Interesting thread Adam. Thanks for sharing some of your experiences. I do believe it's different for everyone though....and it's impossible to predict the future how everything will eventually pan out.
I was employed for 4 years, and then self employed climber for 21+ to the present. For me the freedom, the experiences, the opportunities, the challenges, the money, completely outweighed any perks that employment had to offer. Paid time off at xmas and stuff....never meant anything to me, comparitively.
The key to continuity on my part was to make money for people....and take away their own confidence in their ability. That means constantly evolving and improving ones arsenal. And when you're doing tough jobs everyday, they just become routine. Easy. Whilst if a person only gets a tough job once in a while they're gonna find it a much greater challenge and often take a more cautious and lengthly approach. Interstingly, during many quiet periods when companies don't have much work on, I've found myself really busy....because collectively those companies have only had jobs on the sceduale that suit my skills a lot more than theirs. Just the way it goes sometimes.
More recently I've been doing sourcing a lot more if my own work, with a view to phasing out the freelance climbing etc. I've grown tired of salvaging underbid and poorly negotiated jobs; of hearing how hard it all is to run a full tree service. I'm not sure what kind kind of life they lived but clearly people's perception of hardship is quite varied. Work is not exactly falling at my feet right now at this early stage, but it's coming, and gaining. Because I'm hungry. I don't expect anything to be easy. This week I worked 4 days, and finished at 7 - 8 o clock on three of them. Just me, the whole jobs. No helpers. But I've got a pot of money for it. To keep. Feels good.
Some times bad life changing stuff happens as had with some members here more recently....and can happen to anyone. But outside of that it really is what you make if it. How you as an individual can impose your self on people and situations.
If I could give just 3 pieces of advice to aspiring freelance climbers they would be : always pick the toughest trees on a site. Keep learning and evolving. And always go home with a check at the end of a day or which ever is the last day of the week you work with that company....without exception or excuses.