What have you done and what would you be willing to do to financially support your family?

Because you're a COL, it's very likely that you fit well within the team atmosphere of the military. You've succeeded in that environment, and you find it rewarding to think strategically and build teams to accomplish an objective. I tried positions in two major defense contractors, and the atmosphere was so profit-driven and two-faced that I found it toxic. I now work as a direct support contractor, rubbing elbows with active duty and GS staff officers daily. My pay is much lower, but I am much happier. I would LOVE to teach in an environment where I am allowed to build lesson plans and given the latitude to tailor the course of study to my students. The public school system does not allow that. My advice? Know yourself and know the culture before you leap.

The Army Reserve was my retirement plan. At the time I joined, I was working as a mechanic and just got dumped from a retirement plan. Then I went to work as a professional guide, not much retirement in that. I figured no matter what I got, my Reserve Career was better than nothing, so I did 22yrs, 4 months, 18 days. I knew I couldn't collect until I was 60, that was the plan. In between I also invested in land, bought silver and gold. I've purposely stayed away from stocks because I've never been in the position to watch them.
As a self employed person, I've had to save. So I've set aside money my wife doesn't know I have, and I have the self discipline not to touch it( also it's in a safe deposit box in another country). I've made sure my wife is in DEERS, and she knows where my DD-214 is and all my important papers so she can file for my retirement.
When I was getting deployed I had a Vietnam Vet friend whom I gave a general power of attorney. My wife(Danish) doesn't understand the military system, so it was written in my deployment no notification team could come to my house without my Vietnam Vet Friend because he also spoke Danish and she knew him. I was very lucky this way. This way I was free of mind when deployed.
Now I am self employed as a Farrier. We own a horse transport which my wife drives in the spring, summer and fall. I shoe horses. I came back from Iraq with a collapsed disk in my back and my left shoulder screwed up, but I still have to work 5 more years. I'm 60 now and able to draw my pension, but I am not touching it. I am saving it so we have something when I stop working. Mornings I am glad for the pain in my back and shoulder pains because it lets me know I'm not dead. Yesterday I had a customer ask me how long I was going to be able to work because my work is physically taxing on my body. I told her as long as I could. Between what I've squirreled away, saved and planned for, if I die before my wife she should be able to live good.
You young bucks: PRIOR PLANNING PREVENTS PISS POOR PERFORMANCE; or, you might have a retirement. You are never too young to save and no amount is too small. I am lucky, right now, because of my Army Reserve Career, I am able to save over $2,000 a month. This I will not touch for the next five years.
Looking back I could have done better. But looking back, I think if I die before the wife, I will leave her sitting good.

Since retiring from the USAF in 1992, I've driven commercial vehicles in 48 states, software technical support, software development, software quality assurance, and (for the past 20+ years), caused ones and zeroes to move through copper wires and fiber optic cables. In addition to that, since 1976, I've owned and operated several mobile disk jockey services...which I still do today... Whatever you do, if you're not having fun doing it, it's probably not worth doing.