Should You Start a Business in Uncertain Times? What Research & Real Business Owners Say Looking back, that was a wildly uncertain time. Still, I pushed through, scaled it over a couple of years, and sold it before I moved to Chicago. I recently posted the question of “Should you start a business in uncertain times?” on my Twitter and received a myriad of responses and real experiences, many of which I’ll share below. But one response stuck out to me: “There is no such thing as a certain time to start a business.” It’s true. Starting a new business is one of the most unpredictable, tumultuous adventures on which we could embark.