How Does A Sole Proprietor Retire? 
The answer to the question is that you do it when you 're ready . Now that my feeble effort at humor is out of the way , there are ways to leverage your company success into a retirement . You could work a mutual purchase agreement with a similar competitor . You could groom a key employee as a successor-buyer and help them finance the purchase or down payment . You can secure the sale with life insurance too . 