As a bicycle rider I appreciate the importance of avoiding headwinds on a long ride, especially as I near the finish line. A headwind means it will either take more effort or more time to arrive at my destination by the designated time. When I’m already tired neither option is very appealing. And so it is as you approach the end of your journey as the owner of your business: headwinds mean you will have to put in more effort or more time to exit your business in style.

Like me, I expect you’ve had a long, interesting and challenging journey: starting your business, growing it, contracting it, growing it again until it has reached its current stage.  You’d like to successfully end your journey, but question whether or not that’s possible.

If you are like most Baby-Boomer owners, your excitement about the journey just isn’t what it used to be:  the difficulties and trials never seem to end.  But now that you are within sight of your destination, you find yourself riding into stiff headwinds.

You are not alone.  Every owner faces three significant headwinds that increase the difficulty of a successful business exit. One is our flat economy–today and for the foreseeable future.  The second is the substantially higher tax bill you’ll pay when you sell your business. And last, but not least, is the mediocre investment climate that depresses the amount of income you can expect from your sale proceeds and other investments.

Compared to the pre-Great Recession period (1975-2007), these headwinds can double (if not triple) the time and effort you’ll need to create and preserve financial security upon your business exit.

I doubt that this list of headwinds surprises you, but most of us fail to appreciate (much less react to) the effect they have on our ability to enjoy a financially successful life after we sell our businesses.  Ignoring these headwinds has serious consequences: it makes for an exhausting last leg of the ride.