I am not a lawyer and the following is my personal experience and for entertainment purposes. Telling your boss and/or employer about your side hustle may have negative repercussions including loss of employment. Please consult a lawyer for legal advice on this matter.
Are you sitting around in fear that your employer is going to find out about your side hustle?
You may be wondering “do I have to tell my employer about a second job”. Let’s take a deep dive into sharing your side hustle with your boss:
Before Telling Your Boss
Let’s look at some of the steps you may want to do before telling your boss about your side hustle.
Does your employer allow side hustles?
Many official employee handbooks forbid you from using your talents for outside work. However, this may not be as black and white as your employer wants you to believe.
Many employers will allow you to have outside work if it isn’t in the same sector they operate. For example, you work for a restaurant managing their website and you want to manage a hair salon website. These are unrelated sectors. Unless your employer plans to take on the hair salon industry you may be clear.
Additionally, if your side hustle is in a different field altogether your employer may give you the thumbs up. Let’s say you are an accountant but want to start a freelance writing business. These are clearly unrelated to each other and your employer may have no problem.
Finally, many employee handbooks are vague on the topic of outside employment. Some simply state that you must have the approval of your boss or human resources. In this case you may have no choice but to tell your employer about a second job.
Is your side hustle a conflict of interest?
Oftentimes when browsing your employer’s employee handbook you will find a section on conflicts of interest or a non-compete clause.
In regards to conflicts of interest this can apply to a wide array of things. There are two most obvious examples. You are doing work in the same industry as your employer or the same field as your day job. However, these are not necessarily black or white either and can vary from employer to employer.
Additionally, your employer may have a clause preventing you from working with their clients outside of your day job. Using the example above, if you are an accountant starting a freelance writing business. Your employer may frown on you writing blog posts for one of their clients even if it doesn’t overlap with your accounting job.
Your employer may also not approve of you starting a business with a coworker. They may also deny you working for your boss outside of your day job.
Furthermore, your side hustle should never require the use of proprietary information or software from your employer. Also, you should never use the resources or tools provided by your employer. If your side hustle requires Adobe Photoshop then you better get an Adobe Photoshop subscription yourself. If your day job provides a laptop, then you should never use it for your side hustle. Using anything provided by your employer in your side hustle may create very real problems for you later on.
Conflicts of interest can come up in very diverse ways. Some may even be fine for one employer or boss and against the rules for another.
If you believe there is a conflict of interest it is probably best to consult with a professional.
Do I have to tell my employer about my second job?
Currently you are not legally required to tell your boss or employer about a second job or side hustle. However, not doing so can have huge implications. From losing your boss’ trust to losing your job altogether. I personally believe more harm can come from hiding a side hustle than disclosing it.
Between social media and Google there is a good chance your employer will find out about your side gig anyways. You may talk with a coworker at lunch or share your latest work on social media. All public acknowledgements of your side hustle can lead to you being “outed”.
Rather than be called into human resources or your boss’ office one day at random and asked to explain yourself. I believe it is better to disclose your side hustle on your terms, where you can control the conversation.
Showing a level of transparency can also calm fears your employer may have about you working on the side.
Your Relationship with Your Boss
Whether to disclose your side hustle may also depend on your relationship with your boss or your boss altogether.
Let’s say you have an “old school” boss that does believe things are black and white. They may not understand that selling t-shirts on TeeSpring is not the same as making graphics for your client’s competitor.
Additionally, if your boss has it “out for you”, you may not want to give them another excuse. Honestly, if this is the case, you may want to lean into your side hustle or find a new job.
However, many people have a great relationship with their boss. If that is you, it may be a quick 5 minute conversation that could lead to a positive outcome.
Telling Your Boss
How to Tell Your Boss?
This will very much depend on the relationship you have with your boss. If you have a great relationship with your boss then telling them could be as simple as a The West Wing style “walk-and-talk”.
However, what happens if you have a less than stellar relationship with your boss? You may want to request a formal meeting with your boss and include a member of human resources.
The “how” may also depend on what your employee handbook says. Some require boss approval and some require company approval.
Does your employer require company approval? If so, you may want to chat with your boss first about your side hustle. Gauge if they see any issues and ask for advice on the next steps.
Ensuring your boss is onboard before jumping to human resources may help you get that formal employer approval.
You decide to tell your boss or human resources office, you schedule the meeting, but what’s on the agenda?
First and foremost I would be honest and transparent. You don’t have to provide a minute-by-minute job description or a client list. However, I wouldn’t try to hide anything either.
Start out with what your side hustle is and the type of clients you have or are pursuing. Focus on how your side hustle isn’t a conflict of interest for you or your employer. This may help ease your boss’ tensions right out of the gate.
