Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Trying Not to Screw It Up
Date: April 14, 2026

Brief Overview

In this episode, host Jill Schlesinger consults with listeners Kay and Eric, a couple navigating major life transitions as they approach financial independence in their mid-50s. With their last child nearly out of high school, they seek advice on ensuring their prudent savings and investments are managed wisely as they contemplate next career steps, potential relocation, and the optimal use of pensions and retirement accounts. Jill breaks down actionable steps to help them "not screw it up" and ease their anxieties about the drawdown phase, all in her signature clear, jargon-free style.

Key Discussion Points & Insights

1. Kay and Eric’s Current Situation

• Background: Both professionals, age 54, with high-stress jobs and a strong commitment to financial independence (committed to the "FIRE" philosophy).
• Income: Kay earns $225K/year, Eric earns $175K/year.
  • “We don't want to do something dumb and we have been really boring...save 30% of our net income and dollar cost average and put it in an index fund. Well, that's what we've done.” — Kay [01:34]
• Retirement Savings:
  • 401(k)s totaling ~$2.5M (pre-tax, with $350K in Roth).
  • Brokerage account with $2.1M.
  • Cash reserves: $230K.
• Children: Two, ages 17 and 19; college accounts of $200K for each.
• Home: Paid off, worth $230K.
• Pensions: Kay has a $2,100/month government pension starting at 62; Eric will have a state and federal pension (up to $3K/month at 60 if he works until then).
• Current spending: ~$10K/month, mostly on current lifestyle and kids' expenses.

2. Transition to Next Life Phase

• Timeline: Kay plans to transition careers in the next 11–12 months, considering a new job or endeavor (with an expected minimum income of $60–$75K/year).
• Geographic Flexibility: Considering relocation to a slightly larger or higher-cost area, but aware it may raise expenses.
  • “We do live in a low cost area, we would be assuming a cost even though we. We paid. The house is paid for.” — Kay [05:24]
• Pensions Strategy: Holding off on early withdrawals to maximize payouts, especially Eric's federal pension (doubles from $1,500/month at 57 to $3,000/month at 60).

3. Drawdown Strategy and Tax Planning

• No More Pre-Tax Contributions: Jill strongly recommends that, after Kay’s transition, both should stop making pre-tax retirement contributions.
  • “We have to stop with your pre-tax stuff. I think that what happens is for the years of 55 to 60, you guys keep, this is—again, we don't know what's happening tax law-wise. But let's pretend everything is the same.” — Jill [10:42]
• Switch to Roth and Brokerage: Any future savings should go into Roth IRAs (if allowed) or the taxable brokerage account.
• Withdrawal Discipline: Jill prescribes setting automatic withdrawals from retirement accounts to mimic income, preventing hoarding and supporting lifestyle needs.
  • “You’re going to make it an automatic transfer and you’re going to treat it like it’s income to you...If I have to rely on you to just pull the money out when you need it, you won't spend the money. And that's not good.” — Jill [11:47]
• Bridging Income Before Pensions: From 60 to 62, after Eric’s pension starts, draw necessary funds from retirement accounts to meet living needs.
• Cash Buffer: Keep 1–2 years’ living expenses liquid—approximately $250K in cash at retirement kickoff.
• Social Security: Delay claiming until age 70.

4. Emotional & Psychological Considerations

• Main Anxiety: Difficulty transitioning from “saving” to “spending” mode.
  • “Because you’re the types of people that know how to put money in. You don’t know how to take money out.” — Jill [11:45]
• Jill’s Assurance: Their careful planning earns them “a lot of opportunity,” and the systematic approach should alleviate their worries.
  • “There is nothing here that scares me about where you are. What scares you guys?” — Jill [13:50]
  • “I feel so much better just listening to you lay out the process because I can follow the directions... I feel like a weight has lifted.” — Kay [14:02]

5. Loose Ends and Best Practices

• Estate Planning: Documents are in place (“We do, actually.” — Kay [14:31])
• Life Insurance: Only term life policies, nothing unnecessary.
• Recognition: Jill commends their discipline and low-cost lifestyle.
  • “You are the dream for people on our program because, I don’t know, you guys make a lot of money and you are in a low cost area...You have bought yourself a lot of opportunity. So well done.” — Jill [14:40, 15:06]

Notable Quotes & Memorable Moments

• On Living Beneath Means:
  “We live well beneath our means, obviously, that kind of place. We're very blessed that way.” — Eric [03:17]
• Addressing the Emotional Leap:
  “You’re going to turn your retirement account into an annuity...all we’re doing is automatically making sure it comes to you so you can spend it and have money and have fun.” — Jill [11:45]
• On Future Uncertainty:
  “If something changes, like tax brackets change or, or your plans change, anything that changes, we’re here for you.” — Jill [13:38]
• Listener Relief:
  “Now we have a plan, and I feel like a weight has lifted.” — Kay [14:10]

Timestamps for Important Segments

• [01:34] – Kay and Eric share their financial background and discipline
• [02:46] – Details on retirement and brokerage account balances
• [03:39] – College funding for kids and home value
• [05:24] – Consideration of relocation and cost impacts
• [05:45] – Breakdown of pension values and timing
• [06:28] – Reviewing monthly expenses and lifestyle choices
• [08:09] – Eric considers the trade-offs of retiring before/after pension thresholds
• [10:42] – Jill instructs to halt pre-tax retirement contributions
• [11:45] – Jill outlines the psychological and logistical aspects of the drawdown phase
• [13:38] – Flexibility and contingency planning if tax laws or plans change
• [14:10] – Kay expresses gratitude and relief at the clear, stepwise plan
• [14:31] – Confirmation of estate planning and insurance
• [15:06] – Jill celebrates their financial diligence and opportunity

Recap & Tone

This episode exemplifies Jill’s practical, empathetic approach. With a conversational tone, she dismantles the complexity of asset decumulation, gives concrete action items, and offers emotional reassurance. The conversation is candid, affirming, and offers a model for disciplined savers approaching the psychological shift of retirement.