How to Talk to Your Boss About a Side Hustle

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Clifford Chi
Clifford Chi



In the fifth season of Mad Men, Ken Cosgrove, an account-executive at Sterling Cooper Draper Price, is called into Roger Sterling’s office, a founding partner of the agency.


Roger tells Ken that he knows his secret: Ken’s an accomplished fiction author who writes under a pen name, so no one at the office will find out about his side job. Roger then tells Ken he has to stop writing immediately. He shouldn’t focus any attention away from his high-paying, full-time job.

Ken is initially devastated. But after some encouragement from his colleague and friend, Peggy, he rebels against Roger and adopts a new pen name to continue his pursuit of fiction writing, risking his employment and financial stability for the fulfillment his passion gives him. He could never abandon his stories.

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Fortunately, the Mad Men work culture doesn’t really fly in today’s world, but the story of Ken Cosgrove’s secret side gig still resonates with people today. It’s incredibly nerve-racking to talk to your boss about your side hustle. What if she thinks you care about your side projects more than your regular job? And what if she thinks it will hinder your performance at work?

Side hustles are not only beneficial to you, but they can also bring perks to your boss, team, and company. And we recommend spotlighting these benefits to get your boss on board with your own side hustle.

But before we dive in ...

Eddie Shleyner, who runs a successful side hustle called, knows how exciting it is to build something successful by yourself. But he warns against letting it become your first priority. "If you're employed full-time, your side hustle must be your second priority. As soon as you start giving more time and brain power to your side hustle, you're in the wrong with your full-time manager."

So make sure you hit all your deadlines and your work keeps improving. Once you’ve put in the required time and effort to excel at your regular job, you can then focus on your side hustle.

With this in order, let’s get back on track and go over the seven speaking points you can highlight when bringing up your side hustle to your boss.

How to Explain Your Side Hustle to Your Boss

1. Your side hustle will make you more adaptable.

If you only work one job, you usually use the same thought processes and skills to do the same tasks over and over again. But when you start a side hustle, you’re essentially running an entire business. You’ll have to expose yourself to loads of novel strategies, concepts, and responsibilities to be successful, and you’ll build new skill sets and improve your adaptability along the way.

When you’re more adaptable and well-rounded, you’ll be able to tackle problems from different angles at your regular job, enhancing your team’s overall creativity and effectiveness. You’ll also be more willing to take on new challenges because you already know how to study completely foreign concepts. Learning won’t intimidate you. And this mentality will drive innovation within your team.

2. Your side hustle will boost your confidence.

If you can build something from scratch, then you can definitely help a resource-heavy company grow bigger and better. Starting a successful side hustle will boost your confidence, improving your performance and ability to handle setbacks and disappointments at work.

3. Your side hustle will teach you how to handle big decisions.

When you start a side hustle, you risk losing your money, time, and reputation. That’s a high-stakes decision. Similarly, when you’re growing your side hustle, you have to make quick yet critical decisions that will either build or dismantle your business. Making these pivotal decisions for your side hustle and learning from both the good and bad outcomes will refine your decisiveness and help you make the right decisions at your regular job.

4. Your side hustle will improve your communication skills.

Expanding your network is essential for growing your side hustle. And as you network at industry events, meet connections for coffee, or pitch a guest blog post through email, your communications skills will skyrocket compared to only slacking or chatting with your colleagues. Growing your network and meeting all types of personalities will make you a better communicator at your regular job, helping you give engaging presentations, make articulate points at meetings, and collaborate well with colleagues.

5. Your side hustle will make you feel more fulfilled and happy, leading to higher productivity at your regular job.

You may really enjoy work, but if it’s not your true passion, it can be a grind sometimes. And although dropping a stable job to pursue your passion could be a solution for this, it isn’t ideal for your wallet. Side hustles are unique because they offer the best of both of these worlds. Pursuing your passion, without having to sacrifice the financial stability your regular job provides, makes you feel more fulfilled, happy, and productive.

6. Your side hustle will teach you how to manage your time and take on big responsibilities.

When you work a full-time job and run a side-hustle, time is your most precious asset. You can’t afford to waste it. To take advantage of the limited amount of time you have after work, you need to learn how to prioritize your most important tasks, exercise discipline to actually do them over the many little, unimportant tasks that are time sucks, and take on the responsibility of not only building a top-notch product, but also crafting a compelling brand experience.

These are the requirements for starting a successful side hustle, and if you can follow them, you’ll hone your time-management skills and be able to leverage them at your regular job.

7. If your side hustle is successful, you can help your colleagues get better at their jobs.

Whether you become a star at marketing your personal brand, developing partnerships, or selling your product or service, your can make your colleagues better by teaching them your new skills. For example, if you have a newfound talent of selling, but you work in marketing, you can still teach your colleagues some sales skills to improve their blog post pitches at team brainstorms.

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Topics: Freelancing

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