For example what exactly the move from employee to contractor entailed, or the one from contractor to consultant?
Most contractors tend to try to move from one contract to the next with as little downtime as possible, or work for an agency that sorts it all out for them. For me, the downtime was the big payoff, since contracting pays roughly double what a salaried job does. If you have no attachments, you can spend a fair amount of time slacking off before picking up another contract. I used to push it as far as 9 months off between 3 month contracts and still put plenty into savings.
Repeat the above enough times, and you'll be able to break off work that doesn't require you to be on site, or pick up work from new clients from word of mouth. Some people refer to this as freelancing, but then they don't get to charge as much if they use that term in front of a client. Naturally, it's best to describe yourself as a consultant instead, and double your rate again.
Save up a couple of months salary if you can, make your CV all shiny, and send it out to every job board you can find, with your phone number, email and location at the top. At the same time, send a friendly email and your CV to everyone you've worked with, saying "Hey I'm available for contracts doing X, Y or Z. If you hear about anything, please let me know".
There's no need to quit your job early, you're just going to be leaving like you would for another permanent role.
When someone says they've got a contract for you, sign up for Parasol or a similar umbrella company so paperwork is at a minimum, and away you go!
I'm not hugely experienced at contracting, but since I started doing it a few years ago, another couple of friends have gone down the same route and it's worked out well for them too.
If you're good, learn quickly, and you're honest about what you can do, contracting is a great route for a few years of experience across a range of projects.
After the first couple of contracts, if you're happy with how it's going, then get yourself setup with your own limited company which means you'll end up with more paperwork, but more money in your pocket.
And of course once you've done it a few times, you'll have previous employers bringing you back in for more projects. So at most you might only need to go through that fear stage a few times before you've established yourself.
Does this mean moonlighting and taking side gigs? If so, can it be done without sacrificing personal/family life? Not to mention, possibly living with exhaustion.
Of course, it never hurts to build cool, visible things that you can point to when people ask what you're capable of.
But if you're healthy, 20 - 30 type, and you're seeing the doctor once or twice a year and maybe using prescription meds occasionally for a bacterial infection, then you get the 'high deductible' plan, you end up paying for that stuff yourself but if you happen to be in a wreck or you get cancer or something the insurance will cover it once you get past your deductible.