109. Financial Independence in Midlife: A Life Planning Conversation with Phil Weiss

Money is one of the topics women are least prepared for and most affected by, especially during the transitions that tend to cluster in midlife: divorce, widowhood, career changes, and retirement planning that suddenly feels urgent. On this episode of Women Mastering Midlife, Victoria talks with Phil Weiss, CFA, CPA, and founder of Apprise Wealth Management, about building financial independence before a crisis forces the issue. Phil's path into this work started long before his CFA or CPA credentials. When his mother was diagnosed with stage four breast cancer, he discovered that his father had never handled the family's finances, and he stepped in to negotiate with creditors, catch up on bills, and make sure his mother's care was covered. That experience shaped the practice he has built since: helping women understand and manage their money well before a health or life crisis makes it unavoidable. This conversation covers the practical and the emotional sides of money: how retirement income actually works, what gets overlooked when parents age or a marriage ends, and how a values-based planning process called life planning can change the way you think about both your money and your time. In This Episode Why money is treated like a taboo subject, and how that silence shapes women's financial confidence The shift from accumulating money to spending it in retirement, and why that shift is harder than it sounds Asset allocation versus tax location, and how account type affects what you actually keep The retirement expenses most people don't plan for: healthcare, housing modifications, and long-term care Financial and emotional considerations for women navigating divorce or widowhood The sandwich generation squeeze: caring for aging parents while raising your own kids A simple framework for budgeting that doesn't require obsessive tracking Life planning: a process that starts with your values, not your account balances How childhood experiences with money shape financial decisions decades laterl Key Takeaways Spending money you saved can feel harder than saving it. Phil describes this as a "retirement paycheck." After decades of saving, many people freeze when it's time to draw that money down, even when the numbers clearly support spending more. Account type matters as much as account balance. A traditional 401(k), a Roth IRA, and a taxable brokerage account are all taxed differently. Understanding what Phil calls "tax location," not just asset allocation, can meaningfully change what you keep in retirement. Divorce has a tax dimension that's easy to miss. Splitting retirement accounts evenly by dollar amount can leave one spouse with a much larger future tax bill if the accounts are different types (Roth versus traditional). This is worth raising with an advisor before assets are divided. A written plan protects against the moments no one wants to think about. Access to accounts, passwords, wills, and care preferences for aging parents are logistical details that become urgent and stressful without preparation. Life planning starts with values, not numbers. Through a process built on three reflective questions, Phil helps clients identify what actually matters to them before building the financial plan around it. The goal, in his words, is to help people avoid regret, not sit in it. About Phil Weiss Phil Weiss is a Chartered Financial Analyst (CFA), Certified Public Accountant (CPA), and Registered Life Planner, and the founder of Apprise Wealth Management. He began his career in 1987 as a tax professional at Deloitte and Touche, later worked as an equity research analyst covering oil and gas stocks, and built a practice centered on lon