connect with Lindsay:Website: lindsaygoldwert.comInstagram: instagram.com/lindsay_goldwertMelissa Joy, CFP®, is the founder and president of Pearl Planning, a fee-only financial planning and investment management firm based in Dexter, Michigan. Pearl Planning is a registered investment advisor with the Securities Exchange Commission. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. This podcast offers news, commentary, and generalized research, not personalized investment advice. Nothing on this podcast should be interpreted to state or imply that past performance is an indication of future performance. All investments involve risk and unless otherwise stated, are not guaranteed. Be sure to consult with a tax professional before implementing any investment strategy. Mellissa Joy hosts the Women's Money Wisdom podcast, where she talks with experts and everyday women about the real financial questions and challenges women face. Lindsay Goldwert is not a client of Pearl Planning and is not being compensated for sharing her opinion and experience with our firm.The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...
