Retirement Answer Man

Do you want to have the confidence to truly rock retirement? Are you within 5 years of retirement? If so, this is the series for you. Over the next 5 episodes, we’ll explore what you should be focused on in the years leading up to retirement. 

Today we’ll explore the opportunities and risks that come within this time frame. Next week, we’ll start setting the stage to prepare you for retirement. After that, we’ll explore the financial and non-financial aspects of preparing for retirement. In the 4th episode of this series, you’ll learn how to put it all into a plan. And lastly, you’ll hear an episode full of wisdom from people who are a bit ahead of you in this retirement journey. Are you ready to get started? Press play now!

Preparing for retirement is much like prepping for an adventure

In the 5 years leading up to retirement, you need to get ready. It’s as though you are preparing for an adventure. I liken it to a backpacking trip I took a few years back. First, my partner and I had to decide where we wanted to go. Then we had to arrange the logistics. Next, we had to assess whether we had the right equipment for our journey. Then we had to consider both our physical and mental readiness. After that, we had to acquire the things we needed. Once we finally got to our destination we had to assess the trail ahead. We even had to add extra supplies based on those trail conditions. We had to remain agile throughout the course of our journey. 

The opportunities and barriers to preparing for retirement

At this point in your career, you are probably making more money than you ever have before. You have a reputation and a vast professional network. You may even be at the tail end of the various financial engagements that come with raising a family. Now is a good time to evaluate your life. 

There are some barriers that you may need to overcome as you prepare for retirement. I often refer to the 50s as your not-so-thrifty 50s. It’s easy to save more and spend less now that you are earning more. It’s also easy to create a financial cage for yourself. Be careful of financial obligations like 2nd mortgages, RV or boat payments, or even that adult child that you continue to subsidize. These obligations could force you to work longer than you would like. Listen in to hear about more barriers you might face as you prepare for life in retirement. 

What can you do now to set yourself up for retirement?

There are several steps you can take to begin to set yourself up for retirement. 

  1. Start to assess your risks and opportunities by dialing in your income, expenses, and savings. Think about your expenses. What does it really cost to live your life? Separate your discretionary and non-discretionary spending to realize what it takes to live a good baseline life.
  2. Create your net worth statement listing your assets and liabilities. 
  3. Assess your boundaries at work. You have worked hard to build your career, but have you built up boundaries between work and home life?
  4. Assess your social life. Who would you call to have coffee with tomorrow? Do you need to broaden your social network?
  5. Assess your purpose. If you had 2 weeks to not think or talk about work what would you do each day?

It’s a great time to join the Rock Retirement Club!

Are you signed up for the 6-Shot Saturday newsletter? You’ll want to make sure that you are so that you can get our free net worth and expense worksheets.

Have you been on the fence about joining the Rock Retirement Club? Now is a great time to join because on March 16 we are starting a 3-week sprint to assess your needs, wants, and wishes. You can try it out for 30 days with a money-back guarantee. Go ahead and join now to see whether it is right for you. 



  • [3:30] A Rock Retirement Club update
  • [4:04] The five years leading up to retirement is much like prepping for an adventure
  • [7:27] You have opportunities that you don’t want to miss in the 5 years 
  • [11:37] What can you do now to set yourself up for retirement?


  • [21:51] Using a Roth IRA to fund long term care
  • [27:11] Roth IRAs and the 5-year rule
  • [30:04] Roth IRAs and Game Stop


  • [31:57] Start to dial in your expenses and update your net worth statement

Resources Mentioned In This Episode

Share your wisdom with future retirees!

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Work with Roger

Roger’s Retirement Learning Center

Direct download: RAM367.mp3
Category:general -- posted at: 5:00am CDT