Most people assume it’s about the market, the right buyer at the right time and the right price. You might imagine there will be a moment when all the stars align, when the perfect economic and business cycles match your own life. But those stars rarely line up. If you wait for perfect certainty, you may end up waiting forever.

As the change of seasons approaches and new buds start to show on the trees, there’s reason to feel optimistic about the summer ahead....