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Not to be negative but do not wait. Your boss sounds like a good man but you must start looking right away. September will come quick.
I work in a business with quite a high volume of staff turnover. Often staff need to sign non compete contracts. I know this sounds like a scummy thing to do, but the realities are that if you don't have a NC clause and can take any clients now, that will be a help in securing a new position. You have done well for your current employer, start looking at your competition and see if there is a way you can levy your contacts as a way in. Try and stay positive. Its business and that means you have to look after you and yours.
Good Luck out there.
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