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Advice / Succeeding at Work / Work Relationships

The Not-So-Scary Way to Convince Your Boss to Say Yes to Your Side Gig

Congratulations! You’ve landed a really awesome full-time job that you can’t wait to start. Just one tiny problem: You have a side gig you don’t want to give up. Trust me, you don’t have to convince me about why it’s important for you to keep working on it.

With that said, you might have to convince your new employer that it’s a good idea—and that can be scary to do. Especially since you haven’t even started working yet. So, here’s how to address the topic without making things awkward with your new company.

1. Bring it Up as Early as Possible

From a practical (and sometimes legal) standpoint, you shouldn’t let this linger for very long after receiving a full-time offer. There are some potential landmines along the way if you don’t disclose a side gig you’re working on, especially if you know there’s a potential conflict of interest. And while you could take the gamble of not telling either employer about what you’re up to, you’ll only drive yourself crazy wondering if you’re violating any of your contracts.

In my experience, HR departments are more than happy to walk you through the legalities of what you’re getting yourself into. Remember, your boss is excited to hire you, so you won’t have to worry about having your offer rescinded just because you asked.

2. Have a Realistic Plan

Having this conversation will go a lot smoother if you have a plan of attack. It would be easy to say, “Yeah, I’m a great multitasker and have no doubt I can handle it.” Except anyone who’s eager to start a new job and keep a side gig can say that. I’m not suggesting that you have every minute of your day planned out, but it’s important to do some thinking about how you’ll do all your jobs well.

In my case, I have some really strict guidelines for myself: My day job comes first on weekdays, and I reserve Saturday mornings to write for The Muse. It’s not an elaborate to-do list, but it works for me. And having a similar schedule ready to discuss can ultimately make the conversation much less uncomfortable.

3. Be Honest With Yourself About What You Can Handle

I’m going to level with you: When I was offered my current position, I thought it’d be a great idea to keep all of my freelance gigs and turn them into side jobs. I considered it from a strictly financial standpoint, and after doing some rough math, I was motivated to make it work because it would’ve meant that I’d be making a serious amount of money. But when push came to shove, it was clear that if I worked that much, I would’ve had no time for myself. And the quality of work I’d be able to crank out would’ve gone down.

So, I made the really tough decision to cut back, which meant dropping a project I really enjoyed. But it didn’t take long to see that I had enough money to pay the bills, and I had enough time to do other things I liked—which kept me from working all the time and driving myself nuts.

Asking an employer if you can keep your side gig is a scary thing. And it’s OK if you’re feeling uneasy about it. But you can really make life much easier for yourself if you consider the whole picture, be honest with yourself, and take a deep breath. Even if it’s the first time you’ve had to have this kind of conversation, odds are that your employer has had it plenty times. And I bet the company will be much more empathetic to your request than you realize. Worst case scenario? Your boss says no and you focus on your awesome new job.

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