Jill on Money with Jill Schlesinger

Episode Title: Keeping All the Balls in the Air
Original Air Date: December 4, 2025

Episode Overview

In this candid and relatable episode, Jill Schlesinger is joined by John from Pennsylvania, a high-earning professional and family man struggling with the stress of balancing life, work, and complex financial decisions. The discussion centers on the emotional weight of financial uncertainty, the reality behind “having it all together,” and the practical next steps for those who feel overwhelmed by managing their wealth, planning for retirement, and facing the next life chapter.

Key Discussion Points and Insights

1. The Challenges of "Keeping All the Balls in the Air"

• John's Introduction (04:36–06:30):
  John articulates the universal struggle of juggling career, family responsibilities, household maintenance, and increasingly complex finances.
  • He describes the overwhelm of supporting a family—with his spouse primarily focused on raising kids—and the pressure that comes with being the main breadwinner.
  • Quote:

    "It's hard. It's hard to keep all the balls in the air. So, you know, working, having a family, making sure your kids are safe and bring them up properly, spending time with your spouse, paying bills, mowing the lawn, you know, making sure that the mailbox is straight... And then you Add the financials and it's like, oh my gosh." – John (04:36)

  • John expresses empathy for single parents, admiring how they “rise to the occasion.”

2. John’s Financial Situation Laid Bare

• Assets, Income, and Retirement (07:07–10:53):

  • John is 55, as is his wife; their children are in their 20s, with one working and one about to graduate college.

  • Household income is roughly $350,000/year ($335,000 his, $15,000 wife's part-time).

  • Retirement assets total about $1.3 million, with ~$600k in traditional accounts and $115k in Roth accounts.

  • Substantial non-retirement assets: $3 million in a brokerage account, most of which John has self-managed with some self-admitted “chasing the next thing.”

  • Home is paid off, valued at approximately $650,000. They are considering a nearby move to a more remote area with a higher price point, budgeting $200,000 from savings for this purpose.

  • He maintains a large emergency fund, nearly $560k in cash, driven by job security worries.

  • Memorable Moment:
    Jill reacts lightly to John’s confessed investing jitters:

    "Oh, you're that guy. That's all. Dividends are interesting. Let me open up a dividend fund... Now it should be in index funds. Let's get into index funds. What about international?" – Jill (08:47)

3. Redefining What’s “Enough” and Planning Retirement

• Spending Needs and Moving Goals (10:15–12:00):
  • John tracks expenses closely with his wife, estimating core costs at $65,000/year excluding health insurance.
  • With anticipated ACA health insurance, he projects $90,000/year after taxes to cover everything.
  • Jill probes his willingness to work part-time in the future, possibly in enjoyable settings (e.g., REI, Trader Joe’s), noting that part-time jobs often bring unexpected time commitments relative to pay.

4. The Emotional Reality and the Need for Professional Guidance

• Jill’s Core Advice (12:51–15:43):

  • Jill tells John he’s done “an amazing job” and, despite his anxieties, is in “very good shape”—financially secure and free to choose his next chapter.
  • She urges him to give himself permission to step back at work, potentially seek less stressful part-time or consulting roles, and, most importantly, to hire a real financial planner (not just an investment manager).
  • Her concern is less about the money and more about John’s ongoing emotional distress (“You are the perfect type of person to hire a financial planner. You really are. Because you've got a pile of money. There's really nothing bad that's going to happen except what you do to yourself.” – Jill (13:47))
  • Jill emphasizes the importance of a holistic planner who can address both financial and life questions; someone who can “take the financial baggage off your shoulders.”

• Notable Quote:

  "You have saved so much money that you have now bought yourself the ticket to being able to explore what that next chapter is. You really have." – Jill (15:15)

Notable Quotes & Memorable Exchanges

• On parental pressure and empathy:

  "Sometimes I think about the single parents out there... My heart goes out to those people that just don't have that support.” – John (06:30)

• On investing self-doubt:

  “I've done a good job messing that, that side of it up too.” – John (08:27)

• On financial anxiety despite strong savings:

  "For all of your, your anxiety and self doubt, you've done— and you and your wife have done— an amazing job." – Jill (13:34)

• On what a financial planner can and can’t do:

  “Here's what they cannot solve for, they cannot solve for if you haven't saved enough money. You have saved enough money.” – Jill (15:00)

Important Timestamps

• 02:58 — Jill welcomes listeners, invites financial questions, outlines ways to contact the show
• 04:08 — John introduces his life and money challenges
• 07:07 — Breakdown of John's family and financial snapshot
• 08:27 — Discussion around self-directed investment pitfalls
• 10:15 — Housing plans and moving goals
• 11:25 — Social Security benefit review and retirement budget
• 12:51 — Jill’s key advice: reassess, permission for change, seek professional guidance
• 15:15 — Empowerment for next chapter: “You’ve bought yourself the ticket…”

Tone and Style

Jill delivers her trademark blend of empathy, humor, and practical, actionable advice. The conversation is honest, supportive, and peppered with occasional light-hearted teasing (especially about John’s investing style), ultimately centering on self-kindness and the value of seeking trusted professional help.

Summary Takeaways

• Financial complexity and stress are normal—even for highly successful savers.
• Big financial wins can’t always alleviate the emotional burden of money management.
• Giving yourself permission to change, seek support, and pursue new lifestyles is critical.
• Professional, holistic financial planning can offer relief, structure, and peace of mind for those ready to move into new phases of life.

For more resources or to submit a question for Jill, visit jillonmoney.com.