🤑 Side hustles that work

The best strategies for building a side hustle.

“How to start a side hustle that works?” 

This question came in on Instagram last week during my Ask Me Anything. It really made me reflect on how we think about side hustles. Often it’s easy to fixate on something of your own creation like selling the scarves you crochet (don’t monetize your hobby!), or freelance writing in your spare time, or trying to become a YouTuber, podcaster, Instagram or TikTok influencer and making money through affiliate marketing and brand partnerships. Funnily enough, plugging “side hustle” into Getty Images yields a full page of just influencers in front of cameras…

But really, a side hustle can just be another job that you pick up in addition to your main job. A clock in, clock out sort of job (like retail or being a barista) or gig work that builds to consistent, steady money like babysitting, dog walking, tutoring, photography, freelance editing, etc. 

The hope is that you can quit the side hustle if it becomes untenable or after you’ve reached the goal towards which you were striving (e.g. debt payoff, increased saving, helping a family member). 

Unfortunately, that’s often mere optimism because there are also plenty of folks, myself formerly included, who cobble a bunch of side hustles together in order to create a livable income or to subsidize a primary job that doesn’t provide a livable income. 

While we’re chatting about side hustles, let’s talk about how much to invest into your extra stream of income. Obviously the answer is subjective, but it should be a modest amount. Nothing that could risk putting you into financial trouble if it doesn’t work. You want to focus on a side hustle with little to no start-up costs. Back in my peak side hustling times, I mostly went after jobs to which I could apply for free (e.g. usher at the movies, barista, babysitter). However, I did sometimes strategize to boost my profile. For example, I would pay to run a background check on myself in order to have a badge on my profile for Sittercity and Care.com that confirmed I was legit. It cost something like $20 and paid for itself quickly because it made me a more competitive candidate for jobs. 

In an effort to help brainstorm side hustle opportunities, I asked my Instagram community about their experiences. Here are some of their responses: 

• Selling gently used items

• Focus groups 

• Social media freelancer 

• Babysitting

• Pet sitting

• House sitting 

• Task rabbit / running errands for people

• Mobile notary (mainly doing general notary work)

• Baker (Our state allows home bakers to sell out of their homes with no commercial kitchen required.)

• Detailing/cleaning cars

• Interpreter 

• Gameday staff for local sports teams 

• Uber eats (but disclosed they aren’t confident it’s financially beneficial) 

• Personal trainer 

• Shipt (a delivery service) 

• Front desk at a gym (membership is an extra perk) 

Friendly warning: If you’re going to sell a product, even a digital one, it’s important to understand sales tax and it’s on you to know whether or not you need to make a payment to your state and the state in which a buyer resides. You also need to understand the state and city regulations around your side hustle and if you’d need a license or special equipment to legally be able to sell your goods or services. 

Serious warning: Please don’t mess with multi-level marketing schemes (MLMs) as a means of earning extra income. They’re often marketed as lucrative side hustles, but statistically you’re more likely to end up in debt than with a steady flow of cash. It’s a few years old, but season one of The Dream podcast is an excellent overview on MLMs. There’s also the LuLaRich docuseries on Amazon or this article or this Atlantic story about the Breakaway Movement. 

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Are there any “easy” side hustles that have worked for you? 

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