Sure, there are a variety of challenges with this.
I was thinking about carrying your device into the local bigbox store or grocery store chain.
Everywhere you go, your phone or laptop is looking for it's known ssids.
If people can tie you to your locations via discreet service Id numbers, you're not escaping regardless.
SpaceX is demonstrating with Starlink that watching mobile devices from orbit is incredibly effective. You can hop on Starlink without any special antennas.