Mike,
Good questions for personal thoughts and reflection:
Help us understand where you're going with this goal. You mention "the rat race." And you mentioned "a computer screen 14 hours a day for someone else."
What do you do for money now? I am in the commercial real estate industry making investors lots of money. Which has been great to team me everything about investments up until this point.
How much extra money are you making right now? Above your bare needs? Currently I am making quite a bit but I have been rolling it all into real estate investments. Haven't really pin-pointed a dollar amount as I have been moving/buying places for the past 2 years and haven't ever stayed in one place for more than a few months.
What are the problems with where you are now? What exactly are you trying to change? I currently live next to 7 of my tenants with zero land. I want land, incoming producing land would be an added bonus.
How do you anticipate that being a agricultural business owner will remedy what doesn't suit you about your current situation? I like the sustainable act (or thought of it anyways) of this. I wish to produce more of my own food, work with my hands outside, etc.
I would like to hear the answers to these things, but for an initial bit of feedback with the little information we've got, I wonder if you might be shooting your mosquitoes?
14 hour days are tough. Is there a way to get your work under 40 hours, with the commensurate pay cut, and regain some of your life without necessarily uprooting and changing everything? Absolutely; however, I don't mind working long/hard days. It's just what I do. I am motivated. I would just rather focus this energy towards other endeavors. I am going to keep my rentals, and keep buying more with syndicated funds among people I know earning myself ownership without putting in my own money and taking finders fee's.
I'm in a situation these days where I dread my work. I've been her before, and I got so desperate that I changed fields. I regretted it, and came back. Turns out, the work isn't bad, but an unreasonable workload is. The answer? In my case, go self-employed. People will overwork you when you're salaried, because why the heck wouldn't they? But if they pay you by some unit of work, then they're much more sensitive to things like, "Sorry, that's more than I'll be able to do a good job on right now." - I am currently a commission contractor, and have the freedom to do what I want, I just don't enjoy it. I am all for taking huge risks and leaps of faith. We won't be 30 years old for a few years yet so we have plenty of time to decide we don't like it and undertake the next endeavor should we want too.
Nonetheless, I will be buying land away which I can enjoy, grow some food, etc. We both want to quit or "jobs" and migrate to jobs we fully choose to do which result in us having more time for ourselves, hiking, outside, wilderness, etc. I will keep my investments, I will keep my float business, etc. Just want to add to the portfolio of life by figuring out something that gets me into being outside and creating something (if that makes sense) - food, tree's, whatever it might be.