How Do I Stop Feeling Guilty About Success So I Can Enjoy Retirement?

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By Roger Whitney and RMA. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

There are so many things to take care of in retirement. It can all feel overwhelming. Many people worry about their jobs, the state of the world, retirement, and their uncertain future. On this episode of Retirement Answer Man, you’ll learn what you can do to ease your worries about the unknown as well as discover the answers to questions from listeners like you. Join Tanya Nicols and me as we answer questions about an early retirement package, what to do when you have a significant portion of your net worth in one stock, and how to use second to die life insurance.

What is worry?

Worry is a noun that means a state of anxiety and uncertainty over actual or potential problems. It can also be a verb meaning to give way to anxiety or unease.

Are you a worrier? Although worry is a healthy thing, oftentimes people allow their minds to dwell on difficulties or (perceived) troubles. There is a fine line between healthy worry and overwhelming worry.

The fine line between healthy and unhealthy worry can be hard to walk

Just like how exercise creates stress in your muscles and grows them, worry can do the same to your mind. Worry can spur you into action causing you to improve your situation. However, worry taken to excess can be paralyzing. It can cause you to lose perspective so that you can no longer see clearly. You can’t let worry overwhelm you so much that it steals your life away. Listen in to hear what you can do to help ease your worries about the state of the world, life, and retirement.

How do you perceive the wealth you have created?

It is often said that money is the root of all evil, but this isn’t true. The love of money is the root of evil.

Do you feel guilty about the wealth you have created? Guilt is a common theme for many successful people. Many create an emotional attachment to their money. Rather than judging yourself for creating your wealth, use that wealth as a tool. How you use it is important. What will you do with your wealth to create an amazing life?

What to do when you have a significant portion of your assets in one stock

One listener has ⅓ of her net worth tied up in one particular tech stock. She is looking for some guidance on how to handle this.

A great question to ask is: what would happen to your net worth if that stock simply vanished? This question can get you thinking about how much you need to have a good life. Once you have thought deeply about your life then you can be methodical about this asset. Set a number to help guide you and don’t let taxes sway your decision.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN WHAT DOES THAT MEAN?
  • [1:40] What is worry?
Q&A WITH TANYA NICHOLS
  • [10:56] How do you feel about your wealth?
  • [16:52] What to do when you have a significant portion of your assets in one stock?
  • [22:57] How to balance Social Security, taxes, and an early retirement package
  • [25:46] Second to die life insurance
TODAY’S SMART SPRINT SEGMENT
  • [30:47] Control your input
Resources Mentioned In This Episode

Align Financial

BOOK - The Daily Stoic by Ryan Holiday

BOOK - The Rational Optimist by Matt Ridley

BOOK - The Power of Agency by Anthony Rao

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement by Roger Whitney

Work with Roger

Roger’s Retirement Learning Center

363 episodes