I recently listened to a podcast of one of my fellow FOT team member’s Let’s Fix Work podcasts (which are awesome Laurie, by the way) that was titled Why the Side Hustle is Failing You. The premise of the episode is that side hustle is something that’s been inappropriately glorified by Gary Vee and others, and that it actually can create more harm than good when it comes to living a life of professional satisfaction and fulfillment. The episode focused on side hustles primarily from an individual perspective, but my mind started thinking about what employers think about the same.
Should companies be encouraging side hustles, or discouraging them amongst your employees?
You see, I’ve found that some of those I’ve worked with in the past who have side hustles are some of the very best in their jobs, and oftentimes its because of their side hustle. Not side hustle in the defined traditional sense, but rather in having other interests and “jobs” that provide outside inspiration. Something that fills their energy tank, provides them with broader perspective, and contributes to more success in their day job.
Traditionally companies have frowned on side hustles as conflicts of interest. Another gig where the employee they pay makes money somewhere else, and a side hustle that takes time away from them? Uh, no. Not going to allow that. We swiftly refer our employees to page 16 of the handbook regarding conflicts of interest. That’s an outdated traditional view, and it completely ignores today’s reality and misses the opportunity that side hustles can actually make your employee more valuable.
In today’s economy most people are forced into ensuring they have multiple sources of income. Their W2 job is at-will, increasingly unstable, and the new workforce has been reframed as a freelance and gig economy. It’s a new working world where companies aren’t committed to people, people aren’t committed to companies, and the whole job market has become a free for all. With that in mind, that W2 employee is turning to outside sources in order to obtain financial security for themselves and their family. It would be foolish for them to put all their financial eggs into one basket.
Enter the side hustle.
Maybe they have the benefit of a working partner, but maybe not. And whether they do or don’t, they are trying to develop other sources of financial security. A stand at the local farmers market, writing a book, finding paid speaking gigs, or growing marijuana in your basement (reserved mostly for Colorado residents). But everyone’s trying to find alternative ways to make more money when not working their day job.
Is this bad for professionals and companies alike, or a good thing?
I’m not sure it matters. It’s what is happening. It’s today’s working world.
And the UPSIDE of this new reality is people who have multiple interests, multiple passions, multiple perspectives, and multiple sources of income. These people aren’t wholly committed to your organization. But they bring to your workplace outside inspiration and perspective from these side hustles, and maybe even more financial security and stability. The side hustle makes them better at their day job because what is lost in company loyalty is gained in balance, innovation, perspective, and focus. These aren’t the people an employer will see lackadaisically going through their workday. When they are at their job they are working. Why? Because when the workday is over they are off to do other things.
But there is a DOWNSIDE too. Some can try to do too much, and in doing so they don’t do anything well. They marginalize their contribution to any one thing because they are trying to juggle too many other balls. Sometimes this is because “they have to” in order to pay the bills. Sometimes it’s because they hate their day job and are working diligently to be able to walk into their boss’s office and say “take this job and shove it”. But when they aren’t committed to what they do to make their primary living, they introduce even more risk in financial security equation. They will unknowingly squander opportunities that will benefit their primary employer and the opportunities they have there.
So the side hustle is another tricky topic for each of us to address as HR professionals.
Do you, as the owner of your company’s policies, encourage or discourage it in your workplace? Do you openly talk about side hustles and try to find ways to leverage these outside experiences and bring them into your work environment?
Or do you see more downside to side hustles and constructively attempt to discourage such side hustles? The only way I see this being a potential successful strategy for your company is by ratcheting up your commitment, loyalty and the financial security to employees so that a side hustle is no longer as appealing.
Regardless of your company’s stance here is an inevitable truth: Your employees have side hustles. The stance you and your company take is ultimately up to you, but the only sure-fire failing strategy is to stick your head in the sand and act like they aren’t there.
P.S. Thanks to Laurie Ruettiman for the inspiration, raising intriguing topics such as this to her listeners via her Let’s Fix Work podcast. Check it out if you haven’t already done so.

Ed’s a career HR front man who’s advised business owners and the C-suite on developing great cultures and inspiring work environments since the profession was called “personnel.” Yeah, that makes him seasoned but also quick to call out the fluffy HR theoretical crap from HR strategies that actually work.
His versatility has taken him all over the world, continually acquiring knowledge of how to build a great company through innovative HR practices, learning mostly from real world experience and his own mistakes.
He’s the founder of HRO Partners, a HR consulting firm that specializes in guiding leaders on what they need and don’t need from HR for their business.