Ready For Retirement – Episode Summary

Podcast: Ready For Retirement
Host: James Conole, CFP®
Episode: The Hardest Year of Retirement: What No One Warned Me About | Retirement Reality
Date: December 17, 2025
Guest: Jim (Retired Software Engineer)

Episode Overview

This episode explores the rarely discussed emotional and psychological challenges of retirement through the personal story of Jim, a former software engineer who retired four years ago at age 59. While many focus on the numbers and financial plans, Jim and James dive into loss of identity, finding new purpose, and the process of rebuilding a fulfilling life after the structure of a decades-long career falls away.

Key Discussion Points & Insights

The Psychological Shock of Retirement

• Most Difficult Year:
  Jim reveals that his first year in retirement was his hardest, characterized by a profound loss of identity and routine.

  • “The first year was the hardest. It was the most difficult. Just a psychological component… finding out what I'm going to do, and I'm kind of locking into that now.” (00:11)

• Loss of Structure and Purpose:
  Jim describes struggling to introduce himself and to find motivation for daily activities.

  • “When you go to introduce yourself, what do you say? Okay, my name is Jim. Okay, what do I say after that?... I don't do the software stuff anymore, so I'm not that. What am I?” (08:42)

• Transitioning Identity:
  Retirement requires letting go of previous roles and embracing new chapters of life.

  • “Retirement is just another chapter and so you have to kind of let go of the stuff before that was good, maybe while you had kids… So you just have to embrace the new chapter.” (09:20)

The Importance of Environment and Social Connection

• Living in a Retirement Community:
  Jim credits his living environment with boosting his social life and exposing him to new opportunities and friendships.

  • “I live in a retirement community, so there's a lot of people similar to me around. That's really helpful. That actually helped me retire earlier…” (28:48)
  • “Well, now I know all of my neighbors… so we connect to each other. So that's been the social stuff. I didn't anticipate that. That was just a nice benefit.” (32:55)

• Helping Family:
  Choosing to live close to family, such as his mother, provided both practical assistance and emotional fulfillment during challenges like health issues.

  • “She lives 12 houses down for me. So we do a lot of stuff together…” (33:40)

Discovering and Creating New Purpose

• Experimenting and Volunteering:
  Jim tried various activities — volunteer work at the hospital (including driving golf carts), social events, show choir, and more.

  • “I picked one of those. I was driving a golf cart around the hospital… So that was fulfilling. And then a little bit later… now I'm working in their office, running some numbers for them…” (04:45–07:36)

• Writing as a New Focus:
  A chance meeting with a stranger led Jim to pursue writing seriously, eventually resulting in the publication of a family memoir.

  • “So I did, I started writing for the first year or so… I ended up writing another book that I just published in August. So that was really fun. And it's one about my childhood. My brothers contributed a couple of stories. My mom did a couple of stories and so it's kind of a family project and so that was a lot of fun.” (17:13–21:00)

• Embracing Learning and Challenge:
  Writing carried Jim into learning new business and publishing skills, providing continued growth and purpose.

  • “There's the whole business side. If business is completely different than writing or anything else I've done… It's challenging, but it's fun because it's learning and forcing me to do something.” (21:42)

The Phases of Retirement and Rebuilding Fulfillment

• Freedom From vs. Freedom To:
  James introduces the distinction between freedom from work/stress (immediate relief), and “freedom to” (finding purpose in new endeavors).

  • “There's two different types of freedom. There's the freedom from. And there's freedom to… That freedom, too, I think, is where people struggle. What am I now doing?” (07:36)

• Evolution in Retirement:
  With time, the discomfort of the early years gave way to newfound purpose through community, writing, and volunteering.

  • “The first year was the hardest. It was the most difficult. Just as a psychological components like we talked about before, the, this last year has to be the best. And so it's kind of been a evolution finding out what I'm going to do…” (14:39)

• Trying New Things Leads to Fulfillment:
  James references Dr. Riley Moynes’ phases of retirement: Honeymoon, Loss, Experimentation, Renewal.

