This boss wants you to work your side hustle while on the job

Between the gig economy and Millennials looking to jump-start a new business or pursue a passion, side hustles are officially the new normal. This may prove alarming for bosses who supervise Millennials, who can safely assume that everybody’s hustlin’ in addition to doing the job that they were hired to do.

Chris Tuff, an ad executive at 22squared, doesn’t see it that way. When he was given a young team to supervise, he took inspiration from Facebook’s Fuel and Google’s 20% programs – initiatives where everyone in the company is given a slice of time to pursue their own thing on company hours, be it a new sport or a nonprofit – and decided to create his own program where he would allow his Millennial employees to go after their side hustles at work – under his supervision.

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Tuff has a structured process for his Millennials before they begin working on their projects. First, their hustle can’t compete with the ad agency, and second, it has to “satisfy your deep desire of where you feel your individual purpose lies,” he told Ladders. “I  work with everyone on my team to identify their own individual purpose.”

Ultimately, his team members end up working on their side hustles about 10% out of their workday, but Tuff doesn’t exactly keep count of their hours. It’s a “blurred work-life integration” that Millennials understand instinctively, he said.

There are few real success stories that have come out of the side hustle program, which is perhaps the point. The program allows for exploration and the sense of possibility that his young employees crave, and the projects often simply run their natural course.

“Very few side hustles make it past the concept stage,” said Tuff. “Because just like anything we do in life, follow-through is probably the most difficult. The tenacity and persistence that things require are above and beyond. People grow tired and distracted, or passions evolve.”

There was one hustle, a young woman with an online clothing company, that Tuff helped take “out of incubation” and into a real-world business, but it didn’t make it in the tough world of selling online. “It’s really hard and expensive to grow and online clothing label, and it’s really hard to get people to buy using some of these digital channels,” Tuff explained. “We kind of thought it would be easier.”

Still, Tuff said, it’s better to explore, try, and fail while in the safety of a 9-to-5 job than quit to pursue your passions and flame out. In that way, he said, allowing Millennials to pursue a side hustle on the job promotes retention.

“I think they think they have to leave in order to pursue their side hustle. So we say, you can embrace your side hustle here, and I’ll be a resource for you. The grass isn’t always greener on the other side.”

He knows from personal experience. Tuff left a well-paid advertising job when he was 27 to pursue a start-up. “It was the hardest year of my life. I lost a lot of money.”

His second attempt at a side hustle, however, met with considerably more success. While working at the ad agency, Tuff wrote “The Millennial Whisperer: the Practical, Profit-Focused Playbook for Working With and Motivating the World’s Largest Generation,” about his experience managing Millennials, and decoding their needs and styles of working. The book hit more than one bestseller list.

With the success of his side hustle, Tuff said, his life has become more integrated – exactly what he thinks his Millennial employees are searching for. “For the first time in my life, the lines between my passion, purpose, and professional life have come down.”

He hopes they’re paying attention to all the hard work it took.


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