Episode Overview

Podcast: Ready For Retirement
Host: James Conole, CFP®
Episode: I Threw the First Pitch at a Padres Game—Here’s the Real Lesson | Root Talks
Date: November 6, 2025

This episode centers around a unique, personal experience: James Conole throwing the first pitch at a San Diego Padres game, a childhood dream he never thought he’d achieve. But the heart of the conversation isn’t just about baseball—it’s about living intentionally, making meaningful memories, and using financial planning not just to accumulate wealth, but to fund a fulfilling, adventurous life. James and his guest, Ari, dive into the deeper lesson: breaking out of routines and unwritten rules to live life on your own terms.

Key Discussion Points & Insights

Childhood Dreams and Unexpected Opportunities

• James’ Padres Story:

  • Grew up a huge baseball fan, going to Padres games with friends, always on a budget.
  • Never thought he’d be the person on the field throwing the first pitch ([00:00]-[02:29]).
  • “Never even registered in my mind that that was something that you could do … until one day I get a call from Ari … you’re throwing out the first pitch for the San Diego Padres.” — James ([01:15])

• Ari’s Role as ‘The Initiator’:

  • Ari talks about his proactive approach to life, always being the one to set plans in motion.
  • “My mom always said, you create your own happiness.” ([02:29]-[03:34])
  • “My life will be better if I initiate things, and they often don’t work out. But to me, I’m at a no already—why not try?” — Ari ([03:06])

Drawing Lessons: Living Life on Purpose

• Breaking Out of ‘Manual Mode’:

  • James highlights the importance of not getting stuck in the daily rut and living life intentionally.
  • “Not in this rut, not in this ... wake up, work, go to bed, repeat type situation, but actually live life on purpose.” — James ([01:55])

• Maximizing Experiences for What Matters:

  • The first pitch wasn’t just about baseball; it turned into a memorable event with friends and family, creating lasting memories ([03:34]-[06:52]).
  • “How do we manage that in a way that … the first priority above all else … is translating that into peace of mind … your ability to do the things you want to do with the people you care about.” — James ([05:45])

Challenging the ‘Unwritten Rules’ of Spending

• Meaningful Splurges vs. Responsible Saving:

  • James discusses the tension between frugality and meaningful indulgence.
  • “Sure, we could have just got cheap seats … but there was an experience that went along with that that made it so fun, so meaningful—Truly a once in a lifetime opportunity.” — James ([06:52])

• Ari’s Client Story: Private Jet to Antarctica

  • Ari shares about a client who, after some prodding, splurged on a National Geographic private jet tour with her ailing mother, choosing experience over a new car or home remodel ([07:22]-[10:27]).
  • “She had saved really well … she did a private jet tour with National Geographic, something she totally wrote off in her head because she heard the words private jet.” — Ari ([09:14])

• Designing a Life Well-Lived:

  • Ari makes clear: “The sign of a good financial plan is a life well lived.” ([10:11])
  • Part of their job as financial planners is to help clients dream beyond their default boundaries.

The Trade-Offs and Real Cost of Waiting

• The Pain of Spending vs. The Pain of Regret:

  • James addresses how spending can be difficult for habitual savers, but warns of the greater pain of missed opportunities ([11:25]-[13:56]).
  • “There’s the pain of discipline and there’s a pain of regret. One is in ounces; one is in pounds.” — James ([12:04])
  • “What happens when your mother’s no longer here and you can’t take that trip with her? What happens when your children … [are] so financially responsible … but you’ve missed out on the things you could have done along the way …?” — James ([12:26])

• Living Beyond Limited Expectations:

  • The importance of generating your own list of dreams, even if they seem outlandish.
  • James paraphrases a famous quote: “You have one life, one precious life. What are the things you’re going to do to make it matter?” ([13:43])

Notable Quotes & Memorable Moments

• “Never even registered in my mind that that was something you could do … until one day I get a call from Ari … you’re throwing out the first pitch for the San Diego Padres.” — James ([01:15])
• “It’s not a conscious decision I make … My mom always said: you create your own happiness.” — Ari ([02:29])
• “My life will be better if I initiate things, and they often don’t work out. But to me, I’m at a no already—why not try?” — Ari ([03:06])
• “Not in this rut, not in this ... wake up, work, go to bed, repeat type situation, but actually live life on purpose.” — James ([01:55])
• “The first priority above all else … is translating [wealth] into peace of mind … your ability to do the things you want to do with the people you care about.” — James ([05:45])
• “The sign of a good financial plan is a life well lived.” — Ari ([10:11])
• “There’s the pain of discipline and there’s a pain of regret. One is in ounces; one is in pounds.” — James ([12:04])
• “You have one life, one precious life. What are the things you’re going to do to make it matter?” — James ([13:43])

Key Timestamps

• 00:00 — James recounts his high school days as a Padres fan and the journey to throwing the first pitch.
• 01:15 — The pivotal call from Ari that led to the first pitch experience.
• 02:29 — Ari explains his role as “the initiator” and the importance of creating your own happiness.
• 03:34 — The experience of throwing the pitch, reconnecting with old friends, and the deeper financial planning message.
• 05:45 — Translating financial planning into meaningful, memorable experiences.
• 07:22 — Ari introduces the story of a client’s private jet dream and how advisors can help clients dream bigger.
• 10:11 — “The sign of a good financial plan is a life well lived.”
• 11:25 — James contrasts the pain of responsible spending with the pain of missing out.
• 13:43 — James references the “one wild and precious life” quote and implores listeners to use their resources to create meaning.

Action Items and Takeaways

• Challenge yourself to live intentionally, rather than by default.
• Don’t let unwritten or self-imposed rules hold you back from once-in-a-lifetime experiences, if you have the means and desire.
• In your financial planning, prioritize making memories and doing meaningful things with those you care about.
• Reflect on your own “bucket list”—write down what you’d do if you had a “blank check,” even if they seem out of reach.
• Remember, the greatest regret may not come from money spent, but from missed experiences and opportunities for connection.

This episode is a spirited call to action: live boldly, dream bigger, and use your resources as tools for a richer, more adventurous retirement and life.