Podcast Summary

Podcast: Ready For Retirement
Episode: Most Retirement Advice Fails Singles (Here’s What to Do Instead)
Host: James Conole, CFP®
Date: December 7, 2025

Episode Overview

This episode tackles how most traditional retirement advice doesn’t serve single individuals well. Host James Conole outlines a three-step framework specifically tailored for singles, emphasizing that while the potential risks might be greater without a partner, so is the potential freedom. He walks listeners through a real-life-inspired case study (“Tina”) to highlight the nuances of planning solo, covering how to determine your “freedom number,” map income sources, and design a purpose-driven portfolio.

Key Discussion Points & Insights

The Problem: Retirement Advice Assumes You're Married

• Much of conventional retirement wisdom is tailored to couples (dual incomes, dual Social Security checks, shared expenses).
• For singles, with no “backup plan” or person to fall back on, financial independence strategies must be customized.

Memorable Quote:

“Most retirement advice quietly assumes you have a spouse, two sources of income, two Social Security checks, someone to split expenses with. But what if it's just you? For singles, the rules are different. The margin for error is much smaller, but the potential freedom is much larger.”
(James Conole, 00:00)

The Three Steps for Singles

1. Design Your Freedom Number

• Don't start with calculators or asset spreadsheets—start with your vision.
• Ask: What does your ideal retirement look and feel like? Travel? Hobbies? Giving?
• Determine the real cost of your desired lifestyle (not just a generic monthly figure).

Memorable Quote:

“Don’t start with the spreadsheets. Start with: What do you want life to look like?... What does true freedom feel like?”
(James Conole, 04:30)

• For singles, you have full control over this vision—no compromising with a spouse.
• Example: In Tina’s case, she estimated she needs $6,000/month ($72,000/year) for her ideal retirement (06:00).

2. Map Your Reliable Income Sources

• Identify what “paychecks” continue after you stop working:
  • Social Security (timing is crucial), pensions, annuities, rental income, etc.
• Singles should optimize their Social Security strictly for lifetime income (no need to strategize for a surviving spouse).
• A crucial tip: If you’re divorced but were married for 10+ years, you may still be eligible for spousal or survivor Social Security benefits (14:00).

Memorable Quote:

“If you’re single, it’s all about: how can I maximize my lifetime income? How can I stretch this benefit furthest?”
(James Conole, 11:50)

• Mapping reliable income allows you to identify the gap your portfolio needs to fill.

3. Build a Portfolio With Purpose

• The difference between your freedom number (step 1) and reliable income (step 2) is what your portfolio needs to fund.
  • Example: Tina needs $81,000/year (adjusted for inflation) and Social Security only covers $3,300/month at 67, leaving a gap the portfolio must fill (21:00).
• Calculate what annual withdrawal amount your portfolio must support, then express this as a safe withdrawal rate percentage.
  • Tina’s withdrawals are a low 1.5% of her sizeable portfolio, indicating strong sustainability.

Memorable Quote:

“What does this represent as a percentage of her portfolio to give her a sense of: can she do this or not?”
(James Conole, 27:00)

• If projected portfolio value far exceeds spending needs (as in Tina’s case), singles can consider:
  • Retiring earlier
  • Spending more on meaningful experiences
  • Funding travel or even paying for friends/family to join in

Case Study: Tina (Real-Life Application)

• Tina: Age 62, owns a home, has about $2.1–$2.2 million in investments (primarily in individual stock from her employer), plus 401k and Roth IRA.
• Host stresses: “If you have $2 million, $200,000 or $20 million, these steps are the same. The framework is the same.” (James Conole, 02:40)

Tina’s Retirement Scenarios (33:00+)

• Retire immediately at her target lifestyle: Model shows high odds of success.
• Retire later (age 65) but spend more (e.g., add $20,000/year for travel): Still sustainable.
• Generosity options: Pay for friends to travel with her; still financially viable.

Memorable Moment:

“The goal is not to accumulate the most dollars so you can die with them. The goal is to say: how can you use those dollars to get the most out of life with your money?”
(James Conole, 38:30)

Notable Quotes & Timestamps

• 00:00: "For singles, the rules are different. The margin for error is much smaller, but the potential freedom is much larger."
• 04:30: “Don’t start with the spreadsheets. Start with: What do you want life to look like?... What does true freedom feel like?”
• 11:50: “If you’re single, it’s all about: how can I maximize my lifetime income? How can I stretch this benefit furthest?”
• 14:00: "If you are single but you were previously married, keep in mind you are still eligible for a spousal benefit or a survivor benefit on your ex spouse's Social Security income."
• 27:00: “What does this represent as a percentage of her portfolio to give her a sense of: can she do this or not?”
• 38:30: “The goal is not to accumulate the most dollars so you can die with them. The goal is to say: how can you use those dollars to get the most out of life with your money?”

Takeaways for Single Retirement Planning

• Singles must be both the planner and the backup plan.
• Focus first on your life vision, then map the finances to support it.
• Reliable income (mainly Social Security for many): Optimize for your own lifetime, not for a spouse.
• Build your portfolio to fill the income gap, not just to maximize accumulation.
• If the math enables it, don’t be afraid to retire early or enjoy your money more.

Framework Recap:

1. Design your freedom number – What do you want your retired life to cost?
2. Map reliable income – What predictable monthly income will you have?
3. Build your portfolio with purpose – Make sure your investments bridge the gap to your freedom.