  • “Phase two is that sense of loss, that loss of identity, that loss of structure… And that's where people struggle and people risk staying there indefinitely until they move to step three, which is just the try new things… Phase four is that sense of, okay, renewed purpose, renewed energy, or renewed enthusiasm for what you can do.” (30:54)

Advice for Approaching Retirement

• Consider “Practicing Retirement”:
  Jim suggests reducing work hours pre-retirement to gradually discover new interests — advice he wishes he’d followed.

  • “What I'm doing now is, I'm encouraging what I'm calling practicing retirement… if you could drop down that or drop to 30 hours… you have that extra time to do this expiration. And it's not a cliff like it was for me.” (26:20)

• Embrace the Inevitable Pain of Change:
  One year of discomfort is a small price for long-term fulfillment.

  • “Is one year of self doubt really that bad? Okay, probably not. You know, it caused me to have to learn some things and grow… A painful year in exchange for a stronger retirement going forward.” (27:14, 28:15)

• Don’t Fear the Unknown:
  Jim encourages listeners to be proactive and embrace the opportunity for growth in retirement.

  • “Don't fear it. It's just the different chapter in your life… you'll get through it. You just… seek out opportunities to expand in your new role.” (35:44)

Notable Quotes & Memorable Moments

• On Loss of Identity:
  “When you go to introduce yourself, what do you say? Okay, my name is Jim. Okay, what do I say after that? Who am I? What do I do?” — Jim (08:42)

• On Retirement's Unique Challenge:
  “Retirement is just another chapter… you have to embrace the new chapter and not, you know, you can love the stuff in the past, but now there’s maybe new challenges, new things to think about in your new chapter.” — Jim (09:20)

• On Finding Fulfillment:
  “You can only play so much… It’s not ultimately fulfilling. It’s fun but it’s not fulfilling. And so you have to figure out what your fulfilling [purpose] is.” — Jim (13:09)

• On the Power of Serendipity:
  “The first one is the power of serendipity of putting yourself out there, having lunch with a total stranger. Good things happen when you’re willing to go outside of your comfort zone…” — James (22:07)

• On Growth Through Challenge:
  “Anytime you do something worthwhile that does add purpose to your life, there's an element of challenge to it.” — James (22:07)

• Advice to Pre-Retirees:
  “Just seek out opportunities to expand in your new role… find something outside of yourself to reach out and do… Expand your social network. It'll help.” — Jim (35:44)

Timestamps for Important Segments

• Loss of Identity after Retirement: 02:06–03:22; 08:42
• First-Year Emotional Challenges: 12:31–14:01
• Phases of Retirement Experience: 14:39–16:38; 30:54
• Finding Fulfillment through Volunteering and Writing: 04:45–07:36; 17:13–21:00
• Serendipitous Encounter Inspires Writing: 17:13–21:00
• Importance of Environment/Socializing: 28:48–32:55
• Advice for Approaching Retirement & Practicing Retirement: 26:20–28:15; 35:44
• Peak Moments – Publishing "Growing Up: Our Childhood Survival Guide": 37:14–39:08

Book Mentioned

• Title: Growing Up: Our Childhood Survival Guide
• Author: James Selby (Jim)
• Description: A collection of family stories that serve as a memoir and legacy for future generations.
• Quote: “It’s great. So it gives me a fulfillment there. It gives me another boost to work on the next book.” (37:18)

Final Takeaways

• Retirement is a psychologically challenging transition that requires active self-exploration and effort.
• The sense of loss is real but surmountable with time, experimentation, and new social/community connections.
• Creating new purpose—rather than seeking to simply relax—is often key to fulfillment.
• Social environment, willingness to try new things, and serendipitous encounters can create transformative opportunities.
• Prepare emotionally, not just financially, and if possible, “practice” retirement to ease the transition.

Summary by [Ready For Retirement Podcast]
For more practical insights on the realities of retirement and strategies for fulfillment, listen to the full episode with James Conole and Jim.