Podcast Summary: Jill on Money with Jill Schlesinger

Episode: "Time for a Financial Reset?"

Date: February 12, 2026
Host: Jill Schlesinger
Guest: Jason from Upstate New York

Episode Overview

In this episode, Jill Schlesinger speaks with Jason, a listener looking to reset his financial life after selling his home for a substantial profit. The conversation dives into Jason’s plans for his windfall, shifting careers at age 60, and big-picture questions about home ownership, investment decisions, and long-term planning. Jill provides actionable guidance on managing lump sum proceeds, risk management when building a custom home, and the crucial importance of estate planning.

Key Discussion Points & Insights

1. Jason’s Windfall and Immediate Plans

• Background: Jason sold his renovated home in Woodstock, NY, netting approximately $900,000.
• First Steps: Intends to use about $100,000 to pay down debts (car, credit cards) and set aside living expenses.
  • “My first plan is to pay off credit cards and my car.” (05:09)
  • Confirms the actual consumer debt is “under $100,000.” (05:35–05:41)

2. Housing Decisions – Buy, Build, or Flip?

• Initial Impulse: Jason considered buying and flipping another house—but realized he needed immediate housing.
• Current Situation: Renting at $2,000/month; content but seeks his “forever home” to suit his creative and gardening interests.
• Strategy: Plans to purchase land and build a custom home with a developer, leveraging his own renovation skills.
  • “Buying land and building a home is equal to just buying a home.” (07:07)
  • Expects the build to take “nine months, maybe a year.” (07:58)

3. Career Reset at 60

• New Career Path: Transitioned into real estate and interior design after a corporate layoff, inspired by renovating his house.
  • “This career presented itself when I sold my house. I realized that everything that was happening around selling the house was what I wanted to do for a living.” (08:16)
• Financial Structure: No longer has a corporate salary; income is variable and developing.

4. Planning for Income and Investments

• Living Expense Strategy: Jason plans to pay himself a $60,000–$100,000 “salary” from his windfall this year, and treat future income as savings toward the next year’s living expenses.
  • “Is it wise for me to put the money that I make off of this house into just owning a house, clean and clear?” (10:44)
• Mortgage Considerations: Open to carrying a small mortgage ($200K–$250K) if rates go down, to keep funds invested.

5. Asset Review and Long-Term Outlook

• Personal Assets:
  • IRA: $240,000 (tapped during pandemic for renovation work; plans to replenish with $100,000 from windfall).
  • Anticipated inheritance from mother: $650,000 (conservative estimate).
  • No current Roth IRA assets.
• Spousal Dynamic: Married, but finances kept separate from husband, who owns townhouse in Brooklyn.
• Cash Holdings: None currently, but plans to create an emergency fund with $100,000 from sale proceeds.

6. Risk, Liquidity, and Contingency Plans

• Total Build Budget: Land purchase at $150K–$200K; total build cost $600K–$700K. Plans to spend $500K in cash and consider a small mortgage at completion.
• Plan B: If needed, could sell the new home, rent, or move into husband’s Brooklyn townhouse.
  • “If something bad happened, would your husband be able to help you out?” (17:53)
  • “What I would do is...move into our place in Brooklyn...and I could sell [the house].” (17:58)

7. Jill’s Guidance, Cautions, and Required Next Steps

• Affirms Jason’s Plan: Comfortable given Jason’s experience, separate assets, and backup options. Notes it’s a risk, but calculated and manageable given his skills and fallback plan.
  • Memorable quote: “If you’re doing something really risky like this, Jason, then we must have your bailout plan. And you have it.” (18:53)
• Mark’s Take (Producer): “Jason sounds like this is what he does. He knows what he’s doing...and knowing that inheritance is coming, that also helps.” (18:11)
• Estate Planning Warning: Underscores the critical need for a will, power of attorney, and health care directives, especially with separate finances.
  • Jill bluntly says: “You need a will, you need a power of attorney…” (21:26)
  • Jason sheepishly admits procrastination: “Oh, my God. I know.” (21:02)

Notable Quotes & Memorable Moments

• On Leveraging Experience:
  “The improving, starting from scratch is absolutely...the way that you tend to extract more value...if you can do it.” — Jill (19:59)

• On Knowing Your Limits:
  “You have to know yourself and if you can do it...as long as we have a plan B.” — Jill (20:09)

• On the Importance of Estate Documents:
  “There is no way out of this. You cannot convince me otherwise.” — Jill pressing Jason to create a will and related documents (21:34)

• Humorous Spousal Dynamics:
  Jason: “My husband thinks that I should wait till after the midterms to do anything. And I said, I don’t really think that has anything to do [with it].” (19:15)
  Jill: “Because if the midterms don’t go a certain way, you’re going to move to Canada?” (19:25)

Important Timestamps

• [04:10] Jason introduces himself and explains the home sale
• [06:48] Talks about home rental and desire for a “forever home”
• [08:12] Describes switching careers to real estate & design at age 60
• [10:44] Asks about fully owning the new home vs. keeping a mortgage
• [11:36] Shares retirement/assets overview; mentions future inheritance
• [13:54] States current income from new design/real estate career
• [16:19] Details on land and build process, cash flow for the plan
• [17:53] Discusses worst-case scenarios and fallback plans
• [18:52] Jill and Mark weigh in on risk and the plan’s realism
• [21:01] Jill demands that Jason set up estate documents

Takeaways and Actionable Advice

• For those facing a financial windfall, first assess debts, build your emergency fund, and delay major investments until your job/income situation stabilizes.
• When pursuing risky or large financial moves—like building a home—always have a plan B, especially if employment/income is newly self-directed.
• Keep in mind that personal/family assets and inheritances should be factored conservatively into long-range planning, not as guaranteed present cash flow.
• Estate planning is not optional: wills, powers of attorney, and health care directives are must-haves when you have significant assets, especially for married couples with separate finances.
• Jill’s signature straightforward advice: “You need a will!”

This episode is an engaging look at real-life wealth management questions and the balancing act between financial opportunity, risk, and personal reinvention at any stage of life.