Ready For Retirement Podcast Summary

Episode Title: Ready to Retire? Here's How to Tell Your Company │ Root Talks
Host: James Conole, CFP®
Release Date: May 29, 2025

Introduction

In this enlightening episode of Ready For Retirement, host James Conole engages in a deep discussion with his co-host about the intricacies of announcing retirement to an employer. Prompted by a community post from Eric in the Root Collective, the conversation delves into both the logistical and emotional facets of retiring, offering listeners valuable insights and real-life experiences.

Financial Preparation

Ensuring Financial Readiness

Before even contemplating the emotional challenges of retirement, it's crucial to have a solid financial foundation. Co-host B emphasizes the importance of several key financial considerations:

• Income Replacement: Assess whether your retirement income can adequately replace your current paycheck.
• Insurance Coverage: Ensure that you maintain appropriate health insurance and other necessary coverages post-retirement.
• Investment Adjustments: Make necessary changes to your investment portfolio to align with your retirement goals.
• Tax Strategy: Develop a strategy to minimize tax liabilities as you transition to living off your investments.

Quote:
"The big things I look at is, do you have income to replace your paycheck? Do you have insurance coverage that will see you through?" – B [01:28]

Emotional and Psychological Aspects

Valuing Time Over Money

Transitioning into retirement isn't solely a financial decision; it's also deeply emotional. Co-host B discusses the struggle between valuing time over money and the fear of letting others down:

Quote:
"I need to start valuing my time over money." – B [00:00]

Work Relationships and Loyalty

Many individuals develop strong loyalties to their employers, often viewing work relationships as familial. However, B highlights the importance of recognizing that:

• Work is Not Family: While work can foster meaningful relationships, it doesn't replace the unwavering support of family.
• Replaceability: Employees are often more replaceable than they realize, which can impact how one approaches retirement.

Quote:
"Work is never going to be family. Family is going to be this group that, for better or worse, they're with you through it." – B [03:52]

Overcoming Fear and Regret

Referencing Bronnie Ware's "The Five Regrets of the Dying," the conversation underscores the common regret of spending excessive time at work at the expense of personal life:

Quote:
"One of the top five regrets was too much time spent at work. People who felt like they had to give their all to their employer." – B [07:50]

Telling Your Employer

Preparing for the Conversation

Communicating your decision to retire requires careful preparation, both financially and emotionally. B advises setting clear endpoints and being firm in your decision to prioritize personal freedom and time:

Quote:
"Everything you do to say yes to work, you're saying no to the things you actually want to do." – B [03:52]

Handling Pushback

Employers might attempt to dissuade you from retiring by offering incentives or adjustments. It's essential to remain steadfast in valuing your time and recognizing that:

• Saying No is Okay: Each time you decline additional work or incentives, you affirm your commitment to your retirement goals.
• Role-Playing Scenarios: While it's natural to anticipate various reactions from your employer, B encourages addressing the conversation head-on rather than over-preparing.

Quote:
"Don't worry about hitting it perfectly as much as just making sure that message is heard and that you're staying firm with what the non negotiables for you are." – B [16:13]

Practical Strategies

• Set Clear Timelines: Define a realistic timeline for your departure to ensure a smooth transition.
• Be Honest: Understand and communicate why you're choosing to retire, whether it's to pursue personal passions, reduce commute stress, or other motivations.
• Stay Professional: Maintain professionalism throughout the process, thanking your employer for the opportunities while asserting your decision.

