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Writer's pictureEnthuse Foundation

Guide to Successful Side Hustles

For many people, the idea of entrepreneurship can be scary. It can conjure up visions of long hours, hefty financial investments, or risking an established career to take a chance on a new venture. However, those same people may already be entrepreneurs without even realizing it. How? If they’ve ever earned money through babysitting, driven for a rideshare platform, or sold handmade goods to friends...they’re entrepreneurs.


If you are doing these activities while having a full-time job, these secondary ventures are considered side hustles. There are many reasons people have a side hustle – extra money, a passion project, or a way to gain work experience.


Sometimes a side hustle can turn into a billion-dollar business. One of Sara Blakely’s first jobs was as a saleswoman for a fax machine company. As part of that company’s dress code, she was required to wear pantyhose.  Blakely liked the way the material slimmed her midline but not how her toes felt in certain shoes. She tried different ways to make them more comfortable. After many incarnations, the Spanx prototype was born.


Blakely continued her sales job while pursuing what would become Spanx in her spare time. Slowly, Spanx became the household brand that we know today, and Blakely left her sales job to run the company full-time.


Whether you ultimately want your second venture to be your full-time one or using your side hustle to make additional revenue, there are ways to navigate both opportunities without compromising either one.


Here are tips for pursuing your secondary businesses while keeping your current employer happy.


  1. Review the Employee Handbook – Companies have strict policies about what can be perceived as conflict-of-interest matters. Additionally, there might be language around non-compete clauses. Make sure you fully understand and are compliant with your organization’s rules.

  2. Honesty is Always the Best Policy – Things are bound to come to light. With people documenting all aspects of their life on social media, your company will likely find out about your venture. Being transparent is key to move forward with both opportunities.

  3. Set a Schedule – When you are on company time, make sure you are working on its projects. There should be clear boundaries between your corporate job and your side hustle. Schedule time after the workday ends and on weekends to work on your business, but also include some R&R so you aren’t burning the candle at both ends. If you’re exhausted you’re not going to do the best work for your employer or yourself.

  4. Use Common Sense – If something doesn’t feel right, it probably isn’t. Make sure your side hustle is legal and follows the designated rules for the industry. For example, if you sell homemade cookies, make sure you follow your state’s Cottage Food Laws.

  5. Report All Earnings – Talk to an accountant or financial advisor about the proper way to document your revenue. Remember, your employer takes taxes from your paycheck, but you will have to account for them yourself on your side hustle. Here is a summary from the IRS that provides more information.


Conclusion: Side hustles are a great way to learn new skills, make extra money, and explore a passion project. However, for those juggling full-time employment and a part-time gig, it is a slippery slope. By being transparent and honest, you are poised for success at pursuing both.

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