Why You Should Encourage Your Best Employees to Moonlight

Why You Should Encourage Your Best Employees to Moonlight


Do you encourage your employees to moonlight? Or do you prohibit them from pursuing work outside of their job with your company?

Personally, throughout my career, I’ve always had some sort of a second job or side hustle.

My first job out of school was managing an office for a small magazine, and I moonlighted freelance writing for them, and with a 10-hour-per-week position at my local free weekly newspaper.

Even when I was a full-time employee at Charles Schwab I always had a side hustle or two. The only difference there was that they had a process in place to ask for permission to pursue my outside-of-work job—to make sure it didn’t conflict with my day job or trade on non-public information I had access to as part of my job.

That said, I did eventually have a boss tell me my outside-of-work gig was giving others the impression I wasn’t fully committed to my job. As she requested, I wound down my extracurricular activities… and found a new job elsewhere that didn’t ask the same of me.

Why Employers Should Embrace Moonlighting and Side Hustles

So here’s the thing.

I live in San Francisco, which is an outrageously expensive city. As I was building my career, a second job was necessary to pay off student loans and ensure a reasonable standard of living. It’s also why I left journalism. As fun as that $30,000 per year journalism job sounded, it also looked like a path to a future of having three roommates for the rest of my life.

Further, I’ve never had a full-time job that put all my areas of expertise and interest to use. And even those with solid professional development programs rarely offered the opportunity to try out new skills on the job. Instead, when new skills were needed, we inevitably hired a consultant or agency to do the work. So the only way to build some of the skills that felt necessary for remaining employable meant taking on outside work.

This brings me to the three primary benefits to you, as an employer, of letting your employees moonlight.

  1. Moonlighting allows your employees to build new skills. Many of us learn by doing—not just by watching videos showing us how to do something. These skills can then be put to use in your own organization.
  2. Moonlighting gives employees a different perspective on their job. Sometimes people can romanticize a job or work environment they aren’t a part of. Spending some time on another job, in a different work environment, can make us more appreciative of our current position. I know I’ve stayed in jobs that let me work on my side projects for longer than I would have without that opportunity.
  3. Moonlighting expands our network. Companies tend to do business with the same consultants, and agencies, and service providers. When we’re moonlighting, we often work with a whole different set of providers.

Of course, side hustles don’t always work out in your favor as an employer. Someone may be so happy with and successful at their side hustle that they quit their job. It definitely happens. But here’s the thing: that’s not the side hustle’s fault. The side hustle didn’t magically convert someone who was passionate about their day job into someone completely different.

Rather, that side hustle gave the person something they were missing in their day job. That could be the novelty of stepping out of their usual job. Or the sense of accomplishment from being their own boss. But it’s just as likely that the side hustle allowed them to pair their skills and expertise with doing something they are passionate about.

Finding Our Passion

Not all jobs instill us with passion.

Although there are more and more mission-driven companies out there sharing their vision of a better world with us, many companies…aren’t. They’re here to provide shareholder value. And even as someone who is a shareholder in a number of companies including those I’ve previously worked for, that’s just not a mission that connects with my heart.

Yes, I need to make a living to afford to live here. But making money is not a primary motivator for me. I don’t choose one project over another based just on compensation.

Compensation is always a factor, but the work a company is setting out to do—and that my work will support—is a much bigger consideration. And conversely, I won’t do lucrative work, no matter how innovative, for companies whose values (or whose parent company’s values) I don’t agree with.

I want to do work I’m going to feel good about. Work that makes me feel I’m contributing to something I believe in.

Side hustles can often give your employees a place to channel their passion. And if you’re lucky, they’ll bring that renewed passion back to their day job. Or, they’ll decide they need to pursue something different and leave your company. But that’s not a bad thing.

The typical American workplace is full of disengaged employees. In fact, Gallup research has shown for a number of years that most of your employees are not engaged in their work.

I understand that some of those employees hold important positions in your company. And you may even think of them as irreplaceable. But if they aren’t passionate about what they are doing, and slide into disengagement, that doesn’t benefit you. And it can turn your formerly productive and happy workplace into something else entirely.

Support Your Employees: Embrace the Side Hustle

As a marketing leader, I’ve always said yes to my employees’ requests to moonlight. I ensure they understand their moonlighting must be done 100% outside of work. And it can’t conflict with the work they are doing as part of my team. And I’ve never regretted making that decision. I’ve found that when you hire amazing people and support them in shaping their careers, you always come out ahead.

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