Side Hustling for Beginners: How to Make Money on the side & Keep Your Day Job

If you're here, you have some part of a hustler's spirit.  You work hard.  You see opportunities and you seize them.  

And in this good year of our Lord Two Thousand and Sixteen, you also know that neither tomorrow nor jobs are promised.  You may be killin it at work today and let go in an unfortunate round of layoffs tomorrow.  

So you might have a side hustle.  Or you've thought about one.  Maybe you see your side hustle as your on ramp to a life of freedom and answering to no one.  Maybe you just need some extra cash to float you month to month.  Either way, as long as your side hustle is extra money, not your main source of income, you need to balance its demands and protect your main job.  

First, it goes without saying, but you absolutely cannot let the quality of work at your day job suffer to support the side hustle.  Keep the side hustle squarely on the side, sticking to after hours and weekends, until you are sure you can balance them both. 

Next, you definitely have to figure out if you should let your 9 to 5 know you're working on the side.  And of course, since I'm technically a lawyer, my answer will always be "it depends."  

Most companies claim want their employees to have full lives and pursue their passions outside of work.  A few actually encourage workers to bring all of yourself to work everyday, and the rest are more like "yeah yeah that's cute, where's the TPS report?"  If you work for the former, by all means, share what you're doing on the side (provided it doesn't directly conflict or compete with your full time job).  But, if like most people, you think your side hustle might harm more than help, ask yourself a few more questions first.

How close is my side hustle to my day job?

If your side hustle has zip, zilch, zero to do with your day job, and you feel comfortable sharing, you may want to clue them in.  For example, if you are a PR manager by day but make flower crowns by night (real life example btw), you're probably okay to share that with your team.  It's separate and distinct enough that your manager isn't likely to think that is taking away from your productivity at work.  Honestly, they're more likely to think of it as just a cute hobby on the side.  And let them.  Let them underestimate your side hustle, especially if you have any dreams of making it your main hustle.

On the other hand, if you have any designs on using the skills, contacts, or resources that you have access to by virtue of your day job to benefit your side hustle, keep those lips closed.  At best, it's unethical to use your company's resources in that way; at worst, it's directly counter to your employment agreement or company policy.  Keep it to yourself and work on the sly unless and until you are ready to jump ship.

Do I work with a bunch of haters?

This isn't just about "will my day job care about my side hustle?"  This question gets to the heart of your office or team culture and forces you to ask "will I alienate myself from my colleagues and managers by revealing my side hustle?"  And that's a bigger, more important question to ask. 

Sure, your side hustle may have zip to do with your day job and zero impact on your ability to do said day job.  But, if your team resents your side hustle, you could be screwed.  Ask yourself, do I work in a place where people are supportive of those who go against the grain?  Or, are they more comfortable with everyone living at the same speed they are?

You may have coworkers who are just as broke as you but resent the fact that you had the drive and took the initiative to start something on your own.  You may have older colleagues or managers who've resigned themselves to a life of watching the clock and waiting for the weekends and who begrudge you the spirit and energy of youth to carve out an alternative path.  

If you work with haters, keep your business to yourself.  Cook those cupcakes on the side.  Link your side hustle's social media accounts to an email address and web presence completely separate from the ones your colleagues can see.  Filter them out of your Facebook updates so they don't see your posts about your business.  

If you work with haters but can't keep your side hustle completely separate like church and state, modesty and deflection are your best friends.  Like I said before, make your team think what you're doing is far more of a hobby than a viable source of income and potential alternative to your current employment. 

"Oh the babysitting is going well but I just love little Kennedy so much, I'm just happy to spend time with him, I feel bad for even charging his mom but she insists."

"How's the cupcake business? Well, I'd hardly call it a business. It's mainly an excuse for me to justify my sweet tooth!"

What's my end goal?

Lastly, figure out what your game plan is and what's the end goal.  

If you're truly side hustling just to make ends meet, it's time to do some career planning.  At what point will your current company or industry pay you enough to drop the side gig?  If you don't have a sense of what role or level of experience gets you to that income level, it's time to do some digging.  GlassDoor and LinkedIn are your best friends for this.  Once you know those answers, get proactive and meet with your manager to create a plan for your future. 

If you are side hustling to set yourself up for a career or industry change in the near future (say, you're currently a teacher but doing SEO on the side to make the jump into digital marketing), definitely keep that to yourself until your next big move is imminent. Any sooner and you risk your manager thinking you already have one foot out the door and starting to sideline you and look for your replacement. 

Finally, if your dream is for your side hustle to eventually be your only hustle, ask yourself again if you work for haters.  99% of the time, the answer to that will be yes.  If that's your plan, don't say a word about what else you've got going on until your escape plan is firm and imminent.  If you've built your side business to the point where you will be ready to make the leap within the next 60 days, then you can start to be more honest about what else you've been up to.  But even then, unless your finances are ready, I would keep it under wraps until you give notice.  

Ask yourself these questions first before revealing your side hustle.  And if there's any doubt, keep your mouth shut and your business to yourself.