You're going to get bored
When I got my first 1099 gig, it was awesome!
I made more money, took Friday's off, and felt like Leonard Dicaprio's character in Titanic: "I'm on top of the world!"
Last week, I sat and stared at my screen at work and was literally unable to do ANY of my work because it was so boring. I was supposed to write up some documentation for a dashboard I made and I just did not want to do it.
There are days when I'm driving to the client site and I think "what if I just kept driving" because the thought of doing the same boring thing over and over again was so demoralizing.
Even money and flexibility couldn't solve this problem.
Money and flexibility only solve money problems and flexibility problems
Boredom problems are different. Boredom problems require you to either
a) Become a zen master and achieve Nirvana or
b) Do non-boring things
I was only half joking about the zen master thing. It's important to be mindful of your feelings and observe them without judgement. Doing so will allow you to appreciate the life you have rather than resent the life you don't have.
On the other hand, because you're not going to become a full time monk, you still need to do non-boring things.
Pursuing your first 1099 gig is a non-boring thing. It has clear rewards and concrete actions you can take.
But, it's also worth considering pursuing other non-boring activities you can either do now or when you have more flexibility and money from your new 1099 gig.
I like writing so I have been writing on and off for my other project, The Ancient Wisdom Project, since BEFORE I went 1099.
I also wrote the Going 1099 book, attempted to grow my business with employees, learned the game of travel hacking, had a kid, and watched Yellowstone and considered moving to Montana to become a rancher.
The most non-boring things I do generally involve creating, rather than consuming. So that may be an angle you want to think about when you inevitably find yourself zooming past your office and driving to Florida.