Why Your Team's Side Hustles are the Best Thing to Ever Happen to Your Business

Before I was a CEO of my own company, I was a lawyer. It was an incredible job, but I had a secret. While I was totally dedicated to the firm, I’d spend my vacations working on a side hustle that I also loved: building out an LSAT training website. I never found enough time to spend on it because I was so focused on my career as a lawyer. Eventually, I had to quit so I’d have enough time to take my hustle full time.?

Fast forward to the present, and it’s no exaggeration to say we’re living in the golden age of the side hustle. (I’m talking here about the entrepreneurial variety here — starting an online store, making crafts to sell on Etsy, building an app, etc.) Technology makes entrepreneurship easier than ever, and Covid has only accelerated the trend. For some, a side project is a matter of necessity, for others a preference. (The majority of Gen Z, for instance, aspires to be entrepreneurs.) But whatever the reason, today, an estimated 57 million Americans are pursuing side hustles … a number that’s growing all the time.

For employers, of course, this isn’t necessarily welcome news. I know this personally because,?for me, the script has flipped. As CEO of my own business with hundreds of employees, I’ve had many conversations with my team members about their own side hustles over the years. And they haven’t always been easy ones. For other leaders out there, I wanted to share some learnings from the frontlines and some counterintuitive insights about the hidden power of hustles.

Getting over the hump

A few years after I left the law firm, I found myself at the helm of my own company, an online course platform that was a spin-off of that original side hustle. And, now in a leadership position myself, something funny started to happen. I still remember when my cofounder told me he was working on his own side hustle. I was devastated — although this was odd, as I’m pretty sure I had my own side hustles going on at the time.

I’d liken the feeling to jealousy: I wanted my team members to give Thinkific their all, to devote their undivided time and attention to our collective mission. Just one problem: that’s totally unrealistic. Whether we're on the clock or not, we all have draws on our time and energy: hobbies, personal challenges, kids, and the like. My brother pointed out how much of my own bandwidth was consumed by things as mundane as kiteboarding and as profound as my family. Who was I to begrudge anyone for having their own passions?

Then there was also the fact that our company’s course-creation platform, even in the early days, was being embraced by plenty of side hustlers — from accountants who wanted to teach personal finance, to primary school teachers who want to teach hula hooping (for real). It would be pretty hypocritical of me to discourage our own team from following the same path.

So how did I get over the hump? An important part of accepting this reality was flipping the switch in my brain from a scarcity mentality to one of abundance. I was so worried that employee passion was a finite resource: if they expended energy on other projects, there would be nothing left to spare for our business. But the reality is, passion is renewable and feeds on itself. Enthusiasm about side hustles can bleed into the job in so many ways. And even if those employees spread their wings and start new careers, our business not only stands to reap collateral benefits, it also creates a company culture strong and progressive enough to attract new talent.???

That’s why there are plenty of companies out there who actively encourage employee side hustles: LinkedIn runs InCubator, which gives staff time off from their regular work to develop their own product ideas; Apple’s Blue Sky program offers employees vacation days to pursue pet projects; ad agency Huge encourages workers to pitch startup ideas to the team, awarding funding and office space. These are businesses that understand that employee happiness, creativity, and engagement should be welcomed, not tamped down.?

Establishing rules of engagement

Of course, embracing employees’ side hustle outright is easier said than done when you’ve got a company to run. But I’ve learned that setting clear expectations can help leaders ride that line between being supportive, and making sure that work doesn’t fall by the wayside.?

When Colin, one of our senior digital marketers, came to see me about his side hustle, my heart sank. A former monk — who had a shaved head and all! — Colin was an incredible asset to our team, and when he shared his idea for coaching programs and digital courses on mindfulness in the workplace, I felt like we were surely about to lose him.

But I realized I had two options: I could stifle his initiative (in which case, he’d either resent the company, or pursue it anyway, or both), or I could bring him into the fold. So instead of panicking or shutting him down, we set some ground rules.

To me, the key to creating strong rules of engagement is to not to be proscriptive or punitive; rather, the goal is to create a situation where everyone can benefit. Here are some guidelines that I’ve found helpful to share with my own team when the subject of side hustles comes up:

• Be transparent. The fact that my team comes to me at all to tell me about their side hustles is a great first step, but that honesty needs to extend to their coworkers, too. If your team notices you sneaking around or taking furtive calls and doesn’t know why, they’re going to feel slighted. Conversely, you miss out on input and advice from the people who know you best — your own colleagues. Keeping the lines of communication open is the surest way to make a side hustle work.?
• It’s output that matters. Some employers get fanatical about “company time” vs. “your time.” In my mind, all time is your time, and you choose how to spend it. If you want to work on your side hustle in the middle of the day and dive into that work project on the weekend, that’s fine. What we really care about is deliverables, not which hours you work or how much time you spend at your desk.
• Don’t let your team down. This is huge. If you’re missing team meetings because you’re working 9 to noon on your side hustle, we’ve got a problem. When other people inside the company are depending on you, your first priority is being there for them.
• Understand the trade-off. When you’re pursuing a side project, you might not have the energy to go that extra mile at the office. And that’s absolutely fine, but it could mean missing career advancement opportunities. If climbing the ladder is something that matters to you, you’ve got a choice to make.?

With these rules in mind, Colin built his business and did amazing work for us for two more years before he left the nest to pursue his side hustle full time. Today, he’s brought in to do corporate sessions here … coming full circle, in a way. I’m proud I could put my ego aside (and even offered occasional coaching and guidance) and help him achieve something meaningful.

Reaping the benefits

I’m not going to say I don’t still have instinctive moments of jealousy when an employee tells me they’re working on their side hustle. But I try to fight those raw emotions with data. Looking at all the benefits we’ve seen from side hustling employees, it’s objectively true that it’s made the company better. And I feel this holds true in other companies and contexts.?

For starters, side hustlers sharpen a set of entrepreneurial skills that pay dividends in their current role, including initiative, customer empathy and self-management. Back to the Colin example: it absolutely made him a better marketer in his role. This kind of intrapreneurial acumen — solving problems, innovating, taking calculated risks — is invaluable.?

Maybe it’s selfish in a way, but I also appreciate that people develop more of an understanding of the trials and tribulations of running a business once they’ve tried it themselves: they gain an empathy for what the leadership team might be trying to do, or why decisions get made, in a new way.

Side hustlers also deepen their industry-specific know-how and network, bringing in new expertise and new partners. One employee took some time off to go do some marketing contracts for some SaaS companies in Silicon Valley; when he came back to us, he unloaded a ton of great knowledge. Others who coach leadership teams on the side pick up new perspectives that they can share. Your side-hustling employee is also a link to future collaborators or customers. Even if they strike out and do their own thing, you’ve now got an ambassador for your company out there in the world.

It’s a scary thing to let someone talented go dabble elsewhere, and absolutely a risk. Yes, some will find a new passion and move on to other things. Others will toy with entrepreneurship, only to discover that their current role ticks those boxes — for advancement, for leadership, for creativity — far more effectively. But I’d argue that, regardless of outcome, the company stands to be better for it.??

Ultimately, the cliche, “If you love someone, set them free” applies to employees in a way, too.

Because here’s the thing about employee side hustles: even if you have an issue with it, there’s not much you can do about it. If someone is driven by a passion, they’ll be pursuing it — end of story. Ultimately, you can either be part of someone’s success story or a roadblock. Making the right choice is better for you, your company, and the aspiring side hustler in your ranks.

A version of this article was originally featured in?Forbes. Keep up with my latest posts by following me here or on?Twitter.