The 5 W’s: How to Choose the Right Side Gig

It’s no secret that the gig economy has been gaining popularity over the past few years–and why shouldn’t it? Flexible scheduling, extra income, and mobile technology are all reasons why this industry is growing and attracting a unique and diverse workforce.


If you’re trying to decide if the time is right to get a side gig, you’re in luck. We put together a guide using the 5 W’s (who, what, when, where, why–in no particular order) to help make this decision a little easier.


Simply, a side gig is a way to earn income in addition to your primary job. In some cases, people work multiple side gigs as their main source of income.



There are several reasons people choose to get side gigs, none of which are right or wrong. Thanks to the versatility of the gig economy, there’s no bad time to pick up a gig. Some of the reasons to look for one include:

  • Wanting/needing additional income
  • Interest in gaining more experience
  • Looking to get out of the house
  • Changing careers



This is arguably the most tricky, yet most exciting part of this process. We suggest going about it a few ways:

    • Assess your skills. What industry do you want to work in? What experience do you have that translates to picking up extra work? Thankfully, there are side gigs for virtually every skill or industry, whether they include technical skills or soft skills.
    • Look at options. If you’re open to different types of jobs or have a variety of experience, it’s helpful to look online for options. You’ll have the opportunity to learn about different companies and gather information before making a decision.
  • Decide what’s important to you. There are facets of the gig economy that are going to be more essential when choosing the right job. These may include pay rate, pay schedule (day-of versus weekly versus bi-weekly), or location(s).



Deciding how much time to allocate to working an extra job is completely up to you. You’ll want to be cautious about not getting burned out by too many obligations, which could affect your work or add unnecessary stress. Answering the following questions may help you decide when to work your side gig:

  • What does your schedule look like?
  • How much free time do you have?
  • Do you want something with a more consistent schedule or more flexibility?



It’s helpful to be comfortable working in a team setting or independently. If you have a strong preference for one or the other, you should keep that in mind when choosing the right job. On another note, if you’re choosing a side gig, you may want to consider asking a friend if they want to join you. Having someone to navigate this process with can provide comfort, as well as motivation.

About The Author

Cat is the Marketing Manager at Shiftgig, primarily focused on content marketing and social media. She’s passionate about helping transform the way people work and empowering our Specialists be successful. In her spare time, Cat does stand-up comedy at Chicago’s own Second City!