Emphasize to your employer that this is in fact a side hustle and will never interfere with your day job. Explain how you are going to be doing your side hustle on nights and weekends only. Also, let them know you will always use your own software and equipment.
I do not recommend mentioning transitioning your side hustle into a full time job. Even if that is your goal. This can give the impression you are ready to quit and may have your employer searching for a replacement hire.
Finally, prepare for your boss or employer to not take your side hustle seriously. For example if you are talking with your boss about doing quick tasks on Fiverr, your boss may think that is “chump change” and could never be a threat to their business.
This may hurt if it happens. However, this provides you freedom with minimal concerns about your day job’s future.
My Side Hustle Was Denied, What Can I Do?
If your boss or human resources denies your side hustle then you have a few options.
You can find out what can be done to get it approved. Will dropping a client or two give you the thumbs up? If you focus on another area (Writing blog posts instead of generic SEO) is that approved?
If your current side hustle cannot be approved, will they be fine with another? Can you start an Etsy store or sell on eBay?
What if you cannot find a way for your employer to approve any of the side hustles you want? Then you have to decide between side hustling and your day job.
If you decide to find a new job, it may be important to disclose your side hustle in the interview. This may help avoid the same problem at your new employer.
My Side Hustle Was Approved, What’s Next?
What happens after your boss or human resources department approves your side hustle?
You need to walk-the-talk. If you committed to not taking any clients in your employer’s industry then you better not. If you agreed to not work in your day job’s field then avoid it at all cost.
Continue to watch for any potential conflicts of interest that arise. If you become known as the “graphic gal”, make sure you aren’t helping coworkers create Christmas cards on the clock.
While you are on the day job clock, give 100% to your boss. Then while off the clock give your side hustle 110%. Whatever you do, never let the two jobs mix unless you are given approval to do so.
Sometimes you are actually given permission to mix your side hustle and your day job. I’ve seen a video editor friend get gigs for his side hustle from executives at the company. Nothing wrong with that and it was clearly approved.
Also, keep in mind that you cannot let your work start to decline just because you have a side hustle. If your second job keeps you up until midnight most nights, make sure it doesn’t show at work. This can have very real and painful consequences.
Should I Discuss My Side Hustle in a Job Interview?
Sharing My Second Job
When you are in a job interview you always want to put your best foot forward. You also want to avoid putting out any red flags that can turn off a potential employer.
Is your side hustle inline with the job you are pursuing? If so it may be in your best interest to tell the prospective manager. This may especially be true if it showcases a skill your day job may not allow you to show.
For example, if you are a copywriter at your day job and a freelance editor on the side. If you are applying for an editing job, then your freelancing gig lets you showcase experience. Another example, if you are a data scientist who uses MATLAB in your side hustle but not at work. The additional MATLAB skill may help further your application.
Whereas some side hustles may be unrelated to the job you are applying for. If that is the case you may want to wait until after you are hired to disclose the second job. For example, when I worked at Disney World on weekends, it didn’t provide any benefit in my web development interview. As luck would have it I had an awesome hiring manager. Therefore, my Disney World job came up in casual conversation during the interview.
You may also want to disclose your side hustle if it can be easily found. For example, if you discuss your side hustle on social media or it shows up in a quick Google search. It is always better to share information on your terms than let it look like you are hiding something.
For example, if you are a freelance SEO specialist and are applying for an SEO day job. Then it is better to squash any concerns in the interview than let them think there may be issues later.
How to Share My Side Gig?
If you decide to share your side hustle in a job interview, position it as a strength. Mention that you use your side hustle to continuously improve your craft and learn new skills.
Position it as a way to showcase your strong work ethic and incredible time management skills. Additionally, reassure the hiring manager that your side hustle is second priority. Let them know your second job will only be done on nights and weekends and outside of work hours.
Additionally, inform them you will never let your side hustle become a conflict of interest. Finally, stress that you will always abide by all employer rules and the employee handbook.
Choosing whether to disclose your side hustle to your employer or hiring manager can be a tough decision. Sometimes that decision is made up for you by employer rules.
However, how you disclose your side gig can have a huge impact on getting approved or denied.
If your side hustle is denied, first try to find a way to get it approved. In case that doesn’t work you can find a new job altogether.
If you get approved for a side hustle do not take it for granted. Continue to give your day job 100%. Never use your employer’s proprietary information or the tools they provide in your side hustle.
Are you stressed about your boss finding out about your second job? If so then it may be time to tell your employer. Side hustles are meant to be a fun way to make extra money and achieve financial freedom.