In a medium bowl or jar, whisk together the milk, chia seeds, maple syrup, vanilla extract, and espresso powder until well combined.
Allow the mixture to sit for 5 minutes, then stir again to prevent clumping.
Cover and refrigerate for at least 4 hours or overnight, until the mixture becomes thick and pudding-like.
In a small bowl, whisk together mascarpone cheese, Greek yogurt, powdered sugar, and vanilla until smooth and creamy.
Spoon a layer of the chilled chia pudding into serving glasses or jars. Add a layer of mascarpone cream on top.
Add another spoonful of chia pudding followed by a final dollop of mascarpone cream to mimic the layered look of classic tiramisu.
Dust the top with cocoa powder and sprinkle with chocolate shavings or crushed ladyfinger cookies before serving.