Retirement Answer Man

Are you a bit behind on your retirement savings and wondering how you’ll ever be able to retire? One of our listeners feels the same way. In this Listener Questions episode, I’ll answer his question as well as how to handle net unrealized appreciation (NUA), how to shift retirement savings after a job loss, and we’ll wrap it up by discussing the ramifications of taking Social Security early.

We’re trying a new format this month and releasing 2 episodes a week. On Tuesdays, we’ll release the main segment which focuses on the theme of the month, and on Fridays, you’ll hear listener the questions. Make sure to check out all the episodes and let us know if you like the new structure.

Change is hard!

October has been a month full of change for me and change doesn’t always go smoothly. Not only am I publishing 2 episodes per week, but I’ve stopped drinking alcohol and started exercising in the mornings rather than in the afternoons. 

Any time you bring about changes to the rhythm of your life it can be a challenge. This is why the transition into retirement can bring such trepidation. Even if something new seems daunting, with practice over time the situation will improve. The more you practice the bigger your muscles will get.

With a bit of research, planning, and action, you can learn how to create a paycheck for yourself in retirement, how to tackle your taxes, and how to navigate the healthcare system. Listening to retirement podcasts like this one is a great way to get started. 

How to go from zero to retired

Not everyone has a 7 figure retirement portfolio, in fact the majority of the population finds themselves wondering how they’ll ever be able to stop working. One listener asks how he’s supposed to be able to catch up on retirement savings at age 50. 

The first thing you need to do if you feel behind in your retirement savings is to acknowledge and accept where you are. The next thing you need to understand is that there is only so much catching up that you can do at this point. 

Social Security will be a large part of your retirement equation

After you realize that there is only so much you can do it is time to figure out how to maximize your Social Security benefit. There are a couple of ways that you can do this. The first one is to work longer so that you can increase your benefit. 

The next idea is to navigate when would be the best time for you to file for your Social Security benefit. If you take it early at age 62 you may see your benefit decreased by 30%. Waiting until the full retirement age at 66 or 67 will ensure that you get your full benefit amount, and each year that you wait to file your benefit will increase by 8%. The beauty of Social Security is that it is adjusted each year for inflation and it lasts for the rest of your life.

Retirement is about living out the best version of yourself

To create a retirement plan you can live with, you’ll want to increase your income and decrease your monthly obligations as soon as possible. Identify which bills you can pay off and try using the debt snowball method to pay down your debts. The less you can live on the more prepared for retirement you will be. Try to create a living environment that doesn’t require a lot of money. 

Remember that rocking retirement isn’t about spending loads of money, it’s about creating an environment where you can live the best version of yourself. 

If you have a question to ask head on over to to send a written question or leave a voice message. 


  • [5:00] How to go from zero to retired in 10 years
  • [12:08] How to handle net unrealized appreciation (NUA)
  • [20:23] How to shift retirement savings after a job loss
  • [25:25] The ramifications of taking Social Security early

Resources Mentioned In This Episode

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: RAM399.mp3
Category:general -- posted at: 2:00am CDT