Personally, as a freelancer/consultant, I never think there is a right time for anything in my life. Of course, you might feel differently (and it probably is different). I'm offering advice from my perspective only, and I don't have a home to make, or children to worry about. I've been freelance/consulting/whatever for about 2 years, so make of this what you will, but I'm still early stages having just been where you're at.<p>First I want to say, the risk might not be as big as you might think it is. You've a pretty in-demand skill set right now, more so than most SWEs. If things don't pan out as you expect, you can always get another full-time position despite the 'looming recession'.<p>That said, here is some unsolicited advice. Rebuttal as necessary :)<p>Regarding leads/prospects, if you do decide to make the jump, chances are you'll be tapping your professional network for leads, or pitching strangers if you happen to get on a call with them via cold email. This can work for a while, maybe get your first recurring clients, but I don't recommend working with a matchmaker like Toptal, Fiverr, Upwork, or an agency.<p>The platforms tend to have poor pay and bad clients. Agencies will limit your ability to build a direct relationship with the clients. I know people have built successful businesses using both of them, but for me having a direct relationship with high-value clients seems to have paid off doubly as I can set my own terms (fixed rate / value based) rather than the typical hourly model. If you can/want to build such a relationship, you should *get on the phone with a decision maker* (a huge unlock for closing work). Regular dev/engineer interview channels will yield regular dev work, pay, and circumstances (maybe that's a feature for you).<p>After a few sales calls for clients, You may realize getting leads to come to you is best, or at minimum people should have a reason to answer your emails like having some kind of branding or marketing, so start writing, coding, tweeting, or whatever regularly to get attention. Keep at it. It's hard work.<p>On top of everything, you will fuck up, and that's okay, so give yourself some breathing room financially and mentally.