Well, I explored these options at length this year, and concluded that I couldn't do it and keep a viable relationship with my wife, and support my 3 year old daughter, even though my wife has a well paying job.
There are attractive options for outdoors educators and guides, speakers and consultants on leadership, park rangers etc. None of these gigs pay well, but they do involve significant time outdoors, so if that's the goal... basic starting qualification is WFR and/or some kind of outdoors or environmental certificate or degree (you know, ropes/environment/geology/botany etc) - so that you have something interesting to teach. I had thought to combine with a creative outlet - perhaps poetry on the trail or something...
If you have ability, an interesting message or valuable topic to teach, and are not constrained by family or other obligations, you should go for it and live out your dream. Just remember - "vision without action is a daydream, action without vision is a nightmare". You need to carefully set out your goals, then make a concrete plan of action to get there - just like planning any outdoors adventure! There is work to be done here. Don't assume that if you hang out a "guiding" shingle, people will just come. You need to attract people to your services. Marketing! A good exercise would be to make a "brochure" for yourself... what would you say? Why the hell would anyone hire ME, when they can hire Skurka instead!? What is MY message? How will I make a difference in my clients' lives? If you can't articulate it... it probably isn't a good path for your life! ;-)
In the end, this is your life - you get to choose to waste it or spend it wisely. If you have a passion to teach in the outdoors, combined with something meaningful to teach, if you have gift to give others - go for it! Just my $0.02.
Cheers & good luck!