Listener Responses and Experiences

Community Insights

The Root Collective provided numerous responses to Eric's initial post, offering a wealth of perspectives on retiring. A highlights a few notable experiences:

1. John Hawkins' Seamless Transition:

   • Experience: John gave six months' notice after nearly 30 years with the company.
   • Outcome: The transition was smooth, with phased handovers that reduced his anxiety.
   • Quote:
     "Phase one was where helping people take over my accounts... Phase two, I had them leading discussions, and I found this decreased my anxiety." – A [07:50]

2. Tommy C's Prepared Response:

   • Experience: Tommy was ready to decline offers to stay, focusing on his love for the work.
   • Outcome: He maintained his decision without being swayed by additional incentives.
   • Quote:
     "If they offer me more money to stay one more year, my prepared response was, I just love this." – A [20:27]

3. General Advice:

   • Preparation is Key: Understand that colleagues may react variably—some may congratulate you, while others might distance themselves.
   • Maintaining Relationships: Retirement doesn't mean social isolation; continue to seek connections post-retirement.
   • Value Recognition: Sometimes, employers may not value you as much as you value them, highlighting the transactional nature of professional relationships.

Personal Stories from Hosts

Co-host B's Jet Ski Incident

To illustrate the importance of facing difficult conversations head-on, B recounts a personal story from his youth:

Story Overview: At 18, B was with friends on jet skis. In a playful moment, he threw a friend off his jet ski, leading to a collision. Despite no one being hurt, B felt significant anxiety about reporting the accident to his friend's father.

Lessons Learned:

• Facing the Consequences: Instead of avoiding the situation, B confronted it directly by informing the friend's father.
• Hard Choices vs. Suffering: The act of addressing the issue was hard, but avoiding it would have led to prolonged suffering.
• Core Message:
  "Do the hard, not the suffering. If you want life to go well, make those hard decisions." – B [08:37]

Co-host A's Approach to Client Advising

A shares an experience where he helped a client decide to leave an unfulfilling job by emphasizing quick action over prolonged deliberation:

Story Overview: A client was hesitant to quit their job despite recognizing its non-alignment with their personal happiness. A prompted the client to imagine quitting immediately and pursuing a more meaningful path, which accelerated the client's decision-making process.

Lessons Learned:

• Prompt Decision-Making: Encouraging swift action can help overcome inertia and indecision.
• Accountability: Being present and supportive as an advisor facilitates better client outcomes.
• Client Empowerment: Helping clients recognize their true desires beyond mere financial considerations leads to more fulfilling retirement choices.

Insights and Conclusions

Embracing Change and Prioritizing Personal Goals

The episode concludes with a powerful reminder that retirement is not about abandoning work but about prioritizing what truly matters in one's personal life. B underscores the significance of:

• Understanding Motivations: Clearly define why you want to retire to ensure your decision aligns with your personal aspirations.
• Negotiation: If retirement stems from specific work-related issues (e.g., commute, travel), explore possible adjustments before deciding to leave entirely.
• Holistic Planning: Retirement should be approached comprehensively, balancing financial readiness with emotional well-being.

Final Quote:
"Continuing to say yes to work if you're in a position where you should retire is saying no to the things that you actually want to do." – B [23:28]

Encouragement for Listeners

James and his co-host encourage listeners to engage with the Root Collective for more insights and to seek professional advice to ensure both financial and emotional readiness for retirement. They emphasize that while the path to retirement can be challenging, the rewards of living a life aligned with personal values and passions are invaluable.

Notable Quotes

• "I need to start valuing my time over money." – B [00:00]
• "Work is never going to be family. Family is going to be this group that, for better or worse, they're with you through it." – B [03:52]
• "One of the top five regrets was too much time spent at work." – B [07:50]
• "Everything you do to say yes to work, you're saying no to the things you actually want to do." – B [03:52]
• "Don't worry about hitting it perfectly as much as just making sure that message is heard." – B [16:13]
• "Do the hard, not the suffering. If you want life to go well, make those hard decisions." – B [08:37]
• "Continuing to say yes to work if you're in a position where you should retire is saying no to the things that you actually want to do." – B [23:28]

Final Thoughts

This episode of Ready For Retirement provides a comprehensive guide to navigating the often tricky process of announcing retirement. By blending financial advice with emotional support and real-life stories, James Conole and his co-host empower listeners to make informed, confident decisions about their retirement journeys.

For more insights and community support, visit the Root Collective and join the conversation to ensure a secure and fulfilling retirement.