If you're planning to retire in the next five, ten, or fifteen years, this is the episode to take notes on. Host Richard Erker kicks off a new financial planning series with a simple question: Are you ready? Rich is joined by Patrick O'Reilly, a Certified Financial Planner with Millennia Investments in St. Louis. Patrick followed his father into the business, earned his CFP in 2012, and has spent two decades helping people answer the million-dollar question — "Can I retire, and when?" His answer: there is no magic number, but there is a process. Together they cover why starting early matters (including the new "Trump Accounts" for kids), why time in the market beats timing the market, how to think about risk in your 50s using a three-bucket strategy, and why a good planner plans for you to live to 100. The episode closes with a lightning round — NYSE, S&P 500, ETFs, dividends, bull vs. bear markets and more, all explained like you're a fifth grader. This is the first in a series of financial planning conversations that will go deeper into strategies and taxes in the episodes ahead. Patrick O’Reilly can be reached at poreilly@milleniallc.com. This episode of Fit, Focused & 50 is brought to you by Dr. Kim Simonds and her team at Ballwin Dental Care. You can reach them at 636-227-2525. In this episode - 00:00 — Cold open: retiring in 5, 10, 15 years? Are you ready? - 01:18 — Sponsor: Ballwin Dental Care, plus a listener comment from "Talking Teeth with Dr. Kimberly Simonds" - 01:57 — Why turning 50 changes the money conversation — and Rich's recommended read, The Psychology of Money by Morgan Housel - 03:00 — Meet Patrick O'Reilly, CFP: a second-generation planner's path from the trade desk to independent advisor - 05:25 — Starting early and "Trump accounts": $1,000 seed money for newborns, custodial accounts vs. 529s - 08:07 — Why have a financial planner? A map vs. a guide — and managing emotions when markets swing - 09:45 — Never too late: time in the market vs. timing the market (the yo-yo on the stairs) - 12:11 — "Can I retire?" Why there's no magic number — cash-flow analysis and the lifestyle trade-offs - 14:40 — Do you actually understand your 401(k)? Defaults, target-date funds, and the trap of chasing last year's best fund - 18:10 — Planning to live to 100: a planner's job is making sure you don't outlive your assets - 19:08 — Surprises in both directions — including clients told to spend more - 21:20 — Rich's five-point sticky note: know your risk, make a plan, implement it, stay informed, adjust as needed - 22:20 — Risk numbers and the three-bucket approach: years 1–6 safe, 7–12 balanced, 13+ invested for growth - 26:15 — Staying informed: check-ins with your advisor, and why changing a plan can be one phone call - 29:40 — Lightning round: market terms in plain English - 36:40 — What's ahead in the series — deeper strategies and taxes