Dirty Secrets of Small Business

Dirty Secrets of Small Business


What Are You Retiring To?

August 17, 2023

In This Episode

Are you ready for retirement?  I can’t wait for retirement!!  Can I retire now?  Everywhere you look you can find someone trying to give you advice on retirement.  But as a small business owner, retirement is likely something you’re not looking forward to.  I mean isn’t retiring something old people do?


We have been involved in dozens of business transitions with companies transferring ownership from one generation to the next.  One of the biggest items slowing down business transitions is the current owner figuring out what they are going to do next.  And “retirement” isn’t likely in the cards.  So what’s a business owner supposed to do in retirement?


In addition to coaching folks through transitions, we’ve also helped several of our clients grow and then eventually sell their businesses.  Often they sell when they are in their 40s or 50s and they have enough money from the sale to retire, but what they’ve reinforced is that most small business owners don’t retire well if they are trying to retire to nothing or a life of sitting around.  The key is finding something to retire to.


Here are some thoughts and ideas for how to figure out what you’d like to retire to:


  • Business: knowing what you know now, why not start or buy another business?  How much easier will it be to run a business now with all the successes and mistakes you’ve had in the past to build upon?  Maybe you could be a minority owner in multiple businesses.  How about consulting.
  • Volunteer/Non-Profit: maybe there are organizations you’ve been supporting for a while but now you’ll have more time available to help out.  If you don’t have a cause yet, spend some time looking for one.  Ask some of your friends what they’re involved in.  Visit different groups and check them out.  If one doesn’t exist, maybe you could set up a non-profit.
  • Politics: one of the seeds we plant with many our clients is one about politics.  We encourage them to get involved whether it be at the local level or perhaps national.  Our political system needs more good people who know how to get stuff done and that is the epitome of a small business owner.

Other folks have likely talked to you about traveling and playing golf or pickle ball or spending more time with your family and perhaps kids or grandkids.  And if those sound like fun to you, well then give them a shot.  But don’t feel guilty about trying other things like some of the things we outlined in the show today and above including Jack’s personal journey of trying to retire twice and vowing to never do it again.


People, Companies and Resources We Mentioned in the Show