How To Make A Side Hustle Work

If your employee has a side hustle—something they do away from work that makes money—a leader can worry. Is that team member really committed to the work and paycheck? Does that mean they have one foot out the door?

The struggle is real because more people are working multiple jobs. Federal data shows a 5 percent annual growth rate—7.5 million Americans in 2016 worked more than one job. Couple this with millennials who demand a sense of purpose from their work, and retaining good people is getting harder.

That’s why leaders shouldn’t ignore the side hustle. Learn from what your people choose to do on their own time, to better understand who they are and what motivates them. Team members, make sure the side hustle creates energy and momentum that feeds your day job.

For both leaders and employees, there’s a right way to handle the side hustle. Here’s what my experience can teach you.

“Hidden” talent is revealed and rewarded by the side hustle. When I moved to Atlanta with my very modest life savings after college, I negotiated a side gig with my apartment complex. I taught tennis every Tuesday night in return for free rent. My career focus was getting my career in sports off the ground, and this side hustle took a bunch of financial pressure off me. Even when that career took off, I still taught tennis because I loved it.

• Tip for employees: Your side hustle should give you more energy than it takes from you. If you’re not excited about doing it, find a side hustle that will get your juices going.
• Tip for leaders: Anyone who works a side hustle has to have passion, drive and resourcefulness to solve a problem and get paid for it. How can those attributes help inspire and motivate your team? Can you position this person as a peer leader, to tackle a problem that requires a similar skill set? Asking these questions are important because ….

Curiosity about the side hustle can help your entire team. As my career as a sports agent took off, I became a target for younger people asking me over and over how they could break into this business or other super-competitive jobs. This consistent interest compelled me to write my first book, The 5 Best Tools to Find Your Dream Career.

At that point, I had no idea that this side hustle would eventually lead to my work as a corporate speaker and author. I did know that I owed my job to the owner of the agency, and I didn’t want to jeopardize that relationship. I went to him and laid out my plan for writing my book on my own time. With great generosity, he took an interest in my project. Instead of suffocating my dream, he helped edit the book and make it better.

• Tip for employees: Before you dive too far into your side hustle, consider the people who have a stake in your paycheck. Share your vision as much as possible. With their support, you will go further than you thought. If they aren’t supportive, you may have just saved yourself future headaches.
• Tip for leaders: Curiosity and vision fuels the best leaders. These conversations about side hustles are often casual and best if you are wide open to what you do not know. When you can form a strong trust through generous listening and learning about a team member’s side hustle, you understand what makes them tick, which means …

Respecting the side hustle can retain a talented team member. Remember, a side hustle means different things to different people. Maybe they are trying to form a foundation to chase a bigger dream. Or maybe it’s just a creative outlet and a necessary income source. It could be a step toward greater work-life balance.

The side hustle is almost always personal, and that’s what makes it powerful. There’s usually a sense of pride attached to doing something more than the competition, to going that extra mile, to gain new skills and added income. The future is more open for that person and their next step may be in a new direction.

• Tip for employees: Can you examine your side hustle to see what it’s doing for you that your day job isn’t? How can you get more of your best self and talent into your career? Have you considered every channel?
• Tip for leaders: A leader who supports the side hustle (within reason, not to the detriment of your work product) is establishing a deeper bond. The side hustle is a chance to see this team member as a person with many facets, not just for the service or product that they were hired to provide.

Let’s face it, life is not a sentence with a period at the end; it’s a bunch of commas, as Suzy Welch told me during a conversation recently. As a leader, give your team the opportunity to create their own commas—that’s what the side hustle is often about. Otherwise they will create the period, and move on to work that is more meaningful.

Your Game Changer Takeaway

Everyone has something they love that isn’t part of their career. Smart, strong leaders support that flame. Don’t pay them to build their other business, of course. Know that if you try to suffocate it, you will lose a talented person and the best that person can bring to your team. Leaders, don’t ignore the side hustle—see what you can learn from it.

Molly Fletcher helps inspire and equip game changers to dream, live and grow fearlessly. A keynote speaker and author, Molly draws on her decades of experiences working with elite athletes and coaches as a sports agent, and applies them to the business world. Her new book, Fearless At Work, is now available. Sign up here to receive our monthly newsletter and subscribe to the Game Changers with Molly Fletcher podcast on iTunes.