How to Start a Side Hustle Without Making Your Boss Angry


Whether you’re interested in earning more money, gaining valuable job experience, or pursuing a passion, starting a side hustle can be a great way to achieve your goals. You can conduct your side hustle on your own time, and it offers a low-commitment opportunity to try something new.

Starting a side hustle can even be good for your day job. Your boss may be impressed by your proactive, go-getter attitude.

However, you can’t just assume that your supervisor will be on board with your side hustle. Talking to your boss now, before your launch that hustle, can help you address any concerns and ensure there are no negative repercussions for your full-time gig.

Are You Ready to Manage a Side Hustle Alongside a Full-Time Job?

Before picking up a side gig, it’s important to set clear goals and guidelines. Why do you want to start a side hustle? For extra cash? To improve upon existing skills to advance in your career? Having a clear vision will help you stay focused when life gets busy and you don’t feel like putting in any more hours.

Keep in mind that your side gig will take you away from other things, like spending time with friends, family, and even your beloved Netflix series. Take stock of your priorities. You need to be willing to make tough choices to schedule enough time for your side gig to flourish.

One very important note: Your side gig should not take over your day job or be in direct conflict with it. You definitely don’t want a side gig working for one your full-time employer’s competitors. As soon as you find yourself giving less brain power to your full-time job, you risk getting on the wrong side of your boss.

How to Approach Your Boss

If you’ve decided a side hustle is right for you, it’s time to share your intentions with your boss. It’s best to be open and honest about your activities. Better to err on the side of caution and proactively bring it up, even if your employee handbook doesn’t require disclosure.

Consider scheduling a meeting with your boss rather than popping in for a quick informal conversation. That way, you’ll be able to discuss your side hustle thoroughly and address any of your boss’s concerns without being rushed. You also want to make it clear that you’re interested in maintaining a trusting relationship with your employer and keeping your day job. Assure your boss that you’re committed to your current position.

Once you’ve convinced your boss of your loyalty, fully disclose your side hustle and ask for advice on how to proceed. Perhaps your boss needs to tell their boss, or maybe they’ll want to have regular check-ins to discuss whether your side gig is affecting your performance. Whatever happens, make sure you fully understand what is expected of you before leaving the meeting.

How to Handle Concerns or Hesitations

Your boss may be concerned that you’ll eventually leave your job for the side gig or that the time spent on the side hustle will negatively impact your full-time responsibilities. If so, reassure them that your side gig will actually enhance your job performance. Here are some talking points you can use:

  1. You enjoy your job, but you also want to indulge in other pursuits. Explain to your boss that your side gig offers you the ability to pursue your passion so that you can be more fulfilled and, therefore, a happier and more productive employee.
  2. You took the time to review your employment agreements, so you know that you’re not violating any rules. You will continue to deliver excellent performance, and you will not recruit other employees to your side hustle.
  3. A side gig can help you strengthen your skills and become a better employee at your day job. For example, your side hustle will help you learn how to prioritize projects and exercise discipline to meet deadlines.
  4. Because a successful side hustle requires you to do lots of outreach and expand your network, it will help you develop better communication skills, which will also translate into improved performance at your day job.

Getting Started With Your Side Hustle

Once you have the go-ahead from your boss, the fun part begins: starting your side hustle.

Consider the skills you already have or the ones you want to learn that will benefit your full-time job. In order to start a successful side gig, you need to know what skills someone would be willing to pay you for.

For example, think about your hobbies. Maybe you’re a really great guitar player. If so, you could offer to tutor kids in your area or team up with a band to play at weddings. If you want to improve your communication skills, you could sign up to teach English online. If your side gig is purely a matter of earning extra cash, there are plenty of easy side hustles you could start right now.

As for logistics, consider whether you’ll want to set up an LLC (limited liability company) or operate as a sole proprietor. Rules and regulations differ by state, so you may want to reach out to an experienced tax professional to help you understand the relevant laws in your area. You also want to put systems in place for tracking important things like income and expenses, business credit cards, and necessary insurance. You should take steps to separate your personal and business finances. It can all feel a little overwhelming, but your future self will thank you.

Starting a side gig can boost your happiness and your bottom line. There is a lot of money to be made, and you stand to become an even better employee at your full-time job, provided you balance things properly. As long as you’re up front with your boss about your moonlighting, you should have no problem.

Sarah Li Cain is an experienced content marketing writer specializing in FinTech, credit, loans, personal finance, alternative investments, real estate, banking, international business, and travel.

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