5 Steps To Getting Your Boss To Buy Into Your Side Hustle
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5 Steps To Getting Your Boss To Buy Into Your Side Hustle

It’s never been easier to start a side hustle online, but that doesn’t meaning telling your boss is always easy.

Of course, by definition side hustles mean that their founders work fulltime jobs, dedicating their nights and weekends to their passion project (and fingers crossed, future fulltime business). So the question “how does one juggle fulltime work with side hustling?” usually alludes to an even more daunting question—”how do I get my boss to support my side hustle?”

It can be tough to navigate getting your boss on board, and not getting them on your side means risking a less-than-ideal day work dynamic.

Here are five tips for getting your boss to back your side hustle, thus making life easier for yourself:

Figure out your company’s stance on side hustles

Before you approach your boss, you need to know whether your company supports side hustles or not. This might be obvious—for example, maybe they’re a startup and you know they support entrepreneurial projects, or they might have taken the Agency Side Hustle pledge to show that they support them, or you know that others openly have side hustles in the office.

But maybe they’re on the other end of the spectrum and they don’t support them—no one talks about them, or they have a clause in your employment contract forbidding outside work. The best place to start is your HR department, or if you don’t have one, a trusted colleague who’s been at the company longer than you have.

Knowing where your company stands on the support spectrum will help you plan how to broach the subject.

Know what you’re asking for

There’s a reason you want to disclose your side hustle to your boss, so figure out what that is. What are you hoping to achieve by telling them? Maybe you want to sell your side hustle products in the company’s annual holiday market, or promote the company to your coworkers.

Maybe you’re looking for help or expertise from a colleague, or maybe you just want to disclose it so they don’t question why you’re constantly posting about it on social media. Knowing your “asks” will help you prepare for a meeting with your boss.

Introduce your side hustle

Set up a time to chat with your boss or manager about your side hustle, or bring it up in an existing meeting. I’ve had multiple team members come to me to chat about a side hustle they’re launching, from a designer doing freelance design work, to our former PR director opening up a charcoal ice cream shop.

I even have a side hustle of my own. I’ve worked in startups for a decade, so I’ve always been extremely supportive of side projects, but remember that this may be new territory for your boss. Start by explaining the origin story—why you decided to start it—and outline where you are with it now. Either show them the product, or website, so they get a feel for it and understand that it’s a real thing, instead of just an idea.

Address the fears

Regardless of how supportive your workplace is, most people have fears around side hustles. The most common fears are that it will interfere with your daily work, and that you’ll leave to pursue it fulltime. When you tell your boss about your side hustle, make sure you outline how you’re going to keep it separate from your day job.

Most modern companies should take the approach that if you’re doing great work, it doesn’t matter if you send a couple side hustle-related emails during the day, but check on the policy so you know what’s acceptable in your office.

Your side hustle is a side hustle for a reason right now, so reassure your boss that for now, it’s a side project, and you’re committed to your day job.

Make it a part of hiring

The easiest way to get buy-in on your side hustle is to make it obvious from day one. I’ve had team members who have told me about their side hustles in the job interview, so it’s completely in the open from day one, and it often shows me that they’re a creative, hardworking person who has great time management and knows business fundamentals.

While this won’t help in your current job, if you move positions, make your side hustle known from the beginning. That way you know from the job interview whether it’s the kind of place you want to work.

Erin Bury is the managing director at Toronto creative agency Eighty-Eight. Her side hustle is a bicycle wine tour company in Prince Edward County, and recently launched Agency Side Hustle to encourage agency owners to support their team members’ side hustles.