Regreting something you should have done in the past can only get you to make a mistake now. And it could be bigger than not investing before. So if you find the right amount between the invest something you can lose and regret not investing anything, than you are on the right path.
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That seems to be the sweet spot yes.
Or if you wanna be a tad conservative, don't spend on luxuries and invest only what you're OK with losing.
Although I realize the definition of luxuries may be different from each person.