Most of us have a side-hustle. That job that we do after hours that fulfills our dearest hopes and dreams. That job we do in our free time that gives us joy. That part-time job we hope will someday be our only job. But a good one comes with a dilemma: how to talk to your boss about your side-hustle. Should you even bring it up at work?
lots of people have a side-hustle
More and more workers with full-time jobs have something going on the side. And frequently, their side-hustle is a lot more emotionally engaging to them than their primary gig.
For example, we arrived at an office in Wall Street for a meeting recently. As we walked to reception area, the security guard began chatting with us about his side-hustle, which is writing plays. We know a 10-year old whose full-time gig is going to elementary school, and whose side-hustle is selling designer cupcakes that she bakes on the weekend.
One of our Luminaries, Trent Preszler, is both the CEO of Bedell Cellars and the founder and CEO of the Preszler Woodshop. The dude oversees a winery by day and hand-carves $150,000 canoes by night.
Trent Preszler
The great John Legend – who has a degree from Wharton – had a full-time job as a consultant at Boston Consulting Group, and a side-hustle as a singer-songwriter. That worked out pretty well for him in the end.
John Legend Photo Credit: Getty Images, Monica Schipper
We ourselves had a side-hustle back in the day when the phrase didn’t even exist. As baby consultants at McKinsey & Co, we authored a series of mystery novels. We wrote in the early morning, on long plane rides, and on vacation days. Simon & Schuster published all three of them, and we went on three national book tours while still working full-time. We didn’t get much sleep while we were doing all of this. But man, it was fun.
So we feel you, side-hustlers of the world. We’ve been there.
Enabled by the Internet and social media, it’s easier than ever to have a side-hustle. So if you’re tempted, then why not go ahead and have one? A good side-hustle adds a dimension to your life that’s joyful and precious.
Should you inform your boss about your side-hustle?
We convened our C-Suite Council to debate this pressing matter, and here’s the consensus view. There are 5 questions to ask yourself:
1. Is your side hustle something you can get paid for?
Said another way: is this just a hobby? Or is it a passion project that you hope to turn into a real paying job as soon as possible? Hobbies are private and personal. They don’t pay cash money, and you have every right to keep quiet about them if you like. Side-hustles can be altogether different.
2. Is your side-hustle already public, or likely to become so soon?
Would it be easy for your boss to find out that you’re moonlighting as a singer, novelist, actor, tattoo artist, or Instagram influencer? If so, it’s probably time for a talk.
3. Does your side-hustle conflict with your full-time job?
Could it ever be perceived that way, even if it isn’t? If you’re pursuing something that could someday compete with your current employer, or that relies on information that you gain from your full-time job, you need to disclose it immediately.
4. Could your side-hustle ever cause your employer embarrassment?
Like, if you’re a model or an actor – or even a writer – are you at risk for being seen to be a distraction or a negative for the company’s brand and reputation? If so, see #3 above.
5. Are you prepared to either drop your side-hustle or quit your current job if your boss demands it?
If you feel so strongly about your side-hustle that you’re prepared to quit if you cannot pursue it, then you’re ready to talk to the boss about it. Just be really sure you’re ready if she gives you an ultimatum. Once the genie’s out of the bottle, you can’t put it back.
Depending on how you answered these 5 questions, you’ll know if you need to schedule time with your boss to disclose your situation.
How should you talk to your boss about your side-hustle?
The C-Suite Council advises these 5 steps to create the optimal conditions for a successful conversation:
1. Explain what you’re doing clearly, and with confidence.
No need to be sheepish.
2. Fully disclose what you’re doing, with no hedging and omissions.
You have one chance to get this right, so put it all on the table.
3. Make it clear that you want to have a trust-based relationship with your boss.
Show some vulnerability, ask for advice, and reiterate your commitment to your current role.
4. Schedule the conversation for a time when neither of you are pressed for time.
If either of you gets rushed, you’re going to miss important nuances.
5. End the meeting with a clear agreement on next steps.
For example, will your boss be telling her boss? Will you be telling your peer group? Is there a touch-point between you two that’s needed in the future?
Other considerations
Once you’ve told your boss about your side-hustle, here are some other things to keep an eye on going forward:
Your peers might get jealous. Especially if you start to have some real public success.
Your boss might get jealous – for the same reason.
You might fail – possibly even publicly – and you’ll have to show resilience and optimism in the face of that every day at work. We say, keep your head up. Wear your failure as a badge of honor. At least you tried.
You might succeed. In which case, you’ll have to decide whether or not to make your side-hustle your full-time job. If you do that, and if you leave on good terms, it’s almost a certainty that your boss and colleagues at work will wish you well. They’ll also claim credit for “knowing you when.” And they’ll definitely ask for tickets to the premiere of your first film.
You might tire of your side-hustle and decide to drop it. That’s totally OK. Just disclose that to your boss, and think about what you learned from the experience.
On a personal note, we can honestly say that we have never regretted pursuing our side-hustle. We would have had lifelong regrets if we hadn’t. With a great side-hustle, it’s almost never about the money – it’s almost always about the dream.
Go chase yours. And when the time is right, let the boss in on it. She might become your biggest fan. Or even your first investor.
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