Complete and utter freedom immediately may induce sadness
Did you know it's highly possible to quit your job and then do absolutely nothing for a whole year, drain all of your savings, and then need to find work again?
I know because I did it myself. I was so frustrated with work that I completely quit all money-making activities for other people and gave myself a year to make a go of it on my own.
I promptly sat down and spun my wheels for a year. I got really good at taking walks, cleaning the house, cooking, and browsing the internet. But at the end I was back where I started business-wise, just with a whole lot less money in the bank.
You ask: How in the world can someone sit on their laurels for a whole year? Simple: most people have never experienced the awesome freedom that comes from being completely self-determined. It's an environment completely foreign, since we are forced from birth to live within a highly structured environment of parents, teachers, professors, and bosses telling us what to do. It's amazing, but requires time to learn how to manage it.
So don't quit your job just yet!
Ease into freedom to allow yourself the time to adapt to this new environment without putting your own and/or your family's financial wellbeing on the line.
Fortunately, there are a wide variety of ways to inject more freedom into your current 9-to-5 without quitting your job completely and immediately.
Consider that any of these options are realistic possibilities:
That's a fair question. It would probably be a hard sell to walk into your boss's office the first week on the job and demand working 3 days a week. But if you've been there for years and have provided valuable work, that request could be entertained more seriously.
A book I highly recommend to anyone considering going independent is "So Good They Can't Ignore You" by Cal Newport. He discusses the idea of "career capital". That is, the longer you work at a company, and the more value you provide your employer, the more goodwill you build up which can be used as leverage for more favorable working conditions.
And you can progress even within this continuum slowly but surely. If you've never been allowed any remote work days, consider pitching working 1 day a week from home and see how that goes. See if you can actually handle working remotely. If you are completely unproductive working from home, you might want to master that one day a week of remote work before jumping headfirst into freelance. You might find this working remote thing just isn't for you, and that would be a great thing to learn before quitting.
I hear people often talking about their "runway" - that is, how many months of time they have to become financially solvent before they run out of money. Sometimes this is called the runway of doom, because if your plane gets to the end of the runway without taking off, you just crash and burn. Maybe you work well in that kind of pressure-filled environment, but I absolutely don't. And even if you do, your more risk-averse spouse may not.
I say we can bypass the runway by never taking an all-in risk of ruin. Balance high risk income with low risk income. When you are first building your freelance business (high risk), keep some income from your employer (low risk). If you get to the point of quitting your job, your freelance is secure, and you'd like to work on building an app (high risk), keep some freelance income while you build your app (low risk).
Being completely independent is amazing, but takes some getting used to. For another perspective, David Cain over at Raptitude wrote this insightful essay on his experiences going fully independent.
I first sent this article as a letter to my mailing list. New letters go out each week!
Learn freelancing from someone who's gone down this path before. In the the Less Boring Letters, I'll teach you everything I know about ditching the 9-to-5. Build a profitable new business that you love, benefitting from all of my trial and error.
"I send all my newsletters straight to an email box I almost never read... except David's! Insightful, honest, sometimes downright hilarious, and truly helpful even after years of freelancing."
It Must Bee: Websites with a Buzz!