The Gig 101: The Con of the Side Hustle

From today’s New York Times:

An attractive woman behind the wheel of a gray car says to the camera, “These days anyone can have a side hustle.” She then whisks off to the gym, for her other job as a personal trainer, beaming as she goes from one gig to another. This ad for the ride-share company Uber seeks to entice new drivers to join their ranks by using the “side hustle” come-on. The company isn’t alone.

Similarly laborious “side hustles” are celebrated in popular media and advertising, from self-help articles and other web content that exhort us to, say, work for a design studio part-time or sell CBD oil (great as a side hustle for moms, supposedly). Even pastors can use a side hustle, according to one evangelical blogger.

During tax season, you will also find filing suggestions for side hustlers. (Report all of your income! Deduct expenses!)

The truth is, working multiple gigs creates complications when you do your taxes. Compared with those with salaried jobs, who pay their taxes seamlessly through withholding, for side hustlers “the process will be a lot messier,” according to Steven Dean, the faculty director of the Graduate Tax Program at New York University Law School. You have to estimate and pay taxes on your own, he notes, and your expenses may not be reimbursed by your employer. In other words, paying quarterly tax estimates gives workers with side hustles yet another side hustle — being their own accountant, although this gig doesn’t even pay.

Nevertheless, this nouveau moonlighting continues to be exalted ­as cool, empowering or freeing. This mantra is false: Side hustles are not simply a new version of working as a “wage slave” so that we can do what we love in our off hours. Instead, far more often, people take on second or third side hustles because of wage stagnation or low pay at their full-time jobs.

Read the complete article here.