Your story sounds very familiar to mine Greg! I had been working for my dad off and on since I was 16 and part time while I was in college. I really had no idea what I wanted to do and no matter how hard I fought it I still found myself being pulled back into the family business because I really enjoyed working in landscape. When I was about 22 or 23 I came to work for my dad full time and at that point started trying to really grow the company. At one point in the 80's my Dad had built a pretty big operation but after the recession and loosing a key manager the company kind of languished for most of the 90's. I remember asking him what his long term plan was and he told me that he didn't really have one. He said he planned on running the company until he was no longer able and then sell off any remaining assets. By this point he was pretty burnt out. I remember thinking that his plan was pretty sad.... he had worked his entire life building this company and he was just ready to let it all go. Just as things were starting to happen he died suddenly of a heart attack in early 2002. By this point I was 26 and had spent most of the last 4 years working just about every single field position in the company. Maintenance, Irrigation, Construction, Supervisor etc etc. I knew all of the field operations forwards and backwards and my dad ran all of the back end of the business. Very quickly I found myself behind a desk instead of in a truck. It was quite the abrupt learning experience. By 2008 I had taken the company from 9 employees and $340K in revenue to 50 employees and over $1.5mil in revenue. I learned a lot... some of it the hard way.... but we're still here and the trucks still roll out every day. I guess my advice would be that if you son wants to get involved make him start at the botttom (sounds like he already has some field experience) and learn the basic operations of the company. Once he learns the field end of the operation make sure he knows the business end. Luckily I knew enough of the basics to keep us out of trouble. The other thing would be to have a clear plan for the change in ownership if your company is a Corporation or an LLC as well as a contingency plan just in case one day you're suddenly not there anymore. We had none of that and it made things difficult as we transitioned the ownership of the company to my name. If he intends to grow the business make sure you have a solid map and a written plan. I didn't. It was all in my head and changed frequently which in hindsight was a really stupid way to grow. Pick one or two areas of focus for expansion. When my dad was around we did everything. At the peak of the boom a couple of years back we walked away from commercial construction and focused solely on commercial maintenance. everybody told me i was crazy..... they don't tell me that now. It's better to do one or two things really well than to do everything all halfassed. I think it's great that your son wants to be a part of your business. I'd say let him come on board and see what happens. You'll still be in control of the thing so you can make sure that nothing crazy happens and if things progress in a positive direction you can slowly turn more and more control over to him as you get closer and closer to thinking about retirement. My dad was very much like you say that you are in that he tended to be very risk-averse but he did let me have some freedom to make big decisions. I've made some HUGE decisions that I know he would have never made but I think he would have understood even if he didn't agree with them. I wish that he was still around because he taught me 90% of what I know about the business and there are still things that he could teach me. That said.... Good Luck!