Retirement Answer Man

Why do people start businesses in retirement? Over the next few weeks, we explore this question in the Entrepreneurship in Retirement series. Just because you retire doesn’t mean that you stop living. Many people have so much to give back after they retire that they choose to start their own business. This episode will cover the whys, the ways, and the hows of beginning entrepreneurship in retirement. If you are thinking of starting your own business or having a pretirement phase to your retirement you won’t want to miss this series. Listen to this episode to get started planning your own entrepreneurship dreams.

Why do people start businesses in retirement?

More people between the ages of 55 and 64 start businesses than people under the age of 25. This fact surprised me. Why do baby boomers want to pursue entrepreneurship in retirement? There are several reasons. Just because we retire doesn’t mean we stop living. We still have a purpose. Many people start a business in retirement to pursue their passions. Some people want a bit more money to supplement their lifestyle, others find it a great way to give back to their community. Many want to share their expertise with the world. Why are you thinking of entrepreneurship in retirement? Listen to this episode to hear the many reasons people start businesses in their retirement years.

What are you trying to accomplish?

Before you start a new business you should ask yourself, what are you trying to accomplish? Are you strictly looking to supplement your income? Are you looking to follow your passions? Are you trying to give back to your community? The reason that you choose entrepreneurship in retirement is important. This will shape how you form your business. You don’t want to start a business where your goal is to have flexibility and then find yourself working 60 hours a week. Listen to this episode to hear why it is important to think about why you want to start a business first before you actually begin.

What are the different ways to start a business?

There are many different ways to start a business. A solopreneur is someone who wants to strike out on their own. A solopreneur could make crafts to sell, have a coaching business, or pursue a passion. Usually, a solopreneur doesn’t want to grow too big. A franchise is a way to buy a ready-made business that already has a plan and structure in place. A service business is a business where you can serve others. These different types of businesses have different structures and varying start-up costs. Listen to this episode to help get you thinking about the type of business you would like to start.

Be careful that you don’t commit financial suicide

When you retire you probably will have access to more money than you ever had before. This can be tempting when you want to start your own business. You may want to start your business small so that you can see if it is actually a viable business plan. Test your idea to ensure that it fits your finances as well as the market. You may find that your passion may not be the passion of others. If you start out small you can always find a way to pivot your business without committing financial suicide. Listen to this episode to hear why it is so important not to throw all of your money at your new business.



  • [2:49] Why do people start businesses in retirement?
  • [8:54] What to expect in this series of episodes of Retirement Answer Man


  • [9:51] What are the ways that you could start a business?
  • [12:20] What are you trying to accomplish?
  • [15:50] Be careful that you don’t commit financial suicide
  • [19:55] Make sure that your business idea fits the market
  • [21:17] What are some tools you can use to help you get started?


  • [23:20] Change your mindset to control your life


  • [25:10] Go to the resource section and get a book to help you get started

Resources Mentioned In This Episode

BOOK - 48 Days to the Work You Love by Dan Miller

BOOK - The Lean Start-Up by Eric Ries

BOOK - The Pumpkin Plan by Mike Michalowicz

BOOk - The E-Myth Revisited by Michael E. Gerber

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Ask Roger a question

Work with Roger

3-video Series: 5 Minute Retirement Makeover

Roger’s Retirement Learning Center

The Retirement Answer Man Facebook Page

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Direct download: RAM224.mp3
Category:general -- posted at: 6:00am CDT