Jill on Money with Jill Schlesinger
Episode: Retirement Planning Checkup at 65
Release Date: September 18, 2025
Overview
In this episode, host Jill Schlesinger CFP® is joined by Bob, a listener from Boston approaching age 65, for a detailed retirement planning checkup. Bob seeks Jill’s guidance as he navigates key life and financial changes, including the recent loss of his mother, an inheritance, decisions about his job, and the best tactics for drawing down assets as he approaches full retirement at 70. The episode is a hands-on, candid discussion about transitioning into retirement, using inheritance wisely, optimizing Social Security, and finding a satisfying balance between work and life.
Key Discussion Points & Insights
1. Bob’s Situation: Retirement Planning at 64-65
- Continued full-time work planned until age 70; considering a possible career change or at least a change in work conditions.
- Enjoys the travel aspect of his job, but dislikes the management and working conditions at his company.
- Recognizes generalist background and is concerned about how well it translates in today’s job market.
- Considering hiring a “really good resume writer” if pursuing a job change, mindful of resume screening technology.
[04:54]
Notable Quote:
“I’m not so hot on the management I work for or the conditions that I work under. So I have been contemplating a possible career change. Although with only...five years of full time to go, I’m not sure that’s an easy thing.” – Bob [03:49]
2. Inheritance & Estate Questions
- Recent loss of his mother; he and his sister are co-executors and are “completely in sync.”
- Main inheritance: His half of a $220,000 IRA (Required Minimum Distributions, RMDs, already started) and about $30,000 from cash and tax refund after estate settlement.
- The IRA must be distributed within 10 years, not necessarily in equal increments. Jill emphasizes flexibility in timing the withdrawals to optimize tax strategy.
[07:15]
Notable Quote:
“10 years to get the money out does not have to be equal. Can be in one fell swoop. It could be in five years when you have less income… it’s really up to you.” – Jill [07:15]
- Jill offers a public service reminder for listeners about estate planning:
“If you have aging parents and they do not have their estate documents done, please, please let them get that done. It will make your grieving a lot easier.” – Jill [08:25]
3. Bob’s Financial Snapshot
- 401(k): $1,160,000, with about 97% traditional, 15% contribution rate, includes a 4% match.
- Emergency fund: $32,500 split across CDs.
- Other savings: $12,000 for condo repairs, $19,000 for car expenses.
- Home: Condo valued at ~$300,000, $61,000 remaining on mortgage at 4% interest.
- Salary: 2024 income of $80,800 (salary), $87,400 with bonus.
- Spending: ~$3,000 monthly, $3,500 for planning, Jill encourages $4,000/month for comfort.
- Social Security projection:
- Age 67: $3,058/month
- Age 70: $3,798/month
[11:39]
Notable Exchange:
“With 1.16 million...you have all—you’ve done a great job.” – Jill [11:47]
“Maybe this is not just about a career change. Maybe this is just about you being able to work less or changing other parts of this…you don’t have to make that much to support yourself. You don’t spend a lot of money.” – Jill [12:20]
4. Career Change, Downshifting, and Building a Safety Net
- Jill's guidance:
- Bob has the freedom to leave if unhappy; his financial discipline gives him flexibility to downshift or even stop working for a while and “dribble” withdrawals from the inherited IRA.
- Jill encourages Bob to “start dribbling some of that money out and using it” if he takes time off between jobs, optimizing for tax efficiency by drawing from low-tax-bracket years.
[13:46] - Using years with lower income (possible gap between jobs or part-time work) to withdraw more from inherited IRA.
Notable Quote:
“If for some reason, like at some year where you’re like, ‘Oh, I’m not going to stay here,’ you know, that’s when you get the money, when your income goes down. Right. And…the thing that’s going to be a little bit funny with you is that at age 70, you’ll have that Social Security income. So it would be kind of interesting for you to try to get some of the money out a little bit at a time.” – Jill [16:11]
- Bob expresses intention to work part time after 70 for structure, purpose, and some travel money.
[14:26]
5. Inherited IRA Strategy and Roth Conversions
- Bob’s question: Could he take the inherited IRA withdrawal, pay taxes, and put the remainder into a Roth IRA?
- Jill’s answer: Not ideal. Better to increase 401k Roth contributions at work if cash flow allows; otherwise, use the cash from withdrawals to build up a brokerage/savings cushion for upcoming needs instead. [18:13]
Notable Exchange:
“It’s a little cute for me, honestly. You can just put more money into your Roth 401k at work. I would just…put it into your cash and your brokerage account and build that up and have that available to you rather than have it in the Roth environment…” – Jill [18:28]
- Bob aligns with this, stating his goal to build a larger emergency fund for unexpected expenses or future assessments.
[19:19]
6. Closing Encouragement & Takeaways
- Jill lauds Bob’s preparation and gives her signature stamp of approval:
“If you are feeling comfortable and you wanted us to just give you…the Jill and Mark papal and Jewish girl blessing, we are doing that in spades. You’ve done a really wonderful, wonderful job, truly...you gave yourself options. So well done, Bob.” – Jill [17:24]
- Final advice: Bob should be kind to himself as he deals with his mother’s estate and consider options at work without stress—he has effectively bought himself flexibility through years of careful saving and planning.
Memorable Moments & Notable Quotes (with Timestamps)
- “People really, they don’t know what to say, so they say silly things like that. Anyway, I’m just very sorry.” – Jill, on condolences after a loss [05:41]
- “If you’re the type of person who can manage that – philosophically…it sounds like you’re a real worker. So I guess I’m asking you, do you feel like you can give yourself permission to just say, ‘I’m done at this thing, let me find out the next thing to do?’” – Jill [13:46]
- “I don’t see myself entirely not working anymore. I can see myself easily doing part-time work…” – Bob [14:30]
- “There’s nothing bad that can happen to you. You’ve done a great job of saving. You should be comfortable with where you are.” – Jill [15:43]
- “You take your time with the mom’s estate and be nice to yourself…no matter what, you will have options. Not because we’re giving you options, because you gave yourself options.” – Jill [17:36]
Important Timestamps
- [03:03] Bob introduces his situation and asks about retirement planning at 65
- [04:54] Career satisfaction, job market concerns, resume writing
- [06:01] Bob’s inheritance and estate planning after mother’s passing
- [07:15] Inherited IRA: rules and flexibility in withdrawals
- [08:50] Bob’s current retirement and savings details
- [11:39] Social Security projections at 67 and 70
- [13:46] Discussion on transitioning out of the workforce and flexible withdrawal strategies
- [14:26] Bob’s post-70 work plans and reasons to keep active
- [16:11] Jill's analysis of inherited IRA withdrawals around Social Security
- [17:56] Q&A: Converting inherited IRA distributions into a Roth IRA
- [19:19] Emergency fund strategy and building cash positions
Final Thoughts
This episode provides a relatable, practical roadmap for anyone approaching retirement—or inheriting assets—while giving the reassurance that careful financial habits offer not only future security but also the freedom of choice in later years. Jill’s blend of expertise and empathy offers Bob—and listeners—actionable advice and genuine encouragement for navigating major life transitions with confidence.