Like many others, I tried “outsourcing my life” using a digital assistant. A year and a thousand bucks later, I’ve received one department store recommendation and an admittedly adequate spreadsheet of competitive research.I have since cancelled. Why didn’t it work for me?I think I just didn’t trust it/them/him/her (that I even have this ambiguity is indicative of the issues).Most of my mindless time-sinks involve at least a credit card number and are often a conveniently packaged identity-theft kit.So that was part of it, and the other part was that I had to d...