🤑 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.
Minor IT work is one of my side hustles and probably the one I could expand if I wished. My friend works at the library and they have a constant influx of people wanting help with their devices (phones, computers, iPads, etc). They have issues that aren’t big enough to spend a $100 at an IT store. Instead they’re things like how do I turn notifications on, why is my keyboard typing in strange symbols, how do I connect to the internet, etc.
So I’ve started helping. Most times it’s so easy I don’t charge anything. Most of these people are elderly and want to remain relevant and connected to their children and grandchildren, and I get joy out of seeing how happy they are when we have a new gifted device set up and family contacts added and then showing them how to video chat. Some times I just guide them to fixing the issue via phone or email. They’re happy so that makes me happy and trite as it sounds, that’s payment enough. If they insist on paying, I tell them I accept any homemade foods instead of money.
Some times though there are more serious issues, Eg, someone erased needed operating files by mistake. I’m not an IT person by training but with Google and what little knowledge I have (plus a couple of USB devices with software tools) I can usually fix it. For those ones, I accept a bit of money but make sure it is still far less than what a store would do.
I have little jobs several times a week by word of mouth only. Two big regular ones are for a physiotherapist (she has me look after client lists, conversion of documents to proper format, website maintenance), and one for a police detective who does presentations for other police agencies across the country (I download and embed video for him, do some proof of concept designs which a professional designer (and friend) will work with if the department likes it, and answer basic questions like how to safely transfer large files to a secure laptop that won’t accept USBs—that was yesterday’s question).
If I advertised I likely could do this full time and make enough to live on (I live cheaply in the first place). I may advertise when I retire. For now, I’m happy with it as is. I also shovel driveways, walk dogs, dog-sit, and house-sit too (they usually have Netflix or prime so I get to binge watch all the shows I’ve heard about but never seen). I do have a main job as an independent contractor (take jobs I want, work when I want, don’t work when I don’t want), so I have time to do the fun side gigs.
My side hustle is driving for Uber or Amazon or Shipt. Not great money but since prop22 passed, drivers get paid more fairly. I can usually make an extra $1000 a month if I try hard enough.