Is there ever a right time to do your Thing? Not sure on that one. But what I do know is if you're not doing your Thing yet it's only going to continue to piss you off 'til you start doing it!
Now, I am NOT saying you need to drop everything and start doing your Thing now–that's hardly ever the best plan. But what I am saying is that it's pretty likely that there will come a time where you will have to take a leap of faith into doing your Thing and how big a leap and how much of a safety net (or not!) you have is entirely up to you.
Sometimes it's best to dive in the deep end
If you know you're the sort of person who thrives under pressure, then throwing yourself into the deep end of doing your Thing is probably a great idea–in fact, why not start right now! I am serious here–if you know that to make a Thing work you need to jump in, get on with it and not have other distractions, then it could very well be that now is the perfect time to do your Thing. It might even make sense for you to do this without a harness or safety net too (if you know that will stop you REALLY doing your Thing and just have you dabble instead).
I'm not sure I'm entirely a deep end person. Well, let's put it this way–I will take the dive but with some backup! When I first started my business and gave up my job I made sure I had enough money to 'pay the bills' for a certain amount of time, so I could dive in and see what happened for a few months knowing I could always 'get a job' if it didn't work. To be fair, that was a Plan B I never wanted to make happen so I made sure Plan A worked (and as it turned out, I had my first client within a few weeks and another shortly after, so I was happily working at home in my PJs earning more than I did in my old job within 3 months). Now that makes it sound easy–and the reason it wasn't hard because I went for the 'low-hanging fruit' option of working as a consultant in an industry where I'd already been working (and making connections) for a number of years. It might take you longer in a brand new market, or it might take no time at all. BUT you need to know what's going to give you the best chance to perform your Thing best.
Set yourself up to win
If you know you need to have a 'security blanket' of money in the bank so you can do your Thing without the worry of money, then do it! Do whatever it is you do now (Thing or not) to get this money saved up. Or sell things, or do something you don't even like to 'buy the time' for doing what you want to. Same goes for time. Save up time–outsource things that use up your time now to give yourself more space to do your Thing (and don't just think work here–it might be more child care or cleaning your house, running errands, all sorts of time sucks might be taking you away from doing your Thing). You might need to 'give up' things for a while so you can do your Thing (to get back the time or save money or both!). Perhaps telly needs to go for a while, or meals out, or doodling days?
Don't get rid of everything though–the whole purpose of you working out the right time is so you can do your Thing–so don't go nuts and take out everything that puts you in a good place to do it. All work and no play makes Jack (or Jill) very dull. You need to work out what can go that will still allow you to do your Thing.
Think short term, medium and long term
In the long term (am making an assumption here) you'll want to be doing your Thing full time (or as much as you want to work, this will be what you're doing). But in the short term you might have to do a lot of work that isn't your Thing so you can 'buy time' to do it. It might even be that your short term only allows a tiny amount of time for you do your Thing in, but don't leave it out completely. Not doing your Thing will drive you crazy after a while... so even if you can only carve out an hour or 2 each week to do it, still do it. In the medium term, you'll be doing mostly your Thing with perhaps a degree of 'back up' to get it working for you. How much back up you need is up to you. But don't get stuck here–have a deadline to switch to Thinging only, otherwise you'll always be half in and half out!
How quickly you move through these stages is up to you–if you're the deep end person short term might be days (or hours!) and you'll race through medium term (even skip it!) and get on with your full time Thinging right away. The rest of us (!) will make a plan, plot out a timeline that works for us, set some deadlines, and get on with making the move. But ALL the stages will involve doing our Thing (even if to start you're setting it up ready to sell). Work out how much risk you like, then push a little past that (it needs to stretch you a little!) then make the move.
There's never going to be the perfect time to start doing your Thing, but you can make it the perfect stretch for you.
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