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If you are earning well with a firm that you are currently with - it becomes quite difficult to foray into the unknown with no assurance of a monthly paycheck.
Another factor to consider is where your source of work will come from. If at a High Court level - do you have enough contacts with trial court lawyers who would feed you matters in appeals/ writs. Are you likely to get a few clients from the office where you are currently working. Other determining factors could be age, marriage, children, preference of city, etc.
There are many subjective and objective factors that would need to be considered before one takes the plunge. But there is one important element which usually you cannot be prepared for - some may call it luck, some may call it 'naseeb', some may call its God's wishes - but there is surely that some unknown force/ factor which is not in your control - which could be your guiding light.
However, I feel that in a usual circumstance, about a 5 year work-ex is a good time to consider going independent. I went independent after 6 years of being with a law firm.
I am not sure whether I have answered your question or confused you more. But I do not think there is a straight-jacket formula which is the absolute correct answer/ response. Further, what scenario may work for one person - may not work for another.
Having said that, I have found the world of independent lit practice to be fantastic. Has its own bumps and challenges - but overall is very rewarding. Good luck with whatever decision that you take.