People live deferred lives out of fear. If we rationalize those fears, however, nothing stops us from doing what we aspire to.
We can distinguish two kinds of fears preventing us from making drastic lifestyle changes: social fears, and financial fears.
"What will my boss/partner/friends/neighbors think of me?" is the classic example of social fear put into words. Just realize that your life is yours, and that nobody else should make decisions for you.
If you have duties and responsibilities to oblige, just remember that reality is negotiable. If you really want change, you'll find a way to make time for it to happen. Got young kids? Paint/write/make music while they're asleep. Cumulating too many jobs? Stop buying stuff you don't need, move to a cheaper place, and invest all your time in developing your skills.
Your social status should be irrelevant to your decision-making process. Nobody cares if you're the director of X at Y or the CEO of Z, because it doesn't define you as a person. If a job position is your dream, you're not dreaming big enough.
Financial fears are wicked ones too. You should be afraid of ending up living in the street or not having enough money to have a balanced diet, but you probably don't need the comfort of a house with too many rooms to count or hundreds of shirts. Make compromises to live a simpler life that won't force you into financial slavery if you were to be jobless for a year.
Financial independence is subjective: if you're debtless, you're already richer than 87% of the U.S population in 2018. A debtless beggar is richer than most of the U.S population. It all comes down to how resilient you are. A human doesn't need much to live: a roof above your head, three meals a day, and friends to talk to when life gets rough. When those basic needs are taken care of, you are ready to work toward the projects mattering to you.
What's the worst that could happen?
Failing to make the transition and getting back to your previous situation? It's part of the learning process. A bird didn't teach itself how to fly in a day. Its experience did, and it took many leaps of faith. Don't be afraid to fall.
Running out of savings and living at a friend's/parent's/lover's? You'll find a job again. Just don't limit yourself and use your creativity to get back up financially.
Ending up in the street? Move to the countryside, buy a $20 tent on Amazon, live off bread and canned beans, use public water fountains, and go to the library for free Internet access. Or maybe find a plan B before that happens.
In fact, the worst thing that could happen is you dying tomorrow without having lived fully. Carpe diem.