When you work for yourself you leave behind a major support network, your employer, which provided external accountability and a venue to ask for help.
That void will need to be filled. But you don't have to leave it until after you quit. You can start thinking about it now. In fact, having a "future work" support network already in place will likely help accelerate your journey by providing inspiration, accountability, and access to people who are a few steps ahead of you.
Here's how I might visualize it:
On the X-axis you've got the "typical" payment model. On the Y-axis you've got the level of external help and accountability, which rises on a curve.
With free-to-play communities there's very little formal accountability, conversations as public record, less room for nuance, and little to no filtering on participation. You're incentivized to stay on platform, leading to bad habits. Examples: Twitter/Facebook/Instagram/Reddit.
With pay-to-play it requires some investment (like $10 to $1000). There is usually more accountability, conversations don't leave, there's higher chance for nuance and constructive discussions, and participation is usually filtered to those who are engaged. There's an incentive to be engaged.
Niche communities can be found for free (e.g. subreddits or forums). But the ones that will likely result in better support and accountability have a filter. This filter could be requiring an invite to join but a lot of communities ran by individuals might require payment in varying degrees.
With pay-to-win, it requires a large investment (like $1000 to
Infinity) but they are goal-oriented, they may include coaching, workshops, or mastermind groups. You are paying for a human-powered supercomputer that can help give you specific advice for specific situations to increase the odds of success.
Coaching (both group or 1:1) provides individual attention, accountability and goal-oriented programs. I consider therapy to be in this category as a form of coaching.
The ultra-accountability offering, the mastermind group, is like a "raiding party" of 3-5 high-level endgame characters who all agree to formally help each other reach very specific goals.
Knowing the degrees of support and the level of investment, now you can determine how much support you need.
You might start by following people on Twitter that inspire you. You'll get ideas for what you might like to do in the future. From there, you might join a premium community to accomplish an objective in your quest, like transitioning to a new job, quitting, taking the summer off, or moving into leadership.
It's dangerous to go alone. You don't have to go alone.
Better to grab a sword and go in prepared.