WHEN I MET ARON for dinner, the occasion marked a milestone for both of us. Aron had earned his bachelor’s degree in audio production in 2020—during the thick of the pandemic—and finding his place in the industry had been more difficult than he’d hoped. Now that things were finally falling into place, Aron approached me for help with his finances. In particular, he wanted to understand his tax situation, which had grown into a mixture of self-employed contract work and part-time employment. I’ve known Aron since my wife Sarah began babysitting for the family when she and I were dating in...
