Combine dry ingredients: In a medium bowl, mix chia seeds and cacao powder until evenly distributed.
Add wet ingredients: Pour in milk, maple syrup or alternative sweetener, and vanilla extract. Stir well to combine, ensuring no clumps of cocoa remain.
Optional blending: For a smoother texture, transfer the mixture to a blender and blend for 20-30 seconds until fully incorporated. Return it to the bowl if blended.
Let it set: Cover the bowl and refrigerate for at least 4 hours (or overnight) to allow the chia seeds to thicken the pudding. Stir once after 30 minutes to prevent clumping.
Prepare toppings: Just before serving, wash, hull, and slice strawberries for topping the chia pudding, and prepare the side of mixed fruit as needed.
Whip cream (if using fresh): In a small, chilled bowl, add the heavy cream and maple syrup or confectioner’s sugar, and whip with a chilled whisk or hand mixer until soft peaks form.
Assemble: Divide the thickened pudding into serving bowls or glasses. Top each with whipped cream and sliced strawberries, serve with mixed fruit and orange juice.