Ready For Retirement Podcast

Episode: Retiring at 65 Might Be Too Late (Here’s Why)
Host: James Conole, CFP®
Date: September 5, 2025

Episode Overview

In this episode, James Conole challenges the conventional wisdom of waiting until 65—or even later—to retire. He argues that this traditional timeline can cause retirees to miss their healthiest, most vibrant years, and urges listeners to consider both "health span" and "lifespan" in their planning. With real-world insights and relatable anecdotes, James pushes for a retirement strategy that values purpose and memories as much as just the numbers in your portfolio.

Main Discussion Points & Insights

Lifespan vs Health Span

• Defining the Difference:
  • Lifespan is simply how long you live.
  • Health span is how many years you live in good health, physically and cognitively.
• Notable Stat:
  • The average American’s lifespan: 77 years
  • The average health span: 66 years (01:07)
• Relevance To Retirement:
  • "Very difficult to do [retirement your way] when you no longer have your health." — James (02:50)

Life Expectancy Misunderstandings

• The often-quoted life expectancy (77) is from birth.
• If you're already 60, you can expect to live to 84 on average (85 for women, 82 for men), shifting the planning horizon. (03:18)

The Traditional Retirement Planning Pitfall

• Most plans focus on ensuring you don’t run out of money by your 80s/90s, often at the expense of enjoying the healthiest years.
• Quote:
  • "If all we're looking at is maximizing the terminal value, what are we sacrificing today to do that?" (05:00)
• Many people defer experiences, expecting to "do it all" after retiring at 65+, only to find health issues get in the way.

The True Cost of Delayed Retirement

• Sacrifices:
  • Less time with kids/grandkids while active.
  • Missed trips with a spouse that may never happen.
  • Neglecting health with no opportunity to reclaim it later.
• Key Question:
  • "What’s the cost of a delayed retirement?" (06:16)
• Applying Compounding Elsewhere:
  • "Apply that same [compounding] framework to your health, to your relationships, to your hobbies..." — James (07:08)

The Invisible Scorecard

• Financial gains are easy to track (401k, bonuses, investments).
• Gains in relationships, health, contentment are less visible but often more meaningful.
  • "What I can't see is a scorecard for relationships, for health, for purpose, for contentment. Those are some things that are invisible, but far more meaningful." (08:00)

When Work Is No Longer Serving You

• If work brings joy, structure, and relationships, keep doing it.

• If work brings stress, burnout, and distraction from what matters—and you’re already financially independent—ask what it's really costing you.

• Quote:

  • "What’s it costing you to continue to accrue that Social Security benefit that's getting higher and higher? That feels good. But don't think that it's coming at zero cost." (11:12)

Why People Keep Working

• Higher salary and bonuses are tempting, but at what personal cost?
• Many "success stories" include missing out on relationships, hobbies, and in some cases, life itself.
  • "I've seen far too many people who have sacrificed the things that actually matter just for more money." (13:36)

Action Steps & Final Thoughts

Redefining Wealth

• Wealth isn’t just financial—it’s time, relationships, purpose, experiences.

• Challenge to Listener:

  • "Would you rather have more money in your 80s or more memories in your 60s? Only you can decide that answer." (15:35)

Tangible Steps

• Make a financial plan (with or without an advisor).
• Find your financial independence number.
• Prioritize living intentionally now—don’t just optimize for an abstract financial goal.

Closing Advice

• Don’t drift aimlessly or get stuck optimizing just your finances.

• Build a financial plan that supports the life you truly want, not just the largest account balance.

• Final Quote:

  • "How can you create a financial plan that supports the life you want to live?...Live a life of intention, a life of purpose, a life that supports what you actually want to be doing." (16:50)

Notable Quotes

• On health and wealth:
  "Very difficult to do that [have a fulfilling retirement] when you no longer have your health." (02:50)
• On delayed retirement:
  "What are the costs of continuing to work, continuing to have that toll taken on our bodies? If it's sacrificing the best years of our retirement..." (05:35)
• On invisible value:
  "What I can't see is a scorecard for relationships, for health, for purpose, for contentment. Those are some things that are invisible, but far more meaningful." (08:00)
• On intentional planning:
  "How can you start driving your financial strategy? How can you create a financial plan that supports the life you want to live?" (16:30)
• Provocative question:
  "Would you rather have more money in your 80s or more memories in your 60s?" (15:35)

Key Timestamps

• 01:07 — Health span vs. lifespan explained
• 03:18 — Adjusted life expectancy at age 60
• 05:00 — The focus of traditional retirement planning and its shortcomings
• 06:16 — Real costs of delaying retirement
• 07:08 — Applying compounding to life, not just money
• 08:00 — The invisible scorecard: what really matters
• 11:12 — Social Security and tradeoffs
• 13:36 — Clients’ regrets after putting work above all
• 15:35 — Money vs. memories: the crucial retirement question
• 16:50 — Closing advice on intentionality and living your desired life

This episode reminds listeners that while financial security is essential, time, health, relationships, and purpose cannot be bought back later. James Conole encourages reexamining what wealth means—and acting on it now.