A Cautionary Tale About Generation Gig

Nearly 80% of us would be interested in dropping out of the FT workforce to go freelance.

Two Millennials Discuss Doing Their Taxes

John: I spent, like, four hours one night last week entering tiny numbers into TurboTax, then was crestfallen at the result, and did the same with H&R Block online. Now both of them are emailing me like, HELLO? DO YOUR TAXES AND PAY US… so I'm putting it off. For now. I did actually go to see a human person at an H&R Block office, and she told me it would be $300 just to process my 1099-MISC, nevermind the taxes I will inevitably owe, so I scuttled back to my desk.

Here’s A Surefire Tax Estimating Process for Freelancers (Rebooted and Updated)

A year and a half ago, I wrote about my surefire tax estimation system for freelancers for the Billfold, in the hopes that a system that has worked for me would help the many Billfold readers who live partly or entirely on freelance income avoid quarterly or annual financial panic when it came to dealing with their taxes. "This system is incredibly useful!" some said. "This system is insanely complex, how can you expect anyone to actually do this," said many others. "Please help me," said an unsettling number of emails I've received.