Podcast Summary: Jill on Money with Jill Schlesinger

Episode Title: Is It Time for Us to Get a CFP?
Date: October 14, 2025
Guest: Chris from New Hampshire
Theme: Navigating Retirement Decisions with a CFP

Episode Overview

This episode centers on a listener, Chris, who seeks reassurance and expert guidance about whether he and his wife are truly ready to retire, and how working with a Certified Financial Planner (CFP) can help. Chris describes his journey into, out of, and possibly back into retirement. Jill analyzes Chris’s financial situation, discusses risks and strategies for drawing down assets, and explores the value a CFP brings to complex retirement planning.

Key Discussion Points & Insights

1. Listener Background & Current Situation ([02:31]–[07:17])

• Chris and wife (both nearly 60) have been saving and investing, and Chris recently hired a CFP at Fidelity.
• Chris’s wife is retired; he partially retired but went back to work “out of boredom” and misses true retirement.
• Chris earns between $225,000 and $250,000 annually.
• Primary questions: Did they make the right decision to get a CFP, and can Chris retire confidently considering market uncertainty, healthcare costs, potential government shutdowns, and timing of Social Security?

2. Complete Financial Picture ([04:27]–[07:17])

• Assets:
  • 401(k): $410,000
  • Rollover IRA: $1.775M
  • Roth IRA: $104,000
  • Wife’s IRA (from 403(b)): $561,000
  • Brokerage account: $750,000 (including $370,000 in high-yield savings and $380,000 in stocks)
  • Bank savings: $40,000
  • HSA: $6,000
  • House (fully paid): Estimated $1.3M
  • No other properties after recently selling a vacation/rental home
  • Potential inheritance: Estimated at $1.5M–$2M in 8–10 years (using $1M as a conservative figure)
• Spending:
  • Baseline monthly: $13,000–$13,500
  • Anticipated bump to $15,000/month (mainly pre-Medicare due to healthcare costs, home renovations complete, $50,000 earmarked for an upcoming wedding)

3. Retirement Income Planning, Social Security, & Asset Drawdown ([08:55]–[13:52])

• Chris and wife have not yet drawn Social Security; plan is both to wait until age 70 for maximum benefits:
  • At 67: Joint $5,884/month
  • At 70: Joint $7,300/month
• Jill recommends exploring “substantially equal withdrawals” or an annuity to bridge the gap between retirement and Social Security at age 70.
• Importance of considering the “tax bomb” lurking in large pre-tax accounts.
• Jill encourages running scenarios: If Chris and his wife spent aggressively from their pre-tax accounts, factoring in inheritance and home equity, would they still have enough in the long run?
• Jill notes they're not banking on inheritance but acknowledges it as a meaningful possible cushion.

Memorable moment:
Chris: “It sounds much better when you say it.”
Jill: “You’re doing right, you’re doing great.” ([13:14]–[13:18])

4. The Emotional Side of Retirement Planning ([13:14]–[15:55])

• Chris admits to being “addicted” to monitoring investments daily, which drove the decision to bring in a CFP.
• Jill applauds Chris’s self-awareness and discipline, reiterating that getting help to navigate distributions and tax strategy is wise after years of successful DIY investing.

Quote:
Chris: “I don’t know how to take the money out. I don’t know, you know, all those decisions that would drive me crazy. So I need a professional to do that.” ([13:38]–[13:52])

5. Stress Testing the Plan: Risk and “What Could Go Wrong?” ([13:52]–[16:55])

• Jill’s main suggestion: Ask the CFP, “What could blow up this plan if I retire now? How do we guard against that?”
• Encourages the use of scenario planning, especially considering a potential market downturn or major unexpected expenses.

Quote:
Jill: “What am I guarding against? What am I not seeing? Tell me how this plan implodes.” ([15:52]–[15:54])

6. Healthcare Cost Concerns Before Medicare ([15:59]–[16:55])

• Chris worries about rising healthcare costs pre-Medicare.
• Jill reassures him their plan can absorb premiums up to $1,500/month for two people, and notes many retirees work part-time for benefits if desired.

Quote:
Jill: “If you got really bored again, you could go work and do something equally as boring and get coverage.” ([16:12]–[16:17])

7. Portfolio Allocation: 60/40 vs 70/30 ([17:41]–[19:21])

• Chris’s portfolio was 60/40 stocks to bonds; Fidelity is suggesting 70/30.
• Jill: “Are you willing to forego upside to protect more of your downside?” She encourages Chris to have the advisor show scenarios for each allocation, highlighting there’s no single right answer—comfort and risk tolerance matter most.

Quote:
Jill: “It’s not like right or wrong; it’s how you feel. That’s one of the few feeling questions that we have.” ([19:20]–[19:21])

8. Wrapping Up: Action Steps & Mindset

• Jill encourages Chris to let the CFP prepare scenarios, revisit after the meeting, and not underestimate the emotional relief from having expert guidance.
• She reminds Chris that, with a paid-off house, assets, upcoming inheritance, and no dependents, “You are okay.” ([16:55])
• Jill’s final advice: Ask tough questions of the planner, trust their analysis, and remember to evaluate how much risk and flexibility is tolerable.

Notable Quotes & Timestamps

• Chris: “Did we make the right move in our situation? … Am I good to stop working? My confidence is not there.” ([02:50]–[03:29])
• Jill: “You have a lot of money because of this, this rollover obviously, and the 401k … this is all your pre-tax money, right? Hasn’t been taxed yet.” ([08:32]–[08:58])
• Jill: “You’ve done a really good job managing this … Without the inheritance, I would tell you to keep working, by the way, I really would.” ([13:52]–[14:02])
• Jill: “My number one question for the advisor would be like, ‘Tell me what the scenario looks like if I retire at the end of this year.’ … And what blows this plan up?” ([15:55])
• Jill: “It’s not like right or wrong; it’s how you feel. That’s one of the few feeling questions that we have.” ([19:20])

Important Segment Timestamps

• Listener call-in begins: [02:31]
• Assets walkthrough: [04:27]–[07:17]
• Retirement income drawdown strategy: [08:55]–[13:52]
• Emotional realities of financial planning: [13:14]–[15:55]
• Healthcare cost discussion: [15:59]–[16:55]
• Portfolio allocation decision (60/40 vs 70/30): [17:41]–[19:21]
• Final wrap and action steps: [19:21]–[19:47]

Tone & Style

Friendly, direct, and reassuring. Jill Schlesinger keeps the conversation jargon-free, empathetic, and practical, putting financial decision-making in real-world terms and emphasizing emotional comfort as much as mathematical precision.

Takeaways for Listeners

• Getting a CFP is about not just math but peace of mind and guidance on drawdown strategies, taxes, and risk.
• Stress-test your plan with your advisor: Ask what can go wrong, and be honest about your risk tolerance.
• Healthcare, market downturns, and other variables should be built into your scenario planning.
• Emotional relief from delegation and expert input can be as valuable as investment returns for retirees.

Chris’s story is a relatable example for anyone on the cusp of retirement, wondering if it’s finally “okay” to stop working, and how to approach that new chapter with confidence and clarity.